MiMeDB: Showing metabocard for 2.3-butanediol (MMDBc0008273)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 01:10:33 UTC

Update Date

2024-04-30 19:34:06 UTC

Metabolite ID

MMDBc0008273

Metabolite 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

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-Butylene glycol, (r,r)-isomer	MeSH
2,3-Butylene glycol, (r,r,)-(+-)-isomer	MeSH
2,3-Butylene glycol, (r,s)-isomer	MeSH
2,3-Butylene glycol, (S-(r,r))-isomer	MeSH
2,3-Butylene glycol, R-(r,r)-isomer	MeSH
Butane-2,3-diol	MeSH
2,3-Butandiol	HMDB
2,3-Butanodiol	HMDB
D-2,3-Butane diol	HMDB
2,3-Butanediol	ChEBI

Molecular Formula

C₄H₁₀O₂

Average Mass

90.121

Monoisotopic Mass

90.068079564

IUPAC Name

butane-2,3-diol

Traditional Name

2,3-butanediol

CAS Registry Number

Not Available

SMILES

CC(O)C(C)O

InChI Identifier

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

InChI Key

OWBTYPJTUOEWEK-UHFFFAOYSA-N

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-9000000000-e110e7ce89cc64b78ca2	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-9000000000-39d2dfc0a50d8ba018c7	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-9000000000-e110e7ce89cc64b78ca2	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-9000000000-39d2dfc0a50d8ba018c7	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9000000000-cc27e53ef044f7cb15a5	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-01b9-9520000000-fa7488838e20f2dd123b	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-9000000000-a38d022475e970ac03d7	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03dl-9000000000-c09bcb32a4424164b2b1	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-01p9-9000000000-7e0b3df968981c428a95	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0002-9000000000-f6fb3d0277c373b5e557	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80A) , Positive	splash10-0002-9000000000-94dd097f8cd58f7a22e5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0006-9000000000-973d129e78b29fbf8804	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-373d8ab05d8ca30b9936	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-9000000000-c995422d63c292e20b8f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-5639537d59074e5a4a6c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-aa5e86f920a11ea2d749	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-cef0995334342db934ba	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-c4f65aef56394c6d3a25	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-09fc38b483234e7b66aa	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000f-9000000000-79fde7f9417c0129ac4c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-452a5f79625d3401d495	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-2e058d12c0f9880bd53d	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-77a30103f1d168eecd21	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-4c2f1d8ca7aa89a88c6c	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-05	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)		2016-09-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Adrenal Cortex
Blood
Epidermis
Feces
Fibroblasts
Intestine
Neuron
Platelet
Spleen
Testis
Thyroid Gland
Urine

Tissue Locations

Adrenal Cortex
Epidermis
Fibroblasts
Intestine
Neuron
Platelet
Spleen
Testis
Thyroid Gland

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0193465	Vitamin K epoxide reductase complex subunit 1	Enzyme	Q9BQB6	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Cirrhosis		Association	Human Blood	HMDB	3426740

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	2	Human	Metabolic reconstruction
Bacteria	Proteobacteria	2	Human

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Food			FooDB	31437929
Food			FooDB	31437929
Food			FooDB	31437929
Plant	Endosperm	Cocos nucifera	FooDB	31437929
Plant	Fruit	Capsicum annuum	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	100		5	211	uM	Adult (>18 years old)	Both	Cirrhosis	HMDB	3426740
Human Blood	Detected and Quantified	2		0	5	uM	Adult (>18 years old)	Both	Normal	HMDB	3426740
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Colorectal Cancer	HMDB	27275383
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Bladder cancer	HMDB	28157703
Human Blood	Detected and Quantified	13.8	7.5			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	100.0		5.0	211.0	uM	Adult (>18 years old)	Both	Cirrhosis	HMDB	3426740
Human Blood	Detected and Quantified	2.0		0.0	5.0	uM	Adult (>18 years old)	Both	Normal	HMDB	3426740
Human Blood	Detected and Quantified	13.8	7.5			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Adrenal cortex	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Spleen	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Thyroid gland	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0003156

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011934

KNApSAcK ID

C00050411

Chemspider ID

21106093

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2,3-Butanediol

METLIN ID

Not Available

PubChem Compound

262

PDB ID

Not Available

ChEBI ID

62064

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Herblin WF, Chiu AT, McCall DE, Ardecky RJ, Carini DJ, Duncia JV, Pease LJ, Wong PC, Wexler RR, Johnson AL, et al.: Angiotensin II receptor heterogeneity. Am J Hypertens. 1991 Apr;4(4 Pt 2):299S-302S. doi: 10.1093/ajh/4.4.299s. [PubMed:1854455 ]
Wroblewski VJ: Mechanism of deiodination of 125I-human growth hormone in vivo. Relevance to the study of protein disposition. Biochem Pharmacol. 1991 Jul 25;42(4):889-97. doi: 10.1016/0006-2952(91)90050-f. [PubMed:1867644 ]
Sachs MK, Huang CM, Ost D, Jungkind DL: Failure of dithiothreitol and pronase to reveal a false-positive cryptococcal antigen determination in cerebrospinal fluid. Am J Clin Pathol. 1991 Sep;96(3):381-4. doi: 10.1093/ajcp/96.3.381. [PubMed:1877537 ]
Moshkin AV: [Stabilization of creatine kinase isoenzymes in the cerebrospinal fluid in cranio-cerebral trauma]. Lab Delo. 1989;(2):48-52. [PubMed:2467061 ]
Sakai A, Sakakibara R, Ishiguro M: Human chorionic gonadotropin-ricin A chain hybrid protein: a hormone analog for the study of signal transduction. J Biochem. 1989 Feb;105(2):275-80. doi: 10.1093/oxfordjournals.jbchem.a122653. [PubMed:2542238 ]
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. doi: 10.1016/s0140-6736(83)91130-3. [PubMed:6139706 ]
Chujor CS, Feingold KR, Elias PM, Holleran WM: Glucosylceramide synthase activity in murine epidermis: quantitation, localization, regulation, and requirement for barrier homeostasis. J Lipid Res. 1998 Feb;39(2):277-85. [PubMed:9507988 ]
Hermand P, Gane P, Huet M, Jallu V, Kaplan C, Sonneborn HH, Cartron JP, Bailly P: Red cell ICAM-4 is a novel ligand for platelet-activated alpha IIbbeta 3 integrin. J Biol Chem. 2003 Feb 14;278(7):4892-8. doi: 10.1074/jbc.M211282200. Epub 2002 Dec 10. [PubMed:12477717 ]
Plaisant F, Clippe A, Vander Stricht D, Knoops B, Gressens P: Recombinant peroxiredoxin 5 protects against excitotoxic brain lesions in newborn mice. Free Radic Biol Med. 2003 Apr 1;34(7):862-72. doi: 10.1016/s0891-5849(02)01440-5. [PubMed:12654475 ]
Paul BZ, Vilaire G, Kunapuli SP, Bennett JS: Concurrent signaling from Galphaq- and Galphai-coupled pathways is essential for agonist-induced alphavbeta3 activation on human platelets. J Thromb Haemost. 2003 Apr;1(4):814-20. doi: 10.1046/j.1538-7836.2003.00099.x. [PubMed:12871420 ]
Murray JI, Whitfield ML, Trinklein ND, Myers RM, Brown PO, Botstein D: Diverse and specific gene expression responses to stresses in cultured human cells. Mol Biol Cell. 2004 May;15(5):2361-74. doi: 10.1091/mbc.e03-11-0799. Epub 2004 Mar 5. [PubMed:15004229 ]
Jin Y, Kim DK, Khil LY, Oh U, Kim J, Kwak J: Thimerosal decreases TRPV1 activity by oxidation of extracellular sulfhydryl residues. Neurosci Lett. 2004 Oct 21;369(3):250-5. doi: 10.1016/j.neulet.2004.07.059. [PubMed:15464274 ]
Ohno S, Nakajima Y, Nakajin S: Triphenyltin and Tributyltin inhibit pig testicular 17beta-hydroxysteroid dehydrogenase activity and suppress testicular testosterone biosynthesis. Steroids. 2005 Aug;70(9):645-51. doi: 10.1016/j.steroids.2005.03.005. [PubMed:15899506 ]
Ueda N, Tsuboi K, Lambert DM: A second N-acylethanolamine hydrolase in mammalian tissues. Neuropharmacology. 2005 Jun;48(8):1079-85. doi: 10.1016/j.neuropharm.2004.12.017. [PubMed:15910884 ]
Cooper CA, Bury NR, Grosell M: The effects of pH and the iron redox state on iron uptake in the intestine of a marine teleost fish, gulf toadfish (Opsanus beta). Comp Biochem Physiol A Mol Integr Physiol. 2006 Mar;143(3):292-8. doi: 10.1016/j.cbpa.2005.11.024. Epub 2006 Jan 20. [PubMed:16431145 ]
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 ]

Showing metabocard for 2.3-butanediol (MMDBc0008273)

MOL for #<Metabolite:0x00007fd100013b90>

3D MOL for #<Metabolite:0x00007fd100013b90>

3D SDF for #<Metabolite:0x00007fd100013b90>

3D-SDF for #<Metabolite:0x00007fd100013b90>

PDB for #<Metabolite:0x00007fd100013b90>

3D PDB for #<Metabolite:0x00007fd100013b90>

SMILES for #<Metabolite:0x00007fd100013b90>

INCHI for #<Metabolite:0x00007fd100013b90>

Structure for #<Metabolite:0x00007fd100013b90>

3D Structure for #<Metabolite:0x00007fd100013b90>