(4aS,4bR,7S,8aR,9S,10aR)-7-ethenyl-8a,9-dihydroxy-1,1,4a,7-tetramethyl-4,4b,5,6,8,9,10,10a-octahydro-3H-phenanthren-2-one

Details

• Internal ID: aefefa8d-51a2-4ec9-a4d8-f4bbee1c19bd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (4aS,4bR,7S,8aR,9S,10aR)-7-ethenyl-8a,9-dihydroxy-1,1,4a,7-tetramethyl-4,4b,5,6,8,9,10,10a-octahydro-3H-phenanthren-2-one
• SMILES (Canonical): CC1(C2CC(C3(CC(CCC3C2(CCC1=O)C)(C)C=C)O)O)C
• SMILES (Isomeric): C[C@@]1(CC[C@@H]2[C@]3(CCC(=O)C([C@@H]3C[C@@H]([C@]2(C1)O)O)(C)C)C)C=C
• InChI: InChI=1S/C20H32O3/c1-6-18(4)9-7-13-19(5)10-8-15(21)17(2,3)14(19)11-16(22)20(13,23)12-18/h6,13-14,16,22-23H,1,7-12H2,2-5H3/t13-,14+,16+,18+,19-,20-/m1/s1
• InChI Key: AWTRJROHUHRHRE-LYSHTCLHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.50 g/mol
• Exact Mass: 320.23514488 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.49
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9935	99.35%
Caco-2	+	0.7222	72.22%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7996	79.96%
OATP2B1 inhibitior	-	0.8592	85.92%
OATP1B1 inhibitior	+	0.9320	93.20%
OATP1B3 inhibitior	+	0.9432	94.32%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.7749	77.49%
P-glycoprotein inhibitior	-	0.8279	82.79%
P-glycoprotein substrate	-	0.8601	86.01%
CYP3A4 substrate	+	0.6107	61.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8133	81.33%
CYP3A4 inhibition	-	0.6594	65.94%
CYP2C9 inhibition	-	0.8654	86.54%
CYP2C19 inhibition	-	0.7155	71.55%
CYP2D6 inhibition	-	0.9571	95.71%
CYP1A2 inhibition	-	0.8147	81.47%
CYP2C8 inhibition	-	0.7879	78.79%
CYP inhibitory promiscuity	-	0.9604	96.04%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6785	67.85%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9225	92.25%
Skin irritation	+	0.5642	56.42%
Skin corrosion	-	0.9306	93.06%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4361	43.61%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	-	0.5767	57.67%
skin sensitisation	-	0.5491	54.91%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.6239	62.39%
Acute Oral Toxicity (c)	III	0.7404	74.04%
Estrogen receptor binding	+	0.7344	73.44%
Androgen receptor binding	+	0.5824	58.24%
Thyroid receptor binding	+	0.6220	62.20%
Glucocorticoid receptor binding	+	0.7907	79.07%
Aromatase binding	+	0.6618	66.18%
PPAR gamma	-	0.5663	56.63%
Honey bee toxicity	-	0.7729	77.29%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9933	99.33%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1994	P08235	Mineralocorticoid receptor	89.33%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	88.33%	94.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.10%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.98%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.58%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.12%	99.23%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.87%	82.69%
CHEMBL1902	P62942	FK506-binding protein 1A	82.59%	97.05%
CHEMBL340	P08684	Cytochrome P450 3A4	81.31%	91.19%
CHEMBL2581	P07339	Cathepsin D	81.07%	98.95%

Plants that contains it

• Bromelia pinguin
• Peperomia trineura
• Vellozia piresiana

Cross-Links

• PubChem: 162969903
• LOTUS: LTS0175356
• wikiData: Q105027274