NP-MRD: Showing NP-Card for n-[(3r,4e)-1,3-dihydroxyoctadec-4-en-2-yl]octanimidic acid (NP0178134)

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Record Information

Version

2.0

Created at

2022-09-03 16:04:31 UTC

Updated at

2022-09-03 16:04:31 UTC

NP-MRD ID

NP0178134

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[(3r,4e)-1,3-dihydroxyoctadec-4-en-2-yl]octanimidic acid

Description

OCTANOIC ACID (2-HYDROXY-1-HYDROXYMETHYL-HEPTADEC-3-ENYL)-AMIDE, also known as octanoate (2-hydroxy-1-hydroxymethyl-heptadec-3-enyl)-amide, belongs to the class of organic compounds known as ceramides. These are lipid molecules containing a sphingosine in which the amine group is linked to a fatty acid. n-[(3r,4e)-1,3-dihydroxyoctadec-4-en-2-yl]octanimidic acid is found in Glycine max, Lignincola laevis and Sarcophyton ehrenbergi. Based on a literature review very few articles have been published on OCTANOIC ACID (2-HYDROXY-1-HYDROXYMETHYL-HEPTADEC-3-ENYL)-AMIDE.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032218042D          

 30 29  0  0  1  0            999 V2000
    4.7586    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9020    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6164    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3309    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0454    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7599    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1888    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9033    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6177    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3322    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0467    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.4756    3.9849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.4756    4.8099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1901    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1901    2.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9046    2.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9046    3.9849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6190    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 27 28  1  0  0  0  0
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 29 30  1  0  0  0  0
M  END

     RDKit          3D

 81 80  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309032218042D          

 30 29  0  0  1  0            999 V2000
    4.7586    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0178134

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCC\C=C\[C@@H](O)C(CO)N=C(O)CCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C26H51NO3/c1-3-5-7-9-10-11-12-13-14-15-16-18-19-21-25(29)24(23-28)27-26(30)22-20-17-8-6-4-2/h19,21,24-25,28-29H,3-18,20,22-23H2,1-2H3,(H,27,30)/b21-19+/t24?,25-/m1/s1

> <INCHI_KEY>
APDLCSPGWPLYEQ-KRUWYHBYSA-N

> <FORMULA>
C26H51NO3

> <MOLECULAR_WEIGHT>
425.698

> <EXACT_MASS>
425.386894506

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
55.15581953930831

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]octanimidic acid

> <JCHEM_LOGP>
8.128409950666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.105440798566196

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.241653636240495

> <JCHEM_PKA_STRONGEST_BASIC>
3.166163503901356

> <JCHEM_POLAR_SURFACE_AREA>
73.05

> <JCHEM_REFRACTIVITY>
129.4894

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
N-[(3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]octanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       8.883   6.668   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.216   7.438   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.884   7.438   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.217   6.668   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.551   7.438   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.885   6.668   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.218   7.438   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.552   6.668   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.886   7.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.219   6.668   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.553   7.438   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.887   6.668   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.220   7.438   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.554   6.668   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.888   7.438   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      28.888   8.978   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      30.222   6.668   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.222   5.128   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      31.555   4.358   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0      31.555   7.438   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      32.889   6.668   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      32.889   5.128   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      34.223   7.438   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      35.556   6.668   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      36.890   7.438   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      38.224   6.668   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      39.557   7.438   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      40.891   6.668   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      42.225   7.438   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
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   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   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
OCTANOate (2-hydroxy-1-hydroxymethyl-heptadec-3-enyl)-amide	Generator

Chemical Formula

C₂₆H₅₁NO₃

Average Mass

425.6980 Da

Monoisotopic Mass

425.38689 Da

IUPAC Name

N-[(3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]octanimidic acid

Traditional Name

N-[(3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]octanimidic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCC\C=C\[C@@H](O)C(CO)N=C(O)CCCCCCC

InChI Identifier

InChI=1S/C26H51NO3/c1-3-5-7-9-10-11-12-13-14-15-16-18-19-21-25(29)24(23-28)27-26(30)22-20-17-8-6-4-2/h19,21,24-25,28-29H,3-18,20,22-23H2,1-2H3,(H,27,30)/b21-19+/t24?,25-/m1/s1

InChI Key

APDLCSPGWPLYEQ-KRUWYHBYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Glycine max	LOTUS Database	35616633
Lignincola laevis	LOTUS Database	35616633
Sarcophyton ehrenbergi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ceramides. These are lipid molecules containing a sphingosine in which the amine group is linked to a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Ceramides

Direct Parent

Ceramides

Alternative Parents

Substituents

Ceramide
Fatty amide
N-acyl-amine
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organic nitrogen compound
Carbonyl group
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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	8.13	ChemAxon
pKa (Strongest Acidic)	6.24	ChemAxon
pKa (Strongest Basic)	3.17	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	73.05 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	129.49 m³·mol⁻¹	ChemAxon
Polarizability	55.16 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

Not Available

Chemspider ID

4451374

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5289390

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-[(3r,4e)-1,3-dihydroxyoctadec-4-en-2-yl]octanimidic acid (NP0178134)

MOL for NP0178134 (n-[(3r,4e)-1,3-dihydroxyoctadec-4-en-2-yl]octanimidic acid)

3D MOL for NP0178134 (n-[(3r,4e)-1,3-dihydroxyoctadec-4-en-2-yl]octanimidic acid)

3D SDF for NP0178134 (n-[(3r,4e)-1,3-dihydroxyoctadec-4-en-2-yl]octanimidic acid)

3D-SDF for NP0178134 (n-[(3r,4e)-1,3-dihydroxyoctadec-4-en-2-yl]octanimidic acid)

PDB for NP0178134 (n-[(3r,4e)-1,3-dihydroxyoctadec-4-en-2-yl]octanimidic acid)

3D PDB for NP0178134 (n-[(3r,4e)-1,3-dihydroxyoctadec-4-en-2-yl]octanimidic acid)

SMILES for NP0178134 (n-[(3r,4e)-1,3-dihydroxyoctadec-4-en-2-yl]octanimidic acid)

INCHI for NP0178134 (n-[(3r,4e)-1,3-dihydroxyoctadec-4-en-2-yl]octanimidic acid)

Structure for NP0178134 (n-[(3r,4e)-1,3-dihydroxyoctadec-4-en-2-yl]octanimidic acid)

3D Structure for NP0178134 (n-[(3r,4e)-1,3-dihydroxyoctadec-4-en-2-yl]octanimidic acid)