NP-MRD: Showing NP-Card for Behenyl Alcohol (NP0331734)

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Record Information

Version

1.0

Created at

2023-07-28 20:08:16 UTC

Updated at

2024-04-19 09:49:53 UTC

NP-MRD ID

NP0331734

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Behenyl Alcohol

Description

Docosanol, also known as abreva or behenic alcohol, belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Thus, docosanol is considered to be a fatty alcohol lipid molecule. A long-chain primary fatty alcohol that is docosane substituted by a hydroxy group at position 1. Docosanol is a drug which is used for the topical treatment of recurrent oral-facial herpes simplex episodes (cold sores or fever blisters). Docosanol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Docosanol has been detected, but not quantified in, ginkgo nuts and potato. It was first documented in 2000 (PMID: 11413487). This could make docosanol a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567) (PMID: 12367721).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309272007392D          

 23 22  0  0  0  0            999 V2000
10010.998210011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.713910010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.428710011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.143710010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.858510011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.573210010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.288010011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.003010010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.717810011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.432410010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.147210011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.862010010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.282610010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.567010011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.853510010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.137910011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.422310010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.708810011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.993310010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.279710011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.564110010.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.848510011.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.135010010.8176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331734

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCCCCCCCO

> <INCHI_IDENTIFIER>
InChI=1S/C22H46O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23/h23H,2-22H2,1H3

> <INCHI_KEY>
NOPFSRXAKWQILS-UHFFFAOYSA-N

> <FORMULA>
C22H46O

> <MOLECULAR_WEIGHT>
326.6

> <EXACT_MASS>
326.354866094

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
47.2711929228291

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
docosan-1-ol

> <ALOGPS_LOGP>
9.31

> <JCHEM_LOGP>
8.807557916

> <ALOGPS_LOGS>
-7.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.84394282199214

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9922594096606376

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
104.95289999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.96e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
docosanol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8687.1978687.628   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8688.5338686.859   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8689.8678687.628   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8691.2028686.859   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8692.5368687.628   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8693.8708686.859   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8695.2048687.628   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8696.5398686.859   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8697.8738687.628   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8699.2078686.859   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8700.5418687.628   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8701.8768686.859   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8685.8618686.859   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8684.5258687.628   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8683.1938686.859   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8681.8578687.628   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8680.5228686.859   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8679.1908687.628   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8677.8548686.859   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8676.5228687.628   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8675.1868686.859   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8673.8518687.628   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    8672.5198686.859   0.000  0.00  0.00           O+0
CONECT    1    2   13                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    1   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

View in JSmol

Synonyms

Value	Source
1-Docosanol	ChEBI
Abreva	ChEBI
Behenic alcohol	ChEBI
Behenyl alcohol	ChEBI
Docosyl alcohol	ChEBI
N-Docosanol	ChEBI
Tadenan	ChEBI
IK.2	HMDB
Docosanol	ChEBI
1-Docosonol	PhytoBank

Chemical Formula

C₂₂H₄₆O

Average Mass

326.6000 Da

Monoisotopic Mass

326.35487 Da

IUPAC Name

docosan-1-ol

Traditional Name

docosanol

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCCCCCCO

InChI Identifier

InChI=1S/C22H46O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23/h23H,2-22H2,1H3

InChI Key

NOPFSRXAKWQILS-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Not Available	Not Available	2023-07-28	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Not Available	Not Available	2023-07-28	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Fatty alcohols

Alternative Parents

Substituents

Fatty alcohol
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain primary fatty alcohol (CHEBI:31000 )
fatty alcohol 22:0 (CHEBI:31000 )
Fatty alcohols (LMFA05000008 )
a long-chain alcohol (CPD-7845 )
a primary alcohol (CPD-7845 )
a fatty alcohol (CPD-7845 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	9.31	ALOGPS
logP	8.81	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Acidic)	16.84	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	104.95 m³·mol⁻¹	ChemAxon
Polarizability	47.27 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0014770

DrugBank ID

DB00632

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB007105

KNApSAcK ID

C00030805

Chemspider ID

12100

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Docosanol

METLIN ID

Not Available

PubChem Compound

12620

PDB ID

Not Available

ChEBI ID

31000

Good Scents ID

Not Available

References

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Marcelletti JF: Synergistic inhibition of herpesvirus replication by docosanol and antiviral nucleoside analogs. Antiviral Res. 2002 Nov;56(2):153-66. doi: 10.1016/s0166-3542(02)00105-5. [PubMed:12367721 ]

Showing NP-Card for Behenyl Alcohol (NP0331734)

MOL for NP0331734 (Behenyl Alcohol)

3D MOL for NP0331734 (Behenyl Alcohol)

3D SDF for NP0331734 (Behenyl Alcohol)

3D-SDF for NP0331734 (Behenyl Alcohol)

PDB for NP0331734 (Behenyl Alcohol)

3D PDB for NP0331734 (Behenyl Alcohol)

SMILES for NP0331734 (Behenyl Alcohol)

INCHI for NP0331734 (Behenyl Alcohol)

Structure for NP0331734 (Behenyl Alcohol)

3D Structure for NP0331734 (Behenyl Alcohol)