5-(4-carboxy-3-methylbut-3-enyl)-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid

Details

• Internal ID: b0c4ef55-3d2a-42f6-b0cf-02c4192be33e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 5-(4-carboxy-3-methylbut-3-enyl)-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• SMILES (Canonical): CC(=CC(=O)O)CCC1C(=C)CCC2C1(CCCC2(C)C(=O)O)C
• SMILES (Isomeric): CC(=CC(=O)O)CCC1C(=C)CCC2C1(CCCC2(C)C(=O)O)C
• InChI: InChI=1S/C20H30O4/c1-13(12-17(21)22)6-8-15-14(2)7-9-16-19(15,3)10-5-11-20(16,4)18(23)24/h12,15-16H,2,5-11H2,1,3-4H3,(H,21,22)(H,23,24)
• InChI Key: QYCOHMYDSOZCQD-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.40 g/mol
• Exact Mass: 334.21440943 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 4.66
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9760	97.60%
Caco-2	+	0.7441	74.41%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7101	71.01%
OATP2B1 inhibitior	-	0.8678	86.78%
OATP1B1 inhibitior	+	0.7694	76.94%
OATP1B3 inhibitior	-	0.3527	35.27%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6771	67.71%
BSEP inhibitior	+	0.6524	65.24%
P-glycoprotein inhibitior	-	0.7013	70.13%
P-glycoprotein substrate	-	0.7690	76.90%
CYP3A4 substrate	+	0.6166	61.66%
CYP2C9 substrate	-	0.7829	78.29%
CYP2D6 substrate	-	0.9180	91.80%
CYP3A4 inhibition	-	0.7313	73.13%
CYP2C9 inhibition	-	0.8709	87.09%
CYP2C19 inhibition	-	0.8957	89.57%
CYP2D6 inhibition	-	0.9385	93.85%
CYP1A2 inhibition	-	0.8614	86.14%
CYP2C8 inhibition	-	0.6358	63.58%
CYP inhibitory promiscuity	-	0.8439	84.39%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6941	69.41%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.6798	67.98%
Skin irritation	-	0.6061	60.61%
Skin corrosion	-	0.9752	97.52%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7425	74.25%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.7266	72.66%
skin sensitisation	+	0.7743	77.43%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6313	63.13%
Acute Oral Toxicity (c)	III	0.6888	68.88%
Estrogen receptor binding	+	0.7020	70.20%
Androgen receptor binding	+	0.6630	66.30%
Thyroid receptor binding	+	0.6718	67.18%
Glucocorticoid receptor binding	+	0.7544	75.44%
Aromatase binding	+	0.5849	58.49%
PPAR gamma	+	0.5584	55.84%
Honey bee toxicity	-	0.8834	88.34%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.73%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.05%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.64%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.09%	94.45%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.17%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.92%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.68%	95.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.55%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	82.66%	90.17%
CHEMBL340	P08684	Cytochrome P450 3A4	82.40%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.82%	96.09%

Plants that contains it

• Araucaria angustifolia
• Jasminum sambac
• Juniperus chinensis

Cross-Links

• PubChem: 541901
• LOTUS: LTS0260309
• wikiData: Q104999301