(1S)-1,2,3,4,4a,5,6,7,8,8abeta-Decahydro-1alpha,4abeta-dimethyl-6-methylene-5beta-[(3S)-3-methyl-5-oxohexyl]-1beta-naphthalenecarboxylic acid methyl ester

Details

• Internal ID: f0a85102-bdb6-4a2a-b593-cc7305ac931d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: methyl (1S,4aR,5S,8aS)-1,4a-dimethyl-6-methylidene-5-[(3S)-3-methyl-5-oxohexyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate
• SMILES (Canonical): CC(CCC1C(=C)CCC2C1(CCCC2(C)C(=O)OC)C)CC(=O)C
• SMILES (Isomeric): C[C@@H](CC[C@H]1C(=C)CC[C@H]2[C@@]1(CCC[C@]2(C)C(=O)OC)C)CC(=O)C
• InChI: InChI=1S/C22H36O3/c1-15(14-17(3)23)8-10-18-16(2)9-11-19-21(18,4)12-7-13-22(19,5)20(24)25-6/h15,18-19H,2,7-14H2,1,3-6H3/t15-,18-,19-,21+,22-/m0/s1
• InChI Key: BXFIQIHHUYQVJG-GKYSZPLNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₆O₃
• Molecular Weight: 348.50 g/mol
• Exact Mass: 348.26644501 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 5.33
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• (1S)-1,2,3,4,4a,5,6,7,8,8abeta-Decahydro-1alpha,4abeta-dimethyl-6-methylene-5beta-[(3S)-3-methyl-5-oxohexyl]-1beta-naphthalenecarboxylic acid methyl ester
• 55515-21-4

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9938	99.38%
Caco-2	+	0.6549	65.49%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6578	65.78%
OATP2B1 inhibitior	-	0.8651	86.51%
OATP1B1 inhibitior	+	0.8955	89.55%
OATP1B3 inhibitior	+	0.8645	86.45%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.8638	86.38%
P-glycoprotein inhibitior	-	0.4358	43.58%
P-glycoprotein substrate	-	0.5232	52.32%
CYP3A4 substrate	+	0.6585	65.85%
CYP2C9 substrate	-	0.8017	80.17%
CYP2D6 substrate	-	0.8590	85.90%
CYP3A4 inhibition	-	0.5928	59.28%
CYP2C9 inhibition	-	0.7918	79.18%
CYP2C19 inhibition	-	0.6617	66.17%
CYP2D6 inhibition	-	0.9559	95.59%
CYP1A2 inhibition	-	0.8336	83.36%
CYP2C8 inhibition	-	0.8580	85.80%
CYP inhibitory promiscuity	-	0.6520	65.20%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8020	80.20%
Carcinogenicity (trinary)	Non-required	0.5843	58.43%
Eye corrosion	-	0.9848	98.48%
Eye irritation	-	0.7456	74.56%
Skin irritation	-	0.6462	64.62%
Skin corrosion	-	0.9862	98.62%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4236	42.36%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.6851	68.51%
skin sensitisation	-	0.5333	53.33%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7003	70.03%
Acute Oral Toxicity (c)	III	0.8480	84.80%
Estrogen receptor binding	+	0.6878	68.78%
Androgen receptor binding	+	0.6486	64.86%
Thyroid receptor binding	+	0.6223	62.23%
Glucocorticoid receptor binding	+	0.7921	79.21%
Aromatase binding	+	0.5372	53.72%
PPAR gamma	-	0.5100	51.00%
Honey bee toxicity	-	0.7816	78.16%
Biodegradation	-	0.7750	77.50%
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	98.08%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.29%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.80%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.75%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.18%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.22%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.97%	82.69%
CHEMBL340	P08684	Cytochrome P450 3A4	87.38%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.28%	91.07%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.22%	92.62%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	84.67%	95.71%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.51%	94.33%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.23%	96.47%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.07%	100.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.36%	96.38%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.99%	95.89%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	81.69%	98.75%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.46%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.31%	95.89%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.83%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.54%	95.56%

Plants that contains it

• Breonia chinensis
• Campylotropis hirtella
• Ceropegia dichotoma
• Crinum moorei
• Crotalaria candicans
• Cryptomeria japonica
• Dendrobium loddigesii
• Distephanus angulifolius
• Eucalyptus apodophylla
• Glycosmis macrophylla
• Gypsophila perfoliata
• Hypericum polyanthemum
• Juniperus drupacea
• Lophostemon confertus
• Mentha × gentilis
• Ononis spinosa
• Orbivestus karaguensis
• Pentaclethra macrophylla
• Periploca sepium
• Pinalia japonica
• Plectranthus hereroensis
• Pterocaulon virgatum
• Rhodiola semenovii
• Salvia sessei
• Sonneratia caseolaris
• Stephania zippeliana
• Veronica polita

Cross-Links

• PubChem: 102239830
• NPASS: NPC236785
• LOTUS: LTS0026694
• wikiData: Q104947911