3,9-Dihydroxypterocarpan

Details

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Internal ID 61dff25c-7a60-4208-9eff-62031af5e924
Taxonomy Phenylpropanoids and polyketides > Isoflavonoids > Furanoisoflavonoids > Pterocarpans
IUPAC Name (6aR,11aR)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene-3,9-diol
SMILES (Canonical) C1C2C(C3=C(O1)C=C(C=C3)O)OC4=C2C=CC(=C4)O
SMILES (Isomeric) C1[C@@H]2[C@H](C3=C(O1)C=C(C=C3)O)OC4=C2C=CC(=C4)O
InChI InChI=1S/C15H12O4/c16-8-2-4-11-13(5-8)18-7-12-10-3-1-9(17)6-14(10)19-15(11)12/h1-6,12,15-17H,7H2/t12-,15-/m0/s1
InChI Key ODMIEGVTNZNSLD-WFASDCNBSA-N
Popularity 48 references in papers

Physical and Chemical Properties

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Molecular Formula C15H12O4
Molecular Weight 256.25 g/mol
Exact Mass 256.07355886 g/mol
Topological Polar Surface Area (TPSA) 58.90 Ų
XlogP 2.30
Atomic LogP (AlogP) 2.71
H-Bond Acceptor 4
H-Bond Donor 2
Rotatable Bonds 0

Synonyms

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61135-91-9
demethylmedicarpin
(6aR,11aR)-3,9-Dihydroxypterocarpan
CHEMBL1098413
CHEBI:15648
(6aR,11aR)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene-3,9-diol
(6aR-cis)-6a,11a-Dihydro-6H-benzofuro(3,2-c)(1)benzopyran-3,9-diol
(6aR,11aR)-6a,11a-dihydro-6H-benzo[4,5]furo[3,2-c]chromene-3,9-diol
D0G5PT
C04271
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of 3,9-Dihydroxypterocarpan

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9842 98.42%
Caco-2 - 0.5569 55.69%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.7990 79.90%
OATP2B1 inhibitior - 0.8613 86.13%
OATP1B1 inhibitior + 0.9102 91.02%
OATP1B3 inhibitior + 0.9582 95.82%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.7422 74.22%
P-glycoprotein inhibitior - 0.9002 90.02%
P-glycoprotein substrate - 0.8203 82.03%
CYP3A4 substrate - 0.5891 58.91%
CYP2C9 substrate - 0.7977 79.77%
CYP2D6 substrate + 0.4476 44.76%
CYP3A4 inhibition - 0.6893 68.93%
CYP2C9 inhibition + 0.7793 77.93%
CYP2C19 inhibition + 0.7150 71.50%
CYP2D6 inhibition - 0.5569 55.69%
CYP1A2 inhibition + 0.9391 93.91%
CYP2C8 inhibition + 0.5232 52.32%
CYP inhibitory promiscuity + 0.6953 69.53%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.5017 50.17%
Eye corrosion - 0.9861 98.61%
Eye irritation + 0.7967 79.67%
Skin irritation - 0.5802 58.02%
Skin corrosion - 0.9769 97.69%
Ames mutagenesis + 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6268 62.68%
Micronuclear + 0.7600 76.00%
Hepatotoxicity - 0.6875 68.75%
skin sensitisation - 0.8277 82.77%
Respiratory toxicity - 0.6000 60.00%
Reproductive toxicity + 0.5667 56.67%
Mitochondrial toxicity + 0.5125 51.25%
Nephrotoxicity - 0.6809 68.09%
Acute Oral Toxicity (c) III 0.5017 50.17%
Estrogen receptor binding + 0.6451 64.51%
Androgen receptor binding + 0.6843 68.43%
Thyroid receptor binding + 0.7409 74.09%
Glucocorticoid receptor binding + 0.6272 62.72%
Aromatase binding + 0.5590 55.90%
PPAR gamma + 0.7578 75.78%
Honey bee toxicity - 0.9099 90.99%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.5500 55.00%
Fish aquatic toxicity + 0.8101 81.01%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.17% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.57% 97.09%
CHEMBL4040 P28482 MAP kinase ERK2 87.07% 83.82%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.69% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.88% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 83.44% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.87% 89.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 82.16% 94.45%
CHEMBL2581 P07339 Cathepsin D 82.12% 98.95%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.34% 100.00%
CHEMBL3227 P41594 Metabotropic glutamate receptor 5 80.46% 96.42%

Cross-Links

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PubChem 162933
NPASS NPC262573
ChEMBL CHEMBL1098413
LOTUS LTS0134551
wikiData Q27098166