NP-MRD: Showing NP-Card for 5-Methylmellein (NP0078243)

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Record Information

Version

2.0

Created at

2022-04-28 23:20:46 UTC

Updated at

2022-04-28 23:20:46 UTC

NP-MRD ID

NP0078243

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-Methylmellein

Description

5-Methylmellein 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. 5-Methylmellein is found in Adenocarpus foliolosus, Azadirachta indica, Biscogniauxia mediterranea, Cytospora ceratosperma, Euphorbia plumerioides, Garcinia atroviridis, Phomopsis velata and Picea glauca. 5-Methylmellein was first documented in 2020 (PMID: 31401763). Based on a literature review a small amount of articles have been published on 5-Methylmellein (PMID: 34822596) (PMID: 34806497) (PMID: 33803611) (PMID: 32562274).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201202D          

 14 15  0  0  1  0            999 V2000
    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
   -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
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   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
    1.4289    0.8250    0.0000 O   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
    2.1434   -1.2375    0.0000 C   0  0  1  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
    2.8579   -1.6500    0.0000 C   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
  6  7  1  0  0  0  0
  3  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 13  1  0  0  0  0
 12 14  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0078243

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O3/c1-6-3-4-9(12)10-8(6)5-7(2)14-11(10)13/h3-4,7,12H,5H2,1-2H3/t7-/m1/s1

> <INCHI_KEY>
YETSBBYQOFXYGV-SSDOTTSWSA-N

> <FORMULA>
C11H12O3

> <MOLECULAR_WEIGHT>
192.214

> <EXACT_MASS>
192.078644246

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
20.035586850975267

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-8-hydroxy-3,5-dimethyl-3,4-dihydro-1H-2-benzopyran-1-one

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
3.093042378666666

> <ALOGPS_LOGS>
-1.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.02116390929991

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2515798686191575

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
52.833800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-8-hydroxy-3,5-dimethyl-3,4-dihydro-2-benzopyran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2    6   13                                                  
CONECT    2    1    3    9                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    3                                                            
CONECT    9    2   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    1                                                       
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₂O₃

Average Mass

192.2140 Da

Monoisotopic Mass

192.07864 Da

IUPAC Name

(3R)-8-hydroxy-3,5-dimethyl-3,4-dihydro-1H-2-benzopyran-1-one

Traditional Name

(3R)-8-hydroxy-3,5-dimethyl-3,4-dihydro-2-benzopyran-1-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H12O3/c1-6-3-4-9(12)10-8(6)5-7(2)14-11(10)13/h3-4,7,12H,5H2,1-2H3/t7-/m1/s1

InChI Key

YETSBBYQOFXYGV-SSDOTTSWSA-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
Adenocarpus foliolosus	LOTUS Database	35616633
Azadirachta indica	LOTUS Database	35616633
Biscogniauxia mediterranea	Fungi	KNApSAcK
Cytospora ceratosperma	LOTUS Database	35616633
Euphorbia plumerioides	LOTUS Database	35616633
Garcinia atroviridis	LOTUS Database	35616633
Phomopsis velata	LOTUS Database	35616633
Picea glauca	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

2-benzopyrans

Direct Parent

2-benzopyrans

Alternative Parents

Substituents

2-benzopyran
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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	2.29	ALOGPS
logP	3.09	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	10.02	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	52.83 m³·mol⁻¹	ChemAxon
Polarizability	20.04 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00042155

Chemspider ID

24691759

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14807789

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Savi DC, Noriler SA, Ponomareva LV, Thorson JS, Rohr J, Glienke C, Shaaban KA: Dihydroisocoumarins produced by Diaporthe cf. heveae LGMF1631 inhibiting citrus pathogens. Folia Microbiol (Praha). 2020 Apr;65(2):381-392. doi: 10.1007/s12223-019-00746-8. Epub 2019 Aug 10. [PubMed:31401763 ]
Masi M, Bashiri S, Cimmino A, Bahmani Z, Abdollahzadeh J, Evidente A: Phytotoxins Produced by Two Biscogniauxia rosacearum Strains, Causal Agents of Grapevine Trunk Diseases, and Charcoal Canker of Oak Trees in Iran. Toxins (Basel). 2021 Nov 18;13(11). pii: toxins13110812. doi: 10.3390/toxins13110812. [PubMed:34822596 ]
Ding JH, Fan XY, Liu SW, Li ZH, Feng T, Liu JK: A new dimeric (-)-5-methylmellein from cultures of the basidiomycete Inonotus sinensis. J Asian Nat Prod Res. 2021 Nov 21:1-6. doi: 10.1080/10286020.2021.2004129. [PubMed:34806497 ]
Wu J, Yang B, Xu J, Cuthbertson AGS, Ali S: Characterization and Toxicity of Crude Toxins Produced by Cordyceps fumosorosea against Bemisia tabaci (Gennadius) and Aphis craccivora (Koch). Toxins (Basel). 2021 Mar 18;13(3). pii: toxins13030220. doi: 10.3390/toxins13030220. [PubMed:33803611 ]
Alheety S, Valenti D, Mujumdar N, Ellis N, Campiglia AD, Harper JK, Heider EC: Characterization of a Bio-sourced, Fluorescent, Ratiometric pH Indicator with Alkaline pKa. Photochem Photobiol. 2020 Nov;96(6):1176-1181. doi: 10.1111/php.13299. Epub 2020 Jul 8. [PubMed:32562274 ]

Showing NP-Card for 5-Methylmellein (NP0078243)

MOL for NP0078243 (5-Methylmellein)

3D MOL for NP0078243 (5-Methylmellein)

3D SDF for NP0078243 (5-Methylmellein)

3D-SDF for NP0078243 (5-Methylmellein)

PDB for NP0078243 (5-Methylmellein)

3D PDB for NP0078243 (5-Methylmellein)

SMILES for NP0078243 (5-Methylmellein)

INCHI for NP0078243 (5-Methylmellein)

Structure for NP0078243 (5-Methylmellein)

3D Structure for NP0078243 (5-Methylmellein)