methyl (1R,4aR,7S,9R,10aS)-7-ethenyl-9-hydroxy-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2H-phenanthrene-1-carboxylate

Details

• Internal ID: 413d5a47-951e-467c-8ea9-20cf73297ae8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: methyl (1R,4aR,7S,9R,10aS)-7-ethenyl-9-hydroxy-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2H-phenanthrene-1-carboxylate
• SMILES (Canonical): CC1(CCC2=C(C1)C(CC3C2(CCCC3(C)C(=O)OC)C)O)C=C
• SMILES (Isomeric): C[C@@]1(CCC2=C(C1)[C@@H](C[C@H]3[C@]2(CCC[C@@]3(C)C(=O)OC)C)O)C=C
• InChI: InChI=1S/C21H32O3/c1-6-19(2)11-8-15-14(13-19)16(22)12-17-20(15,3)9-7-10-21(17,4)18(23)24-5/h6,16-17,22H,1,7-13H2,2-5H3/t16-,17+,19+,20+,21-/m1/s1
• InChI Key: PYHBJCJOQMKMQF-GZSKETOLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₂O₃
• Molecular Weight: 332.50 g/mol
• Exact Mass: 332.23514488 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 4.41
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9962	99.62%
Caco-2	+	0.8223	82.23%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7963	79.63%
OATP2B1 inhibitior	-	0.8639	86.39%
OATP1B1 inhibitior	+	0.8701	87.01%
OATP1B3 inhibitior	+	0.9090	90.90%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	+	0.5974	59.74%
P-glycoprotein inhibitior	-	0.6911	69.11%
P-glycoprotein substrate	-	0.7505	75.05%
CYP3A4 substrate	+	0.6724	67.24%
CYP2C9 substrate	-	0.6346	63.46%
CYP2D6 substrate	-	0.7958	79.58%
CYP3A4 inhibition	-	0.8225	82.25%
CYP2C9 inhibition	-	0.5980	59.80%
CYP2C19 inhibition	-	0.6436	64.36%
CYP2D6 inhibition	-	0.9404	94.04%
CYP1A2 inhibition	-	0.7756	77.56%
CYP2C8 inhibition	-	0.5798	57.98%
CYP inhibitory promiscuity	-	0.9504	95.04%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9643	96.43%
Carcinogenicity (trinary)	Non-required	0.5807	58.07%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.8572	85.72%
Skin irritation	-	0.5184	51.84%
Skin corrosion	-	0.9636	96.36%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3663	36.63%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.5621	56.21%
skin sensitisation	-	0.6319	63.19%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.6385	63.85%
Acute Oral Toxicity (c)	III	0.7372	73.72%
Estrogen receptor binding	+	0.6504	65.04%
Androgen receptor binding	+	0.6093	60.93%
Thyroid receptor binding	+	0.6287	62.87%
Glucocorticoid receptor binding	+	0.7842	78.42%
Aromatase binding	+	0.6424	64.24%
PPAR gamma	-	0.5907	59.07%
Honey bee toxicity	-	0.7135	71.35%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9900	99.00%

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	96.92%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.61%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.52%	96.09%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	91.43%	91.07%
CHEMBL340	P08684	Cytochrome P450 3A4	90.31%	91.19%
CHEMBL233	P35372	Mu opioid receptor	89.68%	97.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.46%	95.56%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.66%	91.03%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.55%	93.03%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.84%	100.00%

Plants that contains it

• Mikania triangularis

Cross-Links

• PubChem: 101630388
• LOTUS: LTS0191042
• wikiData: Q105216580