NP-MRD: Showing NP-Card for Dehydroxyhexaspermone C (NP0060863)

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Record Information

Version

2.0

Created at

2022-04-28 05:50:30 UTC

Updated at

2022-04-28 05:50:31 UTC

NP-MRD ID

NP0060863

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dehydroxyhexaspermone C

Description

(2R,3S)-5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-2-[(2S,3R)-7-methoxy-3-(4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]-3,4-dihydro-2H-1-benzopyran-4-one belongs to the class of organic compounds known as 7-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C7 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Dehydroxyhexaspermone C is found in Ochna macrocalyx. Based on a literature review very few articles have been published on (2R,3S)-5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-2-[(2S,3R)-7-methoxy-3-(4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]-3,4-dihydro-2H-1-benzopyran-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207502D          

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M  END

     RDKit          3D

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  Mrv1652304282207502D          

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    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    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
   -5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  1  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 20  1  6  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 30 33  1  0  0  0  0
 23 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 22 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 34 40  1  0  0  0  0
  1 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0060863

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)[C@@H]1[C@H](OC2=CC(OC)=CC=C2C1=O)[C@@H]1OC2=C(C(O)=CC(OC)=C2)C(=O)[C@H]1C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C33H28O9/c1-38-20-10-6-18(7-11-20)27-30(36)23-13-12-21(39-2)15-25(23)41-32(27)33-28(17-4-8-19(34)9-5-17)31(37)29-24(35)14-22(40-3)16-26(29)42-33/h4-16,27-28,32-35H,1-3H3/t27-,28+,32-,33+/m0/s1

> <INCHI_KEY>
XCWXPZXXHWLHDD-TYMAPWMDSA-N

> <FORMULA>
C33H28O9

> <MOLECULAR_WEIGHT>
568.578

> <EXACT_MASS>
568.173332482

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
59.004033707731004

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S)-5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-2-[(2S,3R)-7-methoxy-3-(4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
5.01

> <JCHEM_LOGP>
5.494572914333332

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.552403701839587

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.59941247807477

> <JCHEM_PKA_STRONGEST_BASIC>
-4.263299386866059

> <JCHEM_POLAR_SURFACE_AREA>
120.75000000000001

> <JCHEM_REFRACTIVITY>
152.19039999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.11e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S)-5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-2-[(2S,3R)-7-methoxy-3-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-2-yl]-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2    6   41                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15   19                                                       
CONECT   19   18                                                            
CONECT   20    8   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   37                                                  
CONECT   23   22   24   34                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   20   27                                                  
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
CONECT   33   30                                                            
CONECT   34   23   35   40                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36   22                                                       
CONECT   38   36   39                                                       
CONECT   39   38                                                            
CONECT   40   34                                                            
CONECT   41    1   42                                                       
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₂₈O₉

Average Mass

568.5780 Da

Monoisotopic Mass

568.17333 Da

IUPAC Name

(2R,3S)-5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-2-[(2S,3R)-7-methoxy-3-(4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2R,3S)-5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-2-[(2S,3R)-7-methoxy-3-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-2-yl]-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)[C@@H]1[C@H](OC2=CC(OC)=CC=C2C1=O)[C@@H]1OC2=C(C(O)=CC(OC)=C2)C(=O)[C@H]1C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C33H28O9/c1-38-20-10-6-18(7-11-20)27-30(36)23-13-12-21(39-2)15-25(23)41-32(27)33-28(17-4-8-19(34)9-5-17)31(37)29-24(35)14-22(40-3)16-26(29)42-33/h4-16,27-28,32-35H,1-3H3/t27-,28+,32-,33+/m0/s1

InChI Key

XCWXPZXXHWLHDD-TYMAPWMDSA-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
Ochna macrocalyx	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C7 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

7-O-methylated isoflavonoids

Alternative Parents

Substituents

4p-methoxyisoflavonoid
7-methoxyisoflavonoid-skeleton
Hydroxyisoflavonoid
Isoflavanone
Isoflavan
Chromone
Chromane
Benzopyran
1-benzopyran
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Aryl ketone
Aryl alkyl ketone
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Oxacycle
Ether
Organoheterocyclic compound
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	5.01	ALOGPS
logP	5.49	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	8.6	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	120.75 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	152.19 m³·mol⁻¹	ChemAxon
Polarizability	59 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162863279

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Dehydroxyhexaspermone C (NP0060863)

MOL for NP0060863 (Dehydroxyhexaspermone C)

3D MOL for NP0060863 (Dehydroxyhexaspermone C)

3D SDF for NP0060863 (Dehydroxyhexaspermone C)

3D-SDF for NP0060863 (Dehydroxyhexaspermone C)

PDB for NP0060863 (Dehydroxyhexaspermone C)

3D PDB for NP0060863 (Dehydroxyhexaspermone C)

SMILES for NP0060863 (Dehydroxyhexaspermone C)

INCHI for NP0060863 (Dehydroxyhexaspermone C)

Structure for NP0060863 (Dehydroxyhexaspermone C)

3D Structure for NP0060863 (Dehydroxyhexaspermone C)