NP-MRD: Showing NP-Card for (3r,4s)-4,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione (NP0284747)

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Record Information

Version

2.0

Created at

2022-09-09 12:36:28 UTC

Updated at

2022-09-09 12:36:28 UTC

NP-MRD ID

NP0284747

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,4s)-4,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione

Description

(3R,4S)-4,8-dihydroxy-3-methyl-1,2,3,4,7,12-hexahydrotetraphene-1,7,12-trione belongs to the class of organic compounds known as angucyclines. These are polyketides with a structure based on then benz[a]anthracene skeleton, with the particularity that the central ring of the anthracene moiety is a para-quinone. Based on a literature review very few articles have been published on (3R,4S)-4,8-dihydroxy-3-methyl-1,2,3,4,7,12-hexahydrotetraphene-1,7,12-trione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092214362D          

 24 27  0  0  1  0            999 V2000
    6.1154    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.2566    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7651   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149   -0.8348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449    2.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    0.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6048   -0.6789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    1.9716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2546    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    1.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    2.4393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352    1.0361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5753    1.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  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
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  2  0  0  0  0
  7 23  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0284747

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC(=O)C2=C(C=CC3=C2C(=O)C2=CC=CC(O)=C2C3=O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H14O5/c1-8-7-13(21)14-10(17(8)22)5-6-11-16(14)19(24)9-3-2-4-12(20)15(9)18(11)23/h2-6,8,17,20,22H,7H2,1H3/t8-,17+/m1/s1

> <INCHI_KEY>
WWVNIBVFNYKUQY-RBHXEPJQSA-N

> <FORMULA>
C19H14O5

> <MOLECULAR_WEIGHT>
322.316

> <EXACT_MASS>
322.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
32.9624901491695

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4S)-4,8-dihydroxy-3-methyl-1,2,3,4,7,12-hexahydrotetraphene-1,7,12-trione

> <JCHEM_LOGP>
2.707181364666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.771106725959879

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.822976968298592

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3147203003912793

> <JCHEM_POLAR_SURFACE_AREA>
91.67

> <JCHEM_REFRACTIVITY>
87.38769999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4S)-4,8-dihydroxy-3-methyl-3,4-dihydro-2H-tetraphene-1,7,12-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      11.415   0.188   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.903   0.479   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.895  -0.685   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.383  -0.394   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.375  -1.558   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.879   1.061   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.887   2.225   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.383   3.680   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.870   3.971   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.366   1.352   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.358   0.188   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.862  -1.267   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.846   0.479   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.838  -0.685   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.326  -0.394   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.179   1.061   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.830   2.225   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.326   3.680   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.342   1.934   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.350   3.098   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.846   4.553   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.399   1.934   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.407   3.098   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8   23                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   21                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   14   21                                                  
CONECT   21   20   10   22                                                  
CONECT   22   21                                                            
CONECT   23    7    2   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₄O₅

Average Mass

322.3160 Da

Monoisotopic Mass

322.08412 Da

IUPAC Name

(3R,4S)-4,8-dihydroxy-3-methyl-1,2,3,4,7,12-hexahydrotetraphene-1,7,12-trione

Traditional Name

(3R,4S)-4,8-dihydroxy-3-methyl-3,4-dihydro-2H-tetraphene-1,7,12-trione

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC(=O)C2=C(C=CC3=C2C(=O)C2=CC=CC(O)=C2C3=O)[C@H]1O

InChI Identifier

InChI=1S/C19H14O5/c1-8-7-13(21)14-10(17(8)22)5-6-11-16(14)19(24)9-3-2-4-12(20)15(9)18(11)23/h2-6,8,17,20,22H,7H2,1H3/t8-,17+/m1/s1

InChI Key

WWVNIBVFNYKUQY-RBHXEPJQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angucyclines. These are polyketides with a structure based on then benz[a]anthracene skeleton, with the particularity that the central ring of the anthracene moiety is a para-quinone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Angucyclines

Sub Class

Not Available

Direct Parent

Angucyclines

Alternative Parents

Substituents

Angucycline core
9,10-anthraquinone
Anthraquinone
Phenanthrol
Anthracene
Phenanthrene
Tetralin
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Vinylogous acid
Ketone
Secondary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	2.71	ChemAxon
pKa (Strongest Acidic)	7.82	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	87.39 m³·mol⁻¹	ChemAxon
Polarizability	32.96 Å³	ChemAxon
Number of Rings	4	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

8059291

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9883616

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,4s)-4,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione (NP0284747)

MOL for NP0284747 ((3r,4s)-4,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione)

3D MOL for NP0284747 ((3r,4s)-4,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione)

3D SDF for NP0284747 ((3r,4s)-4,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione)

3D-SDF for NP0284747 ((3r,4s)-4,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione)

PDB for NP0284747 ((3r,4s)-4,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione)

3D PDB for NP0284747 ((3r,4s)-4,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione)

SMILES for NP0284747 ((3r,4s)-4,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione)

INCHI for NP0284747 ((3r,4s)-4,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione)

Structure for NP0284747 ((3r,4s)-4,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione)

3D Structure for NP0284747 ((3r,4s)-4,8-dihydroxy-3-methyl-3,4-dihydro-2h-tetraphene-1,7,12-trione)