(2S)-2-[(1R,12R)-16-hydroxy-6,11,19-trioxapentacyclo[10.8.0.02,10.05,9.013,18]icosa-2(10),3,5(9),7,13(18),14,16-heptaen-7-yl]propane-1,2-diol

Details

• Internal ID: b2c7a017-fee8-4d28-b881-3db7c87c7ea0
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Furanoisoflavonoids > Pterocarpans
• IUPAC Name: (2S)-2-[(1R,12R)-16-hydroxy-6,11,19-trioxapentacyclo[10.8.0.02,10.05,9.013,18]icosa-2(10),3,5(9),7,13(18),14,16-heptaen-7-yl]propane-1,2-diol
• SMILES (Canonical): CC(CO)(C1=CC2=C(O1)C=CC3=C2OC4C3COC5=C4C=CC(=C5)O)O
• SMILES (Isomeric): C[C@](CO)(C1=CC2=C(O1)C=CC3=C2O[C@@H]4[C@H]3COC5=C4C=CC(=C5)O)O
• InChI: InChI=1S/C20H18O6/c1-20(23,9-21)17-7-13-15(25-17)5-4-11-14-8-24-16-6-10(22)2-3-12(16)19(14)26-18(11)13/h2-7,14,19,21-23H,8-9H2,1H3/t14-,19-,20-/m0/s1
• InChI Key: JDKOSPKTKADBCU-GKCIPKSASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₆
• Molecular Weight: 354.40 g/mol
• Exact Mass: 354.11033829 g/mol
• Topological Polar Surface Area (TPSA): 92.30 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.95
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• BDBM50142190
• 2-((11bR,12R)-9-Hydroxy-5b,11b-dihydro-6H-3,7,12-trioxa-benzo[a]cyclopenta[i]fluoren-2-yl)-propane-1,2-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9379	93.79%
Caco-2	-	0.6087	60.87%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5895	58.95%
OATP2B1 inhibitior	-	0.7167	71.67%
OATP1B1 inhibitior	+	0.8516	85.16%
OATP1B3 inhibitior	+	0.9680	96.80%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8312	83.12%
P-glycoprotein inhibitior	-	0.5163	51.63%
P-glycoprotein substrate	+	0.5975	59.75%
CYP3A4 substrate	+	0.6079	60.79%
CYP2C9 substrate	-	0.5873	58.73%
CYP2D6 substrate	-	0.7310	73.10%
CYP3A4 inhibition	-	0.9014	90.14%
CYP2C9 inhibition	-	0.8410	84.10%
CYP2C19 inhibition	-	0.6437	64.37%
CYP2D6 inhibition	-	0.8328	83.28%
CYP1A2 inhibition	-	0.5741	57.41%
CYP2C8 inhibition	+	0.7280	72.80%
CYP inhibitory promiscuity	-	0.7948	79.48%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4235	42.35%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.8070	80.70%
Skin irritation	-	0.7978	79.78%
Skin corrosion	-	0.9534	95.34%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5214	52.14%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.7764	77.64%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.8384	83.84%
Acute Oral Toxicity (c)	III	0.6266	62.66%
Estrogen receptor binding	+	0.8762	87.62%
Androgen receptor binding	+	0.8400	84.00%
Thyroid receptor binding	+	0.7176	71.76%
Glucocorticoid receptor binding	+	0.8251	82.51%
Aromatase binding	+	0.7513	75.13%
PPAR gamma	+	0.8175	81.75%
Honey bee toxicity	-	0.8638	86.38%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	-	0.4475	44.75%

Targets

Proven Targets:

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	98.61%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	97.75%	83.82%
CHEMBL2581	P07339	Cathepsin D	95.04%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	91.09%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.76%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.15%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.83%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.67%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.01%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.80%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.64%	89.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.08%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.76%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.68%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.63%	99.23%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.42%	93.56%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.04%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.36%	99.17%
CHEMBL2535	P11166	Glucose transporter	81.22%	98.75%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	81.09%	90.93%
CHEMBL242	Q92731	Estrogen receptor beta	80.21%	98.35%

Plants that contains it

• Crotalaria pallida
• Crotalaria sericea

Cross-Links

• PubChem: 44264369
• NPASS: NPC476459
• ChEMBL: CHEMBL7054
• LOTUS: LTS0008996
• wikiData: Q105125552