GLYCEOLLIN I

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H18O5
Molecular Weight	338.3539
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12OC3=CC(O)=CC=C3[C@]1(O)COC4=C5C=CC(C)(C)OC5=CC=C24

InChI

InChIKey=YIFYYPKWOQSCRI-AZUAARDMSA-N

InChI=1S/C20H18O5/c1-19(2)8-7-12-15(25-19)6-4-13-17(12)23-10-20(22)14-5-3-11(21)9-16(14)24-18(13)20/h3-9,18,21-22H,10H2,1-2H3/t18-,20+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C20H18O5
Molecular Weight	338.3539
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Phytochemical glyceollins, isolated from soy, mediate antihormonal effects through estrogen receptor alpha and beta.	2001 Apr	11297613
Bradyrhizobium japonicum mutants defective in cyclic beta-glucan synthesis show enhanced sensitivity to plant defense responses.	2001 Jul-Aug	11531093
Induction of H(2)O(2) synthesis by beta-glucan elicitors in soybean is independent of cytosolic calcium transients.	2001 Nov 16	11718714
The role of octadecanoids and functional mimics in soybean defense responses.	2003 Mar	12715894
Effects of soybean glyceollins and estradiol in postmenopausal female monkeys.	2006	17176220
Modification of phenolic metabolism in soybean hairy roots through down regulation of chalcone synthase or isoflavone synthase.	2007 Feb	16924535
Fungal-stressed germination of black soybeans leads to generation of oxooctadecadienoic acids in addition to glyceollins.	2007 Oct 17	17892258
Soybean seed extracts preferentially express genomic loci of Bradyrhizobium japonicum in the initial interaction with soybean, Glycine max (L.) Merr.	2008 Aug	18511436
Total syntheses of racemic, natural (-) and unnatural (+) glyceollin I.	2008 Nov 6	18817403
Copy number variation and transcriptional polymorphisms of Phytophthora sojae RXLR effector genes Avr1a and Avr3a.	2009	19343173
Systemic acquired resistance in soybean is regulated by two proteins, Orthologous to Arabidopsis NPR1.	2009 Aug 5	19656407
Estrogen/isoflavone interactions in cynomolgus macaques (Macaca fascicularis).	2009 Sep	19322873
Molecular effects of soy phytoalexin glyceollins in human prostate cancer cells LNCaP.	2009 Sep	19263441
Induction of glyceollins by fungal infection in varieties of Korean soybean.	2010 Aug	20798587
Glyceollin I, a novel antiestrogenic phytoalexin isolated from activated soy.	2010 Jan	19797619
Inhibitory effect of glyceollin isolated from soybean against melanogenesis in B16 melanoma cells.	2010 Jul	20663406
Antioxidant activity of glyceollins derived from soybean elicited with Aspergillus sojae.	2010 Nov 24	21033668
Abscisic acid deficiency causes changes in cuticle permeability and pectin composition that influence tomato resistance to Botrytis cinerea.	2010 Oct	20709830
Antifungal activity of glyceollins isolated from soybean elicited with Aspergillus sojae.	2010 Sep 8	20666365

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:41:29 GMT 2023` Edited by `admin` on `Fri Dec 15 19:41:29 GMT 2023`
Record UNII	6461TV6UCH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GLYCEOLLIN I

Common Name

English

2H,6H-BENZOFURO(3,2-C)PYRANO(2,3-H)(1)BENZOPYRAN-6A,9(11AH)-DIOL, 2,2-DIMETHYL-, (6AS-CIS)-

Common Name

English

2H,6H-BENZOFURO(3,2-C)PYRANO(2,3-H)(1)BENZOPYRAN-6A,9(11AH)-DIOL, 2,2-DIMETHYL-, (6AS,11AS)-

Common Name

English

(-)-GLYCEOLLIN I

Common Name

English

Code System Code Type Description

MESH

C017343