NP-MRD: Showing NP-Card for Isoreptanthrin (NP0073559)

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Record Information

Version

2.0

Created at

2022-04-28 18:47:20 UTC

Updated at

2022-04-28 18:47:20 UTC

NP-MRD ID

NP0073559

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isoreptanthrin

Description

3,4,5',6',9,10'-Hexamethoxy-[1,1'-biphenanthrene]-2,2',7,7'-tetrol belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached. Isoreptanthrin is found in Bulbophyllum reptans. 3,4,5',6',9,10'-Hexamethoxy-[1,1'-biphenanthrene]-2,2',7,7'-tetrol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161518592D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004161518592D          

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    2.7770   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
  3 22  1  0  0  0  0
 16 22  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 23 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 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  1  0  0  0  0
 36 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 41 44  2  0  0  0  0
 28 44  1  0  0  0  0
 34 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073559

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(O)=C(OC)C(OC)=C2C2=CC=C(O)C=C12)C1=C2C(OC)=CC3=CC(O)=C(OC)C(OC)=C3C2=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C34H30O10/c1-39-23-14-20-26(17-8-7-16(35)13-19(17)23)33(43-5)34(44-6)30(38)28(20)29-21(36)10-9-18-25-15(12-24(40-2)27(18)29)11-22(37)31(41-3)32(25)42-4/h7-14,35-38H,1-6H3

> <INCHI_KEY>
FAEKSGIHDACYAU-UHFFFAOYSA-N

> <FORMULA>
C34H30O10

> <MOLECULAR_WEIGHT>
598.604

> <EXACT_MASS>
598.183897166

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
62.91539506957015

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(2,7-dihydroxy-5,6,10-trimethoxyphenanthren-1-yl)-3,4,9-trimethoxyphenanthrene-2,7-diol

> <ALOGPS_LOGP>
4.98

> <JCHEM_LOGP>
5.418089324

> <ALOGPS_LOGS>
-5.43

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.336539705261377

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.784023907316213

> <JCHEM_PKA_STRONGEST_BASIC>
-4.28962177606187

> <JCHEM_POLAR_SURFACE_AREA>
136.3

> <JCHEM_REFRACTIVITY>
163.69779999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.24e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(2,7-dihydroxy-5,6,10-trimethoxyphenanthren-1-yl)-3,4,9-trimethoxyphenanthrene-2,7-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      13.654   0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.114   0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.034  -1.897   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.494  -1.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.724  -3.231   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.478  -4.136   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.494  -4.565   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.724  -5.898   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.494  -7.232   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.034  -4.565   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.804  -5.898   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.034  -7.232   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.804  -3.231   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.344  -3.231   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.114  -4.565   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.654  -4.565   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.424  -3.231   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      15.964  -3.231   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      13.654  -1.897   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.114  -1.897   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.034   0.770   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.184  -3.231   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.414  -4.565   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -1.746   3.437   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       2.874   3.437   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       2.104   4.771   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7   23                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12    5   16                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21    3   16                                                  
CONECT   23    6   24   29                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   44                                                  
CONECT   29   28   23   30                                                  
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   34                                                       
CONECT   34   33   35   44                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   41                                                  
CONECT   39   38   40                                                       
CONECT   40   39                                                            
CONECT   41   38   42   44                                                  
CONECT   42   41   43                                                       
CONECT   43   42                                                            
CONECT   44   41   28   34                                                  
MASTER        0    0    0    0    0    0    0    0   44    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₃₀O₁₀

Average Mass

598.6040 Da

Monoisotopic Mass

598.18390 Da

IUPAC Name

1-(2,7-dihydroxy-5,6,10-trimethoxyphenanthren-1-yl)-3,4,9-trimethoxyphenanthrene-2,7-diol

Traditional Name

1-(2,7-dihydroxy-5,6,10-trimethoxyphenanthren-1-yl)-3,4,9-trimethoxyphenanthrene-2,7-diol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(O)=C(OC)C(OC)=C2C2=CC=C(O)C=C12)C1=C2C(OC)=CC3=CC(O)=C(OC)C(OC)=C3C2=CC=C1O

InChI Identifier

InChI=1S/C34H30O10/c1-39-23-14-20-26(17-8-7-16(35)13-19(17)23)33(43-5)34(44-6)30(38)28(20)29-21(36)10-9-18-25-15(12-24(40-2)27(18)29)11-22(37)31(41-3)32(25)42-4/h7-14,35-38H,1-6H3

InChI Key

FAEKSGIHDACYAU-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
Bulbophyllum reptans	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Phenanthrols

Direct Parent

Phenanthrols

Alternative Parents

Substituents

Phenanthrol
2-naphthol
Naphthalene
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	4.98	ALOGPS
logP	5.42	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	8.78	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	136.3 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	163.7 m³·mol⁻¹	ChemAxon
Polarizability	62.92 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	Yes	ChemAxon

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100989757

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isoreptanthrin (NP0073559)

MOL for NP0073559 (Isoreptanthrin)

3D MOL for NP0073559 (Isoreptanthrin)

3D SDF for NP0073559 (Isoreptanthrin)

3D-SDF for NP0073559 (Isoreptanthrin)

PDB for NP0073559 (Isoreptanthrin)

3D PDB for NP0073559 (Isoreptanthrin)

SMILES for NP0073559 (Isoreptanthrin)

INCHI for NP0073559 (Isoreptanthrin)

Structure for NP0073559 (Isoreptanthrin)

3D Structure for NP0073559 (Isoreptanthrin)