NP-MRD: Showing NP-Card for bauhinoxepin i (NP0322374)

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Record Information

Version

2.0

Created at

2022-09-12 01:06:44 UTC

Updated at

2022-09-12 01:06:44 UTC

NP-MRD ID

NP0322374

Secondary Accession Numbers

None

Natural Product Identification

Common Name

bauhinoxepin i

Description

Bauhinoxepin I belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. Bauhinoxepin I is an extremely weak basic (essentially neutral) compound (based on its pKa). bauhinoxepin i is found in Bauhinia purpurea. A dibenzooxepine that is 10,11-dihydrodibenzooxepine-1,4-dione substituted by a hydroxy, a methoxy and a methyl group at positions 8, 2 and 3 respectively.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.8776   -1.5682   -0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1432   -1.0317    0.6507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9125   -0.4278    0.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8467    0.8437    0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0643    1.7003    0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5507    1.4506   -0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4188    2.6848   -0.3033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3286    0.6565    0.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.6449    0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6522   -1.6732    0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9078   -1.4980   -0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6058   -0.2412    0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9532   -0.4347    0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8013    0.6495    0.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1450    0.4622    0.6352 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2930    1.9194    0.4832 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9633    2.1334    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1394    1.0512    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7923    1.4056   -0.1180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6954   -1.2207    0.5816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8240   -2.4456    0.8611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1025   -0.7747   -1.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7686   -2.0904   -0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1984   -2.3400   -0.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9229    2.6087    0.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1321    2.0373   -1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9738    1.2020    0.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9576   -1.8272    1.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2112   -2.6582    0.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5747   -2.3517    0.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7013   -1.6004   -1.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4285   -1.4085    0.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5534   -0.4576    0.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9266    2.7768    0.6655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5106    3.1125    0.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
  9 20  1  0
 20 21  2  0
 20  3  1  0
 19  8  1  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  5 26  1  0
  5 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 13 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
M  END


  Mrv1533004191514542D          

 21 23  0  0  0  0            999 V2000
    7.5168    1.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9120    0.6078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1237    0.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9401    1.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5448    2.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1517    1.8985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9682    2.7028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5470    1.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7305    0.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -0.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3912   -0.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    0.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0884    0.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837    0.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6953    0.6078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673    1.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4556    1.8985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0604    1.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037    1.6953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5189    0.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7025   -0.5145    0.0000 O   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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
  9 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0322374

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C)C(=O)C2=C(CCC3=CC(O)=CC=C3O2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-8-13(18)16-11(14(19)15(8)20-2)5-3-9-7-10(17)4-6-12(9)21-16/h4,6-7,17H,3,5H2,1-2H3

> <INCHI_KEY>
ATBQBNKWWGOEFJ-UHFFFAOYSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.283

> <EXACT_MASS>
286.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.8292511750142

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-hydroxy-6-methoxy-5-methyl-2-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),5,11,13-pentaene-4,7-dione

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
2.440709486333333

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.459671777570692

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.664183707469911

> <JCHEM_PKA_STRONGEST_BASIC>
-4.823683346112054

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
77.90879999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-hydroxy-6-methoxy-5-methyl-2-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),5,11,13-pentaene-4,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      14.031   2.182   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.902   1.135   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.431   1.588   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.088   3.090   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.217   4.137   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.617   3.544   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.274   5.045   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.488   2.496   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.830   0.995   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.870  -0.209   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.330  -0.209   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.370   0.995   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.898   0.541   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.770   1.588   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.298   1.135   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.112   3.090   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.584   3.544   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.713   2.496   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.100   3.165   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.302   0.541   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.645  -0.960   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   19                                                  
CONECT    9    8   10   20                                                  
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    8                                                       
CONECT   20    9    3   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
5,6-Dihydro-8-hydroxy-3-methoxy-1,4-dione-2-methyldibenz[b,F]-oxepin	ChEBI

Chemical Formula

C₁₆H₁₄O₅

Average Mass

286.2830 Da

Monoisotopic Mass

286.08412 Da

IUPAC Name

13-hydroxy-6-methoxy-5-methyl-2-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),5,11,13-pentaene-4,7-dione

Traditional Name

13-hydroxy-6-methoxy-5-methyl-2-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),5,11,13-pentaene-4,7-dione

CAS Registry Number

Not Available

SMILES

COC1=C(C)C(=O)C2=C(CCC3=CC(O)=CC=C3O2)C1=O

InChI Identifier

InChI=1S/C16H14O5/c1-8-13(18)16-11(14(19)15(8)20-2)5-3-9-7-10(17)4-6-12(9)21-16/h4,6-7,17H,3,5H2,1-2H3

InChI Key

ATBQBNKWWGOEFJ-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Bauhinia purpurea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-hydroxy-2-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Vinylogous ester
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:65471 )
phenols (CHEBI:65471 )
quinone (CHEBI:65471 )
dibenzooxepine (CHEBI:65471 )

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	2.43	ALOGPS
logP	2.44	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	5.66	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.91 m³·mol⁻¹	ChemAxon
Polarizability	28.83 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

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

16679966

PDB ID

Not Available

ChEBI ID

65471

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for bauhinoxepin i (NP0322374)

MOL for NP0322374 (bauhinoxepin i)

3D MOL for NP0322374 (bauhinoxepin i)

3D SDF for NP0322374 (bauhinoxepin i)

3D-SDF for NP0322374 (bauhinoxepin i)

PDB for NP0322374 (bauhinoxepin i)

3D PDB for NP0322374 (bauhinoxepin i)

SMILES for NP0322374 (bauhinoxepin i)

INCHI for NP0322374 (bauhinoxepin i)

Structure for NP0322374 (bauhinoxepin i)

3D Structure for NP0322374 (bauhinoxepin i)