Valerenic acid

Details

• Internal ID: c28a07b4-c0ae-4755-abba-35291a1eeca7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (E)-3-[(4S,7R,7aR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoic acid
• SMILES (Canonical): CC1CCC(C2=C(CCC12)C)C=C(C)C(=O)O
• SMILES (Isomeric): C[C@@H]1CC[C@H](C2=C(CC[C@H]12)C)/C=C(\C)/C(=O)O
• InChI: InChI=1S/C15H22O2/c1-9-4-6-12(8-11(3)15(16)17)14-10(2)5-7-13(9)14/h8-9,12-13H,4-7H2,1-3H3,(H,16,17)/b11-8+/t9-,12+,13-/m1/s1
• InChI Key: FEBNTWHYQKGEIQ-SUKRRCERSA-N
• Popularity: 207 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.33 g/mol
• Exact Mass: 234.161979940 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.79
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 3569-10-6
• (-)-valerenic acid
• CHEBI:9921
• 34NDB285PM
• DTXSID8034089
• DTXCID6014089
• (2E)-3-[(4S,7R,7aR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylacrylic acid
• (2E)-3-[(4S,7R,7aR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoic acid
• (2E)-3-((4S,7R,7AR)-3,7-DIMETHYL-2,4,5,6,7,7A-HEXAHYDRO-1H-INDEN-4-YL)-2-METHYLACRYLIC ACID
• (E)-3-[(4S,7R,7aR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoic acid
• (2E)-3-((4S,7R,7aR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-2-methylprop-2-enoic acid
• (E)-3-((4S,7R,7aR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-2-methylprop-2-enoic acid
• RefChem:50926
• MFCD00075694
• 2-Propenoic acid,3-[(4S,7R,7aR)-2,4,5,6,7,7a-hexahydro-3,7-dimethyl-1H-inden-4-yl]-2-methyl-, (2E)-
• C15H22O2
• Nardin
• (E)-3-((4S,7R,7aR)-3,7-Dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-2-methylacrylic acid
• VALERENICACID
• Valerian dry extract
• Valerenic acid (Standard)
• UNII-34NDB285PM
• SCHEMBL403082
• orb1684169
• CHEMBL1545045
• VALERENIC ACID [USP-RS]
• FEBNTWHYQKGEIQ-SUKRRCERSA-N
• GLXC-20388
• Valerenic acid, analytical standard
• Tox21_200313
• BDBM50341378
• EX-A10774
• AKOS024457400
• FV71689
• HY-103524R
• NCGC00091912-01
• NCGC00091912-02
• NCGC00257867-01
• (2E)-3-[(4S,7R,7aR)-2,4,5,6,7,7a-Hexadydro-3,7-dimethyl-1H-inden-4-yl]-2-methyl-2-propenoic acid
• 2-Propenoic acid, 3-(2,4,5,6,7,7a-hexahydro-3,7-dimethyl-1H-inden-4-yl)-2-methyl-, (4S-(4alpha(E),7beta,7aalpha))-
• MS-23355
• CAS-3569-10-6
• HY-103524
• CS-0028025
• NS00121273
• C09743
• G12200
• 569V106
• VALERENIC ACID (CONSTITUENT OF VALERIAN) [DSC]
• Valerenic acid - Valeriana officinalis (common valerian)
• Valerenic acid, primary pharmaceutical reference standard
• Valerenic acid, United States Pharmacopeia (USP) Reference Standard
• (2E)-3-[(4S,7R,7aR)-2,4,5,6,7,7a-Hexahydro-3,7-dimethyl-1H-inden-4-yl]-2-methyl-2-propenoic acid
• (2E)-3-[(4S\,7R\,7aR)-3\,7-dimethyl-2\,4\,5\,6\,7\,7a-hexahydro-1H-inden-4-yl]-2-methylacrylic acid
• (E)-3-[(4S,7R,7AR)-3,7-DIMETHYL-2,4,5,6,7,7A-HEXAHYDRO-1H-INDEN-4-YL]-2-METHYL-PROP-2-ENOIC ACID

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8991	89.91%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Plasma membrane	0.5539	55.39%
OATP2B1 inhibitior	-	0.8495	84.95%
OATP1B1 inhibitior	+	0.8818	88.18%
OATP1B3 inhibitior	+	0.8882	88.82%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.8634	86.34%
P-glycoprotein inhibitior	-	0.9174	91.74%
P-glycoprotein substrate	-	0.9273	92.73%
CYP3A4 substrate	-	0.5122	51.22%
CYP2C9 substrate	-	0.5618	56.18%
CYP2D6 substrate	-	0.9140	91.40%
CYP3A4 inhibition	-	0.8961	89.61%
CYP2C9 inhibition	-	0.7437	74.37%
CYP2C19 inhibition	-	0.7671	76.71%
CYP2D6 inhibition	-	0.9253	92.53%
CYP1A2 inhibition	-	0.6404	64.04%
CYP2C8 inhibition	-	0.7615	76.15%
CYP inhibitory promiscuity	-	0.9217	92.17%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6031	60.31%
Eye corrosion	-	0.9031	90.31%
Eye irritation	-	0.8409	84.09%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9838	98.38%
Ames mutagenesis	-	0.6854	68.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5682	56.82%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	+	0.8302	83.02%
skin sensitisation	+	0.7118	71.18%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	-	0.5889	58.89%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8001	80.01%
Acute Oral Toxicity (c)	III	0.8288	82.88%
Estrogen receptor binding	-	0.9202	92.02%
Androgen receptor binding	-	0.5204	52.04%
Thyroid receptor binding	-	0.6484	64.84%
Glucocorticoid receptor binding	-	0.7422	74.22%
Aromatase binding	-	0.6988	69.88%
PPAR gamma	-	0.5765	57.65%
Honey bee toxicity	-	0.9268	92.68%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9948	99.48%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	17782.8 nM	Potency	via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	39810.7 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.49%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.78%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.91%	95.56%
CHEMBL2581	P07339	Cathepsin D	86.61%	98.95%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.73%	93.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.09%	93.56%
CHEMBL340	P08684	Cytochrome P450 3A4	82.50%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.23%	97.09%

Plants that contains it

• Valeriana hardwickii
• Valeriana officinalis
• Valeriana wolgensis

Cross-Links

• PubChem: 6440940
• NPASS: NPC81907
• ChEMBL: CHEMBL1545045
• LOTUS: LTS0067308
• wikiData: Q75850