NP-MRD: Showing NP-Card for 6-hydroxymellein (NP0004219)

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Record Information

Version

2.0

Created at

2020-12-09 01:42:32 UTC

Updated at

2021-07-15 16:48:34 UTC

NP-MRD ID

NP0004219

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-hydroxymellein

Provided By

NPAtlas

Description

6-Hydroxymellein 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. 6-hydroxymellein is found in Aspergillus terreus, Cladonia uncialis, Garcinia atroviridis, Lachnum papyraceum, Pyricularia grisea, Myxotrichum stipitatum, Senna siamea and Tubakia dryina. 6-hydroxymellein was first documented in 2002 (PMID: 12132685). Based on a literature review a small amount of articles have been published on 6-hydroxymellein (PMID: 34114710) (PMID: 33661567) (PMID: 32643425).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118053D          

 24 25  0  0  0  0            999 V2000
   -3.0510    0.0020    0.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2111   -0.0624   -0.7686 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1213   -1.0826   -0.6620 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1668   -0.5316   -0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1081   -1.4420    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3564   -1.0663    0.6357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2947   -1.9879    1.0669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6757    0.2597    0.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7579    1.2430    0.2098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0933    2.5473    0.2208 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5015    0.8135   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5244    1.7374   -0.6861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2991    2.9654   -0.7095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7463    1.2084   -1.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4406   -0.1890    1.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9156   -0.7159    0.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4785    1.0416    0.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9288   -0.3683   -1.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9811   -1.5700   -1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4399   -1.8297    0.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8939   -2.5159    0.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9642   -2.4196    0.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6357    0.5784    0.9695 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894    3.3844   -0.0034 H   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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14  2  1  0  0  0  0
 11  4  1  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  2 18  1  6  0  0  0
  3 19  1  0  0  0  0
  3 20  1  0  0  0  0
  5 21  1  0  0  0  0
  7 22  1  0  0  0  0
  8 23  1  0  0  0  0
 10 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004219

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(=O)O[C@]([H])(C([H])([H])[H])C([H])([H])C2=C1[H]

> <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>
18.857000477041773

> <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                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.051   0.002   0.497  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.211  -0.062  -0.769  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.121  -1.083  -0.662  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.167  -0.532  -0.229  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.108  -1.442   0.202  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.356  -1.066   0.636  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.295  -1.988   1.067  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.676   0.260   0.639  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.758   1.243   0.210  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.093   2.547   0.221  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.501   0.814  -0.222  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.524   1.737  -0.686  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.299   2.965  -0.710  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.746   1.208  -1.096  0.00  0.00           O+0
HETATM   15  H   UNK     0      -2.441  -0.189   1.403  0.00  0.00           H+0
HETATM   16  H   UNK     0      -3.916  -0.716   0.424  0.00  0.00           H+0
HETATM   17  H   UNK     0      -3.478   1.042   0.579  0.00  0.00           H+0
HETATM   18  H   UNK     0      -2.929  -0.368  -1.583  0.00  0.00           H+0
HETATM   19  H   UNK     0      -0.981  -1.570  -1.649  0.00  0.00           H+0
HETATM   20  H   UNK     0      -1.440  -1.830   0.120  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.894  -2.516   0.216  0.00  0.00           H+0
HETATM   22  H   UNK     0       3.964  -2.420   0.427  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.636   0.578   0.970  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.689   3.384  -0.003  0.00  0.00           H+0
CONECT    1    2   15   16   17                                             
CONECT    2    1    3   14   18                                             
CONECT    3    2    4   19   20                                             
CONECT    4    3    5   11                                                  
CONECT    5    4    6   21                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6   22                                                       
CONECT    8    6    9   23                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   24                                                       
CONECT   11    9   12    4                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    2                                                       
CONECT   15    1                                                            
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    2                                                            
CONECT   19    3                                                            
CONECT   20    3                                                            
CONECT   21    5                                                            
CONECT   22    7                                                            
CONECT   23    8                                                            
CONECT   24   10                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol View NMR Assignments

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

Chemical Formula

C₁₀H₁₀O₄

Average Mass

194.1860 Da

Monoisotopic Mass

194.05791 Da

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

C[C@@H]1CC2=C(C(O)=CC(O)=C2)C(=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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus terreus	NPAtlas	12132685
Cladonia uncialis	LOTUS Database	35616633
Daucus carota	KNApSAcK Database	22123792
Garcinia atroviridis	LOTUS Database	35616633
Lachnum papyraceum	LOTUS Database	35616633
Magnaporthe grisea	LOTUS Database	35616633
Myxotrichum stipitatum	LOTUS Database	35616633
Senna siamea	LOTUS Database	35616633
Tubakia dryina	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	18.86 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

External Links

NPAtlas ID

NPA028477

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Not Available

PDB ID

Not Available

ChEBI ID

16368

Good Scents ID

Not Available

References

General References

Shimada A, Kusano M, Takeuchi S, Fujioka S, Inokuchi T, Kimura Y: Aspterric acid and 6-hydroxymellein, inhibitors of pollen development in Arabidopsis thaliana, produced by Aspergillus terreus. Z Naturforsch C J Biosci. 2002 May-Jun;57(5-6):459-64. doi: 10.1515/znc-2002-5-610. [PubMed:12132685 ]
Kahlert L, Bernardi D, Hauser M, Ioca LP, Berlinck RGS, Skellam EJ, Cox RJ: Early Oxidative Transformations During the Biosynthesis of Terrein and Related Natural Products. Chemistry. 2021 Jun 11. doi: 10.1002/chem.202101447. [PubMed:34114710 ]
Kahlert L, Villanueva M, Cox RJ, Skellam EJ: Biosynthesis of 6-Hydroxymellein Requires a Collaborating Polyketide Synthase-like Enzyme. Angew Chem Int Ed Engl. 2021 May 10;60(20):11423-11429. doi: 10.1002/anie.202100969. Epub 2021 Apr 8. [PubMed:33661567 ]
Lin S, Zhang X, Shen L, Mo S, Liu J, Wang J, Hu Z, Zhang Y: A new abietane-type diterpenoid and a new long-chain alkenone from fungus Daldinia sp. TJ403-LS1. Nat Prod Res. 2020 Jul 9:1-8. doi: 10.1080/14786419.2020.1789638. [PubMed:32643425 ]

Showing NP-Card for 6-hydroxymellein (NP0004219)

MOL for NP0004219 (6-hydroxymellein)

3D MOL for NP0004219 (6-hydroxymellein)

3D SDF for NP0004219 (6-hydroxymellein)

3D-SDF for NP0004219 (6-hydroxymellein)

PDB for NP0004219 (6-hydroxymellein)

3D PDB for NP0004219 (6-hydroxymellein)

SMILES for NP0004219 (6-hydroxymellein)

INCHI for NP0004219 (6-hydroxymellein)

Structure for NP0004219 (6-hydroxymellein)

3D Structure for NP0004219 (6-hydroxymellein)