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Vanillin

Odors

Receptor Interaction

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2D Structure
3D Conformer
image of chemical
 

Odor Profile

Strength: medium
Evidences:

11487625

Kajiya K, Inaki K, Tanaka M, Haga T, Kataoka H, Touhara K. Molecular bases of odor discrimination: Reconstitution of olfactory receptors that recognize overlapping sets of odorants. J Neurosci. 2001 Aug 15;21(16):6018-25. doi: 10.1523/JNEUROSCI.21-16-06018.2001

15741602

Matarazzo V, Clot-Faybesse O, Marcet B, Guiraudie-Capraz G, Atanasova B, Devauchelle G, Cerutti M, Etiévant P, Ronin C. Functional characterization of two human olfactory receptors expressed in the baculovirus Sf9 insect cell system. Chem Senses. 2005 Mar;30(3):195-207. doi: 10.1093/chemse/bji015.

17873857

Keller A, Zhuang H, Chi Q, Vosshall LB, Matsunami H. Genetic variation in a human odorant receptor alters odour perception. Nature. 2007 Sep 27;449(7161):468-72. doi: 10.1038/nature06162. 

25784876

Gonzalez-Kristeller DC, do Nascimento JB, Galante PA, Malnic B. Identification of agonists for a group of human odorant receptors. Front Pharmacol. 2015 Mar 3;6:35. doi: 10.3389/fphar.2015.00035.

25977809

Mainland JD, Li YR, Zhou T, Liu WL, Matsunami H. Human olfactory receptor responses to odorants. Sci Data. 2015 Feb 3;2:150002. doi: 10.1038/sdata.2015.2.

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Modena D, Trentini M, Corsini M, Bombaci A, Giorgetti A. OlfactionDB: A Database of Olfactory Receptors and Their Ligands. Adv. In Life Sci. 2011, 1:1-5. doi: 10.5923/j.als.20110101.01

General Information

Common Name: Vanillin
IUPAC Name: 4-hydroxy-3-methoxybenzaldehyde
Molecular Formula: C8H8O3
SMILES: COC1=C(C=CC(=C1)C=O)O
Inchi: 1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
Inchi Key: MWOOGOJBHIARFG-UHFFFAOYSA-N
Cas No: 121-33-5

Functional Group

Aldehydes
Esters
Ethers
Phenol

Drug Likeness

Name Value
Lipinski Violations 0
Ghose Violations 2
Veber Violations 0
Egan Violations 0
Muegge Violations 1

Cross References

PubChem: 1183
Zinc: ZINC2567933
OdoRactor: View
TGSC: View

Physicochemical properties

Name Value
Molecular Weight (g/mol) 152.15
Mass (g/mol) 152.047
Molar Refractivity 40.34
Net Charge -1
HBD 1
HBA 3
Rt Bonds 2
Rings 1
TPSA 46.53
Hetero Atoms 3
Heavy Atoms 11
Aromatic Heavy Atoms 6
Melting Point (°C) 81.00 to 84.00
Boiling Point (°C@760.00mm Hg) 285.00 to 286.00
Vapor Pressure (mmHg@25.00 °C) 0.002
Vapor Density (Air =1) 5.3
Fraction Csp3 0.12
LogP 1.213
iLOGP 1.57
XLOGP3 1.21
WLOGP 1.21
MLOGP 0.51
ESOL Log S -1.82
ESOL Solubility (mg/ml) 2.32
ESOL Solubility (mol/l) 0.015
ESOL Class: esol_class Very soluble
Ali Log S -1.78
Ali Solubility (mg/ml) 2.5
Ali Solubility (mol/l) 0.02
Ali Class Very soluble
Silicos-IT LogSw -1.88
Silicos-IT Solubility (mg/ml) 2
Silicos-IT Solubility (mol/l) 0.01
Silicos-IT Class Soluble

Pharmacokinetic profile

Name Value
GI Absorption High
BBB Permeable 1
PgP Substrate 0
Log Kp (cm/s) -6.37
Bioavailability Score 0.55
Caco2 1
Human Intestinal Absorption 1
Plasm Protein Binding 0.829
CYP1A2 Inhibitor 0
CYP2C19 Inhibitor 0
CYP2C9 Inhibitor 0
CYP2D6 inhibitor 0
CYP3A4 inhibitor 0
Ames mutagenesis 0
Acute Oral Toxicity 1.537
Carcinogenicity (Binary) 0
Carcinogenicity (Trinary) Non-required
Eye Irritation 1
Hepatotoxicity 0
Androgen Receptor Binding 0
Aromatase Binding 0
Estrogen Receptor Binding 0
Glucocorticoid Receptor Binding 0
Thyroid Receptor Binding 0
BRCP inhibitor 1
BSEP inhibitor 0
OATP1B1 inhibitor 1
OATP1B3 inhibitor 1
OATP2B1 inhibitor 0
OCT1 inhibitor 0
OCT2 inhibitor 0