MiMeDB: Showing metabocard for KDO-lipid IV(A) (MMDBc0031618)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:41:37 UTC

Update Date

2022-08-31 18:22:32 UTC

MiMeDB ID

MMDBc0031618

Metabolite Identification

Common Name

KDO-lipid IV(A)

Description

KDO-lipid IV(a) is a part of lipopolysaccharide or LPS. Specifically it is lipid IVA glycosylated with a single 3-deoxy-D-manno-octulosonic acid (KDO) residue. KDO-lipid IV(a) is a saccharolipid. The most familiar saccharolipids are the acylated glucosamine precursors of the lipid A component of the lipopolysaccharides in Gram-negative bacteria. Typical lipid A molecules are disaccharides of glucosamine, which are derivatized with as many as seven fatty-acyl chains. The minimal lipopolysaccharide required for growth in E. coli is Kdo2-Lipid A, a hexa-acylated disaccharide of glucosamine that is glycosylated with two 3-deoxy-D-manno-octulosonic acid (Kdo) residues.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Deoxy-D-manno-octulosonyl-2',3',2',3'-tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate	ChEBI
3-Deoxy-D-manno-octulosonyl-lipid IV(a)	ChEBI
3-Deoxy-D-manno-octulosonyl-2',3',2',3'-tetrakis(b-hydroxymyristoyl)-D-glucosaminyl-1,6-b-D-glucosamine 1,4'-bisphosphate	Generator
3-Deoxy-D-manno-octulosonyl-2',3',2',3'-tetrakis(b-hydroxymyristoyl)-D-glucosaminyl-1,6-b-D-glucosamine 1,4'-bisphosphoric acid	Generator
3-Deoxy-D-manno-octulosonyl-2',3',2',3'-tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphoric acid	Generator
3-Deoxy-D-manno-octulosonyl-2',3',2',3'-tetrakis(β-hydroxymyristoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1,4'-bisphosphate	Generator
3-Deoxy-D-manno-octulosonyl-2',3',2',3'-tetrakis(β-hydroxymyristoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1,4'-bisphosphoric acid	Generator

Chemical Formula

C₇₆H₁₄₂N₂O₃₀P₂

Average Molecular Weight

1625.8836

Monoisotopic Molecular Weight

1624.912264238

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C76H142N2O30P2/c1-5-9-13-17-21-25-29-33-37-41-53(80)45-61(86)77-65-71(104-63(88)47-55(82)43-39-35-31-27-23-19-15-11-7-3)68(91)59(102-74(65)108-110(97,98)99)51-100-73-66(78-62(87)46-54(81)42-38-34-30-26-22-18-14-10-6-2)72(105-64(89)48-56(83)44-40-36-32-28-24-20-16-12-8-4)70(107-109(94,95)96)60(103-73)52-101-76(75(92)93)49-57(84)67(90)69(106-76)58(85)50-79/h53-60,65-74,79-85,90-91H,5-52H2,1-4H3,(H,77,86)(H,78,87)(H,92,93)(H2,94,95,96)(H2,97,98,99)/t53-,54-,55-,56-,57-,58-,59-,60-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,76-/m1/s1

InChI Key

GPNCBCJEDRRCDW-ACUQGRCXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Acylaminosugars

Alternative Parents

Substituents

Acylaminosugar
Saccharolipid
Hexose phosphate
Disaccharide phosphate
N-acyl-alpha-hexosamine
C-glucuronide
C-glycosyl compound
Disaccharide
Glycosyl compound
O-glycosyl compound
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Ketal
Fatty acid ester
Monoalkyl phosphate
Fatty acyl
Fatty amide
Alkyl phosphate
Hydroxy acid
N-acyl-amine
Pyran
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Secondary carboxylic acid amide
Carboxamide group
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organoheterocyclic compound
Carboxylic acid
Oxacycle
Acetal
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Primary alcohol
Alcohol
Carbonyl group
Organonitrogen compound
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

lipid As (CHEBI:27439 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Phylum	Total species	Hosts and Body Sites	Microbial Links
Proteobacteria	172	Human Feces; Human ; Pig	Unknown; Metabolic reconstruction
Firmicutes	22	Pig ; Human Feces	Metabolic reconstruction
Actinobacteria	88	Human Feces; Human	Metabolic reconstruction
Verrucomicrobia	1	Human	Metabolic reconstruction
Bacteroidetes	116	Human Feces; Human	Metabolic reconstruction
Synergistetes	3	Human Feces	Metabolic reconstruction
Spirochaetes	1	Human Feces	Metabolic reconstruction
Thaumarchaeota	1	Human Feces	Metabolic reconstruction
Fusobacteria	19	Human Feces; Human	Metabolic reconstruction
Euryarchaeota	4	Human Feces; Cattle ; Human	Metabolic reconstruction
Planctomycetes	1	Human Feces	Metabolic reconstruction
Crenarchaeota	1	Human Feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

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		details

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C06024

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25203768

PDB ID

Not Available

ChEBI ID

27439

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for KDO-lipid IV(A) (MMDBc0031618)

MOL for #<Metabolite:0x000055b76de04f00>

3D MOL for #<Metabolite:0x000055b76de04f00>

3D SDF for #<Metabolite:0x000055b76de04f00>

3D-SDF for #<Metabolite:0x000055b76de04f00>

PDB for #<Metabolite:0x000055b76de04f00>

3D PDB for #<Metabolite:0x000055b76de04f00>

SMILES for #<Metabolite:0x000055b76de04f00>

INCHI for #<Metabolite:0x000055b76de04f00>

Structure for #<Metabolite:0x000055b76de04f00>

3D Structure for #<Metabolite:0x000055b76de04f00>