(1Z,5E,8S,11S)-11-(hydroxymethyl)-5-methyl-8-prop-1-en-2-ylcyclotetradeca-1,5-diene-1-carboxylic acid

Details

• Internal ID: 6dbd1802-8dcd-4b37-ab74-42a8cb8ce53f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Cembrane diterpenoids
• IUPAC Name: (1Z,5E,8S,11S)-11-(hydroxymethyl)-5-methyl-8-prop-1-en-2-ylcyclotetradeca-1,5-diene-1-carboxylic acid
• SMILES (Canonical): CC1=CCC(CCC(CCCC(=CCC1)C(=O)O)CO)C(=C)C
• SMILES (Isomeric): C/C/1=C\C[C@H](CC[C@H](CCC/C(=C/CC1)/C(=O)O)CO)C(=C)C
• InChI: InChI=1S/C20H32O3/c1-15(2)18-12-10-16(3)6-4-8-19(20(22)23)9-5-7-17(14-21)11-13-18/h8,10,17-18,21H,1,4-7,9,11-14H2,2-3H3,(H,22,23)/b16-10+,19-8-/t17-,18+/m0/s1
• InChI Key: WZMNIACHVDKCII-OGDMOPOQSA-N
• Popularity: 1 reference 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: 4.80
• Atomic LogP (AlogP): 4.88
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9867	98.67%
Caco-2	+	0.5461	54.61%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6518	65.18%
OATP2B1 inhibitior	-	0.8585	85.85%
OATP1B1 inhibitior	+	0.9286	92.86%
OATP1B3 inhibitior	+	0.9189	91.89%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6195	61.95%
BSEP inhibitior	+	0.6862	68.62%
P-glycoprotein inhibitior	-	0.8044	80.44%
P-glycoprotein substrate	-	0.7812	78.12%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.5528	55.28%
CYP2D6 substrate	-	0.9159	91.59%
CYP3A4 inhibition	-	0.6933	69.33%
CYP2C9 inhibition	-	0.7638	76.38%
CYP2C19 inhibition	-	0.8719	87.19%
CYP2D6 inhibition	-	0.8731	87.31%
CYP1A2 inhibition	-	0.7270	72.70%
CYP2C8 inhibition	-	0.6385	63.85%
CYP inhibitory promiscuity	-	0.8528	85.28%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8328	83.28%
Carcinogenicity (trinary)	Non-required	0.6797	67.97%
Eye corrosion	-	0.8621	86.21%
Eye irritation	-	0.5000	50.00%
Skin irritation	-	0.7945	79.45%
Skin corrosion	-	0.9807	98.07%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5334	53.34%
Micronuclear	-	0.9500	95.00%
Hepatotoxicity	-	0.5191	51.91%
skin sensitisation	+	0.5491	54.91%
Respiratory toxicity	-	0.7111	71.11%
Reproductive toxicity	-	0.7556	75.56%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	+	0.4714	47.14%
Acute Oral Toxicity (c)	III	0.5201	52.01%
Estrogen receptor binding	-	0.6153	61.53%
Androgen receptor binding	-	0.7247	72.47%
Thyroid receptor binding	+	0.5177	51.77%
Glucocorticoid receptor binding	-	0.4688	46.88%
Aromatase binding	-	0.6716	67.16%
PPAR gamma	+	0.5451	54.51%
Honey bee toxicity	-	0.9217	92.17%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	+	0.9952	99.52%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.39%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.55%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.82%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.40%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.55%	95.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.08%	93.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.57%	97.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.40%	93.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.97%	96.61%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.23%	93.04%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.80%	96.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.66%	95.50%

Plants that contains it

• Cleome viscosa

Cross-Links

• PubChem: 162931457
• LOTUS: LTS0229654
• wikiData: Q105323327