MiMeDB: Showing metabocard for Isoterrein (MMDBc0019562)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 09:37:12 UTC

Update Date

2022-08-31 06:45:35 UTC

Metabolite ID

MMDBc0019562

Metabolite Identification

Common Name

Isoterrein

Description

Isoterrein belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions. Isoterrein is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152111372D          

 15 15  0  0  1  0            999 V2000
    2.9760    1.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1913    1.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5783    2.2433    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329    0.3323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3028    1.4888    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287    1.4442    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  2  0  0  0  0
  5  3  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  6  2  0  0  0  0
  7 10  1  1  0  0  0
  8 11  1  1  0  0  0
 12  2  1  0  0  0  0
 13  3  1  0  0  0  0
  7 14  1  6  0  0  0
  8 15  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0019562

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(C)=C(\[H])C1=CC(=O)[C@@]([H])(O)[C@@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C8H10O3/c1-2-3-5-4-6(9)8(11)7(5)10/h2-4,7-8,10-11H,1H3/b3-2+/t7-,8+/m0/s1

> <INCHI_KEY>
MHOOPNKRBMHHEC-RIAPOHOLSA-N

> <FORMULA>
C8H10O3

> <MOLECULAR_WEIGHT>
154.165

> <EXACT_MASS>
154.062994182

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.761092452269859

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,5S)-4,5-dihydroxy-3-[(1E)-prop-1-en-1-yl]cyclopent-2-en-1-one

> <ALOGPS_LOGP>
-0.13

> <JCHEM_LOGP>
0.021963966666666473

> <ALOGPS_LOGS>
-0.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.211256114862422

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.311488205100407

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5228885354846042

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
42.04

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.32e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5S)-4,5-dihydroxy-3-[(1E)-prop-1-en-1-yl]cyclopent-2-en-1-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       5.555   3.633   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.091   3.157   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.770   1.651   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0       2.946   4.188   0.000  0.00  0.00           H+0
HETATM   13  H   UNK     0       4.915   0.620   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0       2.432   2.779   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0      -0.427   2.696   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    5   13                                                  
CONECT    4    5    6                                                       
CONECT    5    3    4    7                                                  
CONECT    6    4    8    9                                                  
CONECT    7    5    8   10   14                                             
CONECT    8    6    7   11   15                                             
CONECT    9    6                                                            
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    2                                                            
CONECT   13    3                                                            
CONECT   14    7                                                            
CONECT   15    8                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

Synonyms

Not Available

Molecular Formula

C₈H₁₀O₃

Average Mass

154.165

Monoisotopic Mass

154.062994182

IUPAC Name

(4S,5S)-4,5-dihydroxy-3-[(1E)-prop-1-en-1-yl]cyclopent-2-en-1-one

Traditional Name

(4S,5S)-4,5-dihydroxy-3-[(1E)-prop-1-en-1-yl]cyclopent-2-en-1-one

CAS Registry Number

Not Available

SMILES

[H]\C(C)=C(\[H])C1=CC(=O)[C@@]([H])(O)[C@@]1([H])O

InChI Identifier

InChI=1S/C8H10O3/c1-2-3-5-4-6(9)8(11)7(5)10/h2-4,7-8,10-11H,1H3/b3-2+/t7-,8+/m0/s1

InChI Key

MHOOPNKRBMHHEC-RIAPOHOLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

1,2-diols

Alternative Parents

Substituents

Cyclic ketone
Secondary alcohol
Ketone
1,2-diol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	93.2 g/L	ALOGPS
logP	-0.13	ALOGPS
logP	0.022	ChemAxon
logS	-0.22	ALOGPS
pKa (Strongest Acidic)	12.31	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	42.04 m³·mol⁻¹	ChemAxon
Polarizability	15.76 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

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
Eukaryota/Fungi	Ascomycota	1	Human feces	Metabolic reconstruction

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

9085035

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10909778

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 Isoterrein (MMDBc0019562)

MOL for #<Metabolite:0x00007fece4019fe0>

3D MOL for #<Metabolite:0x00007fece4019fe0>

3D SDF for #<Metabolite:0x00007fece4019fe0>

3D-SDF for #<Metabolite:0x00007fece4019fe0>

PDB for #<Metabolite:0x00007fece4019fe0>

3D PDB for #<Metabolite:0x00007fece4019fe0>

SMILES for #<Metabolite:0x00007fece4019fe0>

INCHI for #<Metabolite:0x00007fece4019fe0>

Structure for #<Metabolite:0x00007fece4019fe0>

3D Structure for #<Metabolite:0x00007fece4019fe0>