NP-MRD: Showing NP-Card for Neochamaejasmin A (NP0054271)

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Record Information

Version

2.0

Created at

2022-04-28 00:41:11 UTC

Updated at

2022-04-28 00:41:11 UTC

NP-MRD ID

NP0054271

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Neochamaejasmin A

Description

Neochamaejasmin 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''. Neochamaejasmin A is found in Stellera chamaejasme and Wikstroemia sikokiana. Neochamaejasmin A was first documented in 2018 (PMID: 29360465). Based on a literature review a small amount of articles have been published on Neochamaejasmin A (PMID: 33357557) (PMID: 32411325) (PMID: 31529668) (PMID: 31153465).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202412D          

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M  END

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 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 26 29  1  0  0  0  0
 18 30  1  0  0  0  0
 16 31  1  0  0  0  0
  8 32  1  1  0  0  0
 32 33  2  0  0  0  0
 33 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
 32 37  1  0  0  0  0
 35 38  1  0  0  0  0
  3 39  1  0  0  0  0
  1 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054271

> <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-OIWKEWRZSA-N

> <FORMULA>
C30H22O10

> <MOLECULAR_WEIGHT>
542.496

> <EXACT_MASS>
542.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
52.34089568452848

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S)-3-[(2S,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>
140.72440000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S)-3-[(2S,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                                 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  O   UNK     0       6.280  -3.790   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       3.613   0.830   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -3.667  -0.352   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.506  -1.884   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.752  -2.789   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -6.159  -2.163   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -6.320  -0.631   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -5.074   0.274   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -7.405  -3.068   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       2.723   2.642   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -0.412   6.958   0.000  0.00  0.00           O+0
CONECT    1    2    6   40                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   39                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   32                                                  
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   31                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   30                                                  
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                                                            
CONECT   30   18                                                            
CONECT   31   16                                                            
CONECT   32    8   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   38                                                  
CONECT   36   35   37                                                       
CONECT   37   36   32                                                       
CONECT   38   35                                                            
CONECT   39    3                                                            
CONECT   40    1                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₂O₁₀

Average Mass

542.4960 Da

Monoisotopic Mass

542.12130 Da

IUPAC Name

(2S,3S)-3-[(2S,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

Traditional Name

(2S,3S)-3-[(2S,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

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-OIWKEWRZSA-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 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
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
logP	4.27	ALOGPS
logP	5.4	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	7.54	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	173.98 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	140.72 m³·mol⁻¹	ChemAxon
Polarizability	52.34 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

C00006422

Chemspider ID

4478229

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5320060

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ren Y, Li Q, Lu L, Jin H, Tao K, Hou T: Toxicity and physiological actions of biflavones on potassium current in insect neuronal cells. Pestic Biochem Physiol. 2021 Jan;171:104735. doi: 10.1016/j.pestbp.2020.104735. Epub 2020 Oct 16. [PubMed:33357557 ]
Ding Y, Xie Q, Liu W, Pan Z, Fan X, Chen X, Li M, Zhao W, Li D, Zheng Q: Neochamaejasmin A Induces Mitochondrial-Mediated Apoptosis in Human Hepatoma Cells via ROS-Dependent Activation of the ERK1/2/JNK Signaling Pathway. Oxid Med Cell Longev. 2020 Jan 20;2020:3237150. doi: 10.1155/2020/3237150. eCollection 2020. [PubMed:32411325 ]
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 ]
Ren Y, Mu Y, Yue Y, Jin H, Tao K, Hou T: Neochamaejasmin A extracted from Stellera chamaejasme L. induces apoptosis involving mitochondrial dysfunction and oxidative stress in Sf9 cells. Pestic Biochem Physiol. 2019 Jun;157:169-177. doi: 10.1016/j.pestbp.2019.03.025. Epub 2019 Apr 1. [PubMed:31153465 ]
Ren Y, Pan L, Zhao W, Xu L, Xu J, Lu H, Chen Y: Neochamaejasmin A inhibits KV1.4 channel activity via direct binding to the pore. Brain Res. 2018 Mar 15;1683:17-26. doi: 10.1016/j.brainres.2018.01.013. Epub 2018 Jan 31. [PubMed:29360465 ]

Showing NP-Card for Neochamaejasmin A (NP0054271)

MOL for NP0054271 (Neochamaejasmin A)

3D MOL for NP0054271 (Neochamaejasmin A)

3D SDF for NP0054271 (Neochamaejasmin A)

3D-SDF for NP0054271 (Neochamaejasmin A)

PDB for NP0054271 (Neochamaejasmin A)

3D PDB for NP0054271 (Neochamaejasmin A)

SMILES for NP0054271 (Neochamaejasmin A)

INCHI for NP0054271 (Neochamaejasmin A)

Structure for NP0054271 (Neochamaejasmin A)

3D Structure for NP0054271 (Neochamaejasmin A)