(+)-Centrolobol

Details

• Internal ID: 1eaac249-517b-41dd-967d-8232bf85b772
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: 4-[(5S)-5-hydroxy-7-(4-hydroxyphenyl)heptyl]phenol
• SMILES (Canonical): C1=CC(=CC=C1CCCCC(CCC2=CC=C(C=C2)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1CCCC[C@@H](CCC2=CC=C(C=C2)O)O)O
• InChI: InChI=1S/C19H24O3/c20-17(10-7-16-8-13-19(22)14-9-16)4-2-1-3-15-5-11-18(21)12-6-15/h5-6,8-9,11-14,17,20-22H,1-4,7,10H2/t17-/m0/s1
• InChI Key: UYJAYWZGEZOHRU-KRWDZBQOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₃
• Molecular Weight: 300.40 g/mol
• Exact Mass: 300.17254462 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 3.80
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

• DTXSID60873813
• 30359-04-7

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9888	98.88%
Caco-2	-	0.5494	54.94%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.9238	92.38%
OATP2B1 inhibitior	-	0.8607	86.07%
OATP1B1 inhibitior	+	0.9162	91.62%
OATP1B3 inhibitior	+	0.8950	89.50%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5584	55.84%
P-glycoprotein inhibitior	-	0.7481	74.81%
P-glycoprotein substrate	-	0.6476	64.76%
CYP3A4 substrate	-	0.5954	59.54%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	+	0.4565	45.65%
CYP3A4 inhibition	-	0.7373	73.73%
CYP2C9 inhibition	-	0.7636	76.36%
CYP2C19 inhibition	+	0.5145	51.45%
CYP2D6 inhibition	-	0.9245	92.45%
CYP1A2 inhibition	-	0.7881	78.81%
CYP2C8 inhibition	-	0.6651	66.51%
CYP inhibitory promiscuity	-	0.6513	65.13%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7811	78.11%
Carcinogenicity (trinary)	Non-required	0.5975	59.75%
Eye corrosion	-	0.9728	97.28%
Eye irritation	+	0.6378	63.78%
Skin irritation	-	0.6427	64.27%
Skin corrosion	-	0.9091	90.91%
Ames mutagenesis	-	0.8670	86.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7061	70.61%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.6047	60.47%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	-	0.5386	53.86%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.6987	69.87%
Acute Oral Toxicity (c)	III	0.7495	74.95%
Estrogen receptor binding	+	0.8941	89.41%
Androgen receptor binding	+	0.8466	84.66%
Thyroid receptor binding	+	0.5897	58.97%
Glucocorticoid receptor binding	-	0.5194	51.94%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.8024	80.24%
Honey bee toxicity	-	0.8871	88.71%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9251	92.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.60%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.21%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.40%	91.11%
CHEMBL242	Q92731	Estrogen receptor beta	91.23%	98.35%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.98%	94.45%
CHEMBL5939	Q9NZ08	Endoplasmic reticulum aminopeptidase 1	86.96%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.48%	99.17%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	83.99%	94.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.65%	95.89%
CHEMBL233	P35372	Mu opioid receptor	82.21%	97.93%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.28%	100.00%

Plants that contains it

• Centrolobium paraense
• Centrolobium tomentosum

Cross-Links

• PubChem: 14427393
• LOTUS: LTS0229434
• wikiData: Q81981271