NP-MRD: Showing NP-Card for n-(1,3,4-trihydroxyoctadecan-2-yl)hexadecanimidic acid (NP0265763)

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Record Information

Version

2.0

Created at

2022-09-08 09:51:45 UTC

Updated at

2022-09-08 09:51:45 UTC

NP-MRD ID

NP0265763

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-(1,3,4-trihydroxyoctadecan-2-yl)hexadecanimidic acid

Description

Armillaramide belongs to the class of organic compounds known as phytoceramides. These are n-acylated 4-hydroxysphinganine. Armillaramide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Armillaramide has been detected, but not quantified in, mushrooms. n-(1,3,4-trihydroxyoctadecan-2-yl)hexadecanimidic acid is found in Daldinia concentrica. This could make armillaramide a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241209502D          

 39 38  0  0  0  0            999 V2000
   -6.3326   -0.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6179   -0.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv0541 02241209502D          

 39 38  0  0  0  0            999 V2000
   -6.3326   -0.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6179   -0.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9031   -0.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1885   -0.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4737   -0.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7591   -0.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0444   -0.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3296   -0.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6150   -0.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0996   -0.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8142   -0.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5290   -0.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2437   -0.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9584   -0.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6731   -0.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3878   -0.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1025   -0.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8173   -0.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6042   -1.6520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1025    0.3822    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3878   -1.6795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6731    0.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5148    1.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9321    1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2188    1.2685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5054    1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7922    1.2685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0787    1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3655    1.2685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6522    1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0611    1.2685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7743    1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4877    1.2685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2010    1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9143    1.2685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6276    1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3410    1.2685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0544    1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3326    1.2039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
 12 13  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
 15 22  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 19  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 39  2  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
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0265763

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCC(=O)NC(CO)C(O)C(O)CCCCCCCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C34H69NO4/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(38)35-31(30-36)34(39)32(37)28-26-24-22-20-18-16-14-12-10-8-6-4-2/h31-32,34,36-37,39H,3-30H2,1-2H3,(H,35,38)

> <INCHI_KEY>
IVBULNXGVIHEKN-UHFFFAOYSA-N

> <FORMULA>
C34H69NO4

> <MOLECULAR_WEIGHT>
555.916

> <EXACT_MASS>
555.522659701

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
74.05936459181606

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(1,3,4-trihydroxyoctadecan-2-yl)hexadecanamide

> <ALOGPS_LOGP>
8.76

> <JCHEM_LOGP>
9.996465733333334

> <ALOGPS_LOGS>
-6.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.4413560488785

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.262014760738879

> <JCHEM_PKA_STRONGEST_BASIC>
0.02944992997796647

> <JCHEM_POLAR_SURFACE_AREA>
89.78999999999999

> <JCHEM_REFRACTIVITY>
166.17459999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
31

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.29e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(1,3,4-trihydroxyoctadecan-2-yl)hexadecanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0     -11.821  -0.826   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.487  -1.596   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.153  -0.826   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.819  -1.596   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.484  -0.826   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.150  -1.596   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.816  -0.826   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.482  -1.596   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.148  -0.826   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.186  -1.596   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.520  -0.826   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.854  -1.596   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.188  -0.826   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.522  -1.596   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.856  -0.826   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.191  -1.596   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.525  -0.826   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.859  -1.596   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.461  -3.084   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0       9.525   0.713   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       8.191  -3.135   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.856   0.713   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.294   2.047   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.207   3.135   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.875   2.368   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.543   3.135   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.212   2.368   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.880   3.135   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.549   2.368   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.217   3.135   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.114   2.368   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.445   3.135   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.777   2.368   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.109   3.135   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.440   2.368   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -6.772   3.135   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -8.103   2.368   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -9.435   3.135   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      11.821   2.247   0.000  0.00  0.00           O+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   22                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   23                                                       
CONECT   21   16                                                            
CONECT   22   15                                                            
CONECT   23   20   24   39                                                  
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   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39   23                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   76    0
END

View in JSmol

Synonyms

Value	Source
(2S,3S,4R)-2-Hexadecanoylamino-octadecane-1,3,4-triol	HMDB
N-(1,3,4-Trihydroxyoctadecan-2-yl)hexadecanimidate	Generator
Armillaramide	MeSH

Chemical Formula

C₃₄H₆₉NO₄

Average Mass

555.9160 Da

Monoisotopic Mass

555.52266 Da

IUPAC Name

N-(1,3,4-trihydroxyoctadecan-2-yl)hexadecanamide

Traditional Name

N-(1,3,4-trihydroxyoctadecan-2-yl)hexadecanamide

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(=O)NC(CO)C(O)C(O)CCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C34H69NO4/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(38)35-31(30-36)34(39)32(37)28-26-24-22-20-18-16-14-12-10-8-6-4-2/h31-32,34,36-37,39H,3-30H2,1-2H3,(H,35,38)

InChI Key

IVBULNXGVIHEKN-UHFFFAOYSA-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
Daldinia concentrica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phytoceramides. These are n-acylated 4-hydroxysphinganine.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Ceramides

Direct Parent

Phytoceramides

Alternative Parents

Substituents

N-acyl-4-hydroxysphinganine
Fatty amide
N-acyl-amine
Fatty acyl
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Carboxylic acid derivative
Polyol
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Carbonyl group
Primary alcohol
Hydrocarbon derivative
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	8.76	ALOGPS
logP	10	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	13.26	ChemAxon
pKa (Strongest Basic)	0.029	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	89.79 Å²	ChemAxon
Rotatable Bond Count	31	ChemAxon
Refractivity	166.17 m³·mol⁻¹	ChemAxon
Polarizability	74.06 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

HMDB0037105

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016096

KNApSAcK ID

Not Available

Chemspider ID

7983535

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9807776

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-(1,3,4-trihydroxyoctadecan-2-yl)hexadecanimidic acid (NP0265763)

MOL for NP0265763 (n-(1,3,4-trihydroxyoctadecan-2-yl)hexadecanimidic acid)

3D MOL for NP0265763 (n-(1,3,4-trihydroxyoctadecan-2-yl)hexadecanimidic acid)

3D SDF for NP0265763 (n-(1,3,4-trihydroxyoctadecan-2-yl)hexadecanimidic acid)

3D-SDF for NP0265763 (n-(1,3,4-trihydroxyoctadecan-2-yl)hexadecanimidic acid)

PDB for NP0265763 (n-(1,3,4-trihydroxyoctadecan-2-yl)hexadecanimidic acid)

3D PDB for NP0265763 (n-(1,3,4-trihydroxyoctadecan-2-yl)hexadecanimidic acid)

SMILES for NP0265763 (n-(1,3,4-trihydroxyoctadecan-2-yl)hexadecanimidic acid)

INCHI for NP0265763 (n-(1,3,4-trihydroxyoctadecan-2-yl)hexadecanimidic acid)

Structure for NP0265763 (n-(1,3,4-trihydroxyoctadecan-2-yl)hexadecanimidic acid)

3D Structure for NP0265763 (n-(1,3,4-trihydroxyoctadecan-2-yl)hexadecanimidic acid)