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

Details

• Internal ID: ae536090-03da-4b67-9a0c-883b1dfb4def
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1S,4aR,5R,7R,8aR)-7-acetyloxy-1,4a-dimethyl-6-methylidene-5-[(2E)-3-methylpenta-2,4-dienyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• SMILES (Canonical): CC(=CCC1C(=C)C(CC2C1(CCCC2(C)C(=O)O)C)OC(=O)C)C=C
• SMILES (Isomeric): C/C(=C\C[C@H]1C(=C)[C@@H](C[C@@H]2[C@@]1(CCC[C@]2(C)C(=O)O)C)OC(=O)C)/C=C
• InChI: InChI=1S/C22H32O4/c1-7-14(2)9-10-17-15(3)18(26-16(4)23)13-19-21(17,5)11-8-12-22(19,6)20(24)25/h7,9,17-19H,1,3,8,10-13H2,2,4-6H3,(H,24,25)/b14-9+/t17-,18+,19+,21+,22-/m0/s1
• InChI Key: ZJXFDQVVYBKPMA-YJFYXXRUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₂O₄
• Molecular Weight: 360.50 g/mol
• Exact Mass: 360.23005950 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.91
• H-Bond Acceptor: 3
• 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	+	0.9878	98.78%
Caco-2	+	0.6483	64.83%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8521	85.21%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8043	80.43%
OATP1B3 inhibitior	-	0.3212	32.12%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.7271	72.71%
BSEP inhibitior	+	0.6949	69.49%
P-glycoprotein inhibitior	-	0.5499	54.99%
P-glycoprotein substrate	-	0.7238	72.38%
CYP3A4 substrate	+	0.6492	64.92%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	-	0.8963	89.63%
CYP3A4 inhibition	-	0.5374	53.74%
CYP2C9 inhibition	-	0.8869	88.69%
CYP2C19 inhibition	-	0.8735	87.35%
CYP2D6 inhibition	-	0.9517	95.17%
CYP1A2 inhibition	-	0.8175	81.75%
CYP2C8 inhibition	+	0.5437	54.37%
CYP inhibitory promiscuity	-	0.8945	89.45%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9643	96.43%
Carcinogenicity (trinary)	Non-required	0.6870	68.70%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.8980	89.80%
Skin irritation	+	0.5947	59.47%
Skin corrosion	-	0.9673	96.73%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8503	85.03%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.5745	57.45%
skin sensitisation	-	0.6854	68.54%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.6344	63.44%
Acute Oral Toxicity (c)	III	0.8138	81.38%
Estrogen receptor binding	+	0.6961	69.61%
Androgen receptor binding	+	0.5445	54.45%
Thyroid receptor binding	+	0.6338	63.38%
Glucocorticoid receptor binding	+	0.7236	72.36%
Aromatase binding	+	0.5376	53.76%
PPAR gamma	+	0.6901	69.01%
Honey bee toxicity	-	0.7583	75.83%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6755	67.55%
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	95.12%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.58%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.18%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	89.79%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.59%	97.25%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.27%	95.50%
CHEMBL2581	P07339	Cathepsin D	83.96%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.89%	86.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.72%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.65%	82.69%
CHEMBL221	P23219	Cyclooxygenase-1	80.01%	90.17%

Plants that contains it

• Chromolaena collina

Cross-Links

• PubChem: 162870908
• LOTUS: LTS0247249
• wikiData: Q105378242