Bilobol

Details

• Internal ID: 0f7c209f-9f90-42eb-8400-2837ba78d4a2
• Taxonomy: Benzenoids > Phenols > Benzenediols > Resorcinols
• IUPAC Name: 5-[(Z)-pentadec-8-enyl]benzene-1,3-diol
• SMILES (Canonical): CCCCCCC=CCCCCCCCC1=CC(=CC(=C1)O)O
• SMILES (Isomeric): CCCCCC/C=C\CCCCCCCC1=CC(=CC(=C1)O)O
• InChI: InChI=1S/C21H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-16-20(22)18-21(23)17-19/h7-8,16-18,22-23H,2-6,9-15H2,1H3/b8-7-
• InChI Key: TUGAUFMQYWZJAB-FPLPWBNLSA-N
• Popularity: 13 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₄O₂
• Molecular Weight: 318.50 g/mol
• Exact Mass: 318.255880323 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 8.10
• Atomic LogP (AlogP): 6.51
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 13

Synonyms

• 22910-86-7
• Cardol monoene
• Trifurcatol A2
• 5-[(8Z)-pentadec-8-enyl]resorcinol
• 5-[(8Z)-pentadec-8-en-1-yl]benzene-1,3-diol
• 5-[(Z)-pentadec-8-enyl]benzene-1,3-diol
• 5-(8Z-Pentadecenyl)resorcinol
• CHEBI:3104
• CHEMBL461628
• 5-{8(Z),-pentadecenyl}resorcinol
• 1,3-Benzenediol, 5-(8Z)-8-pentadecenyl-
• (Z)-5-(Pentadec-8-en-1-yl)benzene-1,3-diol
• 1,3-Benzenediol, 5-(8-pentadecenyl)-, (Z)-
• 5-pentadec-8-enylbenzene-1,3-diol
• 5-(8-Pentadecenyl)-1,3-benzenediol
• Bilobol C15:1
• Cardol C15:1
• D0OE5N
• 21:1-.omega.7-Cardol
• SCHEMBL164545
• 5-(8'Z-heptadecenyl)resorcinol
• DTXSID90872874
• cis-5-Pentadec-8'-enylresorcinol
• TUGAUFMQYWZJAB-FPLPWBNLSA-N
• 5-[8'(Z)-Pentadecenyl]Resorcinol
• cis-5-n-Pentadec-8'-enylresorcino
• 5-[(Z)-Pentadec-8-enyl]resorcinol
• BDBM50241751
• LMPK15030001
• 5-[(Z)-pentadec-8-enylo]resorcinol
• AKOS040735273
• 5-(8Z)-8-Pentadecenyl-1,3-benzenediol
• PD182474
• Resorcinol, 5-(8-pentadecenyl)-, (Z)-
• 1,3-Benzenediol, 5-[(8Z)-8-pentadecen-1-yl]-
• Q4913564

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9906	99.06%
Caco-2	+	0.6591	65.91%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5227	52.27%
OATP2B1 inhibitior	-	0.8555	85.55%
OATP1B1 inhibitior	+	0.7039	70.39%
OATP1B3 inhibitior	+	0.9451	94.51%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8838	88.38%
BSEP inhibitior	+	0.5967	59.67%
P-glycoprotein inhibitior	-	0.6700	67.00%
P-glycoprotein substrate	-	0.8264	82.64%
CYP3A4 substrate	-	0.5700	57.00%
CYP2C9 substrate	-	0.7928	79.28%
CYP2D6 substrate	+	0.3567	35.67%
CYP3A4 inhibition	+	0.8505	85.05%
CYP2C9 inhibition	-	0.5926	59.26%
CYP2C19 inhibition	+	0.5358	53.58%
CYP2D6 inhibition	-	0.7401	74.01%
CYP1A2 inhibition	+	0.7543	75.43%
CYP2C8 inhibition	+	0.5703	57.03%
CYP inhibitory promiscuity	+	0.8169	81.69%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7411	74.11%
Carcinogenicity (trinary)	Non-required	0.6401	64.01%
Eye corrosion	+	0.4493	44.93%
Eye irritation	+	0.6236	62.36%
Skin irritation	+	0.7645	76.45%
Skin corrosion	+	0.6007	60.07%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8765	87.65%
Micronuclear	-	0.9500	95.00%
Hepatotoxicity	-	0.6589	65.89%
skin sensitisation	+	0.8229	82.29%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	-	0.5491	54.91%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	-	0.7027	70.27%
Acute Oral Toxicity (c)	III	0.7916	79.16%
Estrogen receptor binding	+	0.8665	86.65%
Androgen receptor binding	+	0.6247	62.47%
Thyroid receptor binding	+	0.7045	70.45%
Glucocorticoid receptor binding	+	0.5567	55.67%
Aromatase binding	-	0.4891	48.91%
PPAR gamma	+	0.9098	90.98%
Honey bee toxicity	-	0.9886	98.86%
Biodegradation	+	0.7000	70.00%
Crustacea aquatic toxicity	+	0.8737	87.37%
Fish aquatic toxicity	+	0.9895	98.95%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	97.81%	92.08%
CHEMBL2581	P07339	Cathepsin D	97.48%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.90%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.67%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.98%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	88.43%	94.73%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	87.15%	97.29%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.58%	86.33%
CHEMBL230	P35354	Cyclooxygenase-2	86.36%	89.63%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	85.90%	100.00%
CHEMBL240	Q12809	HERG	85.02%	89.76%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.97%	96.95%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	83.88%	92.86%
CHEMBL1781	P11387	DNA topoisomerase I	83.71%	97.00%
CHEMBL242	Q92731	Estrogen receptor beta	80.45%	98.35%

Plants that contains it

• Anacardium occidentale
• Ardisia brevicaulis
• Ardisia gigantifolia
• Aronia arbutifolia
• Clibadium sodiroi
• Discaria serratifolia
• Embelia ribes
• Ginkgo biloba
• Grevillea robusta
• Hakea trifurcata
• Ononis speciosa
• Pteris dactylina
• Pyrostegia venusta
• Rostellularia hayatae
• Silene viscaria

Cross-Links

• PubChem: 5281852
• NPASS: NPC94351
• ChEMBL: CHEMBL461628
• LOTUS: LTS0050977
• wikiData: Q4913564