Bovine Metabolome Database: Showing metabocard for D-Lactic acid (BMDB0001311)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:43:57 UTC

Update Date

2020-06-04 20:34:30 UTC

BMDB ID

BMDB0001311

Secondary Accession Numbers

BMDB01311

Metabolite Identification

Common Name

D-Lactic acid

Description

L-Lactic acid, also known as D-lactate or D-milchsaeure, belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. L-Lactic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. L-Lactic acid exists in all living species, ranging from bacteria to humans. L-Lactic acid participates in a number of enzymatic reactions, within cattle. In particular, L-Lactic acid can be converted into pyruvic acid; which is catalyzed by the enzyme L-lactate dehydrogenase. In addition, L-Lactic acid can be converted into L-lactic acid through the action of the enzyme monocarboxylate transporter. In cattle, L-lactic acid is involved in the metabolic pathway called cancer (via the Warburg effect). L-Lactic acid is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Lactic acid	ChEBI
(R)-(-)-Lactic acid	ChEBI
D-2-Hydroxypropanoic acid	ChEBI
D-2-Hydroxypropionic acid	ChEBI
D-Milchsaeure	ChEBI
LACTIC ACID	ChEBI
D-Lactate	Kegg
(-)-Lactate	Generator
(R)-(-)-Lactate	Generator
D-2-Hydroxypropanoate	Generator
D-2-Hydroxypropionate	Generator
LACTate	Generator
L-Lactate	HMDB
(R)-2-Hydroxypropanoate	HMDB
(R)-2-Hydroxypropanoic acid	HMDB
(R)-2-Hydroxypropionate	HMDB
(R)-2-Hydroxypropionic acid	HMDB
(R)-a-Hydroxypropionate	HMDB
(R)-a-Hydroxypropionic acid	HMDB
(R)-alpha-Hydroxypropionate	HMDB
(R)-alpha-Hydroxypropionic acid	HMDB
(R)-Lactate	HMDB
(R)-Lactic acid	HMDB
D-(-)-Lactate	HMDB
D-(-)-Lactic acid	HMDB
delta-(-)-Lactate	HMDB
delta-(-)-Lactic acid	HMDB
delta-2-Hydroxypropanoate	HMDB
delta-2-Hydroxypropanoic acid	HMDB
delta-2-Hydroxypropionate	HMDB
delta-2-Hydroxypropionic acid	HMDB
delta-Lactate	HMDB
delta-Lactic acid	HMDB
DLA	HMDB
L-(+)-Lactate	HMDB
Propel	HMDB
Tisulac	HMDB
2 Hydroxypropanoic acid	HMDB
2 Hydroxypropionic acid	HMDB
2-Hydroxypropanoic acid	HMDB
Ammonium lactate	HMDB
L Lactic acid	HMDB
2-Hydroxypropionic acid	HMDB
Sarcolactic acid	HMDB
D Lactic acid	HMDB
Lactate, ammonium	HMDB
L-Lactic acid	HMDB
D-Lactic acid	ChEBI

Chemical Formula

C₃H₆O₃

Average Molecular Weight

90.0779

Monoisotopic Molecular Weight

90.031694058

IUPAC Name

(2R)-2-hydroxypropanoic acid

Traditional Name

D-lactic acid

CAS Registry Number

10326-41-7

SMILES

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

InChI Identifier

InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m1/s1

InChI Key

JVTAAEKCZFNVCJ-UWTATZPHSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Alpha hydroxy acids and derivatives

Direct Parent

Alpha hydroxy acids and derivatives

Alternative Parents

Substituents

Alpha-hydroxy acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-hydroxypropanoic acid (CHEBI:42111 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	52.8 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.79	ALOGPS
logP	-0.47	ChemAxon
logS	0.79	ALOGPS
pKa (Strongest Acidic)	3.78	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	18.84 m³·mol⁻¹	ChemAxon
Polarizability	8.05 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00kb-0900000000-fb59ec16914501aa19ab	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014j-0900000000-c4d9e12b4b0150eda54b	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kb-0900000000-fb59ec16914501aa19ab	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-a3691f383d440fb00e1f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-01b9-9620000000-f7faa7db9c1be3d9d975	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000i-9000000000-704f8ff33156c82a02d1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-000m-9000000000-023931446d9bb3330e7f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-000l-9000000000-0fb29afb128baea2240b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-000i-9000000000-d7cd347946e49a57860e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-aee01e43e8ee93db755d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000f-9000000000-581a00222505e9e4b458	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-5bfd9fdf1c0df2054452	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-9000000000-5f417f4a6d08f0ab00ed	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dm-9000000000-df7a94bb1a9cf6e78e1a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004j-9000000000-dc2a1b965287b9dfee9c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-c3686a681cc9bbf039e1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-ddad20647c2ac56efd22	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-b728b45617afcc6b67da	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-b586cb8f053eb4465b4e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-400a5f1c0dfcc32ef2bb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0007-9000000000-ad5eb77c7e0a96f3a40a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-00ba25458eb6c0cc2940	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-00ba25458eb6c0cc2940	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-00ba25458eb6c0cc2940	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-002b-9000000000-50213d6b39ef9741c466	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Bladder
Brain
Epidermis
Fibroblasts
Intestine
Liver
Mammary Gland
Neuron
Placenta
Platelet
Ruminal Fluid
Semen
Skeletal Muscle
Spleen
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Pyruvaldehyde Degradation		Not Available
Gluconeogenesis		Not Available
Pyruvate Metabolism		Not Available
Warburg Effect		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Bladder	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	3560 +/- 270 uM	Adult	Both	Normal	PMID: 15135111	details
Semen	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31533629	details
Semen	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 29634739	details
Skeletal Muscle	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Spleen	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details