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Showing NP-Card for (R)-(-)-Mellein (NP0050398)

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Record Information
Version2.0
Created at2022-04-27 20:57:14 UTC
Updated at2022-04-27 20:57:14 UTC
NP-MRD IDNP0050398
Secondary Accession NumbersNone
Natural Product Identification
Common Name(R)-(-)-Mellein
Description(+)-Mellein belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position. (R)-(-)-Mellein is found in Annulohypoxylon squamulosum, Aphomia sociella, Aspergillus melleus, Aspergillus ochraceus, Aspergillus ochraceus Wilhelm, Botryosphaeria mamane PSU-M76, Cercospora taiwanensis, Cophinforma mamane, Ficus formosana, Fusarium larvarum, Garcinia bancana, Garcinia bancana MIQ , Hypoxylon haematostroma, Hypoxylon venustuissimum, Lasiodiplodia theobromae, Lasiodiplodia theobromae IFO 31059, Marasmiellus ramealis, Phaeohelotium epiphyllum and Phomopsis velata. (R)-(-)-Mellein was first documented in 2021 (PMID: 34304561). Based on a literature review very few articles have been published on (+)-Mellein.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0050398 ((R)-(-)-Mellein)


  Mrv1652304272222572D          

 13 14  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   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
    0.0000   -1.6500    0.0000 C   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
    0.7145   -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
    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 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   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
    1.4289   -2.4750    0.0000 O   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
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  6  0  0  0
  3 13  1  0  0  0  0
M  END
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3D MOL for NP0050398 ((R)-(-)-Mellein)

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3D SDF for NP0050398 ((R)-(-)-Mellein)

  Mrv1652304272222572D          

 13 14  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   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
    0.0000   -1.6500    0.0000 C   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
    0.7145   -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
    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 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   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
    1.4289   -2.4750    0.0000 O   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
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  6  0  0  0
  3 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050398

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O3/c1-6-5-7-3-2-4-8(11)9(7)10(12)13-6/h2-4,6,11H,5H2,1H3/t6-/m0/s1

> <INCHI_KEY>
KWILGNNWGSNMPA-LURJTMIESA-N

> <FORMULA>
C10H10O3

> <MOLECULAR_WEIGHT>
178.187

> <EXACT_MASS>
178.062994182

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
17.746514678498286

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-8-hydroxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
2.5796209893333333

> <ALOGPS_LOGS>
-1.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.652553359850293

> <JCHEM_PKA_STRONGEST_BASIC>
-4.295219685147942

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
47.7926

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-8-hydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0050398 ((R)-(-)-Mellein)
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PDB for NP0050398 ((R)-(-)-Mellein)
HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -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       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8                                                            
CONECT   13    3                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

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3D PDB for NP0050398 ((R)-(-)-Mellein)
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SMILES for NP0050398 ((R)-(-)-Mellein)
C[C@H]1CC2=CC=CC(O)=C2C(=O)O1
Download
INCHI for NP0050398 ((R)-(-)-Mellein)
InChI=1S/C10H10O3/c1-6-5-7-3-2-4-8(11)9(7)10(12)13-6/h2-4,6,11H,5H2,1H3/t6-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H10O3
Average Mass178.1870 Da
Monoisotopic Mass178.06299 Da
IUPAC Name(3S)-8-hydroxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one
Traditional Name(3S)-8-hydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one
CAS Registry NumberNot Available
SMILES
C[C@H]1CC2=CC=CC(O)=C2C(=O)O1
InChI Identifier
InChI=1S/C10H10O3/c1-6-5-7-3-2-4-8(11)9(7)10(12)13-6/h2-4,6,11H,5H2,1H3/t6-/m0/s1
InChI KeyKWILGNNWGSNMPA-LURJTMIESA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Annulohypoxylon squamulosumLOTUS Database
Aphomia sociellaAnimalia
Aspergillus melleusLOTUS Database
Aspergillus ochraceusLOTUS Database
Aspergillus ochraceus WilhelmFungi
Botryosphaeria mamane PSU-M76Fungi
Cercospora taiwanensis-
Cophinforma mamaneLOTUS Database
Ficus formosanaPlant
Fusarium larvarumLOTUS Database
Garcinia bancanaLOTUS Database
Garcinia bancana MIQPlant
Hypoxylon haematostromaFungi
Hypoxylon venustuissimumFungi
Lasiodiplodia theobromaeLOTUS Database
Lasiodiplodia theobromae IFO 31059Fungi
Marasmiellus ramealisLOTUS Database
Phaeohelotium epiphyllumLOTUS Database
Phomopsis velataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzopyrans  
Sub Class2-benzopyrans  
Direct Parent2-benzopyrans  
Alternative Parents
Substituents
  • 2-benzopyran
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Benzenoid
    • 

  • Vinylogous acid
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.27ALOGPS
logP2.58ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)9.65ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.79 m³·mol⁻¹ChemAxon
Polarizability17.75 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9096314  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10921069  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Li Y, Gai Z, Wang C, Li P, Li B: Identification of Mellein as a Pathogenic Substance of Botryosphaeria dothidea by UPLC-MS/MS Analysis and Phytotoxic Bioassay. J Agric Food Chem. 2021 Aug 4;69(30):8471-8481. doi: 10.1021/acs.jafc.1c03249.  Epub 2021 Jul 24. [PubMed:34304561  ]