NP-MRD: Showing NP-Card for (3S)-6-Hydroxy-8-methoxy-3-methyl-3,4-dihydroisocoumarin (NP0043785)

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Record Information

Version

2.0

Created at

2021-06-22 17:17:29 UTC

Updated at

2021-06-22 17:17:29 UTC

NP-MRD ID

NP0043785

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3S)-6-Hydroxy-8-methoxy-3-methyl-3,4-dihydroisocoumarin

Description

ZINC31158115 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. (3S)-6-Hydroxy-8-methoxy-3-methyl-3,4-dihydroisocoumarin is found in Penicillium sp. WN-11-1-3-1-2. (3S)-6-Hydroxy-8-methoxy-3-methyl-3,4-dihydroisocoumarin was first documented in 2015 (SOrfali, et al.). Based on a literature review very few articles have been published on ZINC31158115.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306222119172D          

 15 16  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
    0.0000    0.8250    0.0000 O   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
   -1.4289   -1.6500    0.0000 O   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
    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
    2.8579   -1.6500    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
  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
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
  8 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043785

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=CC2=C1C(=O)O[C@@H](C)C2

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O4/c1-6-3-7-4-8(12)5-9(14-2)10(7)11(13)15-6/h4-6,12H,3H2,1-2H3/t6-/m0/s1

> <INCHI_KEY>
WGUHOBJSLARYHD-LURJTMIESA-N

> <FORMULA>
C11H12O4

> <MOLECULAR_WEIGHT>
208.213

> <EXACT_MASS>
208.073558866

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.787901213922503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-6-hydroxy-8-methoxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one

> <ALOGPS_LOGP>
1.85

> <JCHEM_LOGP>
1.7719497236666661

> <ALOGPS_LOGS>
-1.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.475126760713232

> <JCHEM_PKA_STRONGEST_BASIC>
-4.901711196819986

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
54.25580000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.82e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-6-hydroxy-8-methoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+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  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -2.310   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
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    NP0043785
HETATM    1  C1  UNL     1       3.492  -2.029   0.209  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.131  -1.739   0.243  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.577  -0.476   0.102  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.324   0.661  -0.094  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.682   1.881  -0.225  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.487   3.009  -0.422  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.313   1.967  -0.162  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.463   0.826   0.035  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.197  -0.374   0.163  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.616  -1.565   0.369  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.041  -2.677   0.489  1.00  0.00           O  
HETATM   12  O4  UNL     1      -2.004  -1.434   0.426  1.00  0.00           O  
HETATM   13  C9  UNL     1      -2.564  -0.370  -0.339  1.00  0.00           C  
HETATM   14  C10 UNL     1      -4.051  -0.371  -0.104  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.949   0.948   0.099  1.00  0.00           C  
HETATM   16  H1  UNL     1       4.046  -1.347  -0.446  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.933  -2.017   1.227  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.608  -3.058  -0.204  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.400   0.564  -0.139  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.825   3.533   0.351  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.185   2.907  -0.263  1.00  0.00           H  
HETATM   22  H7  UNL     1      -2.337  -0.545  -1.405  1.00  0.00           H  
HETATM   23  H8  UNL     1      -4.299  -0.835   0.875  1.00  0.00           H  
HETATM   24  H9  UNL     1      -4.448   0.661  -0.169  1.00  0.00           H  
HETATM   25  H10 UNL     1      -4.528  -0.991  -0.883  1.00  0.00           H  
HETATM   26  H11 UNL     1      -2.299   1.711  -0.614  1.00  0.00           H  
HETATM   27  H12 UNL     1      -2.230   1.160   1.140  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   19
CONECT    5    6    7    7
CONECT    6   20
CONECT    7    8   21
CONECT    8    9    9   15
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13
CONECT   13   14   15   22
CONECT   14   23   24   25
CONECT   15   26   27
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₂O₄

Average Mass

208.2130 Da

Monoisotopic Mass

208.07356 Da

IUPAC Name

(3S)-6-hydroxy-8-methoxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one

Traditional Name

(3S)-6-hydroxy-8-methoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=CC2=C1C(=O)O[C@@H](C)C2

InChI Identifier

InChI=1S/C11H12O4/c1-6-3-7-4-8(12)5-9(14-2)10(7)11(13)15-6/h4-6,12H,3H2,1-2H3/t6-/m0/s1

InChI Key

WGUHOBJSLARYHD-LURJTMIESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Penicillium sp. WN-11-1-3-1-2	Linigton's dataset	Raha S.Orfali, Amal H.Aly, Weaam Ebrahim, Rudiyansyah, Peter Proksch. Isochroman and isocoumarin ...

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
Anisole
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Carboxylic acid ester
Lactone
Ether
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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	1.85	ALOGPS
logP	1.77	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	8.48	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	54.26 m³·mol⁻¹	ChemAxon
Polarizability	20.79 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

Not Available

Chemspider ID

75241548

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

38350045

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Raha S.Orfali, Amal H.Aly, Weaam Ebrahim, Rudiyansyah, Peter Proksch (2015). Raha S.Orfali, Amal H.Aly, Weaam Ebrahim, Rudiyansyah, Peter Proksch. Isochroman and isocoumarin derivatives from hypersaline lake sediment-derived fungus Penicillium sp. DOI: 10.1016/j.phytol.2015.06.003. Phytochemistry Letters.

Showing NP-Card for (3S)-6-Hydroxy-8-methoxy-3-methyl-3,4-dihydroisocoumarin (NP0043785)

MOL for NP0043785 ((3S)-6-Hydroxy-8-methoxy-3-methyl-3,4-dihydroisocoumarin)

3D MOL for NP0043785 ((3S)-6-Hydroxy-8-methoxy-3-methyl-3,4-dihydroisocoumarin)

3D SDF for NP0043785 ((3S)-6-Hydroxy-8-methoxy-3-methyl-3,4-dihydroisocoumarin)

3D-SDF for NP0043785 ((3S)-6-Hydroxy-8-methoxy-3-methyl-3,4-dihydroisocoumarin)

PDB for NP0043785 ((3S)-6-Hydroxy-8-methoxy-3-methyl-3,4-dihydroisocoumarin)

3D PDB for NP0043785 ((3S)-6-Hydroxy-8-methoxy-3-methyl-3,4-dihydroisocoumarin)

SMILES for NP0043785 ((3S)-6-Hydroxy-8-methoxy-3-methyl-3,4-dihydroisocoumarin)

INCHI for NP0043785 ((3S)-6-Hydroxy-8-methoxy-3-methyl-3,4-dihydroisocoumarin)

Structure for NP0043785 ((3S)-6-Hydroxy-8-methoxy-3-methyl-3,4-dihydroisocoumarin)

3D Structure for NP0043785 ((3S)-6-Hydroxy-8-methoxy-3-methyl-3,4-dihydroisocoumarin)