NP-MRD: Showing NP-Card for 8,8'-Paepalantine dimer (NP0073828)

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Record Information

Version

2.0

Created at

2022-04-28 19:03:11 UTC

Updated at

2022-04-28 19:03:11 UTC

NP-MRD ID

NP0073828

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8,8'-Paepalantine dimer

Description

CHEMBL1834753 belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. 8,8'-Paepalantine dimer is found in Paepalanthus bromelioides. Based on a literature review very few articles have been published on CHEMBL1834753.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221032D          

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M  END

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   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    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   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  4 12  2  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 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
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 14 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 18 31  1  0  0  0  0
 31 32  2  0  0  0  0
 29 33  1  0  0  0  0
 17 34  1  0  0  0  0
 15 35  1  0  0  0  0
 10 36  1  0  0  0  0
 36 37  1  0  0  0  0
  3 38  1  0  0  0  0
  2 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
  1 43  1  0  0  0  0
 42 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073828

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C(O)=C2C(O)=C3C(=O)OC(C)=CC3=C(OC)C2=C1)C1=C(OC)C=C2C(OC)=C3C=C(C)OC(=O)C3=C(O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C32H26O12/c1-11-7-13-21(31(37)43-11)25(33)19-15(29(13)41-5)9-17(39-3)23(27(19)35)24-18(40-4)10-16-20(28(24)36)26(34)22-14(30(16)42-6)8-12(2)44-32(22)38/h7-10,33-36H,1-6H3

> <INCHI_KEY>
ZFQBRSSPULXABF-UHFFFAOYSA-N

> <FORMULA>
C32H26O12

> <MOLECULAR_WEIGHT>
602.548

> <EXACT_MASS>
602.142426277

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
61.65999665750266

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-{9,10-dihydroxy-5,7-dimethoxy-3-methyl-1-oxo-1H-benzo[g]isochromen-8-yl}-9,10-dihydroxy-5,7-dimethoxy-3-methyl-1H-benzo[g]isochromen-1-one

> <ALOGPS_LOGP>
4.20

> <JCHEM_LOGP>
5.618912792666666

> <ALOGPS_LOGS>
-4.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.514323214626613

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.7064921561733915

> <JCHEM_PKA_STRONGEST_BASIC>
-4.263163800034173

> <JCHEM_POLAR_SURFACE_AREA>
170.44

> <JCHEM_REFRACTIVITY>
160.3652

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-{9,10-dihydroxy-5,7-dimethoxy-3-methyl-1-oxobenzo[g]isochromen-8-yl}-9,10-dihydroxy-5,7-dimethoxy-3-methylbenzo[g]isochromen-1-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      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -9.336  -6.930   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.667  -0.000   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       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -8.002 -12.320   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -10.669 -12.320   0.000  0.00  0.00           C+0
CONECT    1    2    6   43                                                  
CONECT    2    1    3   39                                                  
CONECT    3    2    4   38                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   36                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11    4   13                                                  
CONECT   13   12                                                            
CONECT   14   11   15   23                                                  
CONECT   15   14   16   35                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18   34                                                  
CONECT   18   17   19   31                                                  
CONECT   19   18   20   28                                                  
CONECT   20   19   21   26                                                  
CONECT   21   20   16   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   14   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   20   27                                                       
CONECT   27   26                                                            
CONECT   28   19   29                                                       
CONECT   29   28   30   33                                                  
CONECT   30   29   31                                                       
CONECT   31   30   18   32                                                  
CONECT   32   31                                                            
CONECT   33   29                                                            
CONECT   34   17                                                            
CONECT   35   15                                                            
CONECT   36   10   37                                                       
CONECT   37   36                                                            
CONECT   38    3                                                            
CONECT   39    2   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42    1                                                       
CONECT   44   42                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₂₆O₁₂

Average Mass

602.5480 Da

Monoisotopic Mass

602.14243 Da

IUPAC Name

8-{9,10-dihydroxy-5,7-dimethoxy-3-methyl-1-oxo-1H-benzo[g]isochromen-8-yl}-9,10-dihydroxy-5,7-dimethoxy-3-methyl-1H-benzo[g]isochromen-1-one

Traditional Name

8-{9,10-dihydroxy-5,7-dimethoxy-3-methyl-1-oxobenzo[g]isochromen-8-yl}-9,10-dihydroxy-5,7-dimethoxy-3-methylbenzo[g]isochromen-1-one

CAS Registry Number

Not Available

SMILES

COC1=C(C(O)=C2C(O)=C3C(=O)OC(C)=CC3=C(OC)C2=C1)C1=C(OC)C=C2C(OC)=C3C=C(C)OC(=O)C3=C(O)C2=C1O

InChI Identifier

InChI=1S/C32H26O12/c1-11-7-13-21(31(37)43-11)25(33)19-15(29(13)41-5)9-17(39-3)23(27(19)35)24-18(40-4)10-16-20(28(24)36)26(34)22-14(30(16)42-6)8-12(2)44-32(22)38/h7-10,33-36H,1-6H3

InChI Key

ZFQBRSSPULXABF-UHFFFAOYSA-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
Paepalanthus bromelioides	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Isocoumarin
1-naphthol
Benzopyran
Naphthalene
2-benzopyran
Anisole
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Lactone
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	4.2	ALOGPS
logP	5.62	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	7.71	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	170.44 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	160.37 m³·mol⁻¹	ChemAxon
Polarizability	61.66 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

C00034430

Chemspider ID

4582971

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5473234

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 8,8'-Paepalantine dimer (NP0073828)

MOL for NP0073828 (8,8'-Paepalantine dimer)

3D MOL for NP0073828 (8,8'-Paepalantine dimer)

3D SDF for NP0073828 (8,8'-Paepalantine dimer)

3D-SDF for NP0073828 (8,8'-Paepalantine dimer)

PDB for NP0073828 (8,8'-Paepalantine dimer)

3D PDB for NP0073828 (8,8'-Paepalantine dimer)

SMILES for NP0073828 (8,8'-Paepalantine dimer)

INCHI for NP0073828 (8,8'-Paepalantine dimer)

Structure for NP0073828 (8,8'-Paepalantine dimer)

3D Structure for NP0073828 (8,8'-Paepalantine dimer)