Valerenolic acid

Details

• Internal ID: f2e63c59-9834-434f-956c-1b27b1cebf81
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (E)-3-(1-hydroxy-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-2-methylprop-2-enoic acid
• SMILES (Canonical): CC1CCC(C2=C(CC(C12)O)C)C=C(C)C(=O)O
• SMILES (Isomeric): CC1CCC(C2=C(CC(C12)O)C)/C=C(\C)/C(=O)O
• InChI: InChI=1S/C15H22O3/c1-8-4-5-11(6-10(3)15(17)18)13-9(2)7-12(16)14(8)13/h6,8,11-12,14,16H,4-5,7H2,1-3H3,(H,17,18)/b10-6+
• InChI Key: XJNQXTISSHEQKD-UXBLZVDNSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.76
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 81397-68-4
• (E)-3-(1-hydroxy-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-2-methylprop-2-enoic acid
• 3-(2,4,5,6,7,7a-Hexahydro-1-hydroxy-3,7-dimethyl-1H-inden-4-yl)-2-methyl-2-propenoic acid
• CHEBI:174304
• (2E)-3-(1-hydroxy-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-2-methylprop-2-enoic acid
• 2-Propenoic acid, 3-(2,4,5,6,7,7a-hexahydro-1-hydroxy-3,7-dimethyl-1H-inden-4-yl)-2-methyl-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9960	99.60%
Caco-2	+	0.7785	77.85%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6378	63.78%
OATP2B1 inhibitior	-	0.8520	85.20%
OATP1B1 inhibitior	+	0.8980	89.80%
OATP1B3 inhibitior	+	0.9646	96.46%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.8481	84.81%
P-glycoprotein inhibitior	-	0.9262	92.62%
P-glycoprotein substrate	-	0.7551	75.51%
CYP3A4 substrate	+	0.5111	51.11%
CYP2C9 substrate	-	0.5827	58.27%
CYP2D6 substrate	-	0.8997	89.97%
CYP3A4 inhibition	-	0.8928	89.28%
CYP2C9 inhibition	-	0.9028	90.28%
CYP2C19 inhibition	-	0.9196	91.96%
CYP2D6 inhibition	-	0.8985	89.85%
CYP1A2 inhibition	-	0.6587	65.87%
CYP2C8 inhibition	-	0.8630	86.30%
CYP inhibitory promiscuity	-	0.9190	91.90%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5870	58.70%
Eye corrosion	-	0.9818	98.18%
Eye irritation	-	0.8209	82.09%
Skin irritation	+	0.5928	59.28%
Skin corrosion	-	0.9373	93.73%
Ames mutagenesis	-	0.6454	64.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6948	69.48%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.7698	76.98%
skin sensitisation	-	0.5279	52.79%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.4563	45.63%
Acute Oral Toxicity (c)	III	0.6618	66.18%
Estrogen receptor binding	-	0.8683	86.83%
Androgen receptor binding	-	0.6407	64.07%
Thyroid receptor binding	-	0.6597	65.97%
Glucocorticoid receptor binding	-	0.8661	86.61%
Aromatase binding	-	0.7428	74.28%
PPAR gamma	-	0.6164	61.64%
Honey bee toxicity	-	0.8730	87.30%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9454	94.54%

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	93.48%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.11%	91.11%
CHEMBL2581	P07339	Cathepsin D	89.55%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.64%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	85.98%	91.19%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.24%	93.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.14%	93.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.18%	89.00%

Plants that contains it

• Valeriana officinalis

Cross-Links

• PubChem: 6439586
• LOTUS: LTS0101695
• wikiData: Q105329074