cucurbitacin b (Q27106259)

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chemical compound

1,2-dihydro-alpha-elaterin
2beta,16alpha,20,25-tetrahydroxy-9-methyl-19-nor-9beta,10alpha-lanosta-5,23-diene-3,11,22-trione, 25-acetate
2beta,16alpha,20,25-tetrahydroxy-9-methyl-3,11,22-trioxo-19-nor-9beta,10alpha-lanosta-5,23-dien-25-yl acetate

Language	Label	Description	Also known as
English	cucurbitacin b	chemical compound	1,2-dihydro-alpha-elaterin 2beta,16alpha,20,25-tetrahydroxy-9-methyl-19-nor-9beta,10alpha-lanosta-5,23-diene-3,11,22-trione, 25-acetate 2beta,16alpha,20,25-tetrahydroxy-9-methyl-3,11,22-trioxo-19-nor-9beta,10alpha-lanosta-5,23-dien-25-yl acetate

Statements

type of chemical entity

0 references

0 references

[(E,6R)-6-[(2S,8S,9R,10R,13R,14S,16R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate

1 reference

based on heuristic

inferred from SMILES

558.319268±0 dalton

1 reference

language of work or name

Cucurbitacin B (English)

5 October 2016

stereoisomer of

[(E,6R)-6-[(2S,8S,9R,10S,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate

2 references

based on heuristic

inferred from InChIKey

based on heuristic

inferred from InChI

(3E,6S)-6-[(1S,2S,3aS,3bR,8S,9aR,9bR,11aR)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1H,2H,3H,3bH,4H,8H,9H,9aH,11H-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate

1 reference

based on heuristic

inferred from InChIKey

[(E,6S)-6-[(2R,8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate

1 reference

based on heuristic

inferred from InChI

chemical formula

C₃₂H₄₆O₈

1 reference

language of work or name

Cucurbitacin B (English)

19 November 2016

canonical SMILES

CC(=O)OC(C)(C)C=CC(=O)C(C)(C1C(CC2(C1(CC(=O)C3(C2CC=C4C3CC(C(=O)C4(C)C)O)C)C)C)O)O

1 reference

language of work or name

Cucurbitacin B (English)

19 November 2016

isomeric SMILES

CC(=O)OC(C)(C)/C=C/C(=O)[C@@](C)([C@H]1[C@@H](C[C@@]2([C@@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3C[C@@H](C(=O)C4(C)C)O)C)C)C)O)O

1 reference

language of work or name

Cucurbitacin B (English)

19 November 2016

Cucumis sativus

1 reference

Chromatographic and mass spectral analysis of cucurbitacins of three Cucumis sativus cultivars

Iberis umbellata

2 references

Analysis of cucurbitacins in medicinal plants by high-pressure liquid chromatography-mass spectrometry

Arvenin I (Cucurbitacin B 2-O-β-d-Glucopyranoside) from Iberis umbellata

Begonia nantoensis

4 references

Cytotoxic and anti-HIV principles from the rhizomes of Begonia nantoensis

Cytotoxic and anti-HIV Principles from the Rhizomes of Begonia nantoensis.

Cytotoxic and anti-HIV Principles from the Rhizomes of Begonia nantoensis.

Cytotoxic and anti-HIV principles from the rhizomes of Begonia nantoensis

1 reference

Die cucurbitacine in Bryonia alba und Bryonia dioica

1 reference

Isoleirung und struktur der cucurbitacine aus Bryonia dioica

Casearia arborea

2 references

Novel cytotoxic diterpenes from Casearia arborea.

Novel cytotoxic diterpenes from Casearia arborea.

4 references

Cucurbitane-type triterpenoids from the stems of Cucumis melo

Cucurbitane-type triterpenoids from the stems of Cucumis melo

Cucurbitane-type triterpenoids from the stems of Cucumis melo

Cucurbitane-type triterpenoids from the stems of Cucumis melo

Leucopaxillus gentianeus

4 references

Cucurbitane triterpenes from the fruiting bodies and cultivated mycelia of Leucopaxillus gentianeus.

Cucurbitane triterpenoids from Leucopaxillus gentianeus.

Cucurbitane Triterpenoids from Leucopaxillus gentianeus

Cucurbitane triterpenoids from Leucopaxillus gentianeus.

Licania intrapetiolaris

2 references

Bioactive Constituents of the Roots ofLicaniaintrapetiolaris

Bioactive Constituents of the Roots ofLicaniaintrapetiolaris

Acanthosicyos horridus

1 reference

Cucurbitacins from Acanthosicyos horridus

Begonia heracleifolia

2 references

Phytochemical and biological investigation of Begonia heracleifolia

Phytochemical and biological investigation of Begonia heracleifolia

Begonia parviflora

1 reference

Finding the needle in the haystack. The dereplication of natural product extracts

Begonia plebeja

1 reference

Cucurbitacins: differential cytotoxicity, dereplication and first isolation from Gonystylus keithii

Bryonia verrucosa

1 reference

Cucurbitacins From Bryonia Verrucosa. Isomerization of 2-Hydroxy-3-Keto-Cucurbitacins

Cayaponia angustiloba

1 reference

Isolation and13C-nmr Assignments of Cucurbitacins from Cayaponia Angustiloba, Cayaponia racemosa, and Guraniasubumbellata

Ceratosanthes hilariana

1 reference

Isolation of feeding stimulants of Brazilian leaf beetles (Diabrotica speciosa and Cerotoma arcuata) from the root of Ceratosanthes hilariana.

Chrysosplenium flagelliferum

1 reference

Cytotoxic Principles from Chrysosplenium flagelliferum

Cogniauxia podolaena

1 reference

Cogniauxia podolaena: bioassay-guided fractionation of defoliated stems, isolation of active compounds, antiplasmodial activity and cytotoxicity

Cucumis prophetarum

1 reference

Cucumidisecosterol: A New diseco-sterol from Cucumis prophetarum

Datisca glomerata

1 reference

New cytotoxic principles from Datisca glomerata

Ecballium elaterium

8 references

Antiinflammatory effects of the fruit juice ofEcballium elaterium on edemas in mice

Callus formation and cucurbitacin B accumulation in Ecballium elaterium callus cultures

Isolation of an Anti-inflammatory Principle from the Fruit Juice of Ecballium elaterium

A new cucurbitacin D related 16,23-epoxy derivative and its isomerization products

Isolation of ani-hepatotoxic principle form the juice of Ecballium elaterium

Clinical Effects of the Fruit Juice of Ecbalium elaterium in the Treatment of Sinusits

Isolation of ani-hepatotoxic principle form the juice of Ecballium elaterium

Callus formation and cucurbitacin B accumulation in Ecballium elaterium callus cultures

Gurania subumbellata

1 reference

Isolation and13C-nmr Assignments of Cucurbitacins from Cayaponia Angustiloba, Cayaponia racemosa, and Guraniasubumbellata

Hemsleya endecaphylla

1 reference

Octanorcucurbitane and cucurbitane triterpenoids from the tubers of Hemsleya endecaphylla with HIV-1 inhibitory activity

Ipomopsis aggregata

2 references

Plant anticancer agents. XXX: Cucurbitacins from Ipomopsis aggregata (Polemoniaceae)

Plant anticancer agents. XXX: Cucurbitacins from Ipomopsis aggregata (Polemoniaceae)

Luffa operculata

2 references

Studies on the constituents of Luffa operculata Cogn. I. Isolation and structures of luperosides A-H, dammarane-type triterpene glycosides in the herb.

Two novel cucurbitacins, neocucurbitacins A and B, from the Brazilian folk medicine "Buchinha" (Luffa operculata) and their effect on PEBP2alphaA and OCIF gene expression in a human osteoblast-like Saos-2 cell line

Morierina montana

1 reference

Morierinin: a new cytotoxic cucurbitacin from the leaves of Morierina montana Vieill

Trichosanthes hupehensis

1 reference

Chemical constituents from Trichosanthes cucumeroides

Trichosanthes kirilowii

4 references

Antitumor activity ofTrichosanthes kirilowii

[Studies on the constituents of trichosanthes root. I. Constituents of roots of Trichosanthes kirilowii Maxim. var. japonicum Kitam]

An isoaurone and other constituents from Trichosanthes kirilowii seeds inhibit hypoxia-inducible factor-1 and nuclear factor-kappaB.

Cucurbitacin B markedly inhibits growth and rapidly affects the cytoskeleton in glioblastoma multiforme.

Trichosanthes miyagii

1 reference

[Studies on the constituents of "Trichosanthes root". IV. Constituents of roots of Trichosanthes multiloba Miq., Trichosanthes miyagii Hay. and Chinese crude drug "karo-kon"]

Trichosanthes multiloba

1 reference

[Studies on the constituents of "Trichosanthes root". IV. Constituents of roots of Trichosanthes multiloba Miq., Trichosanthes miyagii Hay. and Chinese crude drug "karo-kon"]

Wilbrandia ebracteata

4 references

Nitric oxide and cyclooxygenase may participate in the analgesic and anti-inflammatory effect of the cucurbitacins fraction from Wilbrandia ebracteata

Anti-inflammatory effects of the products from Wilbrandia ebracteata on carrageenan-induced pleurisy in mice

Anti-inflammatory and analgesic effects of cucurbitacins from Wilbrandia ebracteata

Cucurbitacins as Constituents of Wilbrandia ebracteata

1 reference

A biotransformation process for the production of cucurbitacin B from its glycoside using a selected Streptomyces sp.

Bryonia cretica

1 reference

Cucurbitane-type triterpenes with anti-proliferative effects on U937 cells from an egyptian natural medicine, Bryonia cretica: structures of new triterpene glycosides, bryoniaosides A and B.

Cucurbita foetidissima

1 reference

Foetidissimoside A, a new 3,28-bidesmosidic triterpenoid saponin, and cucurbitacins from Cucurbita foetidissima

1 reference

Bitter Principles from Echinocystis Fabacea1

1 reference

Bitter Principles from Echinocystis Fabacea1

1 reference

Bitter Principles from Echinocystis Fabacea1

1 reference

Bitter Principles from Echinocystis Fabacea1

Cucurbita andreana

1 reference

A new cucurbitacin profile forCucurbita andreana: A candidate for cucurbitacin tissue culture

Picrorhiza kurroa

2 references

New cucurbitacin glycosides from Picrorhiza kurrooa.

Minor cucurbitacin glycosides from Picrorhiza kurrooa

Helicteres angustifolia

1 reference

Two pregnane derivatives and a quinolone alkaloid from Helicteres angustifolia

Citrullus colocynthis

1 reference

Colocynthenins A-D, Ring-A seco-Cucurbitane Triterpenoids from the Fruits of Citrullus colocynthis

Trichosanthes cucumeroides

1 reference

Lipid-Lowering Activities of Cucurbitacins Isolated from Trichosanthes cucumeroides and Their Synthetic Derivatives

Cucumis myriocarpus

1 reference

Cucumidisecosterol: A New diseco-sterol from Cucumis prophetarum

Hymenopus intrapetiolaris

1 reference

Bioactive Constituents of the Roots ofLicaniaintrapetiolaris

Picrorhiza kurrooa

2 references

New cucurbitacin glycosides from Picrorhiza kurrooa.

Minor cucurbitacin glycosides from Picrorhiza kurrooa

Trichosanthes tricuspidata

1 reference

[Studies on the constituents of trichosanthes root. III. Constituents of roots of Trichosanthes bracteata Voigt]

physically interacts with

taste receptor type 2

subject has role

2 references

The human bitter taste receptor TAS2R10 is tailored to accommodate numerous diverse ligands.

The Molecular Receptive Ranges of Human TAS2R Bitter Taste Receptors

Identifiers

InChI=1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12 /t19-,20 ,21-,22 ,25 ,29 ,30-,31 ,32 /m1/s1

1 reference

language of work or name

Cucurbitacin B (English)

19 November 2016

IXQKXEUSCPEQRD-DKRGWESNSA-N

2 references

language of work or name

Cucurbitacin B (English)

19 November 2016

ChEBI release 2020-09-01

CAS Registry Number

2 references

Global Substance Registration System

language of work or name

cucurbitacin b (English)

19 November 2016

IXQKXEUSCPEQRD-DKRGWESNSA-N

CAS Common Chemistry

8 April 2021

https://commonchemistry.cas.org/detail?cas_rn=6199-67-3

1 reference

language of work or name

1,2-Dihydro-a-elaterin (English)

5 October 2016

2 references

language of work or name

Cucurbitacin B (English)

19 November 2016

matched by identifier from

IXQKXEUSCPEQRD-DKRGWESNSA-N

Reaxys registry number

2068869

1 reference

language of work or name

cucurbitacin B (English)

5 October 2016

mapping relation type

2 references

language of work or name

CHEMBL508185 (English)

19 November 2016

matched by identifier from

International Chemical Identifier

InChI=1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12 /t19-,20 ,21-,22 ,25 ,29 ,30-,31 ,32 /m1/s1

1 reference

language of work or name

CHEMBL508185 (English)

19 November 2016

2 references

based on heuristic

inferred from InChIKey

matched by identifier from

IXQKXEUSCPEQRD-DKRGWESNSA-N

UniChem compound ID

1 reference

1 reference

Hazardous Substances Data Bank

publication date

28 October 2019

CUCURBITACIN B (English)

10 May 2021

DSSTox substance ID

DTXSID501316196

1 reference

matched by identifier from

IXQKXEUSCPEQRD-DKRGWESNSA-N

0 references

0 references

1 reference

ECHA Substance Infocard database

ECHA Substance Infocard ID

27 December 2018

CUCURBITACIN B (English)

CAS no.: 6199-67-3 (English)

ECHA Substance Infocard ID

1 reference

ECHA Substance Infocard database

ECHA Substance Infocard ID

20 December 2018

CUCURBITACIN B (English)

CAS no.: 6199-67-3 (English)

0 references

reason for deprecated rank

cannot be confirmed by other sources

1 reference

language of work or name

cucurbitacin B (English)

5 October 2016

2 references

Global Substance Registration System

language of work or name

cucurbitacin b (English)

19 November 2016

matched by identifier from

IXQKXEUSCPEQRD-DKRGWESNSA-N

Probes And Drugs ID

0 references

1 reference

language of work or name

cucurbitacin B (English)

5 October 2016

0 references

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