(+)-Vouacapenic acid

Details

• Internal ID: 7f864a7d-7e9c-4a45-8c43-2f6423a115cb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (4S,4aR,6aS,7R,11aS,11bR)-4,7,11b-trimethyl-1,2,3,4a,5,6,6a,7,11,11a-decahydronaphtho[2,1-f][1]benzofuran-4-carboxylic acid
• SMILES (Canonical): CC1C2CCC3C(C2CC4=C1C=CO4)(CCCC3(C)C(=O)O)C
• SMILES (Isomeric): C[C@@H]1[C@@H]2CC[C@@H]3[C@@]([C@H]2CC4=C1C=CO4)(CCC[C@]3(C)C(=O)O)C
• InChI: InChI=1S/C20H28O3/c1-12-13-5-6-17-19(2,8-4-9-20(17,3)18(21)22)15(13)11-16-14(12)7-10-23-16/h7,10,12-13,15,17H,4-6,8-9,11H2,1-3H3,(H,21,22)/t12-,13+,15+,17-,19-,20+/m1/s1
• InChI Key: CGLTYYYFMFIPDN-FGPOBWDPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.40 g/mol
• Exact Mass: 316.20384475 g/mol
• Topological Polar Surface Area (TPSA): 50.40 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.86
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• CHEMBL2398518

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9955	99.55%
Caco-2	+	0.8789	87.89%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6158	61.58%
OATP2B1 inhibitior	-	0.8693	86.93%
OATP1B1 inhibitior	+	0.8326	83.26%
OATP1B3 inhibitior	+	0.8956	89.56%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.5839	58.39%
P-glycoprotein inhibitior	-	0.7021	70.21%
P-glycoprotein substrate	-	0.7809	78.09%
CYP3A4 substrate	+	0.6336	63.36%
CYP2C9 substrate	-	0.5888	58.88%
CYP2D6 substrate	-	0.8396	83.96%
CYP3A4 inhibition	-	0.7716	77.16%
CYP2C9 inhibition	-	0.6415	64.15%
CYP2C19 inhibition	-	0.6062	60.62%
CYP2D6 inhibition	-	0.9319	93.19%
CYP1A2 inhibition	-	0.6242	62.42%
CYP2C8 inhibition	+	0.4905	49.05%
CYP inhibitory promiscuity	-	0.8880	88.80%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7800	78.00%
Carcinogenicity (trinary)	Non-required	0.5902	59.02%
Eye corrosion	-	0.9855	98.55%
Eye irritation	-	0.9648	96.48%
Skin irritation	-	0.7022	70.22%
Skin corrosion	-	0.9389	93.89%
Ames mutagenesis	-	0.7870	78.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7796	77.96%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.5067	50.67%
skin sensitisation	-	0.8139	81.39%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.7710	77.10%
Acute Oral Toxicity (c)	III	0.6383	63.83%
Estrogen receptor binding	+	0.8237	82.37%
Androgen receptor binding	+	0.6644	66.44%
Thyroid receptor binding	+	0.7268	72.68%
Glucocorticoid receptor binding	+	0.7535	75.35%
Aromatase binding	+	0.7575	75.75%
PPAR gamma	+	0.5825	58.25%
Honey bee toxicity	-	0.8924	89.24%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9890	98.90%

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	93.69%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.60%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.47%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.28%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.52%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.11%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.11%	97.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.96%	93.56%
CHEMBL340	P08684	Cytochrome P450 3A4	80.78%	91.19%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.19%	100.00%

Plants that contains it

• Dipteryx odorata
• Harrisonia perforata
• Vouacapoua americana

Cross-Links

• PubChem: 73350581
• LOTUS: LTS0048973
• wikiData: Q104957848