(3bR,5aS,6S,9aS,9bS)-3b-formyl-6,9a-dimethyl-5,5a,7,8,9,9b,10,11-octahydro-4H-naphtho[1,2-g][1]benzofuran-6-carboxylic acid

Details

• Internal ID: 0c78e9a6-3ec6-4dbb-9c96-9c8b71fbb6b0
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (3bR,5aS,6S,9aS,9bS)-3b-formyl-6,9a-dimethyl-5,5a,7,8,9,9b,10,11-octahydro-4H-naphtho[1,2-g][1]benzofuran-6-carboxylic acid
• SMILES (Canonical): CC12CCCC(C1CCC3(C2CCC4=C3OC=C4)C=O)(C)C(=O)O
• SMILES (Isomeric): C[C@@]12CCC[C@]([C@H]1CC[C@]3([C@H]2CCC4=C3OC=C4)C=O)(C)C(=O)O
• InChI: InChI=1S/C20H26O4/c1-18-8-3-9-19(2,17(22)23)14(18)6-10-20(12-21)15(18)5-4-13-7-11-24-16(13)20/h7,11-12,14-15H,3-6,8-10H2,1-2H3,(H,22,23)/t14-,15-,18+,19-,20+/m0/s1
• InChI Key: VGJOOKOJOFUENK-WOCWYEKDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.40 g/mol
• Exact Mass: 330.18310931 g/mol
• Topological Polar Surface Area (TPSA): 67.50 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.97
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 93372-66-8
• (3bR,5aS,6S,9aS,9bS)-3b-Formyl-3b,4,5,5a,6,7,8,9,9a,9b,10,11-dodecahydro-6,9a-dimethylphenanthro[1,2-b]furan-6-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9860	98.60%
Caco-2	+	0.8282	82.82%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7523	75.23%
OATP2B1 inhibitior	-	0.8639	86.39%
OATP1B1 inhibitior	+	0.8122	81.22%
OATP1B3 inhibitior	+	0.8833	88.33%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6571	65.71%
BSEP inhibitior	-	0.4904	49.04%
P-glycoprotein inhibitior	-	0.7752	77.52%
P-glycoprotein substrate	-	0.7909	79.09%
CYP3A4 substrate	+	0.6208	62.08%
CYP2C9 substrate	-	0.5905	59.05%
CYP2D6 substrate	-	0.8408	84.08%
CYP3A4 inhibition	-	0.8421	84.21%
CYP2C9 inhibition	-	0.7129	71.29%
CYP2C19 inhibition	-	0.7822	78.22%
CYP2D6 inhibition	-	0.9412	94.12%
CYP1A2 inhibition	-	0.5959	59.59%
CYP2C8 inhibition	-	0.6097	60.97%
CYP inhibitory promiscuity	-	0.9237	92.37%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.6194	61.94%
Eye corrosion	-	0.9807	98.07%
Eye irritation	-	0.9036	90.36%
Skin irritation	-	0.7296	72.96%
Skin corrosion	-	0.9292	92.92%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7183	71.83%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.7308	73.08%
skin sensitisation	-	0.8585	85.85%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6936	69.36%
Acute Oral Toxicity (c)	III	0.4394	43.94%
Estrogen receptor binding	+	0.8207	82.07%
Androgen receptor binding	+	0.6230	62.30%
Thyroid receptor binding	+	0.6453	64.53%
Glucocorticoid receptor binding	+	0.7518	75.18%
Aromatase binding	+	0.7224	72.24%
PPAR gamma	+	0.6052	60.52%
Honey bee toxicity	-	0.9202	92.02%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9970	99.70%

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	95.32%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.44%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.45%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.14%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.34%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.38%	93.04%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.36%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.19%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.07%	99.23%

Plants that contains it

• Gutierrezia sarothrae

Cross-Links

• PubChem: 101326877
• LOTUS: LTS0214140
• wikiData: Q105285840