methyl (E)-5-[(1S,4aR,5R,8aR)-5-(acetyloxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoate

Details

• Internal ID: dd884dc9-f33e-4ed1-8510-81a91ce88367
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: methyl (E)-5-[(1S,4aR,5R,8aR)-5-(acetyloxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoate
• SMILES (Canonical): CC(=CC(=O)OC)CCC1C(=C)CCC2C1(CCCC2(C)COC(=O)C)C
• SMILES (Isomeric): C/C(=C\C(=O)OC)/CC[C@H]1C(=C)CC[C@@H]2[C@@]1(CCC[C@@]2(C)COC(=O)C)C
• InChI: InChI=1S/C23H36O4/c1-16(14-21(25)26-6)8-10-19-17(2)9-11-20-22(4,15-27-18(3)24)12-7-13-23(19,20)5/h14,19-20H,2,7-13,15H2,1,3-6H3/b16-14+/t19-,20-,22-,23+/m0/s1
• InChI Key: KMEQUVNVNHTHSM-FAWMQMBESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₆O₄
• Molecular Weight: 376.50 g/mol
• Exact Mass: 376.26135963 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 5.23
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9892	98.92%
Caco-2	+	0.6869	68.69%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7437	74.37%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8487	84.87%
OATP1B3 inhibitior	+	0.8768	87.68%
MATE1 inhibitior	+	0.6000	60.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.9061	90.61%
P-glycoprotein inhibitior	+	0.6515	65.15%
P-glycoprotein substrate	-	0.6475	64.75%
CYP3A4 substrate	+	0.6678	66.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9092	90.92%
CYP3A4 inhibition	-	0.6357	63.57%
CYP2C9 inhibition	-	0.7331	73.31%
CYP2C19 inhibition	-	0.6942	69.42%
CYP2D6 inhibition	-	0.9266	92.66%
CYP1A2 inhibition	-	0.7375	73.75%
CYP2C8 inhibition	+	0.5667	56.67%
CYP inhibitory promiscuity	-	0.5725	57.25%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8220	82.20%
Carcinogenicity (trinary)	Non-required	0.6087	60.87%
Eye corrosion	-	0.9779	97.79%
Eye irritation	-	0.7578	75.78%
Skin irritation	-	0.6686	66.86%
Skin corrosion	-	0.9850	98.50%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6799	67.99%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.7822	78.22%
skin sensitisation	-	0.6627	66.27%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.5530	55.30%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.7112	71.12%
Acute Oral Toxicity (c)	III	0.7406	74.06%
Estrogen receptor binding	+	0.7149	71.49%
Androgen receptor binding	+	0.7214	72.14%
Thyroid receptor binding	+	0.5890	58.90%
Glucocorticoid receptor binding	+	0.8303	83.03%
Aromatase binding	+	0.7199	71.99%
PPAR gamma	+	0.6342	63.42%
Honey bee toxicity	-	0.7770	77.70%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.02%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.27%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.95%	97.25%
CHEMBL4040	P28482	MAP kinase ERK2	92.14%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.05%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	89.80%	90.17%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	89.37%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	88.53%	91.19%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.28%	94.33%
CHEMBL2581	P07339	Cathepsin D	85.49%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.36%	95.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.34%	82.69%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	85.30%	96.38%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.47%	92.62%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.41%	100.00%
CHEMBL5028	O14672	ADAM10	82.96%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.67%	97.09%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.50%	97.50%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	81.43%	91.65%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.38%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.92%	95.89%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.48%	94.00%
CHEMBL233	P35372	Mu opioid receptor	80.37%	97.93%

Plants that contains it

• Pinus sylvestris

Cross-Links

• PubChem: 162939279
• LOTUS: LTS0061235
• wikiData: Q105142948