MiMeDB: Showing metabocard for Fumigatin chlorohydrin (MMDBc0017151)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 07:36:56 UTC

Update Date

2025-10-07 16:06:38 UTC

Metabolite ID

MMDBc0017151

Metabolite Identification

Common Name

Fumigatin chlorohydrin

Description

Fumigatin chlorohydrin is a secondary metabolite belonging to the class of polyketides. Its chemical structure is characterized by a chlorohydrin functional group, which is derived from the biosynthetic pathway involving 3,4-dihydroxytoluquinone, a precursor in the fumigatin biosynthesis pathway. This compound was isolated following the overexpression of the PbrlaeA gene in the fungus Penicillium brocae HDN-12-143, leading to the identification of fumigatin chlorohydrin and iso-fumigatin chlorohydrin (PMID:32373583 ). The metabolic role of fumigatin chlorohydrin is linked to its involvement in the complex biosynthetic pathways of fumigatin, where it plays a crucial part in the transformation of key intermediates into final products (PMID:4598457 ). The precise configuration of fumigatin chlorohydrin has not been previously reported, suggesting potential for further investigation into its structural properties and biological activities. Understanding its chemical structure and the pathways it is involved in may provide insights into the broader metabolic functions of polyketides in fungi.

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171503482D          

 14 14  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0017151

> <DATABASE_NAME>
MIME

> <SMILES>
COC1=C(O)C(=O)C(C)(O)C(Cl)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H9ClO5/c1-8(13)6(9)3(10)5(14-2)4(11)7(8)12/h6,11,13H,1-2H3

> <INCHI_KEY>
RSDSFHMEULFQPZ-UHFFFAOYSA-N

> <FORMULA>
C8H9ClO5

> <MOLECULAR_WEIGHT>
220.61

> <EXACT_MASS>
220.0138511

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.961314470962414

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-chloro-3,5-dihydroxy-2-methoxy-5-methylcyclohex-2-ene-1,4-dione

> <ALOGPS_LOGP>
0.25

> <JCHEM_LOGP>
0.09909802266666631

> <ALOGPS_LOGS>
-0.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.295821631181074

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.848645476113674

> <JCHEM_PKA_STRONGEST_BASIC>
-4.111900418797242

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
49.0855

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.46e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-chloro-3,5-dihydroxy-2-methoxy-5-methylcyclohex-2-ene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.324   3.490   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12 Cl   UNK     0       4.001   2.310   0.000  0.00  0.00          Cl+0
HETATM   13  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    3   14                                                  
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

Synonyms

Not Available

Molecular Formula

C₈H₉ClO₅

Average Mass

220.61

Monoisotopic Mass

220.0138511

IUPAC Name

6-chloro-3,5-dihydroxy-2-methoxy-5-methylcyclohex-2-ene-1,4-dione

Traditional Name

6-chloro-3,5-dihydroxy-2-methoxy-5-methylcyclohex-2-ene-1,4-dione

CAS Registry Number

Not Available

SMILES

COC1=C(O)C(=O)C(C)(O)C(Cl)C1=O

InChI Identifier

InChI=1S/C8H9ClO5/c1-8(13)6(9)3(10)5(14-2)4(11)7(8)12/h6,11,13H,1-2H3

InChI Key

RSDSFHMEULFQPZ-UHFFFAOYSA-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
Acyloin
Alpha-haloketone
Alpha-chloroketone
Vinylogous ester
Vinylogous acid
Tertiary alcohol
Chlorohydrin
Halohydrin
Organic oxide
Organohalogen compound
Organochloride
Hydrocarbon derivative
Alkyl halide
Alkyl chloride
Alcohol
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	34.6 g/L	ALOGPS
logP	0.25	ALOGPS
logP	0.099	ChemAxon
logS	-0.8	ALOGPS
pKa (Strongest Acidic)	3.85	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	49.09 m³·mol⁻¹	ChemAxon
Polarizability	18.96 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (void)	2025-10-23	138.8
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (void)	2025-10-23	29.4
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	331.1
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	523.4
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	458.8
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	349.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	1707.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	101.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	738.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	339.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	351.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	207.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	108.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	137.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	534.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	57.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	348.6
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1251.2
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	884.0

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Fumigatin chlorohydrin_TMS_1	COC1=C(O[Si](C)(C)C)C(=O)C(C)(O)C(Cl)C1=O	standard non polar	2025-10-23	1702.13
Gas Chromatography	Fumigatin chlorohydrin_TMS_2	COC1=C(O)C(=O)C(C)(O[Si](C)(C)C)C(Cl)C1=O	standard non polar	2025-10-23	1876.2
Gas Chromatography	Fumigatin chlorohydrin_TMS_3	COC1=C(O)C(=O)C(C)(O)C(Cl)=C1O[Si](C)(C)C	standard non polar	2025-10-23	1732.97
Gas Chromatography	Fumigatin chlorohydrin_TMS_4	COC1=C(O[Si](C)(C)C)C(=O)C(C)(O[Si](C)(C)C)C(Cl)C1=O	standard non polar	2025-10-23	1907.74
Gas Chromatography	Fumigatin chlorohydrin_TMS_5	COC1=C(O[Si](C)(C)C)C(=O)C(C)(O)C(Cl)=C1O[Si](C)(C)C	standard non polar	2025-10-23	2524.09
Gas Chromatography	Fumigatin chlorohydrin_TMS_6	COC1=C(O)C(=O)C(C)(O[Si](C)(C)C)C(Cl)=C1O[Si](C)(C)C	standard non polar	2025-10-23	1085.32
Gas Chromatography	Fumigatin chlorohydrin_TMS_7	COC1=C(O[Si](C)(C)C)C(=O)C(C)(O[Si](C)(C)C)C(Cl)=C1O[Si](C)(C)C	standard non polar	2025-10-23	2373.05
Gas Chromatography	Fumigatin chlorohydrin_TMS_1	COC1=C(O[Si](C)(C)C)C(=O)C(C)(O)C(Cl)C1=O	standard polar	2025-10-23	2232.12
Gas Chromatography	Fumigatin chlorohydrin_TMS_2	COC1=C(O)C(=O)C(C)(O[Si](C)(C)C)C(Cl)C1=O	standard polar	2025-10-23	2095.5
Gas Chromatography	Fumigatin chlorohydrin_TMS_3	COC1=C(O)C(=O)C(C)(O)C(Cl)=C1O[Si](C)(C)C	standard polar	2025-10-23	2606.86
Gas Chromatography	Fumigatin chlorohydrin_TMS_4	COC1=C(O[Si](C)(C)C)C(=O)C(C)(O[Si](C)(C)C)C(Cl)C1=O	standard polar	2025-10-23	2475.12
Gas Chromatography	Fumigatin chlorohydrin_TMS_5	COC1=C(O[Si](C)(C)C)C(=O)C(C)(O)C(Cl)=C1O[Si](C)(C)C	standard polar	2025-10-23	1977.71
Gas Chromatography	Fumigatin chlorohydrin_TMS_6	COC1=C(O)C(=O)C(C)(O[Si](C)(C)C)C(Cl)=C1O[Si](C)(C)C	standard polar	2025-10-23	2024.88
Gas Chromatography	Fumigatin chlorohydrin_TMS_7	COC1=C(O[Si](C)(C)C)C(=O)C(C)(O[Si](C)(C)C)C(Cl)=C1O[Si](C)(C)C	standard polar	2025-10-23	1341.79

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated 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	1	Human feces	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101321356

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

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 Fumigatin chlorohydrin (MMDBc0017151)

MOL for #<Metabolite:0x00007f9acc666278>

3D MOL for #<Metabolite:0x00007f9acc666278>

3D SDF for #<Metabolite:0x00007f9acc666278>

3D-SDF for #<Metabolite:0x00007f9acc666278>

PDB for #<Metabolite:0x00007f9acc666278>

3D PDB for #<Metabolite:0x00007f9acc666278>

SMILES for #<Metabolite:0x00007f9acc666278>

INCHI for #<Metabolite:0x00007f9acc666278>

Structure for #<Metabolite:0x00007f9acc666278>

3D Structure for #<Metabolite:0x00007f9acc666278>