NP-MRD: Showing NP-Card for (21s,22s,23r)-4-chloro-22-hydroxy-11,23-dimethyl-21-propyl-24-oxa-20-azahexacyclo[19.3.1.0²,¹⁹.0⁵,¹⁸.0⁷,¹⁶.0⁸,¹³]pentacosa-2,4,7(16),8,10,12,14,18-octaene-6,17-dione (NP0198696)

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Record Information

Version

2.0

Created at

2022-09-04 17:11:19 UTC

Updated at

2022-09-04 17:11:19 UTC

NP-MRD ID

NP0198696

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(21s,22s,23r)-4-chloro-22-hydroxy-11,23-dimethyl-21-propyl-24-oxa-20-azahexacyclo[19.3.1.0²,¹⁹.0⁵,¹⁸.0⁷,¹⁶.0⁸,¹³]pentacosa-2,4,7(16),8,10,12,14,18-octaene-6,17-dione

Description

(21S,22S,23R)-4-chloro-22-hydroxy-11,23-dimethyl-21-propyl-24-oxa-20-azahexacyclo[19.3.1.0²,¹⁹.0⁵,¹⁸.0⁷,¹⁶.0⁸,¹³]Pentacosa-2,4,7(16),8(13),9,11,14,18-octaene-6,17-dione 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 (21S,22S,23R)-4-chloro-22-hydroxy-11,23-dimethyl-21-propyl-24-oxa-20-azahexacyclo[19.3.1.0²,¹⁹.0⁵,¹⁸.0⁷,¹⁶.0⁸,¹³]Pentacosa-2,4,7(16),8(13),9,11,14,18-octaene-6,17-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042219112D          

 34 39  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309042219112D          

 34 39  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0198696

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC[C@]12CC(O[C@H](C)[C@H]1O)C1=CC(Cl)=C3C(=O)C4=C5C=CC(C)=CC5=CC=C4C(=O)C3=C1N2

> <INCHI_IDENTIFIER>
InChI=1S/C28H26ClNO4/c1-4-9-28-12-20(34-14(3)27(28)33)18-11-19(29)22-23(24(18)30-28)25(31)17-8-6-15-10-13(2)5-7-16(15)21(17)26(22)32/h5-8,10-11,14,20,27,30,33H,4,9,12H2,1-3H3/t14-,20?,27-,28+/m1/s1

> <INCHI_KEY>
FZQRJKWDBLIHPW-ZVLXKKIOSA-N

> <FORMULA>
C28H26ClNO4

> <MOLECULAR_WEIGHT>
475.97

> <EXACT_MASS>
475.155036

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
51.89963838780207

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(21S,22S,23R)-4-chloro-22-hydroxy-11,23-dimethyl-21-propyl-24-oxa-20-azahexacyclo[19.3.1.0^{2,19}.0^{5,18}.0^{7,16}.0^{8,13}]pentacosa-2,4,7,9,11,13,15,18-octaene-6,17-dione

> <JCHEM_LOGP>
5.894555564000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.423643277807258

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.186497443018105

> <JCHEM_PKA_STRONGEST_BASIC>
0.3884674021908925

> <JCHEM_POLAR_SURFACE_AREA>
75.63

> <JCHEM_REFRACTIVITY>
133.6204

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(21S,22S,23R)-4-chloro-22-hydroxy-11,23-dimethyl-21-propyl-24-oxa-20-azahexacyclo[19.3.1.0^{2,19}.0^{5,18}.0^{7,16}.0^{8,13}]pentacosa-2,4,7,9,11,13,15,18-octaene-6,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       5.044   3.661   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.193   5.194   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.595   5.832   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.743   7.365   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.436   9.416   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.131  11.370   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.491  10.646   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.940   9.173   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.473   9.025   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.216   7.814   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.195   6.625   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.658  10.921   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.843  12.227   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.304  12.174   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0       2.489  13.481   0.000  0.00  0.00          Cl+0
HETATM   16  C   UNK     0       2.580  10.815   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.395   9.509   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.934   9.561   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       5.384   8.088   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       2.672   8.149   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.487   6.843   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.132   8.096   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.409   6.737   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.130   6.684   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.946   7.991   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.485   7.938   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.300   9.245   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.839   9.192   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.576  10.604   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.037  10.657   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.222   9.350   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.317   9.403   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.041  10.762   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.226  12.069   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10   19                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10                                                            
CONECT   12    6   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   33                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   12   19                                                  
CONECT   19   18    4                                                       
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   32                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   25   32                                                  
CONECT   32   31   22   33                                                  
CONECT   33   32   16   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₆ClNO₄

Average Mass

475.9700 Da

Monoisotopic Mass

475.15504 Da

IUPAC Name

(21S,22S,23R)-4-chloro-22-hydroxy-11,23-dimethyl-21-propyl-24-oxa-20-azahexacyclo[19.3.1.0^{2,19}.0^{5,18}.0^{7,16}.0^{8,13}]pentacosa-2,4,7,9,11,13,15,18-octaene-6,17-dione

Traditional Name

(21S,22S,23R)-4-chloro-22-hydroxy-11,23-dimethyl-21-propyl-24-oxa-20-azahexacyclo[19.3.1.0^{2,19}.0^{5,18}.0^{7,16}.0^{8,13}]pentacosa-2,4,7,9,11,13,15,18-octaene-6,17-dione

CAS Registry Number

Not Available

SMILES

CCC[C@]12CC(O[C@H](C)[C@H]1O)C1=CC(Cl)=C3C(=O)C4=C5C=CC(C)=CC5=CC=C4C(=O)C3=C1N2

InChI Identifier

InChI=1S/C28H26ClNO4/c1-4-9-28-12-20(34-14(3)27(28)33)18-11-19(29)22-23(24(18)30-28)25(31)17-8-6-15-10-13(2)5-7-16(15)21(17)26(22)32/h5-8,10-11,14,20,27,30,33H,4,9,12H2,1-3H3/t14-,20?,27-,28+/m1/s1

InChI Key

FZQRJKWDBLIHPW-ZVLXKKIOSA-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 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
Anthraquinone
9,10-anthraquinone
Phenanthrene
Anthracene
Tetrahydroquinoline
Aryl ketone
Aralkylamine
Secondary aliphatic/aromatic amine
Benzenoid
Oxane
Aryl halide
Aryl chloride
Vinylogous amide
Vinylogous halide
Secondary alcohol
Ketone
1,2-aminoalcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary amine
Ether
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Amine
Alcohol
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	5.89	ChemAxon
pKa (Strongest Acidic)	13.19	ChemAxon
pKa (Strongest Basic)	0.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.63 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	133.62 m³·mol⁻¹	ChemAxon
Polarizability	51.9 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

79715591

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162961004

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (21s,22s,23r)-4-chloro-22-hydroxy-11,23-dimethyl-21-propyl-24-oxa-20-azahexacyclo[19.3.1.0²,¹⁹.0⁵,¹⁸.0⁷,¹⁶.0⁸,¹³]pentacosa-2,4,7(16),8,10,12,14,18-octaene-6,17-dione (NP0198696)

MOL for NP0198696 ((21s,22s,23r)-4-chloro-22-hydroxy-11,23-dimethyl-21-propyl-24-oxa-20-azahexacyclo[19.3.1.0²,¹⁹.0⁵,¹⁸.0⁷,¹⁶.0⁸,¹³]pentacosa-2,4,7(16),8,10,12,14,18-octaene-6,17-dione)

3D MOL for NP0198696 ((21s,22s,23r)-4-chloro-22-hydroxy-11,23-dimethyl-21-propyl-24-oxa-20-azahexacyclo[19.3.1.0²,¹⁹.0⁵,¹⁸.0⁷,¹⁶.0⁸,¹³]pentacosa-2,4,7(16),8,10,12,14,18-octaene-6,17-dione)

3D SDF for NP0198696 ((21s,22s,23r)-4-chloro-22-hydroxy-11,23-dimethyl-21-propyl-24-oxa-20-azahexacyclo[19.3.1.0²,¹⁹.0⁵,¹⁸.0⁷,¹⁶.0⁸,¹³]pentacosa-2,4,7(16),8,10,12,14,18-octaene-6,17-dione)

3D-SDF for NP0198696 ((21s,22s,23r)-4-chloro-22-hydroxy-11,23-dimethyl-21-propyl-24-oxa-20-azahexacyclo[19.3.1.0²,¹⁹.0⁵,¹⁸.0⁷,¹⁶.0⁸,¹³]pentacosa-2,4,7(16),8,10,12,14,18-octaene-6,17-dione)

PDB for NP0198696 ((21s,22s,23r)-4-chloro-22-hydroxy-11,23-dimethyl-21-propyl-24-oxa-20-azahexacyclo[19.3.1.0²,¹⁹.0⁵,¹⁸.0⁷,¹⁶.0⁸,¹³]pentacosa-2,4,7(16),8,10,12,14,18-octaene-6,17-dione)

3D PDB for NP0198696 ((21s,22s,23r)-4-chloro-22-hydroxy-11,23-dimethyl-21-propyl-24-oxa-20-azahexacyclo[19.3.1.0²,¹⁹.0⁵,¹⁸.0⁷,¹⁶.0⁸,¹³]pentacosa-2,4,7(16),8,10,12,14,18-octaene-6,17-dione)

SMILES for NP0198696 ((21s,22s,23r)-4-chloro-22-hydroxy-11,23-dimethyl-21-propyl-24-oxa-20-azahexacyclo[19.3.1.0²,¹⁹.0⁵,¹⁸.0⁷,¹⁶.0⁸,¹³]pentacosa-2,4,7(16),8,10,12,14,18-octaene-6,17-dione)

INCHI for NP0198696 ((21s,22s,23r)-4-chloro-22-hydroxy-11,23-dimethyl-21-propyl-24-oxa-20-azahexacyclo[19.3.1.0²,¹⁹.0⁵,¹⁸.0⁷,¹⁶.0⁸,¹³]pentacosa-2,4,7(16),8,10,12,14,18-octaene-6,17-dione)

Structure for NP0198696 ((21s,22s,23r)-4-chloro-22-hydroxy-11,23-dimethyl-21-propyl-24-oxa-20-azahexacyclo[19.3.1.0²,¹⁹.0⁵,¹⁸.0⁷,¹⁶.0⁸,¹³]pentacosa-2,4,7(16),8,10,12,14,18-octaene-6,17-dione)

3D Structure for NP0198696 ((21s,22s,23r)-4-chloro-22-hydroxy-11,23-dimethyl-21-propyl-24-oxa-20-azahexacyclo[19.3.1.0²,¹⁹.0⁵,¹⁸.0⁷,¹⁶.0⁸,¹³]pentacosa-2,4,7(16),8,10,12,14,18-octaene-6,17-dione)