NP-MRD: Showing NP-Card for 10-ethenyl-8-hydroxy-7-methylbenzo[f]chromen-3-one (NP0167405)

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Record Information

Version

2.0

Created at

2022-09-03 02:58:41 UTC

Updated at

2022-09-03 02:58:41 UTC

NP-MRD ID

NP0167405

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-ethenyl-8-hydroxy-7-methylbenzo[f]chromen-3-one

Description

7-Methyl-8-hydroxy-10-vinyl-3H-naphtho[2,1-b]pyran-3-one belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 10-ethenyl-8-hydroxy-7-methylbenzo[f]chromen-3-one is found in Juncus acutus. Based on a literature review very few articles have been published on 7-Methyl-8-hydroxy-10-vinyl-3H-naphtho[2,1-b]pyran-3-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309032204582D          

 19 21  0  0  0  0            999 V2000
    4.5079   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 12 18  2  0  0  0  0
 18 19  1  0  0  0  0
  3 19  2  0  0  0  0
  9 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0167405

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2C=CC3=C(C=CC(=O)O3)C2=C(C=C)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O3/c1-3-10-8-13(17)9(2)11-4-6-14-12(16(10)11)5-7-15(18)19-14/h3-8,17H,1H2,2H3

> <INCHI_KEY>
FRAVQEWNAHYTGR-UHFFFAOYSA-N

> <FORMULA>
C16H12O3

> <MOLECULAR_WEIGHT>
252.269

> <EXACT_MASS>
252.078644246

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
26.797915854391967

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-ethenyl-8-hydroxy-7-methyl-3H-benzo[f]chromen-3-one

> <ALOGPS_LOGP>
3.55

> <JCHEM_LOGP>
3.7193945076666663

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.592586284010057

> <JCHEM_PKA_STRONGEST_BASIC>
-5.975684009249837

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
74.7072

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-ethenyl-8-hydroxy-7-methylbenzo[f]chromen-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       8.415  -4.207   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.875  -4.207   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.795  -1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.255  -1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.565  -0.206   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.795   1.127   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.875   1.127   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415   1.127   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.725  -0.206   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.035  -1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.185  -2.874   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18    3    9                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂O₃

Average Mass

252.2690 Da

Monoisotopic Mass

252.07864 Da

IUPAC Name

10-ethenyl-8-hydroxy-7-methyl-3H-benzo[f]chromen-3-one

Traditional Name

10-ethenyl-8-hydroxy-7-methylbenzo[f]chromen-3-one

CAS Registry Number

Not Available

SMILES

CC1=C2C=CC3=C(C=CC(=O)O3)C2=C(C=C)C=C1O

InChI Identifier

InChI=1S/C16H12O3/c1-3-10-8-13(17)9(2)11-4-6-14-12(16(10)11)5-7-15(18)19-14/h3-8,17H,1H2,2H3

InChI Key

FRAVQEWNAHYTGR-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Juncus acutus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Coumarin
2-naphthol
Benzopyran
Naphthalene
1-benzopyran
Styrene
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	3.55	ALOGPS
logP	3.72	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.59	ChemAxon
pKa (Strongest Basic)	-6	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	1	ChemAxon
Refractivity	74.71 m³·mol⁻¹	ChemAxon
Polarizability	26.8 Å³	ChemAxon
Number of Rings	3	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

9303894

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11128774

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-ethenyl-8-hydroxy-7-methylbenzo[f]chromen-3-one (NP0167405)

MOL for NP0167405 (10-ethenyl-8-hydroxy-7-methylbenzo[f]chromen-3-one)

3D MOL for NP0167405 (10-ethenyl-8-hydroxy-7-methylbenzo[f]chromen-3-one)

3D SDF for NP0167405 (10-ethenyl-8-hydroxy-7-methylbenzo[f]chromen-3-one)

3D-SDF for NP0167405 (10-ethenyl-8-hydroxy-7-methylbenzo[f]chromen-3-one)

PDB for NP0167405 (10-ethenyl-8-hydroxy-7-methylbenzo[f]chromen-3-one)

3D PDB for NP0167405 (10-ethenyl-8-hydroxy-7-methylbenzo[f]chromen-3-one)

SMILES for NP0167405 (10-ethenyl-8-hydroxy-7-methylbenzo[f]chromen-3-one)

INCHI for NP0167405 (10-ethenyl-8-hydroxy-7-methylbenzo[f]chromen-3-one)

Structure for NP0167405 (10-ethenyl-8-hydroxy-7-methylbenzo[f]chromen-3-one)

3D Structure for NP0167405 (10-ethenyl-8-hydroxy-7-methylbenzo[f]chromen-3-one)