NP-MRD: Showing NP-Card for (4r,4as,5ar,6s,12ar)-7-chloro-4-(dimethylamino)-1,4a,6,10,11,12a-hexahydroxy-8-methoxy-6-methyl-3,12-dioxo-5,5a-dihydro-4h-tetracene-2-carboximidic acid (NP0330836)

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Record Information

Version

2.0

Created at

2022-09-12 16:35:07 UTC

Updated at

2022-09-12 16:35:08 UTC

NP-MRD ID

NP0330836

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4r,4as,5ar,6s,12ar)-7-chloro-4-(dimethylamino)-1,4a,6,10,11,12a-hexahydroxy-8-methoxy-6-methyl-3,12-dioxo-5,5a-dihydro-4h-tetracene-2-carboximidic acid

Description

Dactylocyclinone belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups. (4r,4as,5ar,6s,12ar)-7-chloro-4-(dimethylamino)-1,4a,6,10,11,12a-hexahydroxy-8-methoxy-6-methyl-3,12-dioxo-5,5a-dihydro-4h-tetracene-2-carboximidic acid was first documented in 1992 (PMID: 1490881). Based on a literature review very few articles have been published on Dactylocyclinone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122218352D          

 36 39  0  0  1  0            999 V2000
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   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
    2.8579   -1.6500    0.0000 Cl  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
    3.7565   -1.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8171   -1.8430    0.0000 O   0  0  0  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
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    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  3  4  2  0  0  0  0
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  3  9  1  0  0  0  0
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  8 11  1  0  0  0  0
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  7 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309122218352D          

 36 39  0  0  1  0            999 V2000
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0330836

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(O)=C3[C@@H](C[C@]4(O)[C@@H](N(C)C)C(=O)C(C(O)=N)=C(O)[C@]4(O)C3=O)[C@](C)(O)C2=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C23H25ClN2O10/c1-21(33)7-6-22(34)17(26(2)3)16(29)12(20(25)32)19(31)23(22,35)18(30)10(7)15(28)11-8(27)5-9(36-4)14(24)13(11)21/h5,7,17,27-28,31,33-35H,6H2,1-4H3,(H2,25,32)/t7-,17+,21+,22+,23-/m1/s1

> <INCHI_KEY>
ZFQSAYKGPAHJBK-SDPQGDBNSA-N

> <FORMULA>
C23H25ClN2O10

> <MOLECULAR_WEIGHT>
524.91

> <EXACT_MASS>
524.1197727

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.72351248612382

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R,4aS,5aR,6S,12aR)-7-chloro-4-(dimethylamino)-1,4a,6,10,11,12a-hexahydroxy-8-methoxy-6-methyl-3,12-dioxo-3,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboximidic acid

> <JCHEM_LOGP>
-6.025470450402953

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
0.6681957683218731

> <JCHEM_PKA_STRONGEST_ACIDIC>
-4.447421393667825

> <JCHEM_PKA_STRONGEST_BASIC>
13.99467005813639

> <JCHEM_POLAR_SURFACE_AREA>
212.06999999999994

> <JCHEM_REFRACTIVITY>
137.46639999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4R,4aS,5aR,6S,12aR)-7-chloro-4-(dimethylamino)-1,4a,6,10,11,12a-hexahydroxy-8-methoxy-6-methyl-3,12-dioxo-5,5a-dihydro-4H-tetracene-2-carboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0       5.335  -3.080   0.000  0.00  0.00          Cl+0
HETATM   11  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.012  -3.440   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.992  -3.440   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.003  -3.850   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      13.337  -3.080   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      16.004  -4.620   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      17.338  -6.930   0.000  0.00  0.00           N+0
HETATM   27  O   UNK     0      16.004  -9.240   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.003  -8.470   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   35                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9                                                            
CONECT   11    8   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15   34                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18   30                                             
CONECT   17   16                                                            
CONECT   18   16   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   18   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   28                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   24   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   16   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   14   35                                                  
CONECT   35   34    7   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
4-Hydroxy-8-methoxychlortetracycline	MeSH

Chemical Formula

C₂₃H₂₅ClN₂O₁₀

Average Mass

524.9100 Da

Monoisotopic Mass

524.11977 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(O)=C3[C@@H](C[C@]4(O)[C@@H](N(C)C)C(=O)C(C(O)=N)=C(O)[C@]4(O)C3=O)[C@](C)(O)C2=C1Cl

InChI Identifier

InChI=1S/C23H25ClN2O10/c1-21(33)7-6-22(34)17(26(2)3)16(29)12(20(25)32)19(31)23(22,35)18(30)10(7)15(28)11-8(27)5-9(36-4)14(24)13(11)21/h5,7,17,27-28,31,33-35H,6H2,1-4H3,(H2,25,32)/t7-,17+,21+,22+,23-/m1/s1

InChI Key

ZFQSAYKGPAHJBK-SDPQGDBNSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tetracyclines

Sub Class

Not Available

Direct Parent

Tetracyclines

Alternative Parents

Substituents

Tetracycline
Anthracene carboxylic acid or derivatives
1-naphthol
Naphthalene
Anisole
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Aralkylamine
Alkyl aryl ether
Benzenoid
Aryl halide
Aryl chloride
Vinylogous acid
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Tertiary aliphatic amine
Tertiary amine
Primary carboxylic acid amide
Ketone
Carboxamide group
Amino acid or derivatives
Polyol
Ether
Enol
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Carbonyl group
Amine
Alcohol
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

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

101685472

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tymiak AA, Ax HA, Bolgar MS, Kahle AD, Porubcan MA, Andersen NH: Dactylocyclines, novel tetracycline derivatives produced by a Dactylosporangium sp. II. Structure elucidation. J Antibiot (Tokyo). 1992 Dec;45(12):1899-906. doi: 10.7164/antibiotics.45.1899. [PubMed:1490881 ]
LOTUS database [Link]

Showing NP-Card for (4r,4as,5ar,6s,12ar)-7-chloro-4-(dimethylamino)-1,4a,6,10,11,12a-hexahydroxy-8-methoxy-6-methyl-3,12-dioxo-5,5a-dihydro-4h-tetracene-2-carboximidic acid (NP0330836)

MOL for NP0330836 ((4r,4as,5ar,6s,12ar)-7-chloro-4-(dimethylamino)-1,4a,6,10,11,12a-hexahydroxy-8-methoxy-6-methyl-3,12-dioxo-5,5a-dihydro-4h-tetracene-2-carboximidic acid)

3D MOL for NP0330836 ((4r,4as,5ar,6s,12ar)-7-chloro-4-(dimethylamino)-1,4a,6,10,11,12a-hexahydroxy-8-methoxy-6-methyl-3,12-dioxo-5,5a-dihydro-4h-tetracene-2-carboximidic acid)

3D SDF for NP0330836 ((4r,4as,5ar,6s,12ar)-7-chloro-4-(dimethylamino)-1,4a,6,10,11,12a-hexahydroxy-8-methoxy-6-methyl-3,12-dioxo-5,5a-dihydro-4h-tetracene-2-carboximidic acid)

3D-SDF for NP0330836 ((4r,4as,5ar,6s,12ar)-7-chloro-4-(dimethylamino)-1,4a,6,10,11,12a-hexahydroxy-8-methoxy-6-methyl-3,12-dioxo-5,5a-dihydro-4h-tetracene-2-carboximidic acid)

PDB for NP0330836 ((4r,4as,5ar,6s,12ar)-7-chloro-4-(dimethylamino)-1,4a,6,10,11,12a-hexahydroxy-8-methoxy-6-methyl-3,12-dioxo-5,5a-dihydro-4h-tetracene-2-carboximidic acid)

3D PDB for NP0330836 ((4r,4as,5ar,6s,12ar)-7-chloro-4-(dimethylamino)-1,4a,6,10,11,12a-hexahydroxy-8-methoxy-6-methyl-3,12-dioxo-5,5a-dihydro-4h-tetracene-2-carboximidic acid)

SMILES for NP0330836 ((4r,4as,5ar,6s,12ar)-7-chloro-4-(dimethylamino)-1,4a,6,10,11,12a-hexahydroxy-8-methoxy-6-methyl-3,12-dioxo-5,5a-dihydro-4h-tetracene-2-carboximidic acid)

INCHI for NP0330836 ((4r,4as,5ar,6s,12ar)-7-chloro-4-(dimethylamino)-1,4a,6,10,11,12a-hexahydroxy-8-methoxy-6-methyl-3,12-dioxo-5,5a-dihydro-4h-tetracene-2-carboximidic acid)

Structure for NP0330836 ((4r,4as,5ar,6s,12ar)-7-chloro-4-(dimethylamino)-1,4a,6,10,11,12a-hexahydroxy-8-methoxy-6-methyl-3,12-dioxo-5,5a-dihydro-4h-tetracene-2-carboximidic acid)

3D Structure for NP0330836 ((4r,4as,5ar,6s,12ar)-7-chloro-4-(dimethylamino)-1,4a,6,10,11,12a-hexahydroxy-8-methoxy-6-methyl-3,12-dioxo-5,5a-dihydro-4h-tetracene-2-carboximidic acid)