NP-MRD: Showing NP-Card for 9-[5-(dimethylamino)-6-methyloxan-2-yl]-3,8-dihydroxy-3-methyl-2,4-dihydrotetraphene-1,7,12-trione (NP0216489)

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Record Information

Version

2.0

Created at

2022-09-05 16:28:51 UTC

Updated at

2022-09-05 16:28:51 UTC

NP-MRD ID

NP0216489

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-[5-(dimethylamino)-6-methyloxan-2-yl]-3,8-dihydroxy-3-methyl-2,4-dihydrotetraphene-1,7,12-trione

Description

9-[5-(Dimethylamino)-6-methyloxan-2-yl]-3,8-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. 9-[5-(dimethylamino)-6-methyloxan-2-yl]-3,8-dihydroxy-3-methyl-2,4-dihydrotetraphene-1,7,12-trione is found in Streptomyces griseus. Based on a literature review very few articles have been published on 9-[5-(dimethylamino)-6-methyloxan-2-yl]-3,8-dihydroxy-3-methyl-1,2,3,4,7,12-hexahydrotetraphene-1,7,12-trione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052218282D          

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M  END

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  Mrv1652309052218282D          

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M  END
> <DATABASE_ID>
NP0216489

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(CCC1N(C)C)C1=CC=C2C(=O)C3=C4C(=O)CC(C)(O)CC4=CC=C3C(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H29NO6/c1-13-18(28(3)4)9-10-20(34-13)15-7-8-17-23(24(15)30)26(32)16-6-5-14-11-27(2,33)12-19(29)21(14)22(16)25(17)31/h5-8,13,18,20,30,33H,9-12H2,1-4H3

> <INCHI_KEY>
VHNOLQAJFPFISB-UHFFFAOYSA-N

> <FORMULA>
C27H29NO6

> <MOLECULAR_WEIGHT>
463.53

> <EXACT_MASS>
463.199487658

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
51.21111757775816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-[5-(dimethylamino)-6-methyloxan-2-yl]-3,8-dihydroxy-3-methyl-1,2,3,4,7,12-hexahydrotetraphene-1,7,12-trione

> <JCHEM_LOGP>
2.596099802773717

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.099716437254326

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.27202062200251

> <JCHEM_PKA_STRONGEST_BASIC>
7.995252969183568

> <JCHEM_POLAR_SURFACE_AREA>
104.14

> <JCHEM_REFRACTIVITY>
128.44069999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
9-[5-(dimethylamino)-6-methyloxan-2-yl]-3,8-dihydroxy-3-methyl-2,4-dihydrotetraphene-1,7,12-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0     -11.888  -0.085   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.880  -1.249   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -9.367  -0.958   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -8.359  -2.122   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.847  -1.831   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.343  -0.376   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.831  -0.085   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.822  -1.249   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.327  -2.704   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.839  -2.995   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -6.343  -4.450   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.318  -3.868   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.822  -5.323   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.806  -3.577   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.798  -4.741   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.714  -4.450   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.218  -2.995   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.210  -1.831   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.302  -2.122   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.310  -0.958   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.806   0.497   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.714  -0.376   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.294   0.788   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.227  -0.085   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.235  -1.249   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.206  -0.054   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.580  -1.998   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.731  -2.704   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -8.863  -3.577   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -10.376  -3.868   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -11.384  -2.704   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0     -12.896  -2.995   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0     -13.400  -4.450   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -13.904  -1.831   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   29                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19   22                                                  
CONECT   19   18   14   20                                                  
CONECT   20   19    8   21                                                  
CONECT   21   20                                                            
CONECT   22   18   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   17                                                       
CONECT   29    4   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30    2   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₉NO₆

Average Mass

463.5300 Da

Monoisotopic Mass

463.19949 Da

IUPAC Name

9-[5-(dimethylamino)-6-methyloxan-2-yl]-3,8-dihydroxy-3-methyl-1,2,3,4,7,12-hexahydrotetraphene-1,7,12-trione

Traditional Name

9-[5-(dimethylamino)-6-methyloxan-2-yl]-3,8-dihydroxy-3-methyl-2,4-dihydrotetraphene-1,7,12-trione

CAS Registry Number

Not Available

SMILES

CC1OC(CCC1N(C)C)C1=CC=C2C(=O)C3=C4C(=O)CC(C)(O)CC4=CC=C3C(=O)C2=C1O

InChI Identifier

InChI=1S/C27H29NO6/c1-13-18(28(3)4)9-10-20(34-13)15-7-8-17-23(24(15)30)26(32)16-6-5-14-11-27(2,33)12-19(29)21(14)22(16)25(17)31/h5-8,13,18,20,30,33H,9-12H2,1-4H3

InChI Key

VHNOLQAJFPFISB-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
Streptomyces griseus	LOTUS Database	35616633

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
Aralkylamine
Phenol
Oxane
Benzenoid
Vinylogous acid
Tertiary alcohol
Ketone
Tertiary aliphatic amine
Tertiary amine
Oxacycle
Ether
Dialkyl ether
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxide
Organic oxygen compound
Amine
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	2.6	ChemAxon
pKa (Strongest Acidic)	7.27	ChemAxon
pKa (Strongest Basic)	8	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	104.14 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	128.44 m³·mol⁻¹	ChemAxon
Polarizability	51.21 Å³	ChemAxon
Number of Rings	5	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

72976472

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-[5-(dimethylamino)-6-methyloxan-2-yl]-3,8-dihydroxy-3-methyl-2,4-dihydrotetraphene-1,7,12-trione (NP0216489)

MOL for NP0216489 (9-[5-(dimethylamino)-6-methyloxan-2-yl]-3,8-dihydroxy-3-methyl-2,4-dihydrotetraphene-1,7,12-trione)

3D MOL for NP0216489 (9-[5-(dimethylamino)-6-methyloxan-2-yl]-3,8-dihydroxy-3-methyl-2,4-dihydrotetraphene-1,7,12-trione)

3D SDF for NP0216489 (9-[5-(dimethylamino)-6-methyloxan-2-yl]-3,8-dihydroxy-3-methyl-2,4-dihydrotetraphene-1,7,12-trione)

3D-SDF for NP0216489 (9-[5-(dimethylamino)-6-methyloxan-2-yl]-3,8-dihydroxy-3-methyl-2,4-dihydrotetraphene-1,7,12-trione)

PDB for NP0216489 (9-[5-(dimethylamino)-6-methyloxan-2-yl]-3,8-dihydroxy-3-methyl-2,4-dihydrotetraphene-1,7,12-trione)

3D PDB for NP0216489 (9-[5-(dimethylamino)-6-methyloxan-2-yl]-3,8-dihydroxy-3-methyl-2,4-dihydrotetraphene-1,7,12-trione)

SMILES for NP0216489 (9-[5-(dimethylamino)-6-methyloxan-2-yl]-3,8-dihydroxy-3-methyl-2,4-dihydrotetraphene-1,7,12-trione)

INCHI for NP0216489 (9-[5-(dimethylamino)-6-methyloxan-2-yl]-3,8-dihydroxy-3-methyl-2,4-dihydrotetraphene-1,7,12-trione)

Structure for NP0216489 (9-[5-(dimethylamino)-6-methyloxan-2-yl]-3,8-dihydroxy-3-methyl-2,4-dihydrotetraphene-1,7,12-trione)

3D Structure for NP0216489 (9-[5-(dimethylamino)-6-methyloxan-2-yl]-3,8-dihydroxy-3-methyl-2,4-dihydrotetraphene-1,7,12-trione)