MiMeDB: Showing metabocard for 6-hydroxymellein (MMDBc0028223)

Microbial

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 17:51:29 UTC

Update Date

2025-10-07 16:07:50 UTC

Metabolite ID

MMDBc0028223

Metabolite Identification

Common Name

6-hydroxymellein

Description

6-hydroxymellein is a dihydroisocoumarin, a subclass of phenolic compounds characterized by a fused benzene and γ-lactone structure. Its chemical structure features a hydroxyl group at the 6-position, contributing to its diverse biological activities. 6-hydroxymellein is involved in various biosynthetic pathways, serving as a precursor for the synthesis of other metabolites through stages of isoprenylation, cyclization, oxidation, and acetylation (PMID:38921585 ). It has been isolated from several fungal species, including Talaromyces stipitatus and Penicillium chrysogenum, indicating its prevalence in filamentous fungi (PMID:35889347 ; PMID:35684566 ). Biological studies have demonstrated that 6-hydroxymellein exhibits significant anti-inflammatory properties, with strong inhibitory effects on nitric oxide production and tumor necrosis factor-alpha (TNF-α) (PMID:39194878 ). Additionally, it has shown antioxidant activity, effectively scavenging DPPH radicals (PMID:39194878 ). The compound is also noted for its role in alleviating lung injury and protecting macrophages against inflammation via the PI3K/AKT signaling pathway (PMID:36212882 ). Overall, 6-hydroxymellein represents a notable compound in the realm of natural products with potential therapeutic applications.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152119512D          

 15 16  0  0  1  0            999 V2000
    0.0000    0.0000    0.0000 C   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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  6  0  0  0
  5  2  1  0  0  0  0
  6  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  4  1  0  0  0  0
  9  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13 10  2  0  0  0  0
 14  5  1  0  0  0  0
 14 10  1  0  0  0  0
  5 15  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0028223

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(C)CC2=CC(O)=CC(O)=C2C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O4/c1-5-2-6-3-7(11)4-8(12)9(6)10(13)14-5/h3-5,11-12H,2H2,1H3/t5-/m1/s1

> <INCHI_KEY>
DHLPMLVSBRRUGA-RXMQYKEDSA-N

> <FORMULA>
C10H10O4

> <MOLECULAR_WEIGHT>
194.186

> <EXACT_MASS>
194.057908802

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
18.988461006591894

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-6,8-dihydroxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one

> <ALOGPS_LOGP>
1.64

> <JCHEM_LOGP>
2.2760556676666663

> <ALOGPS_LOGS>
-1.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.358345497343887

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.5099264564136

> <JCHEM_PKA_STRONGEST_BASIC>
-4.01050549792257

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
49.773500000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.18e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxymellein

> <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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   15  H   UNK     0       0.000  -1.540   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2    5    6                                                       
CONECT    3    6    7                                                       
CONECT    4    7    8                                                       
CONECT    5    1    2   14   15                                             
CONECT    6    2    3    9                                                  
CONECT    7    3    4   11                                                  
CONECT    8    4    9   12                                                  
CONECT    9    6    8   10                                                  
CONECT   10    9   13   14                                                  
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13   10                                                            
CONECT   14    5   10                                                       
CONECT   15    5                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

Synonyms

Value	Source
(-)-6-Hydroxymellein	ChEBI
(3R)-3,4-Dihydro-6,8-dihydroxy-3-methyl-isocoumarin	ChEBI
(R)-(-)-6-Hydroxymellein	ChEBI
(R)-3,4-Dihydro-6,8-dihydroxy-3-methyl-1H-2-benzopyran-1-one	ChEBI
(R)-6-Hydroxymellein	ChEBI
3,4-Dihydro-6,8-dihydroxy-3-methylisocoumarin	ChEBI
6,8-Dihydroxy-3-methyl-3,4-dihydroisocoumarin	ChEBI
3,4-Dihydro-6,8-dihydroxy-3-methyl-isocoumarin	MeSH
6-Hydroxy-mellein	MeSH

Molecular Formula

C₁₀H₁₀O₄

Average Mass

194.186

Monoisotopic Mass

194.057908802

IUPAC Name

(3R)-6,8-dihydroxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one

Traditional Name

6-hydroxymellein

CAS Registry Number

Not Available

SMILES

[H][C@@]1(C)CC2=CC(O)=CC(O)=C2C(=O)O1

InChI Identifier

InChI=1S/C10H10O4/c1-5-2-6-3-7(11)4-8(12)9(6)10(13)14-5/h3-5,11-12H,2H2,1H3/t5-/m1/s1

InChI Key

DHLPMLVSBRRUGA-RXMQYKEDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hydroxybenzoic acid derivatives

Alternative Parents

Substituents

Dihydroxybenzoic acid
Benzopyran
Isochromane
2-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isochromanes (CHEBI:16368 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	5.18 g/L	ALOGPS
logP	1.64	ALOGPS
logP	2.28	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	8.51	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	49.77 m³·mol⁻¹	ChemAxon
Polarizability	18.99 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 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
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	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	63.5
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (void)	2025-10-23	28.1
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	369.4
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	484.4
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	514.0
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	319.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	1749.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	83.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	497.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	303.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	230.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	194.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	113.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	109.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	447.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	171.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	368.7
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1277.1
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	822.4

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	6-hydroxymellein_TMS_1	C[C@@H]1CC2=CC(O[Si](C)(C)C)=CC(O)=C2C(=O)O1	standard non polar	2025-10-23	1954.18
Gas Chromatography	6-hydroxymellein_TMS_2	C[C@@H]1CC2=CC(O)=CC(O[Si](C)(C)C)=C2C(=O)O1	standard non polar	2025-10-23	2173.88
Gas Chromatography	6-hydroxymellein_TMS_3	C[C@@H]1CC2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C(=O)O1	standard non polar	2025-10-23	2059.57
Gas Chromatography	6-hydroxymellein_TMS_1	C[C@@H]1CC2=CC(O[Si](C)(C)C)=CC(O)=C2C(=O)O1	standard polar	2025-10-23	2231.72
Gas Chromatography	6-hydroxymellein_TMS_2	C[C@@H]1CC2=CC(O)=CC(O[Si](C)(C)C)=C2C(=O)O1	standard polar	2025-10-23	1804.74
Gas Chromatography	6-hydroxymellein_TMS_3	C[C@@H]1CC2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C(=O)O1	standard polar	2025-10-23	2362.06

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
MMDBr0025898	Malonyl-CoA	6-hydroxymellein	6-hydroxymellein synthase cdmE	Synthesis	RHEA	34755880

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
nah	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	2	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

C00000554

Chemspider ID

150838

KEGG Compound ID

C02379

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

6-Hydroxymellein

METLIN ID

Not Available

PubChem Compound

172675

PDB ID

Not Available

ChEBI ID

16368

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

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 6-hydroxymellein (MMDBc0028223)

MOL for #<Metabolite:0x00007f2e05517b30>

3D MOL for #<Metabolite:0x00007f2e05517b30>

3D SDF for #<Metabolite:0x00007f2e05517b30>

3D-SDF for #<Metabolite:0x00007f2e05517b30>

PDB for #<Metabolite:0x00007f2e05517b30>

3D PDB for #<Metabolite:0x00007f2e05517b30>

SMILES for #<Metabolite:0x00007f2e05517b30>

INCHI for #<Metabolite:0x00007f2e05517b30>

Structure for #<Metabolite:0x00007f2e05517b30>

3D Structure for #<Metabolite:0x00007f2e05517b30>