(6aS,11aS)-10-[(2R)-2,3-dihydroxy-3-methylbutyl]-9-methoxy-6,11a-dihydro-[1]benzofuro[3,2-c]chromene-3,6a-diol

Details

• Internal ID: 30902f63-24a5-45de-9f53-75329cd51ade
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Furanoisoflavonoids > Pterocarpans
• IUPAC Name: (6aS,11aS)-10-[(2R)-2,3-dihydroxy-3-methylbutyl]-9-methoxy-6,11a-dihydro-[1]benzofuro[3,2-c]chromene-3,6a-diol
• SMILES (Canonical): CC(C)(C(CC1=C(C=CC2=C1OC3C2(COC4=C3C=CC(=C4)O)O)OC)O)O
• SMILES (Isomeric): CC(C)([C@@H](CC1=C(C=CC2=C1O[C@@H]3[C@]2(COC4=C3C=CC(=C4)O)O)OC)O)O
• InChI: InChI=1S/C21H24O7/c1-20(2,24)17(23)9-13-15(26-3)7-6-14-18(13)28-19-12-5-4-11(22)8-16(12)27-10-21(14,19)25/h4-8,17,19,22-25H,9-10H2,1-3H3/t17-,19+,21-/m1/s1
• InChI Key: TWRMBVPWOVPEPJ-SLYNCCJLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₇
• Molecular Weight: 388.40 g/mol
• Exact Mass: 388.15220310 g/mol
• Topological Polar Surface Area (TPSA): 109.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.79
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9628	96.28%
Caco-2	+	0.5949	59.49%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7118	71.18%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	+	0.8918	89.18%
OATP1B3 inhibitior	+	0.9311	93.11%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7771	77.71%
P-glycoprotein inhibitior	-	0.6678	66.78%
P-glycoprotein substrate	+	0.7213	72.13%
CYP3A4 substrate	+	0.6421	64.21%
CYP2C9 substrate	-	0.5839	58.39%
CYP2D6 substrate	+	0.4324	43.24%
CYP3A4 inhibition	-	0.9031	90.31%
CYP2C9 inhibition	-	0.8649	86.49%
CYP2C19 inhibition	-	0.7854	78.54%
CYP2D6 inhibition	-	0.8728	87.28%
CYP1A2 inhibition	+	0.6340	63.40%
CYP2C8 inhibition	+	0.7405	74.05%
CYP inhibitory promiscuity	-	0.8340	83.40%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5671	56.71%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.8915	89.15%
Skin irritation	-	0.8055	80.55%
Skin corrosion	-	0.9468	94.68%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4449	44.49%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8102	81.02%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.8035	80.35%
Acute Oral Toxicity (c)	III	0.6596	65.96%
Estrogen receptor binding	+	0.8758	87.58%
Androgen receptor binding	+	0.6942	69.42%
Thyroid receptor binding	+	0.8379	83.79%
Glucocorticoid receptor binding	+	0.8052	80.52%
Aromatase binding	+	0.6713	67.13%
PPAR gamma	+	0.8001	80.01%
Honey bee toxicity	-	0.7491	74.91%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.8451	84.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.49%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.18%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.48%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.45%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.22%	86.33%
CHEMBL2535	P11166	Glucose transporter	94.00%	98.75%
CHEMBL2581	P07339	Cathepsin D	93.54%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.62%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.25%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	88.84%	83.82%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.47%	94.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.27%	89.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.01%	95.89%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	86.37%	95.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.23%	95.56%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	85.51%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.10%	97.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.01%	92.62%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	82.80%	89.05%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.65%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.64%	99.17%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.95%	89.50%

Plants that contains it

• Erythrina fusca
• Erythrina variegata

Cross-Links

• PubChem: 163038399
• LOTUS: LTS0240990
• wikiData: Q105266036