(1Z,5E,8R,11Z)-11-(hydroxymethyl)-8-(3-hydroxyprop-1-en-2-yl)-5-methylcyclotetradeca-1,5,11-triene-1-carboxylic acid

Details

• Internal ID: 2d52c0e8-9342-48b7-85a7-a7fbeec61f60
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Cembrane diterpenoids
• IUPAC Name: (1Z,5E,8R,11Z)-11-(hydroxymethyl)-8-(3-hydroxyprop-1-en-2-yl)-5-methylcyclotetradeca-1,5,11-triene-1-carboxylic acid
• SMILES (Canonical): CC1=CCC(CCC(=CCCC(=CCC1)C(=O)O)CO)C(=C)CO
• SMILES (Isomeric): C/C/1=C\C[C@@H](CC/C(=C/CC/C(=C/CC1)/C(=O)O)/CO)C(=C)CO
• InChI: InChI=1S/C20H30O4/c1-15-5-3-7-19(20(23)24)8-4-6-17(14-22)10-12-18(11-9-15)16(2)13-21/h6-7,9,18,21-22H,2-5,8,10-14H2,1H3,(H,23,24)/b15-9+,17-6-,19-7-/t18-/m0/s1
• InChI Key: KZZTXXNLURJVPT-JWRLUTJUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.40 g/mol
• Exact Mass: 334.21440943 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.77
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9516	95.16%
Caco-2	-	0.6211	62.11%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6530	65.30%
OATP2B1 inhibitior	-	0.8548	85.48%
OATP1B1 inhibitior	+	0.9278	92.78%
OATP1B3 inhibitior	+	0.9291	92.91%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6445	64.45%
BSEP inhibitior	+	0.5923	59.23%
P-glycoprotein inhibitior	-	0.7626	76.26%
P-glycoprotein substrate	-	0.8332	83.32%
CYP3A4 substrate	+	0.5349	53.49%
CYP2C9 substrate	-	0.5528	55.28%
CYP2D6 substrate	-	0.9159	91.59%
CYP3A4 inhibition	-	0.8568	85.68%
CYP2C9 inhibition	-	0.8255	82.55%
CYP2C19 inhibition	-	0.8468	84.68%
CYP2D6 inhibition	-	0.8862	88.62%
CYP1A2 inhibition	-	0.7641	76.41%
CYP2C8 inhibition	-	0.6069	60.69%
CYP inhibitory promiscuity	-	0.8994	89.94%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8228	82.28%
Carcinogenicity (trinary)	Non-required	0.6954	69.54%
Eye corrosion	-	0.8282	82.82%
Eye irritation	+	0.5600	56.00%
Skin irritation	-	0.7731	77.31%
Skin corrosion	-	0.9708	97.08%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4416	44.16%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.6365	63.65%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	-	0.8444	84.44%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	+	0.4548	45.48%
Acute Oral Toxicity (c)	III	0.4909	49.09%
Estrogen receptor binding	-	0.6189	61.89%
Androgen receptor binding	-	0.5281	52.81%
Thyroid receptor binding	-	0.5248	52.48%
Glucocorticoid receptor binding	-	0.5316	53.16%
Aromatase binding	-	0.6397	63.97%
PPAR gamma	+	0.6094	60.94%
Honey bee toxicity	-	0.9278	92.78%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9932	99.32%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	95.53%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.24%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.17%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.80%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.42%	95.56%
CHEMBL2581	P07339	Cathepsin D	86.88%	98.95%
CHEMBL4208	P20618	Proteasome component C5	85.89%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.70%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.58%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.43%	93.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.43%	97.09%

Plants that contains it

• Cleome viscosa

Cross-Links

• PubChem: 162935360
• LOTUS: LTS0164399
• wikiData: Q105148524