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Showing NP-Card for (4s,5s)-4-hydroxy-5-[(2r)-2-hydroxy-2-methyloctadecyl]-5-methyloxolan-2-one (NP0330152)

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Record Information
Version2.0
Created at2022-09-12 15:13:41 UTC
Updated at2022-09-12 15:13:41 UTC
NP-MRD IDNP0330152
Secondary Accession NumbersNone
Natural Product Identification
Common Name(4s,5s)-4-hydroxy-5-[(2r)-2-hydroxy-2-methyloctadecyl]-5-methyloxolan-2-one
DescriptionCHEMBL1271054 belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. (4s,5s)-4-hydroxy-5-[(2r)-2-hydroxy-2-methyloctadecyl]-5-methyloxolan-2-one is found in Plakortis halichondrioides. Based on a literature review very few articles have been published on CHEMBL1271054.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0330152 ((4s,5s)-4-hydroxy-5-[(2r)-2-hydroxy-2-methyloctadecyl]-5-methyloxolan-2-one)


  Mrv1652309122217132D          

 28 28  0  0  1  0            999 V2000
   -9.9986   -7.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2842   -7.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5697   -7.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8552   -7.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1408   -7.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4263   -7.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7118   -7.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9973   -7.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2829   -7.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5684   -7.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8539   -7.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1395   -7.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250   -7.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7105   -7.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0040   -7.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7184   -7.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4329   -7.4730    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0204   -8.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8454   -6.7585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1474   -7.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8618   -7.4730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1974   -8.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3769   -6.8055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8618   -6.1381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6069   -5.3535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6465   -6.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6465   -7.2180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3139   -7.7029    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
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  6  0  0  0
 17 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  6  0  0  0
M  END
Download

3D MOL for NP0330152 ((4s,5s)-4-hydroxy-5-[(2r)-2-hydroxy-2-methyloctadecyl]-5-methyloxolan-2-one)

Download
3D SDF for NP0330152 ((4s,5s)-4-hydroxy-5-[(2r)-2-hydroxy-2-methyloctadecyl]-5-methyloxolan-2-one)

  Mrv1652309122217132D          

 28 28  0  0  1  0            999 V2000
   -9.9986   -7.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2842   -7.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5697   -7.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8552   -7.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1408   -7.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4263   -7.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7118   -7.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9973   -7.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2829   -7.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5684   -7.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8539   -7.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1395   -7.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250   -7.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7105   -7.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0040   -7.4730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7184   -7.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4329   -7.4730    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0204   -8.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8454   -6.7585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1474   -7.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8618   -7.4730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1974   -8.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3769   -6.8055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8618   -6.1381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6069   -5.3535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6465   -6.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6465   -7.2180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3139   -7.7029    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
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  6  0  0  0
 17 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0330152

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCC[C@@](C)(O)C[C@]1(C)OC(=O)C[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H46O4/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(2,27)20-24(3)21(25)19-22(26)28-24/h21,25,27H,4-20H2,1-3H3/t21-,23+,24-/m0/s1

> <INCHI_KEY>
BOZAKLGASKUEFD-QTJGBDASSA-N

> <FORMULA>
C24H46O4

> <MOLECULAR_WEIGHT>
398.628

> <EXACT_MASS>
398.339609961

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
50.975222925060145

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,5S)-4-hydroxy-5-[(2R)-2-hydroxy-2-methyloctadecyl]-5-methyloxolan-2-one

> <JCHEM_LOGP>
6.384392022

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.991922272898265

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.682259897027883

> <JCHEM_PKA_STRONGEST_BASIC>
-2.815410654274257

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
114.97669999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5S)-4-hydroxy-5-[(2R)-2-hydroxy-2-methyloctadecyl]-5-methyloxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0330152 ((4s,5s)-4-hydroxy-5-[(2r)-2-hydroxy-2-methyloctadecyl]-5-methyloxolan-2-one)
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PDB for NP0330152 ((4s,5s)-4-hydroxy-5-[(2r)-2-hydroxy-2-methyloctadecyl]-5-methyloxolan-2-one)
HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0     -18.664 -13.950   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -17.330 -13.180   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -15.997 -13.950   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -14.663 -13.180   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -13.329 -13.950   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -11.996 -13.180   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.662 -13.950   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.328 -13.180   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.995 -13.950   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.661 -13.180   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.327 -13.950   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.994 -13.180   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.660 -13.950   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.326 -13.180   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.007 -13.950   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.341 -13.180   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.675 -13.950   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.905 -15.283   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.445 -12.616   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.008 -14.720   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.342 -13.950   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.968 -15.356   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.437 -12.704   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.342 -11.458   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.866  -9.993   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.807 -11.934   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.807 -13.474   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.053 -14.379   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                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22   23   27                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   21   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   56    0
END

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3D PDB for NP0330152 ((4s,5s)-4-hydroxy-5-[(2r)-2-hydroxy-2-methyloctadecyl]-5-methyloxolan-2-one)
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SMILES for NP0330152 ((4s,5s)-4-hydroxy-5-[(2r)-2-hydroxy-2-methyloctadecyl]-5-methyloxolan-2-one)
CCCCCCCCCCCCCCCC[C@@](C)(O)C[C@]1(C)OC(=O)C[C@@H]1O
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INCHI for NP0330152 ((4s,5s)-4-hydroxy-5-[(2r)-2-hydroxy-2-methyloctadecyl]-5-methyloxolan-2-one)
InChI=1S/C24H46O4/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(2,27)20-24(3)21(25)19-22(26)28-24/h21,25,27H,4-20H2,1-3H3/t21-,23+,24-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC24H46O4
Average Mass398.6280 Da
Monoisotopic Mass398.33961 Da
IUPAC Name(4S,5S)-4-hydroxy-5-[(2R)-2-hydroxy-2-methyloctadecyl]-5-methyloxolan-2-one
Traditional Name(4S,5S)-4-hydroxy-5-[(2R)-2-hydroxy-2-methyloctadecyl]-5-methyloxolan-2-one
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC[C@@](C)(O)C[C@]1(C)OC(=O)C[C@@H]1O
InChI Identifier
InChI=1S/C24H46O4/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(2,27)20-24(3)21(25)19-22(26)28-24/h21,25,27H,4-20H2,1-3H3/t21-,23+,24-/m0/s1
InChI KeyBOZAKLGASKUEFD-QTJGBDASSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Plakortis halichondrioidesLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassLactones  
Sub ClassGamma butyrolactones  
Direct ParentGamma butyrolactones  
Alternative Parents
Substituents
  • Gamma butyrolactone
    • 

  • Tertiary alcohol
    • 

  • Oxolane
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.38ChemAxon
pKa (Strongest Acidic)13.68ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity114.98 m³·mol⁻¹ChemAxon
Polarizability50.98 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID26363998  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52943285  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]