NP-MRD: Showing NP-Card for 2-hydroxy-6-[hydroxy({4,6,9,10-tetrahydroxy-5,13-dioxo-8h,9h,10h,12ah-indeno[1,2-a]anthracen-8a-yl})methyl]-4-methylbenzoic acid (NP0316966)

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Record Information

Version

2.0

Created at

2022-09-11 16:31:10 UTC

Updated at

2022-09-11 16:31:10 UTC

NP-MRD ID

NP0316966

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-hydroxy-6-[hydroxy({4,6,9,10-tetrahydroxy-5,13-dioxo-8h,9h,10h,12ah-indeno[1,2-a]anthracen-8a-yl})methyl]-4-methylbenzoic acid

Description

2-Hydroxy-6-[hydroxy({6,7,12,16-tetrahydroxy-14,21-dioxopentacyclo[11.8.0.0²,¹⁰.0³,⁸.0¹⁵,²⁰]Henicosa-1,4,10,12,15(20),16,18-heptaen-8-yl})methyl]-4-methylbenzoic acid belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. 2-hydroxy-6-[hydroxy({4,6,9,10-tetrahydroxy-5,13-dioxo-8h,9h,10h,12ah-indeno[1,2-a]anthracen-8a-yl})methyl]-4-methylbenzoic acid is found in Ramularia collo-cygni. 2-Hydroxy-6-[hydroxy({6,7,12,16-tetrahydroxy-14,21-dioxopentacyclo[11.8.0.0²,¹⁰.0³,⁸.0¹⁵,²⁰]Henicosa-1,4,10,12,15(20),16,18-heptaen-8-yl})methyl]-4-methylbenzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171522072D          

 40 45  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004171522072D          

 40 45  0  0  0  0            999 V2000
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  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
  2 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 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  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 20 32  1  0  0  0  0
 32 33  2  0  0  0  0
 16 33  1  0  0  0  0
 33 34  1  0  0  0  0
 14 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 14 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0316966

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=C(C(O)=O)C(=C1)C(O)C12CC3=CC(O)=C4C(=O)C5=C(O)C=CC=C5C(=O)C4=C3C1C=CC(O)C2O

> <INCHI_IDENTIFIER>
InChI=1S/C30H24O10/c1-11-7-14(22(29(39)40)18(33)8-11)27(37)30-10-12-9-19(34)23-24(20(12)15(30)5-6-17(32)28(30)38)25(35)13-3-2-4-16(31)21(13)26(23)36/h2-9,15,17,27-28,31-34,37-38H,10H2,1H3,(H,39,40)

> <INCHI_KEY>
XQLAAGXBBHMPDD-UHFFFAOYSA-N

> <FORMULA>
C30H24O10

> <MOLECULAR_WEIGHT>
544.512

> <EXACT_MASS>
544.136946973

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
54.254266362729744

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-6-[hydroxy({6,7,12,16-tetrahydroxy-14,21-dioxopentacyclo[11.8.0.0²,¹⁰.0³,⁸.0¹⁵,²⁰]henicosa-1,4,10,12,15,17,19-heptaen-8-yl})methyl]-4-methylbenzoic acid

> <ALOGPS_LOGP>
2.11

> <JCHEM_LOGP>
4.427936848

> <ALOGPS_LOGS>
-3.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.903954117989154

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.6041336699604773

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3170837564057862

> <JCHEM_POLAR_SURFACE_AREA>
192.81999999999996

> <JCHEM_REFRACTIVITY>
143.14149999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-6-[hydroxy({6,7,12,16-tetrahydroxy-14,21-dioxopentacyclo[11.8.0.0²,¹⁰.0³,⁸.0¹⁵,²⁰]henicosa-1,4,10,12,15,17,19-heptaen-8-yl})methyl]-4-methylbenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      10.142   4.339   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.743   3.697   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.486   4.587   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.087   3.945   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.831   4.835   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.944   2.411   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.544   1.769   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.401   0.235   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.288   2.659   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.200   1.521   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.599   2.163   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.057  -0.013   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.657  -0.655   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.313  -0.903   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.616   0.607   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.145   0.785   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.036   2.042   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.569   1.899   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.460   3.155   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      13.212   0.499   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.745   0.356   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      15.636   1.612   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      15.388  -1.044   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.921  -1.187   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      17.812   0.069   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      17.564  -2.586   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.673  -3.843   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.140  -3.699   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.497  -2.300   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.964  -2.157   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.073  -3.413   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.321  -0.757   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.788  -0.614   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.656  -1.658   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.673  -3.198   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.349  -3.983   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.006  -3.229   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.682  -4.014   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       6.988  -1.689   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       5.478  -1.386   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6   11   12                                                  
CONECT   11   10    2                                                       
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   34   39                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   33                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   32                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   29                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   23   30                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   20   33                                                  
CONECT   33   32   16   34                                                  
CONECT   34   33   14   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   14   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
2-Hydroxy-6-[hydroxy({6,7,12,16-tetrahydroxy-14,21-dioxopentacyclo[11.8.0.0,.0,.0,]henicosa-1,4,10,12,15(20),16,18-heptaen-8-yl})methyl]-4-methylbenzoate	Generator
2-Hydroxy-6-[hydroxy({6,7,12,16-tetrahydroxy-14,21-dioxopentacyclo[11.8.0.0²,¹⁰.0³,⁸.0¹⁵,²⁰]henicosa-1,4,10,12,15(20),16,18-heptaen-8-yl})methyl]-4-methylbenzoate	Generator

Chemical Formula

C₃₀H₂₄O₁₀

Average Mass

544.5120 Da

Monoisotopic Mass

544.13695 Da

IUPAC Name

2-hydroxy-6-[hydroxy({6,7,12,16-tetrahydroxy-14,21-dioxopentacyclo[11.8.0.0²,¹⁰.0³,⁸.0¹⁵,²⁰]henicosa-1,4,10,12,15,17,19-heptaen-8-yl})methyl]-4-methylbenzoic acid

Traditional Name

2-hydroxy-6-[hydroxy({6,7,12,16-tetrahydroxy-14,21-dioxopentacyclo[11.8.0.0²,¹⁰.0³,⁸.0¹⁵,²⁰]henicosa-1,4,10,12,15,17,19-heptaen-8-yl})methyl]-4-methylbenzoic acid

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=C(C(O)=O)C(=C1)C(O)C12CC3=CC(O)=C4C(=O)C5=C(O)C=CC=C5C(=O)C4=C3C1C=CC(O)C2O

InChI Identifier

InChI=1S/C30H24O10/c1-11-7-14(22(29(39)40)18(33)8-11)27(37)30-10-12-9-19(34)23-24(20(12)15(30)5-6-17(32)28(30)38)25(35)13-3-2-4-16(31)21(13)26(23)36/h2-9,15,17,27-28,31-34,37-38H,10H2,1H3,(H,39,40)

InChI Key

XQLAAGXBBHMPDD-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Ramularia collo-cygni	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

9,10-anthraquinone
Anthraquinone
Fluorene
Hydroxybenzoic acid
Salicylic acid
Salicylic acid or derivatives
Benzoic acid or derivatives
Benzoic acid
Indane
Benzoyl
Aryl ketone
M-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Monocyclic benzene moiety
Vinylogous acid
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Polyol
Alcohol
Aromatic alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	2.11	ALOGPS
logP	4.43	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	2.6	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	192.82 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	143.14 m³·mol⁻¹	ChemAxon
Polarizability	54.25 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-hydroxy-6-[hydroxy({4,6,9,10-tetrahydroxy-5,13-dioxo-8h,9h,10h,12ah-indeno[1,2-a]anthracen-8a-yl})methyl]-4-methylbenzoic acid (NP0316966)

MOL for NP0316966 (2-hydroxy-6-[hydroxy({4,6,9,10-tetrahydroxy-5,13-dioxo-8h,9h,10h,12ah-indeno[1,2-a]anthracen-8a-yl})methyl]-4-methylbenzoic acid)

3D MOL for NP0316966 (2-hydroxy-6-[hydroxy({4,6,9,10-tetrahydroxy-5,13-dioxo-8h,9h,10h,12ah-indeno[1,2-a]anthracen-8a-yl})methyl]-4-methylbenzoic acid)

3D SDF for NP0316966 (2-hydroxy-6-[hydroxy({4,6,9,10-tetrahydroxy-5,13-dioxo-8h,9h,10h,12ah-indeno[1,2-a]anthracen-8a-yl})methyl]-4-methylbenzoic acid)

3D-SDF for NP0316966 (2-hydroxy-6-[hydroxy({4,6,9,10-tetrahydroxy-5,13-dioxo-8h,9h,10h,12ah-indeno[1,2-a]anthracen-8a-yl})methyl]-4-methylbenzoic acid)

PDB for NP0316966 (2-hydroxy-6-[hydroxy({4,6,9,10-tetrahydroxy-5,13-dioxo-8h,9h,10h,12ah-indeno[1,2-a]anthracen-8a-yl})methyl]-4-methylbenzoic acid)

3D PDB for NP0316966 (2-hydroxy-6-[hydroxy({4,6,9,10-tetrahydroxy-5,13-dioxo-8h,9h,10h,12ah-indeno[1,2-a]anthracen-8a-yl})methyl]-4-methylbenzoic acid)

SMILES for NP0316966 (2-hydroxy-6-[hydroxy({4,6,9,10-tetrahydroxy-5,13-dioxo-8h,9h,10h,12ah-indeno[1,2-a]anthracen-8a-yl})methyl]-4-methylbenzoic acid)

INCHI for NP0316966 (2-hydroxy-6-[hydroxy({4,6,9,10-tetrahydroxy-5,13-dioxo-8h,9h,10h,12ah-indeno[1,2-a]anthracen-8a-yl})methyl]-4-methylbenzoic acid)

Structure for NP0316966 (2-hydroxy-6-[hydroxy({4,6,9,10-tetrahydroxy-5,13-dioxo-8h,9h,10h,12ah-indeno[1,2-a]anthracen-8a-yl})methyl]-4-methylbenzoic acid)

3D Structure for NP0316966 (2-hydroxy-6-[hydroxy({4,6,9,10-tetrahydroxy-5,13-dioxo-8h,9h,10h,12ah-indeno[1,2-a]anthracen-8a-yl})methyl]-4-methylbenzoic acid)