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
Induction of H(2)O(2) synthesis by beta-glucan elicitors in soybean is independent of cytosolic calcium transients.	2001 Nov 16	11718714
Regulation of phenobarbital-mediated induction of CYP102 (cytochrome P450(BM-3)) in Bacillus megaterium by phytochemicals from soy and green tea.	2001 Oct	11600046
The role of octadecanoids and functional mimics in soybean defense responses.	2003 Mar	12715894
Lactofen induces isoflavone accumulation and glyceollin elicitation competency in soybean.	2003 Mar	12590114
Isoflavonoid accumulation in soybean hairy roots upon treatment with Fusarium solani.	2004 Jul-Aug	15331097
Effects of soybean glyceollins and estradiol in postmenopausal female monkeys.	2006	17176220
Fungal-stressed germination of black soybeans leads to generation of oxooctadecadienoic acids in addition to glyceollins.	2007 Oct 17	17892258
Novel process of fermenting black soybean [Glycine max (L.) Merrill] yogurt with dramatically reduced flatulence-causing oligosaccharides but enriched soy phytoalexins.	2008 Nov 12	18831591
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
Molecular cloning and characterization of a cDNA for pterocarpan 4-dimethylallyltransferase catalyzing the key prenylation step in the biosynthesis of glyceollin, a soybean phytoalexin.	2009 Feb	19091879
Identification of the potent phytoestrogen glycinol in elicited soybean (Glycine max).	2009 May	19116342
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
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 UTC 2023` Edited by `admin` on `Fri Dec 15 19:41:29 UTC 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