NP-MRD: Showing NP-Card for Cerebroside (NP0339505)

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Record Information

Version

2.0

Created at

2024-09-11 22:10:07 UTC

Updated at

2024-09-11 22:10:07 UTC

NP-MRD ID

NP0339505

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cerebroside

Description

Cerebroside belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. Cerebroside was first documented in 2024 (PMID: 38974607). Based on a literature review very few articles have been published on Cerebroside (PMID: 38931391).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05272300422D          

 21 20  0  0  0  0            999 V2000
10018.988210015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.272710015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.557510015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.844010015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.128510015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.413110015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.697610015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.982910015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.268010015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.553510015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.839010015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.124210015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.409510015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.694910015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.980410015.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.701510015.6194    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10020.417010015.2073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10021.130310015.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10021.845710015.2073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10020.417010014.3821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10019.701510016.4439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 16  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
 16 17  1  0  0  0  0
 16 21  1  1  0  0  0
 17 18  1  0  0  0  0
 17 20  1  6  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339505

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/s2

> <INCHI_KEY>
WWUZIQQURGPMPG-DEDGOTNNNA-N

> <FORMULA>
C18H37NO2

> <MOLECULAR_WEIGHT>
299.499

> <EXACT_MASS>
299.282429435

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
39.23349410531561

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4E)-2-aminooctadec-4-ene-1,3-diol

> <JCHEM_LOGP>
4.5665800486666654

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.190394596992869

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.116140546669913

> <JCHEM_PKA_STRONGEST_BASIC>
9.234294901231742

> <JCHEM_POLAR_SURFACE_AREA>
66.48

> <JCHEM_REFRACTIVITY>
91.89199999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
sphingosine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  C   UNK     0    8702.1118695.054   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8700.7768695.823   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8699.4418695.054   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8698.1098695.823   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8696.7738695.054   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8695.4388695.823   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8694.1028695.054   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8692.7688695.823   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8691.4348695.054   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8690.1008695.823   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8688.7668695.054   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8687.4328695.823   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8686.0988695.054   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8684.7648695.823   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8683.4308695.054   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8703.4438695.823   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8704.7788695.054   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8706.1108695.823   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8707.4458695.054   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0    8704.7788693.513   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0    8703.4438697.362   0.000  0.00  0.00           O+0
CONECT    1    2   16                                                       
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                                                            
CONECT   16    1   17   21                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17                                                            
CONECT   21   16                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₃₇NO₂

Average Mass

299.4990 Da

Monoisotopic Mass

299.28243 Da

IUPAC Name

(2S,3R,4E)-2-aminooctadec-4-ene-1,3-diol

Traditional Name

sphingosine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/s2

InChI Key

WWUZIQQURGPMPG-DEDGOTNNNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

1,2-aminoalcohols

Alternative Parents

Substituents

Secondary alcohol
1,2-aminoalcohol
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Primary alcohol
Organooxygen compound
Primary aliphatic amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

sphing-4-enine (CHEBI:16393 )
Sphing-4-enines (Sphingosines) (C00319 )
Sphing-4-enines (Sphingosines) (LMSP01010001 )

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	4.57	ChemAxon
pKa (Strongest Acidic)	14.12	ChemAxon
pKa (Strongest Basic)	9.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	66.48 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	91.89 m³·mol⁻¹	ChemAxon
Polarizability	39.23 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Cerebroside

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mangini L, Lawrence R, Lopez ME, Graham TC, Bauer CR, Nguyen H, Su C, Ramphal J, Crawford BE, Hartl TA: Galactokinase 1 is the source of elevated galactose-1-phosphate and cerebrosides are modestly reduced in a mouse model of classic galactosemia. JIMD Rep. 2024 Jun 23;65(4):280-294. doi: 10.1002/jmd2.12438. eCollection 2024 Jul. [PubMed:38974607 ]
El Sayed ZI, Hassan WHB, Abdel-Aal MM, Al-Massarani SM, Abdel-Mageed WM, Basudan OA, Parveen M, Abdelsalam E, Abdelaziz S: Chemical and Biological Characterization of the Ethyl Acetate Fraction from the Red Sea Marine Sponge Hymedesmia sp. Pharmaceuticals (Basel). 2024 Jun 3;17(6):724. doi: 10.3390/ph17060724. [PubMed:38931391 ]

Showing NP-Card for Cerebroside (NP0339505)

MOL for NP0339505 (Cerebroside)

3D MOL for NP0339505 (Cerebroside)

3D SDF for NP0339505 (Cerebroside)

3D-SDF for NP0339505 (Cerebroside)

PDB for NP0339505 (Cerebroside)

3D PDB for NP0339505 (Cerebroside)

SMILES for NP0339505 (Cerebroside)

INCHI for NP0339505 (Cerebroside)

Structure for NP0339505 (Cerebroside)

3D Structure for NP0339505 (Cerebroside)