NP-MRD: Showing NP-Card for (-)-Alterporriol A (NP0081402)

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Record Information

Version

2.0

Created at

2022-04-29 02:22:42 UTC

Updated at

2022-04-29 02:22:42 UTC

NP-MRD ID

NP0081402

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Alterporriol A

Description

Alterporriol A belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. (-)-Alterporriol A is found in Alternaria porri, Alternaria solani and Stemphylium globuliferum. (-)-Alterporriol A was first documented in 2009 (PMID: 19271717). Based on a literature review very few articles have been published on Alterporriol A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204222D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292204222D          

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   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8258   -3.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4385   -4.4121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   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
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 15  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  2  0  0  0  0
 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 18 25  1  0  0  0  0
 24 26  1  0  0  0  0
 23 27  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
  4 32  1  0  0  0  0
 32 33  2  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 30 37  1  0  0  0  0
 37 38  1  1  0  0  0
 36 39  1  1  0  0  0
 36 40  1  6  0  0  0
 35 41  1  6  0  0  0
 34 42  1  1  0  0  0
  3 43  1  0  0  0  0
  1 44  1  0  0  0  0
 44 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0081402

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C3=C(C=C(C)C(O)=C3)C(=O)C2=C1C1=C2C(=O)C3=C([C@H](O)[C@@H](O)[C@@](C)(O)[C@@H]3O)C(=O)C2=C(O)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C32H26O13/c1-9-5-10-11(6-12(9)33)25(36)17-13(34)7-15(44-3)19(21(17)26(10)37)20-16(45-4)8-14(35)18-22(20)28(39)24-23(27(18)38)29(40)31(42)32(2,43)30(24)41/h5-8,29-31,33-35,40-43H,1-4H3/t29-,30+,31+,32-/m0/s1

> <INCHI_KEY>
YHXUFRJJYFYRSH-BVEPWEIPSA-N

> <FORMULA>
C32H26O13

> <MOLECULAR_WEIGHT>
618.547

> <EXACT_MASS>
618.137340897

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
59.46390766974281

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S,6R,7S,8R)-4,4',5,6,6',7,8-heptahydroxy-2,2'-dimethoxy-7,7'-dimethyl-6,7,8,9-tetrahydro-5H,9'H,10H,10'H-[1,1'-bianthracene]-9,9',10,10'-tetrone

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
1.871861110666667

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.559332548551705

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.006573124972858

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5658109312134405

> <JCHEM_POLAR_SURFACE_AREA>
228.34999999999994

> <JCHEM_REFRACTIVITY>
156.5209

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6R,7S,8R)-4,4',5,6,6',7,8-heptahydroxy-2,2'-dimethoxy-7,7'-dimethyl-6,8-dihydro-5H-[1,1'-bianthracene]-9,9',10,10'-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.000 -13.860   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.905  -7.994   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -6.240  -8.946   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0     -10.875  -6.984   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0     -10.152  -8.236   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0     -10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2    6   44                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   43                                                  
CONECT    4    3    5   32                                                  
CONECT    5    4    6   28                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   10                                                            
CONECT   16    9   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   25                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19    8   21                                                  
CONECT   21   20                                                            
CONECT   22   19   23                                                       
CONECT   23   22   24   27                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   18                                                       
CONECT   26   24                                                            
CONECT   27   23                                                            
CONECT   28    5   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   37                                                  
CONECT   31   30   32   34                                                  
CONECT   32   31    4   33                                                  
CONECT   33   32                                                            
CONECT   34   31   35   42                                                  
CONECT   35   34   36   41                                                  
CONECT   36   35   37   39   40                                             
CONECT   37   36   30   38                                                  
CONECT   38   37                                                            
CONECT   39   36                                                            
CONECT   40   36                                                            
CONECT   41   35                                                            
CONECT   42   34                                                            
CONECT   43    3                                                            
CONECT   44    1   45                                                       
CONECT   45   44                                                            
MASTER        0    0    0    0    0    0    0    0   45    0  100    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₂₆O₁₃

Average Mass

618.5470 Da

Monoisotopic Mass

618.13734 Da

IUPAC Name

(5S,6R,7S,8R)-4,4',5,6,6',7,8-heptahydroxy-2,2'-dimethoxy-7,7'-dimethyl-6,7,8,9-tetrahydro-5H,9'H,10H,10'H-[1,1'-bianthracene]-9,9',10,10'-tetrone

Traditional Name

(5S,6R,7S,8R)-4,4',5,6,6',7,8-heptahydroxy-2,2'-dimethoxy-7,7'-dimethyl-6,8-dihydro-5H-[1,1'-bianthracene]-9,9',10,10'-tetrone

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C3=C(C=C(C)C(O)=C3)C(=O)C2=C1C1=C2C(=O)C3=C([C@H](O)[C@@H](O)[C@@](C)(O)[C@@H]3O)C(=O)C2=C(O)C=C1OC

InChI Identifier

InChI=1S/C32H26O13/c1-9-5-10-11(6-12(9)33)25(36)17-13(34)7-15(44-3)19(21(17)26(10)37)20-16(45-4)8-14(35)18-22(20)28(39)24-23(27(18)38)29(40)31(42)32(2,43)30(24)41/h5-8,29-31,33-35,40-43H,1-4H3/t29-,30+,31+,32-/m0/s1

InChI Key

YHXUFRJJYFYRSH-BVEPWEIPSA-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
Alternaria porri	LOTUS Database	35616633
Alternaria solani	LOTUS Database	35616633
Stemphylium globuliferum	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
Biphenol
Anisole
Aryl ketone
Quinone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Cyclitol or derivatives
Vinylogous acid
Tertiary alcohol
Ketone
Secondary alcohol
Ether
Polyol
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
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	2.62	ALOGPS
logP	1.87	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.01	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	228.35 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	156.52 m³·mol⁻¹	ChemAxon
Polarizability	59.46 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

C00047381

Chemspider ID

143754

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163910

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Debbab A, Aly AH, Edrada-Ebel R, Wray V, Muller WE, Totzke F, Zirrgiebel U, Schachtele C, Kubbutat MH, Lin WH, Mosaddak M, Hakiki A, Proksch P, Ebel R: Bioactive metabolites from the endophytic fungus Stemphylium globuliferum isolated from Mentha pulegium. J Nat Prod. 2009 Apr;72(4):626-31. doi: 10.1021/np8004997. [PubMed:19271717 ]

Showing NP-Card for (-)-Alterporriol A (NP0081402)

MOL for NP0081402 ((-)-Alterporriol A)

3D MOL for NP0081402 ((-)-Alterporriol A)

3D SDF for NP0081402 ((-)-Alterporriol A)

3D-SDF for NP0081402 ((-)-Alterporriol A)

PDB for NP0081402 ((-)-Alterporriol A)

3D PDB for NP0081402 ((-)-Alterporriol A)

SMILES for NP0081402 ((-)-Alterporriol A)

INCHI for NP0081402 ((-)-Alterporriol A)

Structure for NP0081402 ((-)-Alterporriol A)

3D Structure for NP0081402 ((-)-Alterporriol A)