MiMeDB: Showing metabocard for 5-Chloroisorotiorin (MMDBc0014404)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 05:26:21 UTC

Update Date

2022-08-31 06:37:36 UTC

Metabolite ID

MMDBc0014404

Metabolite Identification

Common Name

5-Chloroisorotiorin

Description

5-Chloroisorotiorin belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 5-Chloroisorotiorin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152107262D          

 33 35  0  0  1  0            999 V2000
    9.6834   -0.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9034    0.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6888    1.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7651    2.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7565   -0.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8588   -0.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4296    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9950    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6442    0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7358   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4688    0.2837    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2542    1.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3606    1.8953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966    0.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620   -0.2372    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8666   -1.7170    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.1528    2.1256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2174   -1.6655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6989    1.2168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804    1.1137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4608   -0.0406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0396    1.7892    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3850   -0.3660    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2096   -0.3918    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2934    0.2579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  8  7  2  0  0  0  0
 12  2  1  1  0  0  0
 12  6  1  0  0  0  0
 12  9  1  0  0  0  0
 13  3  1  0  0  0  0
 13  7  1  0  0  0  0
 13  9  2  0  0  0  0
 14  4  1  0  0  0  0
 15  8  1  0  0  0  0
 15 10  2  0  0  0  0
 16 10  1  0  0  0  0
 17 11  2  0  0  0  0
 17 16  1  0  0  0  0
 18 14  1  0  0  0  0
 19 17  1  0  0  0  0
 19 18  2  0  0  0  0
 20 16  2  0  0  0  0
 21 20  1  0  0  0  0
 22 18  1  0  0  0  0
 23  5  1  1  0  0  0
 23 19  1  0  0  0  0
 23 21  1  0  0  0  0
 24 20  1  0  0  0  0
 25 14  2  0  0  0  0
 26 21  2  0  0  0  0
 27 22  2  0  0  0  0
 28 11  1  0  0  0  0
 28 15  1  0  0  0  0
 29 22  1  0  0  0  0
 29 23  1  0  0  0  0
 30  7  1  0  0  0  0
 31  8  1  0  0  0  0
 32  9  1  0  0  0  0
 12 33  1  6  0  0  0
M  END


  Mrv1652305152107262D          

 33 35  0  0  1  0            999 V2000
    9.6834   -0.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9034    0.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6888    1.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7651    2.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7565   -0.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8588   -0.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4296    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9950    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6442    0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7358   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4688    0.2837    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2542    1.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3606    1.8953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966    0.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620   -0.2372    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8666   -1.7170    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.1528    2.1256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2174   -1.6655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6989    1.2168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804    1.1137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4608   -0.0406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0396    1.7892    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3850   -0.3660    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2096   -0.3918    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2934    0.2579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  8  7  2  0  0  0  0
 12  2  1  1  0  0  0
 12  6  1  0  0  0  0
 12  9  1  0  0  0  0
 13  3  1  0  0  0  0
 13  7  1  0  0  0  0
 13  9  2  0  0  0  0
 14  4  1  0  0  0  0
 15  8  1  0  0  0  0
 15 10  2  0  0  0  0
 16 10  1  0  0  0  0
 17 11  2  0  0  0  0
 17 16  1  0  0  0  0
 18 14  1  0  0  0  0
 19 17  1  0  0  0  0
 19 18  2  0  0  0  0
 20 16  2  0  0  0  0
 21 20  1  0  0  0  0
 22 18  1  0  0  0  0
 23  5  1  1  0  0  0
 23 19  1  0  0  0  0
 23 21  1  0  0  0  0
 24 20  1  0  0  0  0
 25 14  2  0  0  0  0
 26 21  2  0  0  0  0
 27 22  2  0  0  0  0
 28 11  1  0  0  0  0
 28 15  1  0  0  0  0
 29 22  1  0  0  0  0
 29 23  1  0  0  0  0
 30  7  1  0  0  0  0
 31  8  1  0  0  0  0
 32  9  1  0  0  0  0
 12 33  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0014404

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(\[H])C1=CC2=C(Cl)C(=O)[C@]3(C)OC(=O)C(C(C)=O)=C3C2=CO1)\C(\C)=C(/[H])[C@@]([H])(C)CC

> <INCHI_IDENTIFIER>
InChI=1S/C23H23ClO5/c1-6-12(2)9-13(3)7-8-15-10-16-17(11-28-15)19-18(14(4)25)22(27)29-23(19,5)21(26)20(16)24/h7-12H,6H2,1-5H3/b8-7+,13-9+/t12-,23+/m0/s1

> <INCHI_KEY>
QJSWSNAZIVGTFZ-UNSJDTSZSA-N

> <FORMULA>
C23H23ClO5

> <MOLECULAR_WEIGHT>
414.88

> <EXACT_MASS>
414.1234015

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
44.029018971136125

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6aR)-9-acetyl-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-6a-methyl-6H,6aH,8H-furo[2,3-h]isochromene-6,8-dione

> <ALOGPS_LOGP>
4.66

> <JCHEM_LOGP>
3.7965074753333323

> <ALOGPS_LOGS>
-5.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.282705471633466

> <JCHEM_PKA_STRONGEST_BASIC>
-5.231760847526595

> <JCHEM_POLAR_SURFACE_AREA>
69.67

> <JCHEM_REFRACTIVITY>
115.91479999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6aR)-9-acetyl-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-6a-methylfuro[2,3-h]isochromene-6,8-dione

> <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      18.076  -0.876   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.620   1.839   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.352   3.244   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.295   4.604   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.279  -1.660   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.536  -0.828   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.002   1.983   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.191   0.674   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.269   0.578   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.840  -0.587   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.384   2.127   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.808   0.530   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.541   1.935   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.406   3.538   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.651   0.722   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.301  -0.539   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.573   0.818   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.039   2.042   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.034   0.866   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.490  -1.848   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.950  -1.800   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.614   1.460   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.222  -0.443   0.000  0.00  0.00           C+0
HETATM   24 Cl   UNK     0       7.218  -3.205   0.000  0.00  0.00          Cl+0
HETATM   25  O   UNK     0       5.885   3.968   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.139  -3.109   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.305   2.271   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       8.923   2.079   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.727  -0.076   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0      11.274   3.340   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      11.919  -0.683   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      13.458  -0.731   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      17.348   0.481   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   14                                                            
CONECT    5   23                                                            
CONECT    6    1   12                                                       
CONECT    7    8   13   30                                                  
CONECT    8    7   15   31                                                  
CONECT    9   12   13   32                                                  
CONECT   10   15   16                                                       
CONECT   11   17   28                                                       
CONECT   12    2    6    9   33                                             
CONECT   13    3    7    9                                                  
CONECT   14    4   18   25                                                  
CONECT   15    8   10   28                                                  
CONECT   16   10   17   20                                                  
CONECT   17   11   16   19                                                  
CONECT   18   14   19   22                                                  
CONECT   19   17   18   23                                                  
CONECT   20   16   21   24                                                  
CONECT   21   20   23   26                                                  
CONECT   22   18   27   29                                                  
CONECT   23    5   19   21   29                                             
CONECT   24   20                                                            
CONECT   25   14                                                            
CONECT   26   21                                                            
CONECT   27   22                                                            
CONECT   28   11   15                                                       
CONECT   29   22   23                                                       
CONECT   30    7                                                            
CONECT   31    8                                                            
CONECT   32    9                                                            
CONECT   33   12                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

Synonyms

Not Available

Molecular Formula

C₂₃H₂₃ClO₅

Average Mass

414.88

Monoisotopic Mass

414.1234015

IUPAC Name

(6aR)-9-acetyl-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-6a-methyl-6H,6aH,8H-furo[2,3-h]isochromene-6,8-dione

Traditional Name

(6aR)-9-acetyl-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-6a-methylfuro[2,3-h]isochromene-6,8-dione

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC2=C(Cl)C(=O)[C@]3(C)OC(=O)C(C(C)=O)=C3C2=CO1)\C(\C)=C(/[H])[C@@]([H])(C)CC

InChI Identifier

InChI=1S/C23H23ClO5/c1-6-12(2)9-13(3)7-8-15-10-16-17(11-28-15)19-18(14(4)25)22(27)29-23(19,5)21(26)20(16)24/h7-12H,6H2,1-5H3/b8-7+,13-9+/t12-,23+/m0/s1

InChI Key

QJSWSNAZIVGTFZ-UNSJDTSZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Alpha-acyloxy ketone
2-furanone
Pyran
Alpha-haloketone
Alpha-chloroketone
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Chloroalkene
Monocarboxylic acid or derivatives
Haloalkene
Organoheterocyclic compound
Vinyl halide
Vinyl chloride
Organochloride
Organic oxide
Hydrocarbon derivative
Organohalogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.001 g/L	ALOGPS
logP	4.66	ALOGPS
logP	3.8	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	18.28	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.67 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	115.91 m³·mol⁻¹	ChemAxon
Polarizability	44.03 Å³	ChemAxon
Number of Rings	3	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	5	Human sputum; Human ; Human feces	Metabolic reconstruction
Eukaryota/Fungi	nah	1		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

8539944

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10364495

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 5-Chloroisorotiorin (MMDBc0014404)

MOL for #<Metabolite:0x00007fecabb85868>

3D MOL for #<Metabolite:0x00007fecabb85868>

3D SDF for #<Metabolite:0x00007fecabb85868>

3D-SDF for #<Metabolite:0x00007fecabb85868>

PDB for #<Metabolite:0x00007fecabb85868>

3D PDB for #<Metabolite:0x00007fecabb85868>

SMILES for #<Metabolite:0x00007fecabb85868>

INCHI for #<Metabolite:0x00007fecabb85868>

Structure for #<Metabolite:0x00007fecabb85868>

3D Structure for #<Metabolite:0x00007fecabb85868>