(1R,2S,5R,8R,9S,10S,11R,13R)-13-hydroxy-11-methyl-6-methylidene-16-oxopentacyclo[9.3.2.15,8.01,10.02,8]heptadecane-9-carboxylic acid

Details

• Internal ID: b71fe492-dfc5-4ca0-b95a-608b7bcbd67a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (1R,2S,5R,8R,9S,10S,11R,13R)-13-hydroxy-11-methyl-6-methylidene-16-oxopentacyclo[9.3.2.15,8.01,10.02,8]heptadecane-9-carboxylic acid
• SMILES (Canonical): CC12CC(CC3(C1C(C45C3CCC(C4)C(=C)C5)C(=O)O)CC2=O)O
• SMILES (Isomeric): C[C@@]12C[C@@H](C[C@@]3([C@@H]1[C@@H]([C@]45[C@H]3CC[C@H](C4)C(=C)C5)C(=O)O)CC2=O)O
• InChI: InChI=1S/C20H26O4/c1-10-5-19-6-11(10)3-4-13(19)20-8-12(21)7-18(2,14(22)9-20)16(20)15(19)17(23)24/h11-13,15-16,21H,1,3-9H2,2H3,(H,23,24)/t11-,12+,13-,15-,16-,18+,19+,20-/m1/s1
• InChI Key: YDRPJJOHGMOAKP-OJJROGHBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.40 g/mol
• Exact Mass: 330.18310931 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.80
• 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	+	0.9838	98.38%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7342	73.42%
OATP2B1 inhibitior	-	0.8597	85.97%
OATP1B1 inhibitior	+	0.9094	90.94%
OATP1B3 inhibitior	+	0.8716	87.16%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5716	57.16%
BSEP inhibitior	-	0.9380	93.80%
P-glycoprotein inhibitior	-	0.9140	91.40%
P-glycoprotein substrate	-	0.7785	77.85%
CYP3A4 substrate	+	0.5800	58.00%
CYP2C9 substrate	-	0.8299	82.99%
CYP2D6 substrate	-	0.8471	84.71%
CYP3A4 inhibition	-	0.8816	88.16%
CYP2C9 inhibition	-	0.9318	93.18%
CYP2C19 inhibition	-	0.9415	94.15%
CYP2D6 inhibition	-	0.9399	93.99%
CYP1A2 inhibition	-	0.7435	74.35%
CYP2C8 inhibition	-	0.7459	74.59%
CYP inhibitory promiscuity	-	0.9583	95.83%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5750	57.50%
Eye corrosion	-	0.9939	99.39%
Eye irritation	-	0.8377	83.77%
Skin irritation	+	0.6510	65.10%
Skin corrosion	-	0.9242	92.42%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6964	69.64%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.5632	56.32%
skin sensitisation	-	0.7092	70.92%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.5967	59.67%
Acute Oral Toxicity (c)	III	0.6127	61.27%
Estrogen receptor binding	+	0.8310	83.10%
Androgen receptor binding	+	0.6062	60.62%
Thyroid receptor binding	+	0.5809	58.09%
Glucocorticoid receptor binding	+	0.7618	76.18%
Aromatase binding	+	0.6600	66.00%
PPAR gamma	-	0.6086	60.86%
Honey bee toxicity	-	0.9299	92.99%
Biodegradation	-	0.7500	75.00%
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
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	95.98%	96.38%
CHEMBL221	P23219	Cyclooxygenase-1	93.18%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.18%	91.11%
CHEMBL2581	P07339	Cathepsin D	88.42%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.95%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	85.56%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.46%	95.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.08%	93.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.48%	97.25%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162890216
• LOTUS: LTS0040582
• wikiData: Q105346997