(2S,4aS,8S,8aS)-8-[(3R)-3-hydroxy-3-methylpent-4-enyl]-4,4,8a-trimethyl-7-methylidene-2,3,4a,5,6,8-hexahydro-1H-naphthalen-2-ol

Details

• Internal ID: 1cd50715-e2a5-4ad3-855a-e6b0d79552ba
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (2S,4aS,8S,8aS)-8-[(3R)-3-hydroxy-3-methylpent-4-enyl]-4,4,8a-trimethyl-7-methylidene-2,3,4a,5,6,8-hexahydro-1H-naphthalen-2-ol
• SMILES (Canonical): CC1(CC(CC2(C1CCC(=C)C2CCC(C)(C=C)O)C)O)C
• SMILES (Isomeric): C[C@]12C[C@H](CC([C@@H]1CCC(=C)[C@@H]2CC[C@](C)(C=C)O)(C)C)O
• InChI: InChI=1S/C20H34O2/c1-7-19(5,22)11-10-16-14(2)8-9-17-18(3,4)12-15(21)13-20(16,17)6/h7,15-17,21-22H,1-2,8-13H2,3-6H3/t15-,16-,17-,19-,20+/m0/s1
• InChI Key: JGBAOJFZQJIUKE-VDWQKOAOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₄O₂
• Molecular Weight: 306.50 g/mol
• Exact Mass: 306.255880323 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 4.47
• 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	+	1.0000	100.00%
Caco-2	+	0.6543	65.43%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5305	53.05%
OATP2B1 inhibitior	-	0.8567	85.67%
OATP1B1 inhibitior	+	0.8559	85.59%
OATP1B3 inhibitior	+	0.9307	93.07%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.7117	71.17%
P-glycoprotein inhibitior	-	0.8197	81.97%
P-glycoprotein substrate	-	0.7623	76.23%
CYP3A4 substrate	+	0.6032	60.32%
CYP2C9 substrate	-	0.5811	58.11%
CYP2D6 substrate	-	0.7340	73.40%
CYP3A4 inhibition	-	0.6589	65.89%
CYP2C9 inhibition	-	0.9322	93.22%
CYP2C19 inhibition	-	0.8122	81.22%
CYP2D6 inhibition	-	0.9456	94.56%
CYP1A2 inhibition	-	0.8861	88.61%
CYP2C8 inhibition	+	0.4873	48.73%
CYP inhibitory promiscuity	-	0.7123	71.23%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6671	66.71%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9095	90.95%
Skin irritation	-	0.5968	59.68%
Skin corrosion	-	0.9621	96.21%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5094	50.94%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	-	0.7226	72.26%
skin sensitisation	+	0.6974	69.74%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6617	66.17%
Acute Oral Toxicity (c)	I	0.7564	75.64%
Estrogen receptor binding	+	0.7380	73.80%
Androgen receptor binding	+	0.5835	58.35%
Thyroid receptor binding	+	0.5719	57.19%
Glucocorticoid receptor binding	+	0.7759	77.59%
Aromatase binding	+	0.5577	55.77%
PPAR gamma	+	0.5211	52.11%
Honey bee toxicity	-	0.8481	84.81%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9912	99.12%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.10%	97.25%
CHEMBL1977	P11473	Vitamin D receptor	96.33%	99.43%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.77%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.35%	97.09%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	89.73%	90.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.48%	100.00%
CHEMBL1841	P06241	Tyrosine-protein kinase FYN	85.23%	81.29%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.55%	95.89%
CHEMBL1871	P10275	Androgen Receptor	83.22%	96.43%
CHEMBL2581	P07339	Cathepsin D	81.94%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.32%	96.09%

Plants that contains it

• Aster spathulifolius

Cross-Links

• PubChem: 163092936
• LOTUS: LTS0019702
• wikiData: Q105127174