Glyceollin

Details

• Internal ID: 15308470-fc77-4c4b-bd78-f6eca610bb19
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Furanoisoflavonoids > Pterocarpans
• IUPAC Name: (2S,10S)-17,17-dimethyl-3,12,18-trioxapentacyclo[11.8.0.02,10.04,9.014,19]henicosa-1(13),4(9),5,7,14(19),15,20-heptaene-6,10-diol
• SMILES (Canonical): CC1(C=CC2=C(O1)C=CC3=C2OCC4(C3OC5=C4C=CC(=C5)O)O)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C=CC3=C2OC[C@@]4([C@H]3OC5=C4C=CC(=C5)O)O)C
• InChI: 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
• InChI Key: YIFYYPKWOQSCRI-AZUAARDMSA-N
• Popularity: 113 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₅
• Molecular Weight: 338.40 g/mol
• Exact Mass: 338.11542367 g/mol
• Topological Polar Surface Area (TPSA): 68.20 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 3.29
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• glyceollin I
• (-)-Glyceollin I
• 57103-57-8
• UNII-6461TV6UCH
• 6461TV6UCH
• CHEBI:16470
• 66241-09-6
• (-) - glyceollin I
• Glyceollins
• Glyceolin
• (6aS,11aS)-2,2-dimethyl-2H,6H-[1]benzofuro[3,2-c]pyrano[2,3-h]chromene-6a,9(11aH)-diol
• UNII-Y43CLK47RO
• C01701
• Y43CLK47RO
• SCHEMBL364885
• CHEMBL1774987
• DTXSID10205726
• LMPK12070123
• XG161768
• Q5572526
• 2H,6H-Benzofuro(3,2-c)pyrano(2,3-h)(1)benzopyran-6a,9(11aH)-diol, 2,2-dimethyl-
• (2S,10S)-17,17-dimethyl-3,12,18-trioxapentacyclo[11.8.0.02,10.04,9.014,19]henicosa-1(13),4(9),5,7,14(19),15,20-heptaene-6,10-diol
• 2H,6H-BENZOFURO(3,2-C)PYRANO(2,3-H)(1)BENZOPYRAN-6A,9(11AH)-DIOL, 2,2-DIMETHYL-, (6AS,11AS)-
• 2H,6H-BENZOFURO(3,2-C)PYRANO(2,3-H)(1)BENZOPYRAN-6A,9(11AH)-DIOL, 2,2-DIMETHYL-, (6AS-CIS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9884	98.84%
Caco-2	+	0.6653	66.53%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7697	76.97%
OATP2B1 inhibitior	-	0.8560	85.60%
OATP1B1 inhibitior	+	0.8598	85.98%
OATP1B3 inhibitior	+	0.9573	95.73%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6948	69.48%
P-glycoprotein inhibitior	-	0.6670	66.70%
P-glycoprotein substrate	+	0.6165	61.65%
CYP3A4 substrate	+	0.6229	62.29%
CYP2C9 substrate	+	0.5947	59.47%
CYP2D6 substrate	-	0.7209	72.09%
CYP3A4 inhibition	-	0.7693	76.93%
CYP2C9 inhibition	-	0.6898	68.98%
CYP2C19 inhibition	-	0.6015	60.15%
CYP2D6 inhibition	-	0.5953	59.53%
CYP1A2 inhibition	+	0.6483	64.83%
CYP2C8 inhibition	+	0.6105	61.05%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4437	44.37%
Eye corrosion	-	0.9921	99.21%
Eye irritation	+	0.5979	59.79%
Skin irritation	-	0.7849	78.49%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	+	0.5663	56.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.7448	74.48%
Micronuclear	+	0.6359	63.59%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.6233	62.33%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.5703	57.03%
Acute Oral Toxicity (c)	III	0.6390	63.90%
Estrogen receptor binding	+	0.8375	83.75%
Androgen receptor binding	+	0.7382	73.82%
Thyroid receptor binding	+	0.8149	81.49%
Glucocorticoid receptor binding	+	0.7111	71.11%
Aromatase binding	+	0.6824	68.24%
PPAR gamma	+	0.7976	79.76%
Honey bee toxicity	-	0.8563	85.63%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.8327	83.27%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.11%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.98%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.11%	96.09%
CHEMBL2581	P07339	Cathepsin D	90.65%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.63%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.62%	95.89%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	85.31%	93.40%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.10%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.74%	100.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	84.11%	89.05%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.06%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.01%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.64%	95.56%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.52%	100.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.42%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.69%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	81.46%	95.93%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.38%	95.89%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.60%	93.10%

Plants that contains it

• Glycine latifolia
• Glycine max
• Platymiscium floribundum

Cross-Links

• PubChem: 162807
• NPASS: NPC262585
• ChEMBL: CHEMBL1774987
• LOTUS: LTS0125176
• wikiData: Q5572526