MiMeDB: Showing metabocard for (2R,3R)-2,3-Butanediol (MMDBc0000278)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:48:34 UTC

Update Date

2022-08-31 00:16:49 UTC

Metabolite ID

MMDBc0000278

Metabolite Identification

Common Name

(2R,3R)-2,3-Butanediol

Description

(2R,3R)-2,3-Butanediol is found in cocoa and cocoa products. (2R,3R)-2,3-Butanediol is isolated from cocoa butter and roots of Ruta graveolens (rue).2,3-Butanediol is one of the constitutional isomers of butanediol. The 2R,3R stereoisomer of 2,3-butanediol is produced by a variety of microorganisms, in a process known as butanediol fermentation. It is found in cocoa butter and in the roots of Ruta graveolens. (Wikipedia).

Structure

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

Synonyms

Value	Source
(R,R)-(-)-Butane-2,3-diol	ChEBI
(R,R)-2,3-Butanediol	ChEBI
(R,R)-2,3-Butylene glycol	ChEBI
(-)-(2R,3R)-Butanediol	HMDB
(-)-2,3-Butanediol	HMDB
(2R,3R)-(-)-2,3-Butanediol	HMDB
(2R,3R)-Butane-2,3-diol	HMDB
L-(-)-2,3-Butanediol	HMDB
levo-2,3-Butanediol	HMDB

Molecular Formula

C₄H₁₀O₂

Average Mass

90.121

Monoisotopic Mass

90.068079564

IUPAC Name

(2R,3R)-butane-2,3-diol

Traditional Name

(R,R)-butane-2,3-diol

CAS Registry Number

24347-58-8

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-/m1/s1

InChI Key

OWBTYPJTUOEWEK-QWWZWVQMSA-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

butane-2,3-diol (CHEBI:16982 )

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	9.82 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
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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-373d8ab05d8ca30b9936	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-9000000000-c995422d63c292e20b8f	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-5639537d59074e5a4a6c	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-aa5e86f920a11ea2d749	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-cef0995334342db934ba	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-c4f65aef56394c6d3a25	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-2e058d12c0f9880bd53d	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-77a30103f1d168eecd21	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-4c2f1d8ca7aa89a88c6c	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-09fc38b483234e7b66aa	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000f-9000000000-79fde7f9417c0129ac4c	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-452a5f79625d3401d495	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192231	Ubiquitin-conjugating enzyme E2 D2	Enzyme	P62837	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0008242	(2R,3R)-2,3-Butanediol	(R)-acetoin	Not Available	R R butanediol dehydrogenase	VMH	30371894
MMDBr0008256	(2R,3R)-2,3-Butanediol	(2R,3R)-2,3-Butanediol	Not Available	R R butanediol transport inout via diffusion reversible	VMH	30371894
MMDBr0014441	(2R,3R)-2,3-Butanediol	(R)-acetoin	Alcohol dehydrogenase	Dehydrogenation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	121	Human ; Human saliva; Human feces; Human pleural fluid plaque; Human subgingival plaque; Cattle	Microbial culture; Metabolic reconstruction
Bacteria	Actinobacteria	21	Human feces; Human	Microbial culture; Metabolic reconstruction
Bacteria	Proteobacteria	49	Human ; Human sputum; Human subgingival plaque; Human feces	Microbial culture; Metabolic reconstruction
Bacteria	Bacteroidetes	1		Microbial culture
Bacteria	Spirochaetes	1		Microbial culture
Bacteria	Fusobacteria	1	Human ; Human feces	Metabolic reconstruction
Bacteria/NULL	Proteobacteria	1	Human ; Human sputum; Human subgingival plaque; Human feces	Microbial culture; Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant		Theobroma cacao	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0033007

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010997

KNApSAcK ID

Not Available

Chemspider ID

196452

KEGG Compound ID

C03044

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

225936

PDB ID

Not Available

ChEBI ID

16982

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Hermann T: Industrial production of amino acids by coryneform bacteria. J Biotechnol. 2003 Sep 4;104(1-3):155-72. doi: 10.1016/s0168-1656(03)00149-4. [PubMed:12948636 ]
Aklujkar M, Haveman SA, DiDonato R Jr, Chertkov O, Han CS, Land ML, Brown P, Lovley DR: The genome of Pelobacter carbinolicus reveals surprising metabolic capabilities and physiological features. BMC Genomics. 2012 Dec 10;13:690. doi: 10.1186/1471-2164-13-690. [PubMed:23227809 ]
Venkataraman A, Rosenbaum MA, Werner JJ, Winans SC, Angenent LT: Metabolite transfer with the fermentation product 2,3-butanediol enhances virulence by Pseudomonas aeruginosa. ISME J. 2014 Jun;8(6):1210-20. doi: 10.1038/ismej.2013.232. Epub 2014 Jan 9. [PubMed:24401856 ]
Paek J, Shin JH, Shin Y, Park IS, Jin TE, Kook JK, Wie SH, Cho HG, Park SJ, Chang YH: Myroides injenensis sp. nov., a new member isolated from human urine. Antonie Van Leeuwenhoek. 2015 Jan;107(1):201-7. doi: 10.1007/s10482-014-0317-y. Epub 2014 Dec 17. [PubMed:25515411 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for (2R,3R)-2,3-Butanediol (MMDBc0000278)

MOL for #<Metabolite:0x000055d24b2d8d68>

3D MOL for #<Metabolite:0x000055d24b2d8d68>

3D SDF for #<Metabolite:0x000055d24b2d8d68>

3D-SDF for #<Metabolite:0x000055d24b2d8d68>

PDB for #<Metabolite:0x000055d24b2d8d68>

3D PDB for #<Metabolite:0x000055d24b2d8d68>

SMILES for #<Metabolite:0x000055d24b2d8d68>

INCHI for #<Metabolite:0x000055d24b2d8d68>

Structure for #<Metabolite:0x000055d24b2d8d68>

3D Structure for #<Metabolite:0x000055d24b2d8d68>