MiMeDB: Showing metabocard for 3-(L-alanyl-L-homoserinyl-L-aspartyl-Î²carboxy)-4-hydroxy-5-oxopyrazole (MMDBc0008546)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 01:22:12 UTC

Update Date

2022-08-31 06:28:46 UTC

Metabolite ID

MMDBc0008546

Metabolite Identification

Common Name

3-(L-alanyl-L-homoserinyl-L-aspartyl-Î²carboxy)-4-hydroxy-5-oxopyrazole

Description

SCHEMBL17867436 belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Based on a literature review very few articles have been published on SCHEMBL17867436.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152103222D          

 31 31  0  0  1  0            999 V2000
   -4.1212    3.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2337    0.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462    0.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8288    3.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7087    2.3424    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6462    1.6280    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0038    3.0569    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2413    3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2992    4.5721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8837    2.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2337    2.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4708    5.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4788    4.4858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4087    3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1212    1.6280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4712    1.6280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4087    2.3424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7563    5.7915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1432    5.2395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2337   -0.5155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8288    4.4858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8513    3.9590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4712    3.0569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462    3.0569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2245    5.7146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2337    3.7714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0038    4.4858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0663    3.7714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2962    3.0569    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    1.6280    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4163    3.7714    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  4  1  0  0  0  0
  8  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 14  7  1  0  0  0  0
  5 15  1  6  0  0  0
  6 16  1  1  0  0  0
 16 10  2  0  0  0  0
  7 17  1  1  0  0  0
 17 11  2  0  0  0  0
 18 12  1  0  0  0  0
 19 13  2  0  0  0  0
 19 18  1  0  0  0  0
 20  3  1  0  0  0  0
 21  8  2  0  0  0  0
 22  9  1  0  0  0  0
 10 23  1  4  0  0  0
 11 24  1  4  0  0  0
 25 12  1  0  0  0  0
 26 14  2  0  0  0  0
 27 14  1  0  0  0  0
 28  8  1  0  0  0  0
 28 13  1  0  0  0  0
  5 29  1  6  0  0  0
  6 30  1  1  0  0  0
  7 31  1  1  0  0  0
M  END


  Mrv1652305152103222D          

 31 31  0  0  1  0            999 V2000
   -4.1212    3.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2337    0.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462    0.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8288    3.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7087    2.3424    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6462    1.6280    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0038    3.0569    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2413    3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2992    4.5721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8837    2.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2337    2.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4708    5.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4788    4.4858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4087    3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1212    1.6280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4712    1.6280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4087    2.3424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7563    5.7915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1432    5.2395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2337   -0.5155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8288    4.4858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8513    3.9590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4712    3.0569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462    3.0569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2245    5.7146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2337    3.7714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0038    4.4858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0663    3.7714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2962    3.0569    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    1.6280    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4163    3.7714    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  4  1  0  0  0  0
  8  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 14  7  1  0  0  0  0
  5 15  1  6  0  0  0
  6 16  1  1  0  0  0
 16 10  2  0  0  0  0
  7 17  1  1  0  0  0
 17 11  2  0  0  0  0
 18 12  1  0  0  0  0
 19 13  2  0  0  0  0
 19 18  1  0  0  0  0
 20  3  1  0  0  0  0
 21  8  2  0  0  0  0
 22  9  1  0  0  0  0
 10 23  1  4  0  0  0
 11 24  1  4  0  0  0
 25 12  1  0  0  0  0
 26 14  2  0  0  0  0
 27 14  1  0  0  0  0
 28  8  1  0  0  0  0
 28 13  1  0  0  0  0
  5 29  1  6  0  0  0
  6 30  1  1  0  0  0
  7 31  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0008546

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](C)(N)C(O)=N[C@@]([H])(CCO)C(O)=N[C@@]([H])(CC(=O)OC1=NNC(O)=C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H21N5O9/c1-5(15)10(23)16-6(2-3-20)11(24)17-7(14(26)27)4-8(21)28-13-9(22)12(25)18-19-13/h5-7,20,22H,2-4,15H2,1H3,(H,16,23)(H,17,24)(H,26,27)(H2,18,19,25)/t5-,6-,7-/m0/s1

> <INCHI_KEY>
OSMOXHWFOQKIKE-ACZMJKKPSA-N

> <FORMULA>
C14H21N5O9

> <MOLECULAR_WEIGHT>
403.348

> <EXACT_MASS>
403.133927276

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
37.48072051523445

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1,4-dihydroxybutylidene]amino}-4-[(4,5-dihydroxy-1H-pyrazol-3-yl)oxy]-4-oxobutanoic acid

> <ALOGPS_LOGP>
-1.96

> <JCHEM_LOGP>
-3.376226812406124

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.1927854061751475

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.6289150819721385

> <JCHEM_PKA_STRONGEST_BASIC>
7.495061555077432

> <JCHEM_POLAR_SURFACE_AREA>
244.16999999999993

> <JCHEM_REFRACTIVITY>
90.3427

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1,4-dihydroxybutylidene]amino}-4-[(4,5-dihydroxy-1H-pyrazol-3-yl)oxy]-4-oxobutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      -7.693   5.706   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.303   1.705   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.073   0.371   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.547   5.706   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.923   4.373   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.073   3.039   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.007   5.706   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.317   7.040   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.159   8.535   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.383   4.373   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.303   4.373   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.479  10.041   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.627   8.374   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.763   7.040   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -7.693   3.039   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      -4.613   3.039   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      -0.763   4.373   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       5.145  10.811   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       4.001   9.780   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      -2.303  -0.962   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.547   8.374   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.189   7.390   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.613   5.706   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -3.073   5.706   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.886  10.667   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -2.303   7.040   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.007   8.374   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       3.857   7.040   0.000  0.00  0.00           O+0
HETATM   29  H   UNK     0      -6.153   5.706   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.533   3.039   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.777   7.040   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2    3    6                                                       
CONECT    3    2   20                                                       
CONECT    4    7    8                                                       
CONECT    5    1   10   15   29                                             
CONECT    6    2   11   16   30                                             
CONECT    7    4   14   17   31                                             
CONECT    8    4   21   28                                                  
CONECT    9   12   13   22                                                  
CONECT   10    5   16   23                                                  
CONECT   11    6   17   24                                                  
CONECT   12    9   18   25                                                  
CONECT   13    9   19   28                                                  
CONECT   14    7   26   27                                                  
CONECT   15    5                                                            
CONECT   16    6   10                                                       
CONECT   17    7   11                                                       
CONECT   18   12   19                                                       
CONECT   19   13   18                                                       
CONECT   20    3                                                            
CONECT   21    8                                                            
CONECT   22    9                                                            
CONECT   23   10                                                            
CONECT   24   11                                                            
CONECT   25   12                                                            
CONECT   26   14                                                            
CONECT   27   14                                                            
CONECT   28    8   13                                                       
CONECT   29    5                                                            
CONECT   30    6                                                            
CONECT   31    7                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   62    0
END

Synonyms

Not Available

Molecular Formula

C₁₄H₂₁N₅O₉

Average Mass

403.348

Monoisotopic Mass

403.133927276

IUPAC Name

(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1,4-dihydroxybutylidene]amino}-4-[(4,5-dihydroxy-1H-pyrazol-3-yl)oxy]-4-oxobutanoic acid

Traditional Name

(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1,4-dihydroxybutylidene]amino}-4-[(4,5-dihydroxy-1H-pyrazol-3-yl)oxy]-4-oxobutanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](C)(N)C(O)=N[C@@]([H])(CCO)C(O)=N[C@@]([H])(CC(=O)OC1=NNC(O)=C1O)C(O)=O

InChI Identifier

InChI=1S/C14H21N5O9/c1-5(15)10(23)16-6(2-3-20)11(24)17-7(14(26)27)4-8(21)28-13-9(22)12(25)18-19-13/h5-7,20,22H,2-4,15H2,1H3,(H,16,23)(H,17,24)(H,26,27)(H2,18,19,25)/t5-,6-,7-/m0/s1

InChI Key

OSMOXHWFOQKIKE-ACZMJKKPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Aspartic acid or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alanine or derivatives
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Fatty acid ester
Dicarboxylic acid or derivatives
N-acyl-amine
Pyrazolinone
Fatty amide
Fatty acyl
Vinylogous amide
Heteroaromatic compound
Pyrazole
Azole
Carboxylic acid ester
Secondary carboxylic acid amide
Carboxamide group
Amino acid or derivatives
Amino acid
Lactam
Azacycle
Organoheterocyclic compound
Carboxylic acid
Primary alcohol
Organic oxygen compound
Primary amine
Organic nitrogen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Amine
Organic oxide
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.73 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3.4	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	2.63	ChemAxon
pKa (Strongest Basic)	7.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	244.17 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	90.34 m³·mol⁻¹	ChemAxon
Polarizability	37.48 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

Not Available

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	Proteobacteria	1		Metabolic reconstruction

Exposure Sources

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

78437203

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25150672

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for 3-(L-alanyl-L-homoserinyl-L-aspartyl-Î²carboxy)-4-hydroxy-5-oxopyrazole (MMDBc0008546)

MOL for #<Metabolite:0x00007fdb4d2235c8>

3D MOL for #<Metabolite:0x00007fdb4d2235c8>

3D SDF for #<Metabolite:0x00007fdb4d2235c8>

3D-SDF for #<Metabolite:0x00007fdb4d2235c8>

PDB for #<Metabolite:0x00007fdb4d2235c8>

3D PDB for #<Metabolite:0x00007fdb4d2235c8>

SMILES for #<Metabolite:0x00007fdb4d2235c8>

INCHI for #<Metabolite:0x00007fdb4d2235c8>

Structure for #<Metabolite:0x00007fdb4d2235c8>

3D Structure for #<Metabolite:0x00007fdb4d2235c8>