(2S,3S)-2-[(2S,3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran-2-yl]-3-chlorobutane-1,2,4-triol

Details

• Internal ID: f0b361df-b829-441c-b783-0d309542ce3e
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (2S,3S)-2-[(2S,3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran-2-yl]-3-chlorobutane-1,2,4-triol
• SMILES (Canonical): CC1(CCCC2(C1CCC3(C2CC(O3)C(CO)(C(CO)Cl)O)C)C)C
• SMILES (Isomeric): C[C@]12CCCC([C@@H]1CC[C@@]3([C@@H]2C[C@H](O3)[C@@](CO)([C@H](CO)Cl)O)C)(C)C
• InChI: InChI=1S/C20H35ClO4/c1-17(2)7-5-8-18(3)13(17)6-9-19(4)14(18)10-16(25-19)20(24,12-23)15(21)11-22/h13-16,22-24H,5-12H2,1-4H3/t13-,14+,15-,16-,18-,19+,20+/m0/s1
• InChI Key: UVTUWVZTALXLNU-MMOSDQNESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₅ClO₄
• Molecular Weight: 374.90 g/mol
• Exact Mass: 374.2223873 g/mol
• Topological Polar Surface Area (TPSA): 69.90 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.10
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9334	93.34%
Caco-2	-	0.5471	54.71%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.4949	49.49%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.8981	89.81%
OATP1B3 inhibitior	+	0.9355	93.55%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.5470	54.70%
P-glycoprotein inhibitior	-	0.8135	81.35%
P-glycoprotein substrate	-	0.8308	83.08%
CYP3A4 substrate	+	0.6469	64.69%
CYP2C9 substrate	-	0.5872	58.72%
CYP2D6 substrate	-	0.7843	78.43%
CYP3A4 inhibition	-	0.8903	89.03%
CYP2C9 inhibition	-	0.7671	76.71%
CYP2C19 inhibition	-	0.7249	72.49%
CYP2D6 inhibition	-	0.8909	89.09%
CYP1A2 inhibition	-	0.8140	81.40%
CYP2C8 inhibition	+	0.4903	49.03%
CYP inhibitory promiscuity	-	0.8444	84.44%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7800	78.00%
Carcinogenicity (trinary)	Non-required	0.6166	61.66%
Eye corrosion	-	0.9851	98.51%
Eye irritation	-	0.9495	94.95%
Skin irritation	-	0.7637	76.37%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	-	0.5470	54.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5705	57.05%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.5547	55.47%
skin sensitisation	-	0.8299	82.99%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6150	61.50%
Acute Oral Toxicity (c)	III	0.5659	56.59%
Estrogen receptor binding	+	0.8098	80.98%
Androgen receptor binding	+	0.5502	55.02%
Thyroid receptor binding	+	0.7410	74.10%
Glucocorticoid receptor binding	+	0.8391	83.91%
Aromatase binding	+	0.7683	76.83%
PPAR gamma	+	0.5500	55.00%
Honey bee toxicity	-	0.8332	83.32%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.8594	85.94%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.63%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.48%	96.61%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.09%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.03%	97.09%
CHEMBL233	P35372	Mu opioid receptor	91.66%	97.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.59%	96.09%
CHEMBL237	P41145	Kappa opioid receptor	90.60%	98.10%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.15%	82.69%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	90.10%	95.50%
CHEMBL226	P30542	Adenosine A1 receptor	89.95%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.52%	94.45%
CHEMBL259	P32245	Melanocortin receptor 4	89.48%	95.38%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	89.21%	89.05%
CHEMBL2431	P31751	Serine/threonine-protein kinase AKT2	87.47%	98.33%
CHEMBL1977	P11473	Vitamin D receptor	85.22%	99.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.11%	95.89%
CHEMBL4816	Q9Y243	Serine/threonine-protein kinase AKT3	84.65%	96.28%
CHEMBL4370	P16662	UDP-glucuronosyltransferase 2B7	84.24%	100.00%
CHEMBL1871	P10275	Androgen Receptor	83.40%	96.43%
CHEMBL5555	O00767	Acyl-CoA desaturase	83.25%	97.50%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.20%	96.38%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	82.50%	95.58%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.27%	97.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.16%	92.62%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.28%	91.03%

Plants that contains it

• Silphium perfoliatum

Cross-Links

• PubChem: 101925915
• LOTUS: LTS0068528
• wikiData: Q105280096