shikimic acid (Q410830)

chemical structure

Shikimi.svg
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German Wikipedia

Shikimic-acid-skeletal.png
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mass

174.053 dalton

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shikimic acid (English)

19 October 2016

2 references

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inferred from InChI

( )-5-epi-Shikimic acid

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(3S)-3alpha,4beta,5alpha-Trihydroxy-1-cyclohexene-1-carboxylic acid

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chemical formula

C₇H₁₀O₅

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shikimic acid (English)

19 October 2016

canonical SMILES

C1C(C(C(C=C1C(=O)O)O)O)O

1 reference

shikimic acid (English)

19 October 2016

isomeric SMILES

C1[C@H]([C@@H]([C@@H](C=C1C(=O)O)O)O)O

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shikimic acid (English)

19 October 2016

melting point

186 degree Celsius

1 reference

Jean-Claude Bradley Open Melting Point Dataset

found in taxon

Pteridium aquilinum

2 references

Should we be frightened of bracken? A review of the evidence

Isolation of 5-hydroxypyrrolidin-2-one and other constituents from the young fronds of Pteridium aquilinum

Alicyclobacillus acidocaldarius

1 reference

Biosynthesis of the cyclohexanecarboxylic acid starter unit of .omega.-cyclohexyl fatty acids in Alicyclobacillus acidocaldarius

Hydrangea chinensis

1 reference

Secoiridoid glycoside and alkaloid constituents of Hydrangea chinensis.

Hypericum beanii

1 reference

Anti-staphylococcal acylphloroglucinols from Hypericum beanii

Blasia pusilla

1 reference

Phenolic constituents of the liverwort: Four novel cyclic bisbibenzyl dimers from Blasia pusilla L

Callitris columellaris

1 reference

flavonol glycosides from Callitris Glauca

Cleistopholis patens

1 reference

Partially acetylated tri- and tetrarhamnoside dodecanyl ether derivatives from Cleistopholis patens

Daucus carota

1 reference

Regulation of the shikimate pathway of carrot cells in suspension culture

Dendrobium fuscescens

1 reference

Defuscin, a new phenolic ester from Dendrobium fuscescens: Conformation of shikimic acid☆

Dioscorea bulbifera

1 reference

Glycosides from Dioscorea bulbifera

Stenostomum acreanum

1 reference

Phytochemical and pharmacological studies of Guettarda acreana

Hedyosmum bonplandianum

1 reference

The Analgesic Activity ofHedyosmum bonplandianum: Flavonoid Glycosides

Hypericum laricifolium

1 reference

Constituents of Hypericum laricifolium and their cyclooxygenase (COX) enzyme activities

Hypericum monogynum

1 reference

Chemical constituents of Hypericum ssp.

Illicium anisatum

1 reference

The shikimate pathway. Part 8. Synthesis of (−)-3(R)-amino-4(R),5(R)-dihydroxy-1-cyclohexene-1-carboxylic acid: The 3(R)-amino analogue of (−)-shikimic acid

Illicium majus

1 reference

Isolation of Neoanisatin Derivatives from the Pericarps of Illicium majus with Other Constituents.

Illicium simonsii

1 reference

Studies on chemical constituents of Illicium simonsii

Kielmeyera pumila

1 reference

Xanthones and phenylcoumarins from Kielmeyera pumila

Leucopogon parviflorus

1 reference

Iridoid glucosides in epacridaceae

Magnolia denudata

1 reference

Chemical constituents from the leaves of Magnolia denudata

Neurospora crassa

1 reference

Sequential appearance of radiolabel-tagged cyclohexadienyl derivatives of shikimate in Neurospora

Phycomyces blakesleeanus

1 reference

Acidic metabolites from Phycomyces blakesleeanus

Pinus pinaster

1 reference

Carboxylic Acids of Moroccan Pinus Pinaster Bark Extract

Pinus ponderosa

1 reference

Chemistry of toxic range plants. Water-soluble lignols of Ponderosa pine needles

Piptostigma fugax

1 reference

Aporphinoid alkaloids and terpenoids from Piptostigma fugax

Populus lasiocarpa

1 reference

Phenolic analysis of bud exudate of Populus lasiocarpa by GC/MS

Prunus domestica

1 reference

LC/MS/MS characterization of phenolic constituents in dried plums

Pseudocyclosorus esquirolii

1 reference

Chemical and Chemotaxonomical Studies of Filices. LXVI. : Chemical Studies on the Constituents of Pseudocyclosorus subochthodes CHING and P. esquirolii CHING (Organic)

Sequoiadendron giganteum

1 reference

(3S,4S,5R)-3,4,5-trihydroxy-1-cyclohexene-carboxylic acid from Sequoiadendron giganteum

Terminalia chebula

1 reference

Chemical Constituents of Terminalia chebula

Vaccinium macrocarpon

1 reference

Hydrophilic carboxylic acids and iridoid glycosides in the juice of American and European cranberries (Vaccinium macrocarpon and V. oxycoccos), lingonberries (V. vitis-idaea), and blueberries (V. myrtillus).

Vaccinium myrtillus

1 reference

Hydrophilic carboxylic acids and iridoid glycosides in the juice of American and European cranberries (Vaccinium macrocarpon and V. oxycoccos), lingonberries (V. vitis-idaea), and blueberries (V. myrtillus).

Vaccinium oxycoccos

1 reference

Hydrophilic carboxylic acids and iridoid glycosides in the juice of American and European cranberries (Vaccinium macrocarpon and V. oxycoccos), lingonberries (V. vitis-idaea), and blueberries (V. myrtillus).

Vaccinium vitis-idaea

1 reference

Hydrophilic carboxylic acids and iridoid glycosides in the juice of American and European cranberries (Vaccinium macrocarpon and V. oxycoccos), lingonberries (V. vitis-idaea), and blueberries (V. myrtillus).

Vismia micrantha

1 reference

Constituents of Bridelia micrantha

Vismia parviflora

1 reference

Xanthones and other constituents of vismia parviflora

Escherichia coli

1 reference

A comprehensive genome-scale reconstruction of Escherichia coli metabolism--2011.

Brainea insignis

1 reference

Phenolic constituents from Brainea insignis

Calophyllum brasiliense

1 reference

Cytotoxic effects of mammea type coumarins from Calophyllum brasiliense.

Castanopsis fissa

1 reference

Triterpene hexahydroxydiphenoyl esters and a quinic acid purpurogallin carbonyl ester from the leaves of Castanopsis fissa

Corymbia citriodora

1 reference

The isolation of shikimic acid from Eucalyptus citriodora Hook

Excoecaria cochinchinensis

1 reference

New megastigmane glucosides from Excoecaria cochinchinensis LOUR. var. cochinchinensis

Ginkgo biloba

2 references

Extraction and isolation of shikimic acid from Ginkgo biloba leaves utilizing an ionic liquid that dissolves cellulose

Shikimin-säure aus der Blätter von Ginkgo biloba. L

Illicium verum

1 reference

Sur l'illicium religiosum

Liquidambar styraciflua

1 reference

Liquidambar styraciflua: a renewable source of shikimic acid

Pinus sylvestris

1 reference

Chemistry of Pinus sylvestris cones

Streptomyces lincolnensis

1 reference

New carbasugars from Streptomyces lincolnensis

Magnolia arcabucoana

1 reference

Chemical constituents of Talauma arcabucoana (Magnoliaceae): their brine shrimp lethality and antimicrobial activity

Vaccinium dunalianum

1 reference

Caffeoyl arbutin and related compounds from the buds of Vaccinium dunalianum

Dicranopteris dichotoma

1 reference

Chemical and Chemotaxonomical Studies on Filices. XLII. Chemical Studies on the Constituents of Dicranopteris dichotoma (THUNB.) BERNH. and Microlepia obtusiloba HAYATA

Juniperus oxycedrus

1 reference

Identification of hypoglycaemic compounds from berries of Juniperus oxycedrus subsp. oxycedrus through bioactivity guided isolation technique

Perilla frutescens

1 reference

Genetic control of the chemical composition of volatile oils in Perilla frutescens

Pelargonium reniforme

1 reference

Fascinating metabolic pools of Pelargonium sidoides and Pelargonium reniforme, traditional and phytomedicinal sources of the herbal medicine Umckaloabo

Pelargonium sidoides

1 reference

Fascinating metabolic pools of Pelargonium sidoides and Pelargonium reniforme, traditional and phytomedicinal sources of the herbal medicine Umckaloabo

potato

1 reference

Identification of metabolites associated with water stress responses in Solanum tuberosum L. clones

Streptomyces arenae

1 reference

Biosynthesis of the antibiotic 2,5-dihydrophenylalanine by Streptomyces arenae

Streptomyces nigra

1 reference

Streptomyces nigra sp. nov. Is a Novel Actinobacterium Isolated From Mangrove Soil and Exerts a Potent Antitumor Activity in Vitro

Senecio serratifolius

1 reference

Eremophilane, germacrane and shikimic acid derivatives from chilean Senecio species

Quercus mongolica

1 reference

Gallic acid esters of proto-quercitol, quinic acid and (−)-shikimic acid from quercus mongolica and q. myrsin aefolia

Senecio adenophyllus

1 reference

Eremophilane, germacrane and shikimic acid derivatives from chilean Senecio species

Culcitium serratifolium

1 reference

Eremophilane, germacrane and shikimic acid derivatives from chilean Senecio species

Senecio ovatus

1 reference

Eremophilane, germacrane and shikimic acid derivatives from chilean Senecio species

Nicotiana tabacum

1 reference

Phenylpropanoid Defences in Nicotiana tabacum Cells: Overlapping Metabolomes Indicate Common Aspects to Priming Responses Induced by Lipopolysaccharides, Chitosan and Flagellin-22

Apium graveolens

1 reference

Phytochemical and biological characterization of Italian "sedano bianco di Sperlonga" Protected Geographical Indication celery ecotype: A multimethodological approach

common sunflower

1 reference

Metabolic profiles of sunflower genotypes with contrasting response to Sclerotinia sclerotiorum infection

Brassica oleracea

2 references

Metabolic differentiation of diamondback moth ( Plutella xylostella (L.)) resistance in cabbage ( Brassica oleracea L. ssp. capitata).

Metabolic and bioactivity insights into Brassica oleracea var. acephala.

Capsella bursa-pastoris

1 reference

Chemical composition and biological screening of Capsella bursa-pastoris

Medicago sativa

1 reference

Metabolite profiles of nodulated alfalfa plants indicate that distinct stages of nodule organogenesis are accompanied by global physiological adaptations

Phaseolus vulgaris

1 reference

Metabolite Profiling of Root Exudates of Common Bean under Phosphorus Deficiency

Picea abies

1 reference

Analysis of phenolic compounds in spruce needle extracts using an UV-VIS-diode array detector

Triticum aestivum

1 reference

Comparative metabolic responses and adaptive strategies of wheat (Triticum aestivum) to salt and alkali stress

Prunus avium

3 references

Chemical characterisation and bioactive properties of Prunus avium L.: The widely studied fruits and the unexplored stems

Postharvest responses of sweet cherry fruit and stem tissues revealed by metabolomic profiling

Postharvest changes in primary and secondary metabolites of sweet cherry cultivars induced by Monilinia laxa

tomato

2 references

Metabolomic analysis of tomato seed germination

Metabolite content of harvested Micro-Tom tomato (Solanum lycopersicum L.) fruit is altered by chilling and protective heat-shock treatments as shown by GC–MS metabolic profiling

Dicranopteris pedata

1 reference

Chemical and Chemotaxonomical Studies on Filices. XLII. Chemical Studies on the Constituents of Dicranopteris dichotoma (THUNB.) BERNH. and Microlepia obtusiloba HAYATA

Choerospondias axillaris

1 reference

Studies on the constituents of the leaves of Rhus and of some species of related genera in Japan

Toxicodendron sylvestre

1 reference

Studies on the constituents of the leaves of Rhus and of some species of related genera in Japan

Rhus chinensis

1 reference

Studies on the constituents of the leaves of Rhus and of some species of related genera in Japan

Toxicodendron succedaneum

1 reference

Studies on the constituents of the leaves of Rhus and of some species of related genera in Japan

Neoshirakia japonica

1 reference

Studies on the constituents of the leaves of Rhus and of some species of related genera in Japan

Triadica sebifera

1 reference

Studies on the constituents of the leaves of Rhus and of some species of related genera in Japan

Saccharomyces cerevisiae

1 reference

In vivo instability of chorismate causes substrate loss during fermentative production of aromatics.

Caenorhabditis elegans

1 reference

Metabotyping of the C. elegans sir-2.1 mutant using in vivo labeling and (13)C-heteronuclear multidimensional NMR metabolomics

1 reference

https://plantreactome.gramene.org/PathwayBrowser/#/R-OSA-2744345&DTAB=MT

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Shikimic acid

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Identifiers

GND ID

4328368-8

1 reference

InChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1

German Wikipedia

InChI

1 reference

shikimic acid (English)

19 October 2016

2 references

shikimic acid (English)

19 October 2016

ChEBI release 2020-09-01

2 references

shikimic acid (English)

19 October 2016

https://commonchemistry.cas.org/detail?cas_rn=138-59-0

9 April 2021

1 reference

(-)-Shikimic acid (English)

19 October 2016

2 references

shikimic acid (English)

19 October 2016

Reaxys registry number

2210055

1 reference

shikimic acid (English)

19 October 2016

ChEBI ID

16119

mapping relation type

2 references

shikimic acid (English)

19 October 2016

International Chemical Identifier

InChI

InChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1

1 reference

SHIKIMIC ACID (English)

19 October 2016

2 references

MSBNK-BGC_Munich-RP017501

1 reference

MassBank accession ID

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MSBNK-BGC_Munich-RP017502

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MSBNK-BGC_Munich-RP017503

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MSBNK-BGC_Munich-RP017511

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MSBNK-BGC_Munich-RP017512

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MSBNK-BGC_Munich-RP017513

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MSBNK-Osaka_Univ-OUF00458

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MSBNK-RIKEN-PR010005

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MSBNK-RIKEN-PR100485

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MSBNK-GL_Sciences_Inc-GLS00087

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MSBNK-Kazusa-KZ000072

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MSBNK-Keio_Univ-KO001789

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MSBNK-Keio_Univ-KO001790

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MSBNK-Keio_Univ-KO001791

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MSBNK-Keio_Univ-KO001792

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MSBNK-Keio_Univ-KO001793

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SPLASH

splash10-0udj-0970000000-42465cd3f3e138b0bc12

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splash10-01b9-1950000000-6cba5b9b7c4891522045

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splash10-0a4i-9300000000-12d15a049b141a37f34e

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splash10-0a4i-9500000000-ed28bc20ae43473043c9

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splash10-0a4i-9500000000-9864f7359ffed65d6ef0

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splash10-0a4i-9500000000-26dfc876ae35c2cdb845

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splash10-0udi-0795000000-1100443abb8605953f58

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splash10-00di-9450000000-e6ca954dc1a9c1cc4285

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splash10-006x-9600000000-3a5ab91754d9d837d8b4

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splash10-00di-0950000000-b6178c499312eb95287e

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splash10-004i-0950000000-e6ca4ce5acb44dc23a74

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splash10-004r-9700000000-18afe769b0ef5ba3fbdb

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splash10-0udi-0491000000-49993b9b18e12b9461fc

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splash10-000i-9100000000-7d0218e803b828de53b2

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NMRShiftDB structure ID

20096803

1 reference

HSDB ID

3537

1 reference

Hazardous Substances Data Bank

28 October 2019

SHIKIMIC ACID (English)

10 May 2021

2 references

Mapping file of InChIStrings, InChIKeys and DTXSIDs for the EPA CompTox Dashboard

DSSTOX compound identifier

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0 references

1 reference

Global Substance Registration System

UNII

29MS2WI2NU

shikimic acid (English)

ECHA Substance Infocard ID

19 October 2016

100.004.850

1 reference

ECHA Substance Infocard database

ECHA Substance Infocard ID

100.004.850

27 December 2018

D02.455.426.392.368.367.379.750

(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid (English)

quotation

CAS no.: 138-59-0 (English)

1 reference

28 December 2019

SHIKIMIC ACID (English)

quotation

CAS no.: 138-59-0 (English)

1 reference

Shikimic Acid

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MeSH tree code

D02.241.223.268.792

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D02.241.511.852

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Human Metabolome Database ID

HMDB0003070

2 references

1 reference

Global Substance Registration System

shikimic acid (English)

19 October 2016

2 references

UNII

29MS2WI2NU

shikimic acid (English)

19 October 2016

0 references

1 reference

Great Russian Encyclopedia portal ID

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1 reference

6 April 2020

1 reference

28 October 2013

shikimovaia-kislota-f96bb4

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Microsoft Academic ID

0 references

1 reference

26 January 2022

https://docs.openalex.org/download-snapshot/snapshot-data-format

1 reference

4FSH (English)

19 October 2016

1 reference

3PHI (English)

19 October 2016

1 reference

3PHH (English)

19 October 2016

1 reference

4P4G (English)

19 October 2016

1 reference

3DOO (English)

19 October 2016

1 reference

4FOS (English)

19 October 2016

1 reference

4GUJ (English)

19 October 2016

1 reference

3BAF (English)

19 October 2016

1 reference

2GPT (English)

19 October 2016

1 reference

2AAY (English)

19 October 2016

1 reference

2DFN (English)

19 October 2016

1 reference

1ZUI (English)

19 October 2016

1 reference

2G1K (English)

19 October 2016

1 reference

4Y0A (English)

19 October 2016

1 reference

3PGJ (English)

19 October 2016

1 reference

2EV9 (English)

19 October 2016

1 reference

1ZYU (English)

19 October 2016

1 reference

2HK9 (English)

19 October 2016

1 reference

4FR5 (English)

19 October 2016

1 reference

3TNL (English)

19 October 2016

1 reference

3JYQ (English)

19 October 2016

1 reference

3SLH (English)

19 October 2016

1 reference

2AA9 (English)

19 October 2016

1 reference

2IYS (English)

19 October 2016

1 reference

1U8A (English)

19 October 2016

1 reference

3T39 (English)

19 October 2016

1 reference

2D5C (English)

19 October 2016

1 reference

4FQ8 (English)

19 October 2016

1 reference

4P4L (English)

19 October 2016

1 reference

3NVS (English)

19 October 2016

1 reference

2IYX (English)

19 October 2016

1 reference

2IYQ (English)

19 October 2016

1 reference

2IYR (English)

19 October 2016

1 reference

3SEF (English)

19 October 2016

1 reference

inferred by common MeSH mappings on source and on Wikidata

1 reference

UMLS 2023