NP-MRD: Showing NP-Card for Usambarin K (NP0331579)

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Record Information

Version

2.0

Created at

2023-04-15 00:03:10 UTC

Updated at

2024-09-03 04:16:10 UTC

NP-MRD ID

NP0331579

Natural Product DOI

https://doi.org/10.57994/0558

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Usambarin K

Description

3-(3-Methoxy-4-hydroxyphenyl)-2,3-dihydro-1-benzooxepin-8-ol belongs to the class of organic compounds known as benzoxepines. These are organic compounds containing a benzene ring fused to an oxepine ring (an unsaturated seven-membered heterocycle with one oxygen atom replacing a carbon atom). Based on a literature review very few articles have been published on 3-(3-Methoxy-4-hydroxyphenyl)-2,3-dihydro-1-benzooxepin-8-ol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304152302032D          

 21 23  0  0  0  0            999 V2000
   -0.2228   -1.9441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -1.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -0.7066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2062   -0.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206   -0.7066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5656   -0.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700   -0.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7279   -1.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5529   -1.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9654   -0.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7904   -0.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2029   -1.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0279   -1.1191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7904   -1.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2029   -2.5481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7904   -3.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9654   -1.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700   -1.8624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5656   -2.0460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206   -1.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2062   -1.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  2  0  0  0  0
  9 17  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  0  0  0  0
  5 20  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  2 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331579

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C1COC2=CC(O)=CC=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O4/c1-20-17-8-12(5-7-15(17)19)13-3-2-11-4-6-14(18)9-16(11)21-10-13/h2-9,13,18-19H,10H2,1H3

> <INCHI_KEY>
XVYCGNIDLFDDRI-UHFFFAOYSA-N

> <FORMULA>
C17H16O4

> <MOLECULAR_WEIGHT>
284.311

> <EXACT_MASS>
284.104858995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
30.01299607150272

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzoxepin-8-ol

> <JCHEM_LOGP>
3.199353619999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.101810075540527

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.437664788620687

> <JCHEM_PKA_STRONGEST_BASIC>
-4.581212468692535

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
81.141

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzoxepin-8-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-23         0                                  
HETATM    1  O   UNK     0      -0.416  -3.629   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.918  -2.859   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.918  -1.319   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.251  -0.549   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.585  -1.319   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.789  -0.359   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.291  -0.702   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.959  -2.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.499  -2.089   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.269  -0.755   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.809  -0.755   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.579  -2.089   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      13.119  -2.089   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.809  -3.423   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.579  -4.756   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.809  -6.090   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.269  -3.423   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.291  -3.477   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.789  -3.819   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.585  -2.859   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.251  -3.629   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   20                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14    9                                                       
CONECT   18    8   19                                                       
CONECT   19   18   20                                                       
CONECT   20    5   19   21                                                  
CONECT   21   20    2                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₆O₄

Average Mass

284.3110 Da

Monoisotopic Mass

284.10486 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C1COC2=CC(O)=CC=C2C=C1

InChI Identifier

InChI=1S/C17H16O4/c1-20-17-8-12(5-7-15(17)19)13-3-2-11-4-6-14(18)9-16(11)21-10-13/h2-9,13,18-19H,10H2,1H3

InChI Key

XVYCGNIDLFDDRI-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-04-15	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-04-15	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-04-15	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-04-15	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-04-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-04-15	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-04-15	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoxepines. These are organic compounds containing a benzene ring fused to an oxepine ring (an unsaturated seven-membered heterocycle with one oxygen atom replacing a carbon atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxepines

Sub Class

Not Available

Direct Parent

Benzoxepines

Alternative Parents

Substituents

Benzoxepine
Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Ether
Oxacycle
Organooxygen compound
Hydrocarbon derivative
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

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101890466

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Usambarin K (NP0331579)

MOL for NP0331579 (Usambarin K)

3D MOL for NP0331579 (Usambarin K)

3D SDF for NP0331579 (Usambarin K)

3D-SDF for NP0331579 (Usambarin K)

PDB for NP0331579 (Usambarin K)

3D PDB for NP0331579 (Usambarin K)

SMILES for NP0331579 (Usambarin K)

INCHI for NP0331579 (Usambarin K)

Structure for NP0331579 (Usambarin K)

3D Structure for NP0331579 (Usambarin K)