MiMeDB: Showing metabocard for Diprotin A (MMDBc0020920)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 11:04:20 UTC

Update Date

2022-08-31 06:47:11 UTC

Metabolite ID

MMDBc0020920

Metabolite Identification

Common Name

Diprotin A

Description

diprotin A, also known as ile-pro-ile, belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. Based on a literature review a significant number of articles have been published on diprotin A.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152113042D          

 29 29  0  0  1  0            999 V2000
   -0.5029   -2.8867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0301    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7232   -1.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0301   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2817   -3.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7445    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1570   -3.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4120   -2.5474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3320   -3.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8948   -2.5896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7445    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7445   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6794   -2.8445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4590   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7445   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2925   -2.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1735    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8509   -3.6515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4590   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0771   -2.5474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0301   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1210   -1.4855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1735    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8880   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1101   -2.3346    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0301    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4796   -1.6880    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5079   -2.0375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4590    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 10  3  1  6  0  0  0
 10  5  1  0  0  0  0
 11  4  1  1  0  0  0
 11  6  1  0  0  0  0
 12  8  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 12 15  1  6  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 13 18  1  6  0  0  0
 14 19  1  6  0  0  0
 19 15  2  0  0  0  0
 20  9  1  0  0  0  0
 20 12  1  0  0  0  0
 20 16  1  0  0  0  0
 15 21  1  4  0  0  0
 22 16  2  0  0  0  0
 23 17  2  0  0  0  0
 24 17  1  0  0  0  0
 10 25  1  1  0  0  0
 11 26  1  6  0  0  0
 12 27  1  1  0  0  0
 13 28  1  6  0  0  0
 14 29  1  6  0  0  0
M  END


  Mrv1652305152113042D          

 29 29  0  0  1  0            999 V2000
   -0.5029   -2.8867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0301    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7232   -1.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0301   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2817   -3.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7445    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1570   -3.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4120   -2.5474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3320   -3.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8948   -2.5896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7445    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7445   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6794   -2.8445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4590   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7445   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2925   -2.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1735    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8509   -3.6515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4590   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0771   -2.5474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0301   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1210   -1.4855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1735    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8880   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1101   -2.3346    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0301    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4796   -1.6880    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5079   -2.0375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4590    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 10  3  1  6  0  0  0
 10  5  1  0  0  0  0
 11  4  1  1  0  0  0
 11  6  1  0  0  0  0
 12  8  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 12 15  1  6  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 13 18  1  6  0  0  0
 14 19  1  6  0  0  0
 19 15  2  0  0  0  0
 20  9  1  0  0  0  0
 20 12  1  0  0  0  0
 20 16  1  0  0  0  0
 15 21  1  4  0  0  0
 22 16  2  0  0  0  0
 23 17  2  0  0  0  0
 24 17  1  0  0  0  0
 10 25  1  1  0  0  0
 11 26  1  6  0  0  0
 12 27  1  1  0  0  0
 13 28  1  6  0  0  0
 14 29  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0020920

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](C)(CC)[C@]([H])(N)C(=O)N1CCC[C@@]1([H])C(O)=N[C@]([H])(C(O)=O)[C@@]([H])(C)CC

> <INCHI_IDENTIFIER>
InChI=1S/C17H31N3O4/c1-5-10(3)13(18)16(22)20-9-7-8-12(20)15(21)19-14(17(23)24)11(4)6-2/h10-14H,5-9,18H2,1-4H3,(H,19,21)(H,23,24)/t10-,11-,12-,13-,14-/m0/s1

> <INCHI_KEY>
JNTMAZFVYNDPLB-PEDHHIEDSA-N

> <FORMULA>
C17H31N3O4

> <MOLECULAR_WEIGHT>
341.452

> <EXACT_MASS>
341.23145649

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
36.99280285304974

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S)-2-({[(2S)-1-[(2S,3S)-2-amino-3-methylpentanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-3-methylpentanoic acid

> <ALOGPS_LOGP>
-0.81

> <JCHEM_LOGP>
-0.3198043906701196

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.933267068862581

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6288093256630076

> <JCHEM_PKA_STRONGEST_BASIC>
8.499584178682536

> <JCHEM_POLAR_SURFACE_AREA>
116.21999999999998

> <JCHEM_REFRACTIVITY>
90.49609999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S)-2-({[(2S)-1-[(2S,3S)-2-amino-3-methylpentanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-3-methylpentanoic 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      -0.939  -5.388   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.656   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.350  -3.328   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.656  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.526  -5.864   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.990   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.760  -6.220   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.236  -4.755   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.220  -6.220   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.670  -4.834   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.990   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.990  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.135  -5.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.323  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.990  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.279  -4.279   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.657   0.770   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       3.455  -6.816   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       8.323  -1.540   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       5.744  -4.755   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       5.656  -1.540   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.959  -2.773   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.657   2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      10.991  -0.000   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0       0.206  -4.358   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       5.656   1.540   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       8.362  -3.151   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.815  -3.803   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       8.323   1.540   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3   10                                                            
CONECT    4   11                                                            
CONECT    5    1   10                                                       
CONECT    6    2   11                                                       
CONECT    7    8    9                                                       
CONECT    8    7   12                                                       
CONECT    9    7   20                                                       
CONECT   10    3    5   13   25                                             
CONECT   11    4    6   14   26                                             
CONECT   12    8   15   20   27                                             
CONECT   13   10   16   18   28                                             
CONECT   14   11   17   19   29                                             
CONECT   15   12   19   21                                                  
CONECT   16   13   20   22                                                  
CONECT   17   14   23   24                                                  
CONECT   18   13                                                            
CONECT   19   14   15                                                       
CONECT   20    9   12   16                                                  
CONECT   21   15                                                            
CONECT   22   16                                                            
CONECT   23   17                                                            
CONECT   24   17                                                            
CONECT   25   10                                                            
CONECT   26   11                                                            
CONECT   27   12                                                            
CONECT   28   13                                                            
CONECT   29   14                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   58    0
END

Synonyms

Value	Source
Ile-pro-ile	MeSH
Isoleucyl-prolyl-isoleucine	MeSH

Molecular Formula

C₁₇H₃₁N₃O₄

Average Mass

341.452

Monoisotopic Mass

341.23145649

IUPAC Name

(2S,3S)-2-({[(2S)-1-[(2S,3S)-2-amino-3-methylpentanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-3-methylpentanoic acid

Traditional Name

(2S,3S)-2-({[(2S)-1-[(2S,3S)-2-amino-3-methylpentanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-3-methylpentanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@](C)(CC)[C@]([H])(N)C(=O)N1CCC[C@@]1([H])C(O)=N[C@]([H])(C(O)=O)[C@@]([H])(C)CC

InChI Identifier

InChI=1S/C17H31N3O4/c1-5-10(3)13(18)16(22)20-9-7-8-12(20)15(21)19-14(17(23)24)11(4)6-2/h10-14H,5-9,18H2,1-4H3,(H,19,21)(H,23,24)/t10-,11-,12-,13-,14-/m0/s1

InChI Key

JNTMAZFVYNDPLB-PEDHHIEDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
Isoleucine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
N-acylpyrrolidine
Branched fatty acid
Heterocyclic fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Pyrrolidine
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Organoheterocyclic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Carboximidic acid
Carboximidic acid derivative
Monocarboxylic acid or derivatives
Carboxylic acid
Organooxygen compound
Organic oxide
Primary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organopnictogen compound
Amine
Primary amine
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.33 g/L	ALOGPS
logP	-0.81	ALOGPS
logP	-0.32	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.63	ChemAxon
pKa (Strongest Basic)	8.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	116.22 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	90.5 m³·mol⁻¹	ChemAxon
Polarizability	36.99 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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	Firmicutes	1	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	1	Human feces; Human	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	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

C00018579

Chemspider ID

85449

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

94701

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 Diprotin A (MMDBc0020920)

MOL for #<Metabolite:0x00007f9210f5f380>

3D MOL for #<Metabolite:0x00007f9210f5f380>

3D SDF for #<Metabolite:0x00007f9210f5f380>

3D-SDF for #<Metabolite:0x00007f9210f5f380>

PDB for #<Metabolite:0x00007f9210f5f380>

3D PDB for #<Metabolite:0x00007f9210f5f380>

SMILES for #<Metabolite:0x00007f9210f5f380>

INCHI for #<Metabolite:0x00007f9210f5f380>

Structure for #<Metabolite:0x00007f9210f5f380>

3D Structure for #<Metabolite:0x00007f9210f5f380>