MiMeDB: Showing metabocard for 3-deoxy-D-manno-2-octulosonate (MMDBc0051559)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 20:27:38 UTC

Update Date

2022-09-01 02:18:35 UTC

Metabolite ID

MMDBc0051559

Metabolite Identification

Common Name

3-deoxy-D-manno-2-octulosonate

Description

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303082006182D          

 20 20  0  0  1  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7144   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2414    0.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5235    0.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717   -0.4887    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.7111   -0.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  6  0  0  0
  6  5  1  0  0  0  0
  8  1  1  0  0  0  0
  8  7  1  6  0  0  0
  9  2  1  0  0  0  0
  3 10  1  6  0  0  0
  4 11  1  1  0  0  0
  5 12  1  1  0  0  0
 13  7  2  0  0  0  0
 14  7  1  0  0  0  0
  8 15  1  1  0  0  0
 16  6  1  0  0  0  0
 16  8  1  0  0  0  0
  3 17  1  1  0  0  0
  4 18  1  1  0  0  0
  5 19  1  1  0  0  0
  6 20  1  1  0  0  0
M  CHG  1  14  -1
M  END
> <DATABASE_ID>
MMDBc0051559

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](O)(CO)[C@@]1([H])O[C@](O)(C[C@@]([H])(O)[C@@]1([H])O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H14O8/c9-2-4(11)6-5(12)3(10)1-8(15,16-6)7(13)14/h3-6,9-12,15H,1-2H2,(H,13,14)/p-1/t3-,4-,5-,6-,8-/m1/s1

> <INCHI_KEY>
NNLZBVFSCVTSLA-HXUQBWEZSA-M

> <FORMULA>
C8H13O8

> <MOLECULAR_WEIGHT>
237.185

> <EXACT_MASS>
237.061590959

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
20.487564427970643

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,4R,5R,6R)-6-[(1R)-1,2-dihydroxyethyl]-2,4,5-trihydroxyoxane-2-carboxylate

> <ALOGPS_LOGP>
-2.30

> <JCHEM_LOGP>
-2.6455673833333333

> <ALOGPS_LOGS>
0.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.111294812920784

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.890134275479364

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9745201549719393

> <JCHEM_POLAR_SURFACE_AREA>
150.51

> <JCHEM_REFRACTIVITY>
57.5547

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.63e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4R,5R,6R)-6-[(1R)-1,2-dihydroxyethyl]-2,4,5-trihydroxyoxane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-MAR-20         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.184   0.267   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.711   1.715   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.174  -0.912   0.000  0.00  0.00           O-1
HETATM   15  O   UNK     0       3.194  -1.447   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0       0.000   3.080   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0      -1.334   0.770   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       0.000  -1.540   0.000  0.00  0.00           H+0
CONECT    1    3    8                                                       
CONECT    2    4    9                                                       
CONECT    3    1    5   10   17                                             
CONECT    4    2    6   11   18                                             
CONECT    5    3    6   12   19                                             
CONECT    6    4    5   16   20                                             
CONECT    7    8   13   14                                                  
CONECT    8    1    7   15   16                                             
CONECT    9    2                                                            
CONECT   10    3                                                            
CONECT   11    4                                                            
CONECT   12    5                                                            
CONECT   13    7                                                            
CONECT   14    7                                                            
CONECT   15    8                                                            
CONECT   16    6    8                                                       
CONECT   17    3                                                            
CONECT   18    4                                                            
CONECT   19    5                                                            
CONECT   20    6                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

Synonyms

Value	Source
3-Deoxy-D-manno-2-octulosonic acid	Generator
3-Deoxy-a-D-manno-oct-2-ulosonate	Generator
3-Deoxy-a-D-manno-oct-2-ulosonic acid	Generator
3-Deoxy-alpha-D-manno-oct-2-ulosonic acid	Generator
3-Deoxy-α-D-manno-oct-2-ulosonate	Generator
3-Deoxy-α-D-manno-oct-2-ulosonic acid	Generator

Molecular Formula

C₈H₁₃O₈

Average Mass

237.185

Monoisotopic Mass

237.061590959

IUPAC Name

(2R,4R,5R,6R)-6-[(1R)-1,2-dihydroxyethyl]-2,4,5-trihydroxyoxane-2-carboxylate

Traditional Name

(2R,4R,5R,6R)-6-[(1R)-1,2-dihydroxyethyl]-2,4,5-trihydroxyoxane-2-carboxylate

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(CO)[C@@]1([H])O[C@](O)(C[C@@]([H])(O)[C@@]1([H])O)C([O-])=O

InChI Identifier

InChI=1S/C8H14O8/c9-2-4(11)6-5(12)3(10)1-8(15,16-6)7(13)14/h3-6,9-12,15H,1-2H2,(H,13,14)/p-1/t3-,4-,5-,6-,8-/m1/s1

InChI Key

NNLZBVFSCVTSLA-HXUQBWEZSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through a C-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

C-glucuronides

Alternative Parents

Substituents

C-glucuronide
C-glycosyl compound
Glycosyl compound
Monosaccharide
Oxane
Pyran
Hemiacetal
Secondary alcohol
Polyol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organic anion
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

carbohydrate acid anion (CHEBI:85986 )
monocarboxylic acid anion (CHEBI:85986 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	863 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-2.6	ChemAxon
logS	0.53	ALOGPS
pKa (Strongest Acidic)	2.89	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	150.51 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	57.55 m³·mol⁻¹	ChemAxon
Polarizability	20.49 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

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

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0013015	3-deoxy-alpha-D-manno-2-octulosonate-8-phosphate	3-deoxy-D-manno-2-octulosonate	3-deoxy-D-manno-octulosonate 8-phosphate phosphatase KdsC	Dephosphorylation	RHEA	34755880
MMDBr0014337	3-deoxy-D-manno-2-octulosonate	CMP-3-deoxy-beta-D-manno-octulosonate	3-deoxy-manno-octulosonate cytidylyltransferase	Transfer of a cytidylyl group	RHEA	34755880
MMDBr0016261	3-deoxy-D-manno-2-octulosonate	3,8-dideoxy-8-oxo-alpha-D-manno-octulosonic acid	3-deoxy-alpha-D-manno-octulosonate 8-oxidase	Oxidation	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
Bacteria	Proteobacteria	323	Human ; Human feces; Pig ; Cattle ; River trout ; Rat ; Turkey ; Sheep ; Lion ; Chicken ; American dog tick ; Human feces; pleural fluid plaque; bal; Human stool
Bacteria	Cyanobacteria	3
Bacteria	Acidobacteria	3
Bacteria	Aquificae	1
Bacteria	Bacteroidetes	9	Human ; Human feces
Bacteria	Chlamydiae	10	Human ; Sheep ; Cat
Bacteria	Chlorobi	11
Bacteria/NULL	Proteobacteria	2	Human ; Human feces; Pig ; Cattle ; River trout ; Rat ; Turkey ; Sheep ; Lion ; Chicken ; American dog tick ; Human feces; pleural fluid plaque; bal; Human stool
Bacteria	Elusimicrobia	1
Bacteria	Fusobacteria	1	Human ; Human feces
Bacteria	Gemmatimonadetes	1
Bacteria	Spirochaetes	6	Human
Bacteria	Planctomycetes	1
Bacteria	Nitrospirae	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21681234

PDB ID

Not Available

ChEBI ID

85986

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 3-deoxy-D-manno-2-octulosonate (MMDBc0051559)

MOL for #<Metabolite:0x00007f5a908d8f78>

3D MOL for #<Metabolite:0x00007f5a908d8f78>

3D SDF for #<Metabolite:0x00007f5a908d8f78>

3D-SDF for #<Metabolite:0x00007f5a908d8f78>

PDB for #<Metabolite:0x00007f5a908d8f78>

3D PDB for #<Metabolite:0x00007f5a908d8f78>

SMILES for #<Metabolite:0x00007f5a908d8f78>

INCHI for #<Metabolite:0x00007f5a908d8f78>

Structure for #<Metabolite:0x00007f5a908d8f78>

3D Structure for #<Metabolite:0x00007f5a908d8f78>