MiMeDB: Showing metabocard for Citreoisocoumarin (MMDBc0002751)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 21:00:53 UTC

Update Date

2022-08-31 06:19:46 UTC

Metabolite ID

MMDBc0002751

Metabolite Identification

Common Name

Citreoisocoumarin

Description

Citreoisocoumarin belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1. Based on a literature review a significant number of articles have been published on Citreoisocoumarin.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305142123002D          

 21 22  0  0  1  0            999 V2000
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  2  1  0  0  0  0
  9  5  1  0  0  0  0
 10  3  1  0  0  0  0
 10  6  2  0  0  0  0
 11  4  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  8  1  0  0  0  0
 13 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15  7  2  0  0  0  0
  9 16  1  6  0  0  0
 17 10  1  0  0  0  0
 18 12  1  0  0  0  0
 19 14  2  0  0  0  0
 20 11  1  0  0  0  0
 20 14  1  0  0  0  0
  9 21  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0002751

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](O)(CC(C)=O)CC1=CC2=CC(O)=CC(O)=C2C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O6/c1-7(15)2-9(16)5-11-4-8-3-10(17)6-12(18)13(8)14(19)20-11/h3-4,6,9,16-18H,2,5H2,1H3/t9-/m1/s1

> <INCHI_KEY>
OSPHTXUUCFLMQA-SECBINFHSA-N

> <FORMULA>
C14H14O6

> <MOLECULAR_WEIGHT>
278.26

> <EXACT_MASS>
278.079038171

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.34199141642825

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,8-dihydroxy-3-[(2S)-2-hydroxy-4-oxopentyl]-1H-isochromen-1-one

> <ALOGPS_LOGP>
1.05

> <JCHEM_LOGP>
1.4157708076666669

> <ALOGPS_LOGS>
-2.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.269088023511232

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.428039684673012

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8247561579819855

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
71.68130000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.73e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,8-dihydroxy-3-[(2S)-2-hydroxy-4-oxopentyl]isochromen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-21         0                                  
HETATM    1  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   9.240   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   9.240   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0      -1.334   3.850   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2    7    9                                                       
CONECT    3    8   10                                                       
CONECT    4    8   11                                                       
CONECT    5    9   11                                                       
CONECT    6   10   12                                                       
CONECT    7    1    2   15                                                  
CONECT    8    3    4   13                                                  
CONECT    9    2    5   16   21                                             
CONECT   10    3    6   17                                                  
CONECT   11    4    5   20                                                  
CONECT   12    6   13   18                                                  
CONECT   13    8   12   14                                                  
CONECT   14   13   19   20                                                  
CONECT   15    7                                                            
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   12                                                            
CONECT   19   14                                                            
CONECT   20   11   14                                                       
CONECT   21    9                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

Synonyms

Not Available

Molecular Formula

C₁₄H₁₄O₆

Average Mass

278.26

Monoisotopic Mass

278.079038171

IUPAC Name

6,8-dihydroxy-3-[(2S)-2-hydroxy-4-oxopentyl]-1H-isochromen-1-one

Traditional Name

6,8-dihydroxy-3-[(2S)-2-hydroxy-4-oxopentyl]isochromen-1-one

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(CC(C)=O)CC1=CC2=CC(O)=CC(O)=C2C(=O)O1

InChI Identifier

InChI=1S/C14H14O6/c1-7(15)2-9(16)5-11-4-8-3-10(17)6-12(18)13(8)14(19)20-11/h3-4,6,9,16-18H,2,5H2,1H3/t9-/m1/s1

InChI Key

OSPHTXUUCFLMQA-SECBINFHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isocoumarins and derivatives

Sub Class

Not Available

Direct Parent

Isocoumarins and derivatives

Alternative Parents

Substituents

Isocoumarin
Benzopyran
2-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Beta-hydroxy ketone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Ketone
Lactone
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.57 g/L	ALOGPS
logP	1.05	ALOGPS
logP	1.42	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	8.43	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	71.68 m³·mol⁻¹	ChemAxon
Polarizability	27.34 Å³	ChemAxon
Number of Rings	2	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

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	3	Human feces	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

C00033726

Chemspider ID

31143389

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15071544

PDB ID

Not Available

ChEBI ID

177816

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 Citreoisocoumarin (MMDBc0002751)

MOL for #<Metabolite:0x00007fdb40009088>

3D MOL for #<Metabolite:0x00007fdb40009088>

3D SDF for #<Metabolite:0x00007fdb40009088>

3D-SDF for #<Metabolite:0x00007fdb40009088>

PDB for #<Metabolite:0x00007fdb40009088>

3D PDB for #<Metabolite:0x00007fdb40009088>

SMILES for #<Metabolite:0x00007fdb40009088>

INCHI for #<Metabolite:0x00007fdb40009088>

Structure for #<Metabolite:0x00007fdb40009088>

3D Structure for #<Metabolite:0x00007fdb40009088>