OlfactionBase: A repository of Odors, Odorants, Olfactory Receptors and related information
  1. Home
  2. Odorants

Aurantiol

Odors

Receptor Interaction

Image
2D Structure
3D Conformer
image of chemical
 

Odor Profile

Strength: medium
Evidences:

17601748

Schmiedeberg K, Shirokova E, Weber HP, Schilling B, Meyerhof W, Krautwurst D. Structural determinants of odorant recognition by the human olfactory receptors OR1A1 and OR1A2. J Struct Biol. 2007 Sep;159(3):400-12. doi: 10.1016/j.jsb.2007.04.013.

19261596

Saito H, Chi Q, Zhuang H, Matsunami H, Mainland JD. Odor coding by a Mammalian receptor repertoire. Sci Signal. 2009 Mar 3;2(60):ra9. doi: 10.1126/scisignal.2000016.

General Information

Common Name: Aurantiol
IUPAC Name: methyl 2-[(7-hydroxy-3,7-dimethyloctylidene)amino]benzoate
Molecular Formula: C18H27NO3
SMILES: CC(CCCC(C)(C)O)CC=NC1=CC=CC=C1C(=O)OC
Inchi: 1S/C18H27NO3/c1-14(8-7-12-18(2,3)21)11-13-19-16-10-6-5-9-15(16)17(20)22-4/h5-6,9-10,13-14,21H,7-8,11-12H2,1-4H3
Inchi Key: BFBPISPWJZMWJN-UHFFFAOYSA-N
Cas No: 89-43-0

Functional Group

Alcohols
Amines
Esters

Drug Likeness

Name Value
Lipinski Violations 0
Ghose Violations 0
Veber Violations 0
Egan Violations 0
Muegge Violations 0

Cross References

PubChem: 98118
Zinc: ZINC17353434
OdoRactor: View
TGSC: View

Physicochemical properties

Name Value
Molecular Weight (g/mol) 305.41
Mass (g/mol) 305.199
Molar Refractivity 91.39
Net Charge
HBD 1
HBA 4
Rt Bonds 9
Rings 1
TPSA 58.89
Hetero Atoms 4
Heavy Atoms 22
Aromatic Heavy Atoms 6
Melting Point (°C)
Boiling Point (°C@760.00mm Hg) 162.00 @ 101.00 mm Hg
Vapor Pressure (mmHg@25.00 °C) 0.004
Vapor Density (Air =1)
Fraction Csp3 0.56
LogP 4.143
iLOGP 3.66
XLOGP3 3.33
WLOGP 4.14
MLOGP 3.10
ESOL Log S -3.44
ESOL Solubility (mg/ml) 0.111
ESOL Solubility (mol/l) 0
ESOL Class: esol_class Soluble
Ali Log S -4.24
Ali Solubility (mg/ml) 0.02
Ali Solubility (mol/l) 0
Ali Class Moderately soluble
Silicos-IT LogSw -4.86
Silicos-IT Solubility (mg/ml) 0
Silicos-IT Solubility (mol/l) 0
Silicos-IT Class Moderately soluble

Pharmacokinetic profile

Name Value
GI Absorption High
BBB Permeable 1
PgP Substrate 0
Log Kp (cm/s) -5.80
Bioavailability Score 0.55
Caco2 1
Human Intestinal Absorption 1
Plasm Protein Binding 1.059
CYP1A2 Inhibitor 0
CYP2C19 Inhibitor 0
CYP2C9 Inhibitor 0
CYP2D6 inhibitor 1
CYP3A4 inhibitor 1
Ames mutagenesis 0
Acute Oral Toxicity 2.357
Carcinogenicity (Binary) 0
Carcinogenicity (Trinary) Non-required
Eye Irritation 0
Hepatotoxicity 0
Androgen Receptor Binding 0
Aromatase Binding 1
Estrogen Receptor Binding 1
Glucocorticoid Receptor Binding 1
Thyroid Receptor Binding 1
BRCP inhibitor 0
BSEP inhibitor 1
OATP1B1 inhibitor 1
OATP1B3 inhibitor 1
OATP2B1 inhibitor 0
OCT1 inhibitor 0
OCT2 inhibitor 0