(1R,4aR,7R,8aS,10aS)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid

Details

• Internal ID: 471eee06-5187-4b08-a66c-a1c1665a598b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1R,4aR,7R,8aS,10aS)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid
• SMILES (Canonical): CC12CCCC(C1CCC3C2=CCC(C3)(C)C=C)(C)C(=O)O
• SMILES (Isomeric): C[C@@]12CCC[C@@]([C@H]1CC[C@@H]3C2=CC[C@@](C3)(C)C=C)(C)C(=O)O
• InChI: InChI=1S/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,9,14,16H,1,6-8,10-13H2,2-4H3,(H,21,22)/t14-,16-,18+,19-,20+/m0/s1
• InChI Key: TVHDZSRRHQKNEZ-ARSBKQPYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₂
• Molecular Weight: 302.50 g/mol
• Exact Mass: 302.224580195 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 5.50
• Atomic LogP (AlogP): 5.21
• H-Bond Acceptor: 1
• 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	+	0.8058	80.58%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.4127	41.27%
OATP2B1 inhibitior	-	0.8584	85.84%
OATP1B1 inhibitior	+	0.9052	90.52%
OATP1B3 inhibitior	-	0.4703	47.03%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	+	0.6731	67.31%
P-glycoprotein inhibitior	-	0.7433	74.33%
P-glycoprotein substrate	-	0.8829	88.29%
CYP3A4 substrate	+	0.5580	55.80%
CYP2C9 substrate	-	0.5859	58.59%
CYP2D6 substrate	-	0.8733	87.33%
CYP3A4 inhibition	-	0.8276	82.76%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	+	0.7575	75.75%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.7748	77.48%
CYP2C8 inhibition	+	0.5131	51.31%
CYP inhibitory promiscuity	-	0.8959	89.59%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5883	58.83%
Eye corrosion	-	0.9683	96.83%
Eye irritation	-	0.8844	88.44%
Skin irritation	-	0.6521	65.21%
Skin corrosion	-	0.9781	97.81%
Ames mutagenesis	-	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5308	53.08%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	+	0.5033	50.33%
skin sensitisation	+	0.7018	70.18%
Respiratory toxicity	-	0.6889	68.89%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.6491	64.91%
Acute Oral Toxicity (c)	III	0.7692	76.92%
Estrogen receptor binding	+	0.5710	57.10%
Androgen receptor binding	-	0.5706	57.06%
Thyroid receptor binding	+	0.6021	60.21%
Glucocorticoid receptor binding	+	0.6732	67.32%
Aromatase binding	+	0.6169	61.69%
PPAR gamma	-	0.6490	64.90%
Honey bee toxicity	-	0.9125	91.25%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2808	Q13133	LXR-alpha	180 nM	EC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.10%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.75%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	89.19%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.63%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.36%	95.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.76%	93.00%
CHEMBL340	P08684	Cytochrome P450 3A4	84.30%	91.19%
CHEMBL4246	P42680	Tyrosine-protein kinase TEC	82.53%	82.05%

Plants that contains it

• Helichrysum setosum

Cross-Links

• PubChem: 92859215
• LOTUS: LTS0027930
• wikiData: Q105265295