NP-MRD: Showing NP-Card for 1,2,3,5-tetrahydroxy-7-methoxy-2-methyl-3,4-dihydro-1h-anthracene-9,10-dione (NP0328696)

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Record Information

Version

2.0

Created at

2022-09-12 12:24:12 UTC

Updated at

2022-09-12 12:24:12 UTC

NP-MRD ID

NP0328696

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,2,3,5-tetrahydroxy-7-methoxy-2-methyl-3,4-dihydro-1h-anthracene-9,10-dione

Description

1,2,3,5-Tetrahydroxy-7-methoxy-2-methyl-1,2,3,4,9,10-hexahydroanthracene-9,10-dione 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. 1,2,3,5-tetrahydroxy-7-methoxy-2-methyl-3,4-dihydro-1h-anthracene-9,10-dione is found in Alternaria porri, Alternaria solani and Stemphylium botryosum. 1,2,3,5-Tetrahydroxy-7-methoxy-2-methyl-1,2,3,4,9,10-hexahydroanthracene-9,10-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161523432D          

 23 25  0  0  0  0            999 V2000
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1401   -0.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6704   -1.7933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    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  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 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
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328696

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C3=C(C(O)C(C)(O)C(O)C3)C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O7/c1-16(22)10(18)5-8-12(15(16)21)14(20)7-3-6(23-2)4-9(17)11(7)13(8)19/h3-4,10,15,17-18,21-22H,5H2,1-2H3

> <INCHI_KEY>
VEGRZYSJCNPLRM-UHFFFAOYSA-N

> <FORMULA>
C16H16O7

> <MOLECULAR_WEIGHT>
320.297

> <EXACT_MASS>
320.089602855

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
31.496911716018534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2,3,5-tetrahydroxy-7-methoxy-2-methyl-1,2,3,4,9,10-hexahydroanthracene-9,10-dione

> <ALOGPS_LOGP>
0.87

> <JCHEM_LOGP>
-0.20044784333333326

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.727962780491943

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.160541688608296

> <JCHEM_PKA_STRONGEST_BASIC>
-3.310822040249194

> <JCHEM_POLAR_SURFACE_AREA>
124.29000000000002

> <JCHEM_REFRACTIVITY>
79.61799999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2,3,5-tetrahydroxy-7-methoxy-2-methyl-3,4-dihydro-1H-anthracene-9,10-dione

> <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      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.861  -1.633   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.851  -3.347   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001  -5.390   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  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   22                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   19                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10                                                       
CONECT   20   11   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    7   23                                                  
CONECT   23   22    3                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆O₇

Average Mass

320.2970 Da

Monoisotopic Mass

320.08960 Da

IUPAC Name

1,2,3,5-tetrahydroxy-7-methoxy-2-methyl-1,2,3,4,9,10-hexahydroanthracene-9,10-dione

Traditional Name

1,2,3,5-tetrahydroxy-7-methoxy-2-methyl-3,4-dihydro-1H-anthracene-9,10-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C3=C(C(O)C(C)(O)C(O)C3)C(=O)C2=C1

InChI Identifier

InChI=1S/C16H16O7/c1-16(22)10(18)5-8-12(15(16)21)14(20)7-3-6(23-2)4-9(17)11(7)13(8)19/h3-4,10,15,17-18,21-22H,5H2,1-2H3

InChI Key

VEGRZYSJCNPLRM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alternaria porri	LOTUS Database	35616633
Alternaria solani	LOTUS Database	35616633
Stemphylium botryosum	LOTUS Database	35616633

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
Anisole
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Cyclitol or derivatives
Vinylogous acid
Tertiary alcohol
Secondary alcohol
Ketone
Ether
Polyol
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	0.87	ALOGPS
logP	-0.2	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	8.16	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	79.62 m³·mol⁻¹	ChemAxon
Polarizability	31.5 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

14524493

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,2,3,5-tetrahydroxy-7-methoxy-2-methyl-3,4-dihydro-1h-anthracene-9,10-dione (NP0328696)

MOL for NP0328696 (1,2,3,5-tetrahydroxy-7-methoxy-2-methyl-3,4-dihydro-1h-anthracene-9,10-dione)

3D MOL for NP0328696 (1,2,3,5-tetrahydroxy-7-methoxy-2-methyl-3,4-dihydro-1h-anthracene-9,10-dione)

3D SDF for NP0328696 (1,2,3,5-tetrahydroxy-7-methoxy-2-methyl-3,4-dihydro-1h-anthracene-9,10-dione)

3D-SDF for NP0328696 (1,2,3,5-tetrahydroxy-7-methoxy-2-methyl-3,4-dihydro-1h-anthracene-9,10-dione)

PDB for NP0328696 (1,2,3,5-tetrahydroxy-7-methoxy-2-methyl-3,4-dihydro-1h-anthracene-9,10-dione)

3D PDB for NP0328696 (1,2,3,5-tetrahydroxy-7-methoxy-2-methyl-3,4-dihydro-1h-anthracene-9,10-dione)

SMILES for NP0328696 (1,2,3,5-tetrahydroxy-7-methoxy-2-methyl-3,4-dihydro-1h-anthracene-9,10-dione)

INCHI for NP0328696 (1,2,3,5-tetrahydroxy-7-methoxy-2-methyl-3,4-dihydro-1h-anthracene-9,10-dione)

Structure for NP0328696 (1,2,3,5-tetrahydroxy-7-methoxy-2-methyl-3,4-dihydro-1h-anthracene-9,10-dione)

3D Structure for NP0328696 (1,2,3,5-tetrahydroxy-7-methoxy-2-methyl-3,4-dihydro-1h-anthracene-9,10-dione)