NP-MRD: Showing NP-Card for Chamaejasmine (NP0140195)

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Record Information

Version

2.0

Created at

2022-06-29 20:50:28 UTC

Updated at

2022-06-29 20:50:28 UTC

NP-MRD ID

NP0140195

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chamaejasmine

Description

Chamaejasmine 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''. Chamaejasmine is found in Enkleia siamensis and Stellera chamaejasme. Chamaejasmine was first documented in 2019 (PMID: 31529668). Based on a literature review a small amount of articles have been published on Chamaejasmine (PMID: 31726807) (PMID: 31694198) (PMID: 31018627) (PMID: 30463909).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292222502D          

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M  END

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 20 29  1  1  0  0  0
 29 30  2  0  0  0  0
 27 31  1  0  0  0  0
 25 32  1  0  0  0  0
 21 33  1  6  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
  3 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140195

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=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(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H22O10/c31-15-5-1-13(2-6-15)29-25(27(37)23-19(35)9-17(33)11-21(23)39-29)26-28(38)24-20(36)10-18(34)12-22(24)40-30(26)14-3-7-16(32)8-4-14/h1-12,25-26,29-36H/t25-,26-,29+,30+/m1/s1

> <INCHI_KEY>
RNQBLQALVMHBKH-HHGOQMMWSA-N

> <FORMULA>
C30H22O10

> <MOLECULAR_WEIGHT>
542.496

> <EXACT_MASS>
542.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
52.02124174814083

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.27

> <JCHEM_LOGP>
5.403325424666667

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.10429997917402

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.539643703555772

> <JCHEM_PKA_STRONGEST_BASIC>
-5.063540984738151

> <JCHEM_POLAR_SURFACE_AREA>
173.98

> <JCHEM_REFRACTIVITY>
140.7244

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.98e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -3.756  -3.802   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.002  -2.897   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.841  -1.365   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.434  -0.739   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.189  -1.644   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.350  -3.176   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.104  -4.081   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.303  -3.454   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.549  -4.360   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.956  -3.733   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.388  -5.891   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.634  -6.796   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.473  -8.328   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.066  -8.954   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.180  -8.049   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.019  -6.518   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.265  -5.612   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.905 -10.486   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.041  -6.170   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.913  -3.985   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -6.087  -0.460   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   40                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16    7                                                       
CONECT   18   14                                                            
CONECT   19   12                                                            
CONECT   20    8   21   29                                                  
CONECT   21   20   22   33                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   23   29                                                  
CONECT   29   28   20   30                                                  
CONECT   30   29                                                            
CONECT   31   27                                                            
CONECT   32   25                                                            
CONECT   33   21   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                                                            
CONECT   40    3                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
DL-Chamaejasmine	MeSH

Chemical Formula

C₃₀H₂₂O₁₀

Average Mass

542.4960 Da

Monoisotopic Mass

542.12130 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC1=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(O)C=C1

InChI Identifier

InChI=1S/C30H22O10/c31-15-5-1-13(2-6-15)29-25(27(37)23-19(35)9-17(33)11-21(23)39-29)26-28(38)24-20(36)10-18(34)12-22(24)40-30(26)14-3-7-16(32)8-4-14/h1-12,25-26,29-36H/t25-,26-,29+,30+/m1/s1

InChI Key

RNQBLQALVMHBKH-HHGOQMMWSA-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
Enkleia siamensis	LOTUS Database	35616633
Stellera chamaejasme	LOTUS Database	35616633

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
Flavanone
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Flavan
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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

136825

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

155320

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hou W, Xia J, Liu C, Li S, Wu T, Huang Y: Development of a method to screen and isolate bioactive constituents from Stellera chamaejasme by ultrafiltration and liquid chromatography combined with semi-preparative high-performance liquid chromatography and high-speed counter current chromatography. J Sep Sci. 2019 Nov;42(22):3421-3431. doi: 10.1002/jssc.201900772. Epub 2019 Oct 23. [PubMed:31529668 ]
Wang J, Li X: Chamaejasmine induces apoptosis in human non-small-cell lung cancer A549 cells through increasing the Bax/Bcl-2 ratio, caspase-3 and activating the Fas/FasL. Minerva Med. 2021 Jun;112(3):413-414. doi: 10.23736/S0026-4806.19.06209-8. Epub 2019 Nov 11. [PubMed:31726807 ]
Kim TY, Park NJ, Jegal J, Choi S, Lee SW, Hang J, Kim SN, Yang MH: Chamaejasmine Isolated from Wikstroemia dolichantha Diels Suppresses 2,4-Dinitrofluoro-benzene-Induced Atopic Dermatitis in SKH-1 Hairless Mice. Biomolecules. 2019 Nov 5;9(11). pii: biom9110697. doi: 10.3390/biom9110697. [PubMed:31694198 ]
Jegal J, Park NJ, Kim TY, Choi S, Lee SW, Hang J, Kim SN, Yang MH: Effect of Topically Applied Wikstroemia dolichantha Diels on the Development of Atopic Dermatitis-Like Skin Symptoms in Mice. Nutrients. 2019 Apr 23;11(4). pii: nu11040914. doi: 10.3390/nu11040914. [PubMed:31018627 ]
Yang D, Zhang H, Wu J, Ma R, Li Z, Wang K, Yang F: The role of chamaejasmine in cellular apoptosis and autophagy in MG-63 cells. Biosci Rep. 2019 Jan 15;39(1). pii: BSR20181707. doi: 10.1042/BSR20181707. Print 2019 Jan 31. [PubMed:30463909 ]

Showing NP-Card for Chamaejasmine (NP0140195)

MOL for NP0140195 (Chamaejasmine)

3D MOL for NP0140195 (Chamaejasmine)

3D SDF for NP0140195 (Chamaejasmine)

3D-SDF for NP0140195 (Chamaejasmine)

PDB for NP0140195 (Chamaejasmine)

3D PDB for NP0140195 (Chamaejasmine)

SMILES for NP0140195 (Chamaejasmine)

INCHI for NP0140195 (Chamaejasmine)

Structure for NP0140195 (Chamaejasmine)

3D Structure for NP0140195 (Chamaejasmine)