NP-MRD: Showing NP-Card for Chamaejasmenin A (NP0054276)

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Record Information

Version

2.0

Created at

2022-04-28 00:41:23 UTC

Updated at

2022-04-28 00:41:23 UTC

NP-MRD ID

NP0054276

Secondary Accession Numbers

NP0137752

Natural Product Identification

Common Name

Chamaejasmenin A

Description

Chamaejasmenin A 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''. Chamaejasmenin A 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. Chamaejasmenin A is found in Stellera chamaejasme , Wikstroemia indica and Wikstroemia sikokiana. Chamaejasmenin A was first documented in 2005 (PMID: 15997133). Based on a literature review very few articles have been published on chamaejasmenin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202412D          

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   -2.7183    0.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9669   -1.6434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8807   -2.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4589    1.4155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2210    3.7276    0.0000 O   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  6  0  0  0
 12 13  1  6  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  2  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
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 18 31  1  0  0  0  0
 16 32  1  0  0  0  0
  8 33  1  1  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 33 38  1  0  0  0  0
 36 39  1  0  0  0  0
 39 40  1  0  0  0  0
  3 41  1  0  0  0  0
  1 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054276

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)[C@H]1OC2=CC(O)=CC(O)=C2C(=O)[C@@H]1[C@H]1[C@@H](OC2=CC(O)=CC(O)=C2C1=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-COWFKMKXSA-N

> <FORMULA>
C32H26O10

> <MOLECULAR_WEIGHT>
570.55

> <EXACT_MASS>
570.152597037

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
57.50193083576247

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R)-3-[(2R,3S)-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>
8.132243758664567

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.54990456198088

> <JCHEM_PKA_STRONGEST_BASIC>
-4.523877271171124

> <JCHEM_POLAR_SURFACE_AREA>
151.98000000000002

> <JCHEM_REFRACTIVITY>
149.68900000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.88e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-3-[(2R,3S)-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      -0.252   5.427   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.155   4.800   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.316   3.269   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.070   2.363   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.336   2.990   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.497   4.521   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.582   2.085   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.421   0.553   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.014  -0.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.231   0.832   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.638   0.205   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.388  -1.480   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.946  -0.710   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.191   0.195   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.279  -1.480   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.613  -0.710   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.947  -1.480   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.947  -3.020   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.613  -3.790   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.279  -3.020   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.946  -3.790   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.388  -3.020   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.722  -3.790   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.722  -5.330   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.055  -6.100   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.389  -5.330   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.389  -3.790   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.055  -3.020   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -5.723  -6.100   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -5.723  -7.640   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.280  -3.790   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       3.613   0.830   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -3.667  -0.352   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.506  -1.884   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.752  -2.789   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -6.159  -2.163   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -6.320  -0.631   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -5.074   0.274   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -7.405  -3.068   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -7.244  -4.599   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       2.723   2.642   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -0.412   6.958   0.000  0.00  0.00           O+0
CONECT    1    2    6   42                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   41                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   33                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13   22                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   20                                                  
CONECT   16   15   17   32                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   12   23                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   26   30                                                       
CONECT   30   29                                                            
CONECT   31   18                                                            
CONECT   32   16                                                            
CONECT   33    8   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   39                                                  
CONECT   37   36   38                                                       
CONECT   38   37   33                                                       
CONECT   39   36   40                                                       
CONECT   40   39                                                            
CONECT   41    3                                                            
CONECT   42    1                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Value	Source
Rel-(-)-(3,3'-bi-4H-1-benzopyran)-4,4'-dione,2,2',3,3'-tetrahydro-5,5',7,7'-tetrahydroxy-2,2'-bis(4-methoxyphenyl)	ChEBI

Chemical Formula

C₃₂H₂₆O₁₀

Average Mass

570.5500 Da

Monoisotopic Mass

570.15260 Da

IUPAC Name

(2S,3R)-3-[(2R,3S)-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,3R)-3-[(2R,3S)-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=CC(O)=CC(O)=C2C(=O)[C@@H]1[C@H]1[C@@H](OC2=CC(O)=CC(O)=C2C1=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-COWFKMKXSA-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
Wikstroemia indica	LOTUS Database	35616633
Wikstroemia sikokiana	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:65614 )
biflavonoid (CHEBI:65614 )
hydroxyflavanone (CHEBI:65614 )
methoxyflavanone (CHEBI:65614 )

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	57.5 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

C00006427

Chemspider ID

29367948

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71728343

PDB ID

Not Available

ChEBI ID

65614

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 Chamaejasmenin A (NP0054276)

MOL for NP0054276 (Chamaejasmenin A)

3D MOL for NP0054276 (Chamaejasmenin A)

3D SDF for NP0054276 (Chamaejasmenin A)

3D-SDF for NP0054276 (Chamaejasmenin A)

PDB for NP0054276 (Chamaejasmenin A)

3D PDB for NP0054276 (Chamaejasmenin A)

SMILES for NP0054276 (Chamaejasmenin A)

INCHI for NP0054276 (Chamaejasmenin A)

Structure for NP0054276 (Chamaejasmenin A)

3D Structure for NP0054276 (Chamaejasmenin A)