NP-MRD: Showing NP-Card for Nonacosan-10-ol (NP0050651)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 22:00:35 UTC

Updated at

2022-04-27 22:00:35 UTC

NP-MRD ID

NP0050651

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nonacosan-10-ol

Description

(S)-nonacosan-10-ol, also known as ginnol, belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms. Nonacosan-10-ol is found in Abies balsamea, Abies nordmanniana, Chamaecyparis pisifera, Chelidonium majus , Clematis vitalba, Cocculus hirsutus, Corydalis balansae, Corydalis pallida, Crataegus pinnatifida, Entodon luridus, Euphorbia ebracteolata, Ginkgo biloba , Juniperus chinensis, Juniperus pinchotii, Juniperus sabina, Juniperus scopulorum, Lonicera hypoleuca, Lophocolea heterophylla, Metasequoia glyptostroboides, Papaver bracteatum, Pinus koraiensis , Pinus nigra, Pinus pumila, Pinus radiata, Pinus sibirica, Pinus sylvestris, Platycladus orientalis, Senecio nemorensis, Spiraea formosana and Taxus baccata. Nonacosan-10-ol was first documented in 2007 (PMID: 17611192). Thus, (S)-nonacosan-10-ol is considered to be a fatty alcohol lipid molecule (s)-nonacosan-10-ol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 23576353) (PMID: 23495163) (PMID: 22700233) (PMID: 21886346).

Structure

MOL SDF PDB SMILES InChI

  Mrv1652309272006282D          

 30 29  0  0  0  0            999 V2000
10004.121510006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.405810006.7625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.690210006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.974610006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.258910006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.543310006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.829710006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.114110006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.400510006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.684910006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.969310006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.405810007.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.835010006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.550710006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.264210006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.979910006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.694710006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.409510006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.124510006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.839310006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.554010006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.268810006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.983810006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.698610006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.413410006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.128210006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.845110006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.560110006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.274910006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.989710006.3509    0.0000 C   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
  2 12  1  6  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
 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
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

  Mrv1652309272006282D          

 30 29  0  0  0  0            999 V2000
10004.121510006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.405810006.7625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.690210006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.974610006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.258910006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.543310006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.829710006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.114110006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.400510006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.684910006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.969310006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.405810007.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.835010006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.550710006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.264210006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.979910006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.694710006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.409510006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.124510006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.839310006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.554010006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.268810006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.983810006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.698610006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.413410006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.128210006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.845110006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.560110006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.274910006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.989710006.3509    0.0000 C   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
  2 12  1  6  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
 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
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050651

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCCCC[C@@H](O)CCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C29H60O/c1-3-5-7-9-11-12-13-14-15-16-17-18-19-20-22-24-26-28-29(30)27-25-23-21-10-8-6-4-2/h29-30H,3-28H2,1-2H3/t29-/m0/s1

> <INCHI_KEY>
CPGCVOVWHCWVTP-LJAQVGFWSA-N

> <FORMULA>
C29H60O

> <MOLECULAR_WEIGHT>
424.798

> <EXACT_MASS>
424.464416552

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
61.59261854861533

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(10S)-nonacosan-10-ol

> <ALOGPS_LOGP>
10.34

> <JCHEM_LOGP>
11.969498660666666

> <ALOGPS_LOGS>
-7.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.484172992642346

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2748227330182367

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
136.9007

> <JCHEM_ROTATABLE_BOND_COUNT>
26

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.16e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(S)-nonacosan-10-ol

> <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    8674.3608678.522   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8673.0248679.290   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8671.6888678.522   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8670.3538679.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8669.0178678.522   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8667.6818679.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8666.3498678.522   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.0138679.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8663.6818678.522   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.3458679.290   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8661.0098678.522   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8673.0248680.831   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8675.6928679.290   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8677.0288678.522   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8678.3608679.290   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8679.6968678.522   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8681.0308679.290   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8682.3648678.522   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8683.6998679.290   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8685.0338678.522   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8686.3688679.290   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8687.7028678.522   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8689.0378679.290   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8690.3718678.522   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8691.7058679.290   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8693.0398678.522   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8694.3788679.290   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8695.7128678.522   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8697.0478679.290   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8698.3818678.522   0.000  0.00  0.00           C+0
CONECT    1    2   13                                                       
CONECT    2    1    3   12                                                  
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                                                            
CONECT   12    2                                                            
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   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   58    0
END

View in JSmol

Synonyms

Value	Source
Ginnol	ChEBI
(±)-10-Nonacosanol	PhytoBank
Celidoniol	PhytoBank
(10S)-10-Nonacosanol	PhytoBank
(S)-(+)-Ginnol	PhytoBank
Nonacosan-10-ol	PhytoBank

Chemical Formula

C₂₉H₆₀O

Average Mass

424.7980 Da

Monoisotopic Mass

424.46442 Da

IUPAC Name

(10S)-nonacosan-10-ol

Traditional Name

(S)-nonacosan-10-ol

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCCC[C@@H](O)CCCCCCCCC

InChI Identifier

InChI=1S/C29H60O/c1-3-5-7-9-11-12-13-14-15-16-17-18-19-20-22-24-26-28-29(30)27-25-23-21-10-8-6-4-2/h29-30H,3-28H2,1-2H3/t29-/m0/s1

InChI Key

CPGCVOVWHCWVTP-LJAQVGFWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abies balsamea	LOTUS Database	35616633
Abies nordmanniana	LOTUS Database	35616633
Chamaecyparis pisifera	LOTUS Database	35616633
Chelidonium majus	Plant	KNApSAcK
Clematis vitalba	LOTUS Database	35616633
Cocculus hirsutus	LOTUS Database	35616633
Corydalis balansae	LOTUS Database	35616633
Corydalis pallida	LOTUS Database	35616633
Crataegus pinnatifida	LOTUS Database	35616633
Entodon luridus	LOTUS Database	35616633
Euphorbia ebracteolata	LOTUS Database	35616633
Ginkgo biloba	Plant	KNApSAcK
Juniperus chinensis	Plant	KNApSAcK
Juniperus pinchotii	LOTUS Database	35616633
Juniperus sabina	LOTUS Database	35616633
Juniperus scopulorum	LOTUS Database	35616633
Lonicera hypoleuca	LOTUS Database	35616633
Lophocolea heterophylla	LOTUS Database	35616633
Metasequoia glyptostroboides	LOTUS Database	35616633
Papaver bracteatum	LOTUS Database	35616633
Pinus koraiensis	Plant	KNApSAcK
Pinus nigra	LOTUS Database	35616633
Pinus pumila	LOTUS Database	35616633
Pinus radiata	LOTUS Database	35616633
Pinus sibirica	Plant	KNApSAcK
Pinus sylvestris	LOTUS Database	35616633
Platycladus orientalis	LOTUS Database	35616633
Senecio nemorensis	LOTUS Database	35616633
Spiraea formosana	LOTUS Database	35616633
Taxus baccata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Long-chain fatty alcohols

Alternative Parents

Substituents

Long chain fatty alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

nonacosan-10-ol (CHEBI:32948 )
Fatty alcohols (LMFA05000088 )

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	10.34	ALOGPS
logP	11.97	ChemAxon
logS	-7.6	ALOGPS
pKa (Strongest Acidic)	18.48	ChemAxon
pKa (Strongest Basic)	-1.3	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	26	ChemAxon
Refractivity	136.9 m³·mol⁻¹	ChemAxon
Polarizability	61.59 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001261

Chemspider ID

303871

KEGG Compound ID

C08385

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16057860

PDB ID

Not Available

ChEBI ID

32948

Good Scents ID

Not Available

References

General References

Nikolic B, Tesevic V, Bojovic S, Marin PD: Chemotaxonomic implications of the n-alkane composition and the nonacosan-10-ol content in Picea omorika, Pinus heldreichii, and Pinus peuce. Chem Biodivers. 2013 Apr;10(4):677-86. doi: 10.1002/cbdv.201200353. [PubMed:23576353 ]
Nikolic B, Tesevic V, Ethordevic I, Todosijevic M, Jadranin M, Bojovic S, Marin PD: Variability of n-alkanes and nonacosan-10-ol in natural populations of Picea omorika. Chem Biodivers. 2013 Mar;10(3):473-83. doi: 10.1002/cbdv.201200271. [PubMed:23495163 ]
Nikolic B, Tesevic V, Dordevic I, Todosijevic M, Jadranin M, Bojovic S, Marin PD: Population variability of nonacosan-10-ol and n-alkanes in needle cuticular waxes of Macedonian pine (Pinus peuce GRISEB.). Chem Biodivers. 2012 Jun;9(6):1155-65. doi: 10.1002/cbdv.201100316. [PubMed:22700233 ]
Coward JL: FTIR spectroscopy of synthesized racemic nonacosan-10-ol: a model compound for plant epicuticular waxes. J Biol Phys. 2010 Sep;36(4):405-25. doi: 10.1007/s10867-010-9192-6. Epub 2010 Aug 5. [PubMed:21886346 ]
Dragota S, Riederer M: Epicuticular wax crystals of Wollemia nobilis: morphology and chemical composition. Ann Bot. 2007 Aug;100(2):225-31. doi: 10.1093/aob/mcm120. Epub 2007 Jul 3. [PubMed:17611192 ]

Showing NP-Card for Nonacosan-10-ol (NP0050651)

MOL for NP0050651 (Nonacosan-10-ol)

3D MOL for NP0050651 (Nonacosan-10-ol)

3D SDF for NP0050651 (Nonacosan-10-ol)

3D-SDF for NP0050651 (Nonacosan-10-ol)

PDB for NP0050651 (Nonacosan-10-ol)

3D PDB for NP0050651 (Nonacosan-10-ol)

SMILES for NP0050651 (Nonacosan-10-ol)

INCHI for NP0050651 (Nonacosan-10-ol)

Structure for NP0050651 (Nonacosan-10-ol)

3D Structure for NP0050651 (Nonacosan-10-ol)