MiMeDB: Showing metabocard for Tryprostatin A (MMDBc0006683)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 00:08:35 UTC

Update Date

2022-08-31 06:25:50 UTC

Metabolite ID

MMDBc0006683

Metabolite Identification

Common Name

Tryprostatin A

Description

Tryprostatin A belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Based on a literature review a significant number of articles have been published on Tryprostatin A.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152102082D          

 30 33  0  0  1  0            999 V2000
    4.3940   -6.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7917   -6.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8225   -0.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3961   -3.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8810   -2.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8356   -5.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3126   -1.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0577   -2.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4487   -5.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8810   -4.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6716   -2.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8090   -4.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0071   -6.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1196   -1.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6097   -3.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5235   -3.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2772   -4.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4167   -2.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0945   -3.9325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6656   -3.1075    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3801   -2.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3801   -4.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8292   -3.6549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0945   -3.1075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6656   -3.9325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3801   -1.8700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3801   -5.1700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3745   -0.7581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0945   -4.7575    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5794   -2.2870    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  6  1  0  0  0  0
 10  4  1  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  6  2  0  0  0  0
 14  7  1  0  0  0  0
 14 11  2  0  0  0  0
 15  8  1  0  0  0  0
 16 12  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 17 16  2  0  0  0  0
 18 11  1  0  0  0  0
 18 15  2  0  0  0  0
 19 12  1  1  0  0  0
 20  5  1  0  0  0  0
 21 20  1  0  0  0  0
 22 19  1  0  0  0  0
 23 17  1  0  0  0  0
 23 18  1  0  0  0  0
 24 19  1  0  0  0  0
 24 21  2  0  0  0  0
 25 10  1  0  0  0  0
 25 20  1  0  0  0  0
 25 22  1  0  0  0  0
 26 21  1  0  0  0  0
 27 22  2  0  0  0  0
 28  3  1  0  0  0  0
 28 14  1  0  0  0  0
 19 29  1  6  0  0  0
 20 30  1  6  0  0  0
M  END


  Mrv1652305152102082D          

 30 33  0  0  1  0            999 V2000
    4.3940   -6.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7917   -6.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8225   -0.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3961   -3.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8810   -2.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8356   -5.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3126   -1.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0577   -2.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4487   -5.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8810   -4.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6716   -2.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8090   -4.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0071   -6.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1196   -1.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6097   -3.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5235   -3.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2772   -4.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4167   -2.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0945   -3.9325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6656   -3.1075    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3801   -2.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3801   -4.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8292   -3.6549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0945   -3.1075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6656   -3.9325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3801   -1.8700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3801   -5.1700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3745   -0.7581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0945   -4.7575    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5794   -2.2870    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  6  1  0  0  0  0
 10  4  1  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  6  2  0  0  0  0
 14  7  1  0  0  0  0
 14 11  2  0  0  0  0
 15  8  1  0  0  0  0
 16 12  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 17 16  2  0  0  0  0
 18 11  1  0  0  0  0
 18 15  2  0  0  0  0
 19 12  1  1  0  0  0
 20  5  1  0  0  0  0
 21 20  1  0  0  0  0
 22 19  1  0  0  0  0
 23 17  1  0  0  0  0
 23 18  1  0  0  0  0
 24 19  1  0  0  0  0
 24 21  2  0  0  0  0
 25 10  1  0  0  0  0
 25 20  1  0  0  0  0
 25 22  1  0  0  0  0
 26 21  1  0  0  0  0
 27 22  2  0  0  0  0
 28  3  1  0  0  0  0
 28 14  1  0  0  0  0
 19 29  1  6  0  0  0
 20 30  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0006683

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12CCCN1C(=O)[C@]([H])(CC1=C(CC=C(C)C)NC3=C1C=CC(OC)=C3)N=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C22H27N3O3/c1-13(2)6-9-17-16(15-8-7-14(28-3)11-18(15)23-17)12-19-22(27)25-10-4-5-20(25)21(26)24-19/h6-8,11,19-20,23H,4-5,9-10,12H2,1-3H3,(H,24,26)/t19-,20-/m0/s1

> <INCHI_KEY>
XNRPVPHNDQHWLJ-PMACEKPBSA-N

> <FORMULA>
C22H27N3O3

> <MOLECULAR_WEIGHT>
381.476

> <EXACT_MASS>
381.205241741

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
42.287243321340554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,8aS)-1-hydroxy-3-{[6-methoxy-2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-3H,4H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
3.109309468

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.558939242505367

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.42209989526939

> <JCHEM_PKA_STRONGEST_BASIC>
1.3296847410470438

> <JCHEM_POLAR_SURFACE_AREA>
77.92

> <JCHEM_REFRACTIVITY>
109.24860000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,8aS)-1-hydroxy-3-{[6-methoxy-2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-3H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one

> <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       8.202 -13.041   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.811 -12.486   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.002  -0.271   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.739  -6.571   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.645  -5.325   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.026 -10.504   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.050  -3.200   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.574  -4.665   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.171  -9.473   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.645  -7.816   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.587  -4.024   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.110  -8.111   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.347 -12.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.557  -2.880   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.605  -5.809   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.444  -7.341   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.851  -7.967   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.111  -5.489   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.776  -7.341   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.109  -5.801   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.443  -5.031   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.443  -8.111   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      10.881  -6.823   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0       5.776  -5.801   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0       3.109  -7.341   0.000  0.00  0.00           N+0
HETATM   26  O   UNK     0       4.443  -3.491   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.443  -9.651   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      10.032  -1.415   0.000  0.00  0.00           O+0
HETATM   29  H   UNK     0       5.776  -8.881   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.948  -4.269   0.000  0.00  0.00           H+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   28                                                            
CONECT    4    5   10                                                       
CONECT    5    4   20                                                       
CONECT    6    9   13                                                       
CONECT    7    8   14                                                       
CONECT    8    7   15                                                       
CONECT    9    6   17                                                       
CONECT   10    4   25                                                       
CONECT   11   14   18                                                       
CONECT   12   16   19                                                       
CONECT   13    1    2    6                                                  
CONECT   14    7   11   28                                                  
CONECT   15    8   16   18                                                  
CONECT   16   12   15   17                                                  
CONECT   17    9   16   23                                                  
CONECT   18   11   15   23                                                  
CONECT   19   12   22   24   29                                             
CONECT   20    5   21   25   30                                             
CONECT   21   20   24   26                                                  
CONECT   22   19   25   27                                                  
CONECT   23   17   18                                                       
CONECT   24   19   21                                                       
CONECT   25   10   20   22                                                  
CONECT   26   21                                                            
CONECT   27   22                                                            
CONECT   28    3   14                                                       
CONECT   29   19                                                            
CONECT   30   20                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

Synonyms

Not Available

Molecular Formula

C₂₂H₂₇N₃O₃

Average Mass

381.476

Monoisotopic Mass

381.205241741

IUPAC Name

(3S,8aS)-1-hydroxy-3-{[6-methoxy-2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-3H,4H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one

Traditional Name

(3S,8aS)-1-hydroxy-3-{[6-methoxy-2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-3H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCCN1C(=O)[C@]([H])(CC1=C(CC=C(C)C)NC3=C1C=CC(OC)=C3)N=C2O

InChI Identifier

InChI=1S/C22H27N3O3/c1-13(2)6-9-17-16(15-8-7-14(28-3)11-18(15)23-17)12-19-22(27)25-10-4-5-20(25)21(26)24-19/h6-8,11,19-20,23H,4-5,9-10,12H2,1-3H3,(H,24,26)/t19-,20-/m0/s1

InChI Key

XNRPVPHNDQHWLJ-PMACEKPBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
3-alkylindole
Indole or derivatives
Indole
Anisole
Dioxopiperazine
2,5-dioxopiperazine
Alkyl aryl ether
N-alkylpiperazine
Piperazine
Substituted pyrrole
1,4-diazinane
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Heteroaromatic compound
Pyrrole
Carboxamide group
Secondary carboxylic acid amide
Lactam
Azacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:72761 )
indoles (CHEBI:72761 )
dipeptide (CHEBI:72761 )
indole alkaloid (CHEBI:72761 )
pyrrolopyrazine (CHEBI:72761 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.05 g/L	ALOGPS
logP	3.07	ALOGPS
logP	3.11	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.42	ChemAxon
pKa (Strongest Basic)	1.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	77.92 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	109.25 m³·mol⁻¹	ChemAxon
Polarizability	42.29 Å³	ChemAxon
Number of Rings	4	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
Eukaryota/Fungi	Ascomycota	4	Human sputum; 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

C00016083

Chemspider ID

8105464

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9929833

PDB ID

Not Available

ChEBI ID

72761

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 Tryprostatin A (MMDBc0006683)

MOL for #<Metabolite:0x00007f922d3bb750>

3D MOL for #<Metabolite:0x00007f922d3bb750>

3D SDF for #<Metabolite:0x00007f922d3bb750>

3D-SDF for #<Metabolite:0x00007f922d3bb750>

PDB for #<Metabolite:0x00007f922d3bb750>

3D PDB for #<Metabolite:0x00007f922d3bb750>

SMILES for #<Metabolite:0x00007f922d3bb750>

INCHI for #<Metabolite:0x00007f922d3bb750>

Structure for #<Metabolite:0x00007f922d3bb750>

3D Structure for #<Metabolite:0x00007f922d3bb750>