Livestock Metabolome Database: Showing metabocard for Alpha-Lactose (LMDB00082)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:41:58 UTC

Update Date

2016-09-23 18:44:38 UTC

Lmdb

LMDB00082

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Alpha-Lactose

Description

alpha-Lactose is the major sugar present in milk and the main source of energy supplied to the newborn mammalian in its mother's milk. Lactose is also an important osmotic regulator of lactation. It is digested by the intestinal lactase (EC 3.2.1.108), an enzyme expressed in newborns. Its activity declines following weaning. As a result, adult mammals are normally lactose-intolerant and more than 75% of the animal adult population suffers from lactase deficiency. Lactase deficiency is present in up to 80 percent of blacks and Latinos, and up to 100 percent of American Indians and Asians. Persons with lactose intolerance are unable to digest significant amounts of lactose. Common symptoms include abdominal pain and bloating, excessive flatus, and watery stool following the ingestion of foods containing lactose. A sizable number of adults believe they are lactose intolerant but do not actually have impaired lactose digestion, and some persons with lactase deficiency can tolerate moderate amounts of ingested lactose. A diagnosis of lactose intolerance can usually be made with a careful history supported by dietary manipulation. If necessary, diagnosis can be confirmed by using a breath hydrogen or lactose tolerance test. These mostly uncomfortable symptoms of lactose maldigestion are blamed for a variably dairy consumption. There is, however, emerging evidence that certain lactic acid-producing bacteria, which selectively consume prebiotics, may be beneficial against some lower intestinal diseases. Lactose maldigestion and lactose should perhaps be re-evaluated as a potential provider of such a prebiotic. Treatment consists primarily of avoiding lactose-containing foods. Lactase enzyme supplements may be helpful. The degree of lactose malabsorption varies greatly among patients with lactose intolerance, but most of them can ingest up to 350 mL of milk daily without symptoms. Lactose-intolerant patients must ensure adequate calcium intake. (PMID: 13130292 , 12216958 , 12197838 , 12018807 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-beta-D-Galactopyranosyl-4-alpha-D-glucopyranose	ChEBI
4-O-beta-D-Galactopyranosyl-alpha-D-glucopyranose	ChEBI
Anhydrous lactose	ChEBI
beta-D-Galp-(1->4)-alpha-D-GLCP	ChEBI
Lactose	ChEBI
Milk sugar	ChEBI
1-b-D-Galactopyranosyl-4-a-D-glucopyranose	Generator
1-Β-D-galactopyranosyl-4-α-D-glucopyranose	Generator
4-O-b-D-Galactopyranosyl-a-D-glucopyranose	Generator
4-O-Β-D-galactopyranosyl-α-D-glucopyranose	Generator
b-D-Galp-(1->4)-a-D-GLCP	Generator
Β-D-galp-(1->4)-α-D-GLCP	Generator
a-Lactose	Generator
Α-lactose	Generator
(+)-Lactose	HMDB
1-beta-delta-Galactopyranosyl-4-alpha-delta-glucopyranose	HMDB
4-O-Hexopyranosylhexose	HMDB
Aletobiose	HMDB
Dilactose	HMDB
Fast-flo lactose	HMDB
Flowlac 100	HMDB
Galactinum	HMDB
GLC-(4-1)Gal	HMDB
Granulac 140m	HMDB
Lactin	HMDB
Lactin (carbohydrate)	HMDB
Lactobiose	HMDB
Lactohale 300	HMDB
Lactose anhydride	HMDB
Lactose fast-flo	HMDB
Osmolactan	HMDB
Pharmatosa DCL 21	HMDB
Pharmatose 21	HMDB
Pharmatose 325m	HMDB
Pharmatose DCL 15	HMDB
Prismalac	HMDB
Respitose ML 003	HMDB
Respitose SV 003	HMDB
Saccharum lactin	HMDB
Sachelac	HMDB
Sorbalac 400	HMDB
Sorbolac 400	HMDB
Spherolac	HMDB
Super-tab	HMDB
Tablettose	HMDB
Tablettose 70	HMDB
Tablettose 80	HMDB
Zeparox ep	HMDB
Lactose, anhydrous	HMDB

Chemical Formula

C₁₂H₂₂O₁₁

Average Molecular Weight

342.2965

Monoisotopic Molecular Weight

342.116211546

IUPAC Name

(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol

Traditional Name

α-lactose

CAS Registry Number

63-42-3

SMILES

OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5+,6+,7-,8-,9-,10-,11+,12+/m1/s1

InChI Key

GUBGYTABKSRVRQ-XLOQQCSPSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
Disaccharide
Oxane
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

lactose (CHEBI:36219 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	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	-3	ALOGPS
logP	-4.7	ChemAxon
logS	0.23	ALOGPS
pKa (Strongest Acidic)	11.25	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	189.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	68.34 m³·mol⁻¹	ChemAxon
Polarizability	30.92 Å³	ChemAxon
Number of Rings	2	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	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)	splash10-0uxs-0972000000-af8ca1bf1faa3d01a08d	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS; 1 MEOX)	splash10-00di-9741000000-a61bf0223a1683f0402e	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS; 1 MEOX)	splash10-00di-9641000000-12611bfab50cb066e8af	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03e9-4897000000-332d470623cd7f1e1ced	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-014i-3513539000-d702fa4adb45f44530b6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_16) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_11) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_12) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_20) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_32) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_33) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Alpha-Lactose,3TBDMS,#3" TMS) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-0901000000-bcb7aaa42261d980d488	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000f-9300000000-1bc18b05388cd2213573	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-01p9-9000000000-4483af567feecb34a651	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03gl-0907000000-a1de7813fbe8b5258c10	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-0900000000-79cc5059a3f338e8c1dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-3900000000-851d0bc84d91b6e09579	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002f-0749000000-af1d18f2bc3ab8e02883	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0200-2902000000-67218697344afb9e70fa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01td-4900000000-40aa2d8125769803cfbb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000x-1069000000-9cd867711bca0eecf935	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9365000000-65403961bfb5e35eaa0d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000l-9200000000-0de9785c1c5df1430dd2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0109000000-9d0f9a68a67bafd734ab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01rw-3898000000-7f495a1bcfdbed6466c4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ti-9210000000-b8a83657f0266d372bee	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Colostrum
Milk
Ruminal Fluid

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Colostrum	Detected and Quantified	116857.753-146072.192 uM	Not Available	Bovine	11242449	details
Colostrum	Detected and Quantified	27-46 uM	Not Available	Bovine	11242449	details
Colostrum	Detected and Quantified	78878.984-134386.416 uM	Not Available	Bovine	11242449	details
Milk	Detected and Quantified	134386.416 uM	Not Available	Bovine	11242449	details
Milk	Detected and Quantified	46200+/-400 mg/kg	Not Available	Bovine	23040012	details
Milk	Detected and Quantified	46200+/-400 mg/kg	Not Available	Bovine	23040012	details
Milk	Detected and Quantified	47100+/-700 mg/kg	Not Available	Bovine	23040012	details
Milk	Detected and Quantified	47500+/-400 mg/kg	Not Available	Bovine	23040012	details
Milk	Detected and Quantified	47800+/-300 mg/kg	Not Available	Bovine	23040012	details
Milk	Detected and Quantified	45600 mg/kg	Not Available	Ovine	22004605	details
Milk	Detected and Quantified	46000 mg/kg	Not Available	Ovine	22004605	details
Milk	Detected and Quantified	47100 mg/kg	Not Available	Ovine	22004605	details
Milk	Detected and Quantified	47300 mg/kg	Not Available	Ovine	22004605	details
Milk	Detected and Quantified	48300 mg/kg	Not Available	Ovine	22004605	details
Milk	Detected and Quantified	49100 mg/kg	Not Available	Ovine	22004605	details
Milk	Detected and Quantified	43200-43300 mg/kg	Not Available	Caprine	24704223	details
Milk	Detected and Quantified	43100 mg/kg	Not Available	Caprine	24704223	details
Milk	Detected and Quantified	42400-44100 mg/kg	Not Available	Caprine	24704223	details
Milk	Detected and Quantified	41500-44100 mg/kg	Not Available	Caprine	24704223	details
Milk	Detected and Quantified	45792 - 61243 uM	Not Available	Bovine	20338431	details
Milk	Detected and Quantified	18.989 uM	Not Available	Bovine	25087032	details
Milk	Detected and Quantified	124736-153216 uM	Not Available	Bovine	22098372	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23182357	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Ovine	5829180	details
Milk	Detected and Quantified	44900 mg/kg	Not Available	Bovine	9718493	details
Milk	Detected and Quantified	44900 mg/kg	Not Available	Bovine	9718493	details
Milk	Detected and Quantified	46400 mg/kg	Not Available	Bovine	9718493	details
Milk	Detected and Quantified	47500 mg/kg	Not Available	Bovine	9718493	details
Milk	Detected and Quantified	47500 mg/kg	Not Available	Bovine	9718493	details
Milk	Detected and Quantified	47800 mg/kg	Not Available	Bovine	9718493	details
Milk	Detected and Quantified	48100 mg/kg	Not Available	Bovine	9718493	details
Milk	Detected and Quantified	48100 mg/kg	Not Available	Bovine	9718493	details
Milk	Detected and Quantified	48900 mg/kg	Not Available	Bovine	9718493	details
Milk	Detected and Quantified	49000 mg/kg	Not Available	Bovine	9718493	details
Milk	Detected and Quantified	49200 mg/kg	Not Available	Bovine	9718493	details
Milk	Detected and Quantified	72-116 g/d	Not Available	Caprine	Park, Y. W; Juáre...	details
Milk	Detected and Quantified	49200 mg/kg	Not Available	Bovine	9718493	details
Milk	Detected and Quantified	52-84 g/d	Not Available	Caprine	Park, Y. W; Juáre...	details
Milk	Detected and Quantified	49300 mg/kg	Not Available	Bovine	9718493	details
Milk	Detected and Quantified	64-120 g/d	Not Available	Caprine	Park, Y. W; Juáre...	details
Milk	Detected and Quantified	49400 mg/kg	Not Available	Bovine	9718493	details
Milk	Detected and Quantified	43-104 g/d	Not Available	Caprine	Park, Y. W; Juáre...	details
Milk	Detected and Quantified	49900 mg/kg	Not Available	Bovine	9718493	details
Milk	Detected and Quantified	43800-44100 mg/kg	Not Available	Caprine	Park, Y. W; Juáre...	details
Milk	Detected and Quantified	42400-42800 mg/kg	Not Available	Caprine	Park, Y. W; Juáre...	details
Milk	Detected and Quantified	41500-42900 mg/kg	Not Available	Caprine	Park, Y. W; Juáre...	details
Milk	Detected and Quantified	41600-44100 mg/kg	Not Available	Caprine	Park, Y. W; Juáre...	details
Ruminal Fluid	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000186

FooDB ID

FDB021789

Phenol Explorer ID

Not Available

KNApSAcK ID

BiGG ID

BioCyc ID

METLIN ID

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

ECMDB00186

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Delaveau P: [Milk lactose. Hypothesis on its biological importance]. Ann Pharm Fr. 2003;61(5):340-2. [13130292 ]
Vilotte JL: Lowering the milk lactose content in vivo: potential interests, strategies and physiological consequences. Reprod Nutr Dev. 2002 Mar-Apr;42(2):127-32. [12216958 ]
Szilagyi A: Review article: lactose--a potential prebiotic. Aliment Pharmacol Ther. 2002 Sep;16(9):1591-602. [12197838 ]
Swagerty DL Jr, Walling AD, Klein RM: Lactose intolerance. Am Fam Physician. 2002 May 1;65(9):1845-50. [12018807 ]

Showing metabocard for Alpha-Lactose (LMDB00082)

Structure for LMDB00082 (Alpha-Lactose)