NP-MRD: Showing NP-Card for (-)-Agrostonin (NP0073351)

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Record Information

Version

2.0

Created at

2022-04-28 18:37:20 UTC

Updated at

2022-04-28 18:37:20 UTC

NP-MRD ID

NP0073351

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Agrostonin

Description

CHEMBL3984480 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. (-)-Agrostonin is found in Agrostophyllum callosum and Agrostophyllum khasiyanum. CHEMBL3984480 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201503322D          

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M  END

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 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
 25 26  1  0  0  0  0
 18 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
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  2  0  0  0  0
 25 37  1  0  0  0  0
 29 37  1  0  0  0  0
  6 38  2  0  0  0  0
 38 39  1  0  0  0  0
  3 39  2  0  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073351

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C32H26O8/c1-37-25-11-19-15(9-21(25)33)5-7-17-29(19)27(39-3)13-23(35)31(17)32-18-8-6-16-10-22(34)26(38-2)12-20(16)30(18)28(40-4)14-24(32)36/h5-14,33-36H,1-4H3

> <INCHI_KEY>
YPXFNDKNNGQAKQ-UHFFFAOYSA-N

> <FORMULA>
C32H26O8

> <MOLECULAR_WEIGHT>
538.552

> <EXACT_MASS>
538.162767797

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
57.79901146330481

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(2,7-dihydroxy-4,6-dimethoxyphenanthren-1-yl)-4,6-dimethoxyphenanthrene-2,7-diol

> <ALOGPS_LOGP>
5.32

> <JCHEM_LOGP>
5.733431855333332

> <ALOGPS_LOGS>
-5.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.087497208895996

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.401892311889908

> <JCHEM_PKA_STRONGEST_BASIC>
-4.277359381457718

> <JCHEM_POLAR_SURFACE_AREA>
117.84000000000002

> <JCHEM_REFRACTIVITY>
150.77139999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.12e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(2,7-dihydroxy-4,6-dimethoxyphenanthren-1-yl)-4,6-dimethoxyphenanthrene-2,7-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       6.724 -11.233   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.494  -9.899   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.724  -8.566   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.494  -7.232   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.724  -5.898   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184  -5.898   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414  -4.565   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.184  -3.231   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.724  -3.231   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.494  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.034  -1.897   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.804  -0.564   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.804  -3.231   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.034  -4.565   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.804  -5.898   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.034  -7.232   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.494  -4.565   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.034   0.770   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.414   3.437   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.564   4.771   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.414  -7.232   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.184  -8.566   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       4.414  -9.899   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   39                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7   38                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14    5    9                                                  
CONECT   18   10   19   26                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   37                                                  
CONECT   26   25   18   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   37                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   37                                                       
CONECT   37   36   25   29                                                  
CONECT   38    6   39                                                       
CONECT   39   38    3   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₂₆O₈

Average Mass

538.5520 Da

Monoisotopic Mass

538.16277 Da

IUPAC Name

1-(2,7-dihydroxy-4,6-dimethoxyphenanthren-1-yl)-4,6-dimethoxyphenanthrene-2,7-diol

Traditional Name

1-(2,7-dihydroxy-4,6-dimethoxyphenanthren-1-yl)-4,6-dimethoxyphenanthrene-2,7-diol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C32H26O8/c1-37-25-11-19-15(9-21(25)33)5-7-17-29(19)27(39-3)13-23(35)31(17)32-18-8-6-16-10-22(34)26(38-2)12-20(16)30(18)28(40-4)14-24(32)36/h5-14,33-36H,1-4H3

InChI Key

YPXFNDKNNGQAKQ-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
Agrostophyllum callosum	Plant	KNApSAcK
Agrostophyllum khasiyanum	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
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
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	5.32	ALOGPS
logP	5.73	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	8.4	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	117.84 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	150.77 m³·mol⁻¹	ChemAxon
Polarizability	57.8 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

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

44600287

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Agrostonin (NP0073351)

MOL for NP0073351 ((-)-Agrostonin)

3D MOL for NP0073351 ((-)-Agrostonin)

3D SDF for NP0073351 ((-)-Agrostonin)

3D-SDF for NP0073351 ((-)-Agrostonin)

PDB for NP0073351 ((-)-Agrostonin)

3D PDB for NP0073351 ((-)-Agrostonin)

SMILES for NP0073351 ((-)-Agrostonin)

INCHI for NP0073351 ((-)-Agrostonin)

Structure for NP0073351 ((-)-Agrostonin)

3D Structure for NP0073351 ((-)-Agrostonin)