NP-MRD: Showing NP-Card for Isochamaejasmenin B (NP0072157)

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Record Information

Version

2.0

Created at

2022-04-28 17:32:14 UTC

Updated at

2022-04-28 17:32:15 UTC

NP-MRD ID

NP0072157

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isochamaejasmenin B

Description

Isochamaejasmenin B belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Isochamaejasmenin B is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Isochamaejasmenin B is found in Stellera chamaejasme . Isochamaejasmenin B was first documented in 2005 (PMID: 15997133). Based on a literature review very few articles have been published on isochamaejasmenin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219322D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282219322D          

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   -2.8579   -1.6500    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
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    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
  3  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 13  1  0  0  0  0
 12 14  1  1  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 11 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  1  0  0  0
 27 28  2  0  0  0  0
 26 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
 25 32  1  0  0  0  0
 31 33  1  0  0  0  0
 29 34  1  0  0  0  0
 23 35  1  1  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 35 40  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0072157

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C32H26O10/c1-39-19-7-3-15(4-8-19)31-27(29(37)25-21(35)11-17(33)13-23(25)41-31)28-30(38)26-22(36)12-18(34)14-24(26)42-32(28)16-5-9-20(40-2)10-6-16/h3-14,27-28,31-36H,1-2H3/t27-,28+,31-,32+

> <INCHI_KEY>
BTCICADMSGBCKA-WVKQWSHJSA-N

> <FORMULA>
C32H26O10

> <MOLECULAR_WEIGHT>
570.55

> <EXACT_MASS>
570.152597037

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
57.510611394257594

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.86

> <JCHEM_LOGP>
5.695113536666668

> <ALOGPS_LOGS>
-4.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.132243758664563

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.54990456198088

> <JCHEM_PKA_STRONGEST_BASIC>
-4.523877271171124

> <JCHEM_POLAR_SURFACE_AREA>
151.98000000000002

> <JCHEM_REFRACTIVITY>
149.68899999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.88e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S)-3-[(2R,3R)-5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)-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      -2.686   3.438   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.279   2.811   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.033   3.716   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.194   5.248   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.601   5.874   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.847   4.969   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.762   7.406   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.374   3.090   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.118   1.280   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.289   0.653   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.364   0.374   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.771   1.001   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.932   2.532   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -5.017   0.096   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.856  -1.436   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.102  -2.341   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -7.509  -1.715   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -7.670  -0.183   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.424   0.722   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -8.755  -2.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0     -10.161  -1.994   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.246   0.905   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -0.770   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  -3.080   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2    6   13                                                  
CONECT    2    1    3    9                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5                                                            
CONECT    8    3                                                            
CONECT    9    2   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   22                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    1                                                       
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   17   21                                                       
CONECT   21   20                                                            
CONECT   22   11   23   27                                                  
CONECT   23   22   24   35                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   32                                                  
CONECT   26   25   27   29                                                  
CONECT   27   26   22   28                                                  
CONECT   28   27                                                            
CONECT   29   26   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31   25                                                       
CONECT   33   31                                                            
CONECT   34   29                                                            
CONECT   35   23   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   41                                                  
CONECT   39   38   40                                                       
CONECT   40   39   35                                                       
CONECT   41   38   42                                                       
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Value	Source
Meso- 2,2',3,3'-tetrahydro-5,5',7',7-tetrahydroxy-2,2'-bis(4-methoxyphenyl)-[3,3'-bi-4H-1-benzopyran]-4,4'-dione	ChEBI
Rel-(2S,3S)-3-[(2R,3R)-5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one	ChEBI

Chemical Formula

C₃₂H₂₆O₁₀

Average Mass

570.5500 Da

Monoisotopic Mass

570.15260 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C32H26O10/c1-39-19-7-3-15(4-8-19)31-27(29(37)25-21(35)11-17(33)13-23(25)41-31)28-30(38)26-22(36)12-18(34)14-24(26)42-32(28)16-5-9-20(40-2)10-6-16/h3-14,27-28,31-36H,1-2H3/t27-,28+,31-,32+

InChI Key

BTCICADMSGBCKA-WVKQWSHJSA-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
Stellera chamaejasme	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

Bi- and polyflavonoid skeleton
4p-methoxyflavonoid-skeleton
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Chromone
Chromane
Benzopyran
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Organoheterocyclic compound
Ether
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

ring assembly (CHEBI:66091 )
biflavonoid (CHEBI:66091 )
hydroxyflavanone (CHEBI:66091 )
methoxyflavanone (CHEBI:66091 )

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	4.86	ALOGPS
logP	5.7	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	7.55	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	151.98 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	149.69 m³·mol⁻¹	ChemAxon
Polarizability	57.51 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00031893

Chemspider ID

9928108

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11753405

PDB ID

Not Available

ChEBI ID

66091

Good Scents ID

Not Available

References

General References

Yang G, Liao Z, Xu Z, Zhang H, Chen D: Antimitotic and antifungal C-3/C-3''-biflavanones from Stellera chamaejasme. Chem Pharm Bull (Tokyo). 2005 Jul;53(7):776-9. doi: 10.1248/cpb.53.776. [PubMed:15997133 ]

Showing NP-Card for Isochamaejasmenin B (NP0072157)

MOL for NP0072157 (Isochamaejasmenin B)

3D MOL for NP0072157 (Isochamaejasmenin B)

3D SDF for NP0072157 (Isochamaejasmenin B)

3D-SDF for NP0072157 (Isochamaejasmenin B)

PDB for NP0072157 (Isochamaejasmenin B)

3D PDB for NP0072157 (Isochamaejasmenin B)

SMILES for NP0072157 (Isochamaejasmenin B)

INCHI for NP0072157 (Isochamaejasmenin B)

Structure for NP0072157 (Isochamaejasmenin B)

3D Structure for NP0072157 (Isochamaejasmenin B)