NP-MRD: Showing NP-Card for n-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icos-10-en-2-yl)-2-hydroxyhexacos-17-enimidic acid (NP0177392)

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Record Information

Version

2.0

Created at

2022-09-03 15:13:33 UTC

Updated at

2022-09-03 15:13:33 UTC

NP-MRD ID

NP0177392

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icos-10-en-2-yl)-2-hydroxyhexacos-17-enimidic acid

Description

N-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icos-10-en-2-yl)-2-hydroxyhexacos-17-enimidic acid belongs to the class of organic compounds known as glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.G. S-,C-, or N-type) has been reported. n-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icos-10-en-2-yl)-2-hydroxyhexacos-17-enimidic acid is found in Euphorbia rigida. N-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icos-10-en-2-yl)-2-hydroxyhexacos-17-enimidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251507292D          

 63 63  0  0  0  0            999 V2000
   -7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
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 11 12  1  0  0  0  0
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 62 63  1  0  0  0  0
M  END


  Mrv1533004251507292D          

 63 63  0  0  0  0            999 V2000
   -7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0177392

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCC=CCCCCCC(O)C(O)C(COC1OC(CO)C(O)C(O)C1O)NC(=O)C(O)CCCCCCCCCCCCCCC=CCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C52H99NO10/c1-3-5-7-9-11-13-15-17-19-20-21-22-23-24-25-26-28-30-32-34-36-38-40-45(56)51(61)53-43(42-62-52-50(60)49(59)48(58)46(41-54)63-52)47(57)44(55)39-37-35-33-31-29-27-18-16-14-12-10-8-6-4-2/h17,19,27,29,43-50,52,54-60H,3-16,18,20-26,28,30-42H2,1-2H3,(H,53,61)

> <INCHI_KEY>
NVIDKWIMIJDSNO-UHFFFAOYSA-N

> <FORMULA>
C52H99NO10

> <MOLECULAR_WEIGHT>
898.361

> <EXACT_MASS>
897.726898392

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
162

> <JCHEM_AVERAGE_POLARIZABILITY>
114.43894619916992

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icos-10-en-2-yl)-2-hydroxyhexacos-17-enamide

> <ALOGPS_LOGP>
8.26

> <JCHEM_LOGP>
11.965544833666666

> <ALOGPS_LOGS>
-5.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.617095298232389

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.04684198095031

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810834177580157

> <JCHEM_POLAR_SURFACE_AREA>
189.17

> <JCHEM_REFRACTIVITY>
257.5253000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
44

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.38e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icos-10-en-2-yl)-2-hydroxyhexacos-17-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0     -14.670   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -13.337   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -13.337   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -12.003   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -12.003   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   35  N   UNK     0       4.001  -5.390   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      18.672  -4.620   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      20.005  -5.390   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      21.339  -4.620   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      22.673  -5.390   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      24.006  -4.620   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      25.340  -5.390   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      26.674  -4.620   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      28.007  -5.390   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      29.341  -4.620   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      29.341  -3.080   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      30.675  -2.310   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      30.675  -0.770   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      32.008   0.000   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      32.008   1.540   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      33.342   2.310   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      33.342   3.850   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                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   35                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   33                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   24   34                                                  
CONECT   34   33                                                            
CONECT   35   21   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  126    0
END

View in JSmol

Synonyms

Value	Source
N-(3,4-Dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icos-10-en-2-yl)-2-hydroxyhexacos-17-enimidate	Generator

Chemical Formula

C₅₂H₉₉NO₁₀

Average Mass

898.3610 Da

Monoisotopic Mass

897.72690 Da

IUPAC Name

N-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icos-10-en-2-yl)-2-hydroxyhexacos-17-enamide

Traditional Name

N-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icos-10-en-2-yl)-2-hydroxyhexacos-17-enamide

CAS Registry Number

Not Available

SMILES

CCCCCCCCCC=CCCCCCC(O)C(O)C(COC1OC(CO)C(O)C(O)C1O)NC(=O)C(O)CCCCCCCCCCCCCCC=CCCCCCCCC

InChI Identifier

InChI=1S/C52H99NO10/c1-3-5-7-9-11-13-15-17-19-20-21-22-23-24-25-26-28-30-32-34-36-38-40-45(56)51(61)53-43(42-62-52-50(60)49(59)48(58)46(41-54)63-52)47(57)44(55)39-37-35-33-31-29-27-18-16-14-12-10-8-6-4-2/h17,19,27,29,43-50,52,54-60H,3-16,18,20-26,28,30-42H2,1-2H3,(H,53,61)

InChI Key

NVIDKWIMIJDSNO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Euphorbia rigida	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.G. S-,C-, or N-type) has been reported.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Glycosphingolipids

Direct Parent

Glycosphingolipids

Alternative Parents

Substituents

Glycosphingolipid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Monosaccharide
Fatty acyl
Oxane
Secondary alcohol
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organoheterocyclic compound
Carboximidic acid
Carboximidic acid derivative
Oxacycle
Acetal
Polyol
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Alcohol
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	8.26	ALOGPS
logP	11.97	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	12.05	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	189.17 Å²	ChemAxon
Rotatable Bond Count	44	ChemAxon
Refractivity	257.53 m³·mol⁻¹	ChemAxon
Polarizability	114.44 Å³	ChemAxon
Number of Rings	1	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icos-10-en-2-yl)-2-hydroxyhexacos-17-enimidic acid (NP0177392)

MOL for NP0177392 (n-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icos-10-en-2-yl)-2-hydroxyhexacos-17-enimidic acid)

3D MOL for NP0177392 (n-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icos-10-en-2-yl)-2-hydroxyhexacos-17-enimidic acid)

3D SDF for NP0177392 (n-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icos-10-en-2-yl)-2-hydroxyhexacos-17-enimidic acid)

3D-SDF for NP0177392 (n-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icos-10-en-2-yl)-2-hydroxyhexacos-17-enimidic acid)

PDB for NP0177392 (n-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icos-10-en-2-yl)-2-hydroxyhexacos-17-enimidic acid)

3D PDB for NP0177392 (n-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icos-10-en-2-yl)-2-hydroxyhexacos-17-enimidic acid)

SMILES for NP0177392 (n-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icos-10-en-2-yl)-2-hydroxyhexacos-17-enimidic acid)

INCHI for NP0177392 (n-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icos-10-en-2-yl)-2-hydroxyhexacos-17-enimidic acid)

Structure for NP0177392 (n-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icos-10-en-2-yl)-2-hydroxyhexacos-17-enimidic acid)

3D Structure for NP0177392 (n-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icos-10-en-2-yl)-2-hydroxyhexacos-17-enimidic acid)