NP-MRD: Showing NP-Card for Prisconnatanone N (NP0332534)

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Record Information

Version

1.0

Created at

2024-02-22 00:08:30 UTC

Updated at

2024-05-02 04:36:28 UTC

NP-MRD ID

NP0332534

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Prisconnatanone N

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02222400082D          

 21 23  0  0  1  0            999 V2000
    2.1434    2.0625    0.0000 O   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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  1  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
    4.2868    0.8250    0.0000 C   0  0  2  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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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
  6  5  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
  3 10  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 12 20  1  0  0  0  0
  2 20  1  0  0  0  0
 11 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332534

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2C(=O)C3=C(C[C@@H](O)[C@H](C)C3)C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O5/c1-7-3-8-9(4-12(7)17)16(20)11-6-14(21-2)13(18)5-10(11)15(8)19/h5-7,12,17-18H,3-4H2,1-2H3/t7-,12-/m1/s1

> <INCHI_KEY>
KYNUEBXTPXUPDR-JMCQJSRRSA-N

> <FORMULA>
C16H16O5

> <MOLECULAR_WEIGHT>
288.299

> <EXACT_MASS>
288.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
29.841442437048748

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-2,6-dihydroxy-7-methoxy-3-methyl-1,2,3,4,9,10-hexahydroanthracene-9,10-dione

> <JCHEM_LOGP>
1.227848068666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.860715319223052

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.816262628039605

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8597231366370446

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
76.8824

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(6R,7R)-2,6-dihydroxy-3-methoxy-7-methyl-5,6,7,8-tetrahydroanthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-FEB-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-FEB-24         0                                  
HETATM    1  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    3                                                       
CONECT   11    4   12   21                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   12    2                                                  
CONECT   21   11                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆O₅

Average Mass

288.2990 Da

Monoisotopic Mass

288.09977 Da

IUPAC Name

(2R,3R)-2,6-dihydroxy-7-methoxy-3-methyl-1,2,3,4,9,10-hexahydroanthracene-9,10-dione

Traditional Name

(6R,7R)-2,6-dihydroxy-3-methoxy-7-methyl-5,6,7,8-tetrahydroanthracene-9,10-dione

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2C(=O)C3=C(C[C@@H](O)[C@H](C)C3)C(=O)C2=C1

InChI Identifier

InChI=1S/C16H16O5/c1-7-3-8-9(4-12(7)17)16(20)11-6-14(21-2)13(18)5-10(11)15(8)19/h5-7,12,17-18H,3-4H2,1-2H3/t7-,12-/m1/s1

InChI Key

KYNUEBXTPXUPDR-JMCQJSRRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	chenxinyi@imm.ac.cn	Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College	Xinyi Chen	2024-05-02	View Spectrum
1D_NOESY NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	chenxinyi@imm.ac.cn	Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College	Xinyi Chen	2024-05-02	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	chenxinyi@imm.ac.cn	Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College	Xinyi Chen	2024-05-02	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	chenxinyi@imm.ac.cn	Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College	Xinyi Chen	2024-02-22	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	chenxinyi@imm.ac.cn	Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College	Xinyi Chen	2024-02-22	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 800 MHz, CD3OD, experimental)	chenxinyi@imm.ac.cn	Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College	Xinyi Chen	2024-02-22	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	chenxinyi@imm.ac.cn	Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College	Xinyi Chen	2024-02-22	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 800 MHz, CD3OD, experimental)	chenxinyi@imm.ac.cn	Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College	Xinyi Chen	2024-02-22	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	chenxinyi@imm.ac.cn	Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College	Xinyi Chen	2024-02-22	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 800 MHz, CD3OD, experimental)	chenxinyi@imm.ac.cn	Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College	Xinyi Chen	2024-02-22	View Spectrum
INADEQUATE NMR	[¹³C, ¹³C] NMR Spectrum (2D, 101 MHz, CD3OD, experimental)	chenxinyi@imm.ac.cn	Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College	Xinyi Chen	2024-02-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800.23494142 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 499.640181603 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
tetrandra		Not Available

Chemical Taxonomy

Classification

Not classified

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	1.23	ChemAxon
pKa (Strongest Acidic)	7.82	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.88 m³·mol⁻¹	ChemAxon
Polarizability	29.84 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Chen X, Guan J, Zhang C, Li S, Zang Y, Chen J, Jin H, Lai F, Zhang D: Previously undescribed tetrahydroanthraquinones from Prismatomeris tetrandra (roxb.) K. Schum with antitumor cell proliferation activities. Phytochemistry. 2024 Apr;220:113995. doi: 10.1016/j.phytochem.2024.113995. Epub 2024 Feb 1. [PubMed:38307313 ]

Showing NP-Card for Prisconnatanone N (NP0332534)

MOL for NP0332534 (Prisconnatanone N)

3D MOL for NP0332534 (Prisconnatanone N)

3D SDF for NP0332534 (Prisconnatanone N)

3D-SDF for NP0332534 (Prisconnatanone N)

PDB for NP0332534 (Prisconnatanone N)

3D PDB for NP0332534 (Prisconnatanone N)

SMILES for NP0332534 (Prisconnatanone N)

INCHI for NP0332534 (Prisconnatanone N)

Structure for NP0332534 (Prisconnatanone N)

3D Structure for NP0332534 (Prisconnatanone N)