1-[(1S,4aR,5S,8aR)-5-[(3R)-3-hydroxy-3-methylpent-4-enyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalen-1-yl]ethanone

Details

• Internal ID: ff613b12-546b-4688-a972-376ef3c82516
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 1-[(1S,4aR,5S,8aR)-5-[(3R)-3-hydroxy-3-methylpent-4-enyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalen-1-yl]ethanone
• SMILES (Canonical): CC(=O)C1(CCCC2(C1CCC(=C)C2CCC(C)(C=C)O)C)C
• SMILES (Isomeric): CC(=O)[C@]1(CCC[C@]2([C@H]1CCC(=C)[C@@H]2CC[C@](C)(C=C)O)C)C
• InChI: InChI=1S/C21H34O2/c1-7-19(4,23)14-11-17-15(2)9-10-18-20(5,16(3)22)12-8-13-21(17,18)6/h7,17-18,23H,1-2,8-14H2,3-6H3/t17-,18-,19-,20+,21+/m0/s1
• InChI Key: ZJPLPNZOEWUQNS-ALGQRKQJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₄O₂
• Molecular Weight: 318.50 g/mol
• Exact Mass: 318.255880323 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 5.07
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 5

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	+	0.8517	85.17%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.4887	48.87%
OATP2B1 inhibitior	-	0.8623	86.23%
OATP1B1 inhibitior	+	0.8295	82.95%
OATP1B3 inhibitior	+	0.9294	92.94%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.6829	68.29%
P-glycoprotein substrate	-	0.7532	75.32%
CYP3A4 substrate	+	0.6460	64.60%
CYP2C9 substrate	-	0.8375	83.75%
CYP2D6 substrate	-	0.8168	81.68%
CYP3A4 inhibition	-	0.5222	52.22%
CYP2C9 inhibition	-	0.8188	81.88%
CYP2C19 inhibition	-	0.8061	80.61%
CYP2D6 inhibition	-	0.9468	94.68%
CYP1A2 inhibition	-	0.8334	83.34%
CYP2C8 inhibition	-	0.5847	58.47%
CYP inhibitory promiscuity	-	0.8130	81.30%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.6236	62.36%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9507	95.07%
Skin irritation	-	0.5472	54.72%
Skin corrosion	-	0.9727	97.27%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4250	42.50%
Micronuclear	-	0.9500	95.00%
Hepatotoxicity	-	0.7298	72.98%
skin sensitisation	+	0.7113	71.13%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7451	74.51%
Acute Oral Toxicity (c)	III	0.7906	79.06%
Estrogen receptor binding	+	0.6159	61.59%
Androgen receptor binding	+	0.6277	62.77%
Thyroid receptor binding	+	0.6458	64.58%
Glucocorticoid receptor binding	+	0.6666	66.66%
Aromatase binding	+	0.5541	55.41%
PPAR gamma	-	0.5369	53.69%
Honey bee toxicity	-	0.8655	86.55%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9920	99.20%

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	98.07%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.37%	91.11%
CHEMBL1977	P11473	Vitamin D receptor	91.72%	99.43%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.01%	100.00%
CHEMBL2581	P07339	Cathepsin D	85.78%	98.95%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	85.50%	90.93%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	85.40%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.05%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.44%	97.09%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.36%	91.07%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.28%	96.09%
CHEMBL5028	O14672	ADAM10	81.73%	97.50%

Plants that contains it

• Chamaecyparis lawsoniana

Cross-Links

• PubChem: 163037887
• LOTUS: LTS0232046
• wikiData: Q105378043