(1S,3R,4aR,5S,8aR)-3-hydroxy-1,4a-dimethyl-6-methylidene-5-[(2Z)-3-methylpenta-2,4-dienyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid

Details

• Internal ID: 0c17379c-8664-4293-b7ad-ff4663759485
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1S,3R,4aR,5S,8aR)-3-hydroxy-1,4a-dimethyl-6-methylidene-5-[(2Z)-3-methylpenta-2,4-dienyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• SMILES (Canonical): CC(=CCC1C(=C)CCC2C1(CC(CC2(C)C(=O)O)O)C)C=C
• SMILES (Isomeric): C/C(=C/C[C@H]1C(=C)CC[C@@H]2[C@@]1(C[C@H](C[C@]2(C)C(=O)O)O)C)/C=C
• InChI: InChI=1S/C20H30O3/c1-6-13(2)7-9-16-14(3)8-10-17-19(16,4)11-15(21)12-20(17,5)18(22)23/h6-7,15-17,21H,1,3,8-12H2,2,4-5H3,(H,22,23)/b13-7-/t15-,16+,17-,19-,20+/m1/s1
• InChI Key: USNLWGSHMJHWQY-MXJDMVJCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.40 g/mol
• Exact Mass: 318.21949481 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 4.34
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9949	99.49%
Caco-2	+	0.7084	70.84%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7637	76.37%
OATP2B1 inhibitior	-	0.8649	86.49%
OATP1B1 inhibitior	+	0.8640	86.40%
OATP1B3 inhibitior	+	0.9151	91.51%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.6115	61.15%
P-glycoprotein inhibitior	-	0.8638	86.38%
P-glycoprotein substrate	-	0.6967	69.67%
CYP3A4 substrate	+	0.6418	64.18%
CYP2C9 substrate	-	0.8398	83.98%
CYP2D6 substrate	-	0.8724	87.24%
CYP3A4 inhibition	-	0.6204	62.04%
CYP2C9 inhibition	-	0.9145	91.45%
CYP2C19 inhibition	-	0.8750	87.50%
CYP2D6 inhibition	-	0.9549	95.49%
CYP1A2 inhibition	-	0.9325	93.25%
CYP2C8 inhibition	-	0.7151	71.51%
CYP inhibitory promiscuity	-	0.8842	88.42%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6482	64.82%
Eye corrosion	-	0.9949	99.49%
Eye irritation	-	0.9449	94.49%
Skin irritation	+	0.6340	63.40%
Skin corrosion	-	0.9585	95.85%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3941	39.41%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.7069	70.69%
skin sensitisation	-	0.5282	52.82%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.6297	62.97%
Acute Oral Toxicity (c)	III	0.7422	74.22%
Estrogen receptor binding	+	0.5998	59.98%
Androgen receptor binding	+	0.5609	56.09%
Thyroid receptor binding	+	0.5666	56.66%
Glucocorticoid receptor binding	+	0.7333	73.33%
Aromatase binding	+	0.7217	72.17%
PPAR gamma	-	0.5346	53.46%
Honey bee toxicity	-	0.8579	85.79%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9969	99.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	95.76%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.40%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	88.82%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.57%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.28%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.60%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.27%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.66%	95.56%
CHEMBL5028	O14672	ADAM10	81.56%	97.50%
CHEMBL4246	P42680	Tyrosine-protein kinase TEC	80.65%	82.05%

Plants that contains it

• Juniperus chinensis

Cross-Links

• PubChem: 162940763
• LOTUS: LTS0006274
• wikiData: Q105278350