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Showing NP-Card for (r,r)-2,3-butanediol (NP0198915)

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Record Information
Version2.0
Created at2022-09-04 17:27:17 UTC
Updated at2022-09-04 17:27:17 UTC
NP-MRD IDNP0198915
Secondary Accession NumbersNone
Natural Product Identification
Common Name(r,r)-2,3-butanediol
Description (r,r)-2,3-butanediol is found in Aster koraiensis. (r,r)-2,3-butanediol was first documented in 1978 (PMID: 25056).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0198915 ((r,r)-2,3-butanediol)


  Mrv0541 02231216112D          

  6  5  0  0  1  0            999 V2000
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  6  0  0  0
M  END
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3D MOL for NP0198915 ((r,r)-2,3-butanediol)

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3D SDF for NP0198915 ((r,r)-2,3-butanediol)

  Mrv0541 02231216112D          

  6  5  0  0  1  0            999 V2000
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0198915

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)[C@H](C)O

> <INCHI_IDENTIFIER>
InChI=1S/C4H10O2/c1-3(5)4(2)6/h3-6H,1-2H3/t3-,4+

> <INCHI_KEY>
OWBTYPJTUOEWEK-ZXZARUISSA-N

> <FORMULA>
C4H10O2

> <MOLECULAR_WEIGHT>
90.121

> <EXACT_MASS>
90.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
9.827093542014602

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S)-butane-2,3-diol

> <ALOGPS_LOGP>
-0.59

> <JCHEM_LOGP>
-0.37552903133333315

> <ALOGPS_LOGS>
0.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.678062098346835

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.224481598439645

> <JCHEM_PKA_STRONGEST_BASIC>
-3.006341228739074

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
23.391199999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.03e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(R,R)-2,3-butanediol

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0198915 ((r,r)-2,3-butanediol)
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PDB for NP0198915 ((r,r)-2,3-butanediol)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END

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3D PDB for NP0198915 ((r,r)-2,3-butanediol)
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SMILES for NP0198915 ((r,r)-2,3-butanediol)
C[C@@H](O)[C@H](C)O
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INCHI for NP0198915 ((r,r)-2,3-butanediol)
InChI=1S/C4H10O2/c1-3(5)4(2)6/h3-6H,1-2H3/t3-,4+
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Synonyms
ValueSource
(2Rs,3Sr)-2,3-ButanediolChEBI
(2Rs,3Sr)-Butane-2,3-diolChEBI
(2S,3R)-2,3-ButananediolChEBI
(2S,3R)-Butanane-2,3-diolChEBI
(R*,s*)-2,3-butanediolChEBI
(R*,s*)-butane-2,3-diolChEBI
(R,S)-2,3-ButanediolChEBI
(R,S)-Butane-2,3-diolChEBI
(R,S)-Butylene glycolChEBI
Erythro-2,3-butanediolChEBI
Erythro-butane-2,3-diolChEBI
Meso-2,3-butanediolChEBI
Meso-2,3-dihydroxybutaneChEBI
Meso-butanediolChEBI
Meso-butylene glycolChEBI
Meso-dimethyl ethyleneglycolChEBI
NSC 2164ChEBI
UNII-F5ia8X9O8mChEBI
Chemical FormulaC4H10O2
Average Mass90.1210 Da
Monoisotopic Mass90.06808 Da
IUPAC Name(2R,3S)-butane-2,3-diol
Traditional Name(R,R)-2,3-butanediol
CAS Registry NumberNot Available
SMILES
C[C@@H](O)[C@H](C)O
InChI Identifier
InChI=1S/C4H10O2/c1-3(5)4(2)6/h3-6H,1-2H3/t3-,4+
InChI KeyOWBTYPJTUOEWEK-ZXZARUISSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aster koraiensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassAlcohols and polyols  
Direct Parent1,2-diols  
Alternative Parents
Substituents
  • Secondary alcohol
    • 

  • 1,2-diol
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
logP-0.59ALOGPS
logP-0.38ChemAxon
logS0.83ALOGPS
pKa (Strongest Acidic)14.22ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity23.39 m³·mol⁻¹ChemAxon
Polarizability9.83 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB02418  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-12004  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound220010  
PDB IDNot Available
ChEBI ID75460  
Good Scents IDNot Available
References
General References
  1. Casazza JP, Frietas J, Stambuk D, Morgan MY, Veech RL: The measurement of 1,2-propanediol, D, L-2,3-butanediol and meso-2,3-butanediol in controls and alcoholic cirrhotics. Alcohol Alcohol Suppl. 1987;1:607-9. [PubMed:3426740  ] 
  2. Hohn-Bentz H, Radler F: Bacterial 2,3-butanediol dehydrogenases. Arch Microbiol. 1978 Feb;116(2):197-203. doi: 10.1007/BF00406037. [PubMed:25056  ] 
  3. LOTUS database [Link]