NP-MRD: Showing NP-Card for 2,3-Butanediol (NP0000210)

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Record Information

Version

2.0

Created at

2006-05-22 15:12:37 UTC

Updated at

2022-04-04 18:15:48 UTC

NP-MRD ID

NP0000210

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3-Butanediol

Description

2,3-Butanediol is an isomer of butanediol. The 2R,3R stereoisomer of 2,3-butanediol is produced by a variety of microorganisms, in a process known as butanediol fermentation. 2,3-Butanediol fermentation is the anaerobic fermentation of glucose with 2,3-butanediol as one of the end products. The overall stoichiometry of the reaction is 2 pyruvate + NADH --> 2CO2 + 2,3-butanediol. Butanediol fermentation is typical for Enterobacter species or microbes found in the gut. 2,3-Butanediol has been identified in the sera of alcoholics and it may be a specific marker of alcohol abuse (PMID: 6139706 ). In humans, 2,3-butanediol is oxidized to acetyl-CoA via acetoin. 2,3-Butanediol is also found in cocoa butter. 2,3-Butanediol can also be found in Bacillus, Klebsiella and Serratia (PMID: 21272631 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306242117433D          

 16 15  0  0  0  0            999 V2000
    1.1694    0.8726    0.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8174    0.0001   -0.4634 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7867   -0.9688   -0.6299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5582   -0.5739   -0.2388 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5383    0.5639   -0.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5797   -1.3701    0.9029 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5649    0.6273    1.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9912    1.9250    0.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2633    0.7758    0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7869    0.5960   -1.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6340   -1.5641   -1.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9203   -1.1762   -1.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3679    0.2531    0.6339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9855    1.4233    0.3852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9608    0.8302   -1.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1031   -2.2143    0.7426 H   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1  8  1  0  0  0  0
  1  9  1  0  0  0  0
  2 10  1  6  0  0  0
  3 11  1  0  0  0  0
  4 12  1  6  0  0  0
  5 13  1  0  0  0  0
  5 14  1  0  0  0  0
  5 15  1  0  0  0  0
  6 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000210

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
OWBTYPJTUOEWEK-UHFFFAOYSA-N

> <FORMULA>
C4H10O2

> <MOLECULAR_WEIGHT>
90.121

> <EXACT_MASS>
90.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
9.86836471486291

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
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>
23.3912

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.03e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-butanediol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       1.169   0.873   0.700  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.817   0.000  -0.463  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.787  -0.969  -0.630  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.558  -0.574  -0.239  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.538   0.564  -0.047  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.580  -1.370   0.903  0.00  0.00           O+0
HETATM    7  H   UNK     0       0.565   0.627   1.613  0.00  0.00           H+0
HETATM    8  H   UNK     0       0.991   1.925   0.409  0.00  0.00           H+0
HETATM    9  H   UNK     0       2.263   0.776   0.924  0.00  0.00           H+0
HETATM   10  H   UNK     0       0.787   0.596  -1.398  0.00  0.00           H+0
HETATM   11  H   UNK     0       1.634  -1.564  -1.389  0.00  0.00           H+0
HETATM   12  H   UNK     0      -0.920  -1.176  -1.085  0.00  0.00           H+0
HETATM   13  H   UNK     0      -2.368   0.253   0.634  0.00  0.00           H+0
HETATM   14  H   UNK     0      -0.986   1.423   0.385  0.00  0.00           H+0
HETATM   15  H   UNK     0      -1.961   0.830  -1.059  0.00  0.00           H+0
HETATM   16  H   UNK     0      -1.103  -2.214   0.743  0.00  0.00           H+0
CONECT    1    2    7    8    9                                             
CONECT    2    1    3    4   10                                             
CONECT    3    2   11                                                       
CONECT    4    2    5    6   12                                             
CONECT    5    4   13   14   15                                             
CONECT    6    4   16                                                       
CONECT    7    1                                                            
CONECT    8    1                                                            
CONECT    9    1                                                            
CONECT   10    2                                                            
CONECT   11    3                                                            
CONECT   12    4                                                            
CONECT   13    5                                                            
CONECT   14    5                                                            
CONECT   15    5                                                            
CONECT   16    6                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol

Synonyms

Value	Source
2,3-Butylene glycol	ChEBI
2,3-Dihydroxybutane	ChEBI
Dimethylene glycol	ChEBI
Dimethylethylene glycol	ChEBI
Pseudobutylene glycol	ChEBI
Sym-dimethylethylene glycol	ChEBI
2,3-Butandiol	HMDB
2,3-Butanodiol	HMDB
D-2,3-Butane diol	HMDB
2,3-Butylene glycol, (r,r)-isomer	HMDB
2,3-Butylene glycol, (r,r,)-(+-)-isomer	HMDB
2,3-Butylene glycol, R-(r,r)-isomer	HMDB
2,3-Butylene glycol, (S-(r,r))-isomer	HMDB
2,3-Butylene glycol, (r,s)-isomer	HMDB
Butane-2,3-diol	HMDB
2,3-Butanediol	ChEBI

Chemical Formula

C₄H₁₀O₂

Average Mass

90.1210 Da

Monoisotopic Mass

90.06808 Da

IUPAC Name

butane-2,3-diol

Traditional Name

2,3-butanediol

CAS Registry Number

513-85-9

SMILES

[H]O[C@@]([H])(C([H])([H])[H])[C@]([H])(O[H])C([H])([H])[H]

InChI Identifier

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

InChI Key

OWBTYPJTUOEWEK-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, simulated)	Ahselim			2022-04-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Arabidopsis thaliana	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Capsicum annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Cocos nucifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Coffea arabica	KNApSAcK Database	22123792
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Corynebacterium glutamicum	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Mandragora autumnalis	KNApSAcK Database	22123792
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Streptomyces xanthophaeus	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Vitis vinifera	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Bacillus subtilis GB03	KNApSAcK Database	22123792
Erwinia amylovora	KNApSAcK Database	22123792
Serratia odorifera	KNApSAcK Database	22123792

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

1,2-diols

Alternative Parents

Substituents

Secondary alcohol
1,2-diol
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

secondary alcohol (CHEBI:62064 )
glycol (CHEBI:62064 )
butanediol (CHEBI:62064 )
a 2,3-butanediol (CPD-346 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	25 °C	Not Available
Boiling Point	182.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1000 mg/mL at 20 °C	Not Available
LogP	-0.92	Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted Properties

Property	Value	Source
Water Solubility	603 g/L	ALOGPS
logP	-0.59	ALOGPS
logP	-0.38	ChemAxon
logS	0.83	ALOGPS
pKa (Strongest Acidic)	14.22	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	23.39 m³·mol⁻¹	ChemAxon
Polarizability	9.87 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0003156

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

62064

Good Scents ID

rw1161171

References

General References

Walker V, Mills GA: Urinary organic acid excretion by babies born before 33 weeks of gestation. Clin Chem. 1989 Jul;35(7):1460-6. [PubMed:2758593 ]
Kuehnle J, Holzbaur J: 2,3-Butanediol in serum of alcoholics. Lancet. 1983 Dec 10;2(8363):1369-70. [PubMed:6139706 ]
Ji XJ, Huang H, Ouyang PK: Microbial 2,3-butanediol production: a state-of-the-art review. Biotechnol Adv. 2011 May-Jun;29(3):351-64. doi: 10.1016/j.biotechadv.2011.01.007. Epub 2011 Jan 24. [PubMed:21272631 ]
Nan H, Seo SO, Oh EJ, Seo JH, Cate JH, Jin YS: 2,3-butanediol production from cellobiose by engineered Saccharomyces cerevisiae. Appl Microbiol Biotechnol. 2014 Jun;98(12):5757-64. doi: 10.1007/s00253-014-5683-x. Epub 2014 Apr 18. [PubMed:24743979 ]

Showing NP-Card for 2,3-Butanediol (NP0000210)

MOL for NP0000210 (2,3-Butanediol)

3D MOL for NP0000210 (2,3-Butanediol)

3D SDF for NP0000210 (2,3-Butanediol)

3D-SDF for NP0000210 (2,3-Butanediol)

PDB for NP0000210 (2,3-Butanediol)

3D PDB for NP0000210 (2,3-Butanediol)

SMILES for NP0000210 (2,3-Butanediol)

INCHI for NP0000210 (2,3-Butanediol)

Structure for NP0000210 (2,3-Butanediol)

3D Structure for NP0000210 (2,3-Butanediol)