NP-MRD: Showing NP-Card for 2,4-bis(acetyloxy)-5-cyano-1,7-dihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-3-yl 2-methylpropanoate (NP0241750)

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Record Information

Version

2.0

Created at

2022-09-07 01:54:25 UTC

Updated at

2022-09-07 01:54:25 UTC

NP-MRD ID

NP0241750

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,4-bis(acetyloxy)-5-cyano-1,7-dihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-3-yl 2-methylpropanoate

Description

2,4-Bis(acetyloxy)-5-cyano-1,7-dihydroxy-3-methyl-6,11-dioxo-1H,2H,3H,4H,5H,6H,11H-benzo[b]carbazol-3-yl 2-methylpropanoate belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. 2,4-bis(acetyloxy)-5-cyano-1,7-dihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-3-yl 2-methylpropanoate is found in Streptomyces chattanoogensis. 2,4-Bis(acetyloxy)-5-cyano-1,7-dihydroxy-3-methyl-6,11-dioxo-1H,2H,3H,4H,5H,6H,11H-benzo[b]carbazol-3-yl 2-methylpropanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251505372D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004251505372D          

 38 41  0  0  0  0            999 V2000
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 34 35  2  0  0  0  0
 29 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 16 38  1  0  0  0  0
 26 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0241750

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)OC1(C)C(OC(C)=O)C(O)C2=C(C1OC(C)=O)N(C#N)C1=C2C(=O)C2=CC=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H24N2O10/c1-10(2)25(35)38-26(5)23(36-11(3)29)19-17(22(34)24(26)37-12(4)30)16-18(28(19)9-27)21(33)15-13(20(16)32)7-6-8-14(15)31/h6-8,10,22-24,31,34H,1-5H3

> <INCHI_KEY>
MLTKYZACIJTYFJ-UHFFFAOYSA-N

> <FORMULA>
C26H24N2O10

> <MOLECULAR_WEIGHT>
524.482

> <EXACT_MASS>
524.143094981

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
51.92844049125401

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,4-bis(acetyloxy)-5-cyano-1,7-dihydroxy-3-methyl-6,11-dioxo-1H,2H,3H,4H,5H,6H,11H-benzo[b]carbazol-3-yl 2-methylpropanoate

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
2.389334477333332

> <ALOGPS_LOGS>
-3.86

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.899746704866821

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.738160505591797

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7190610982864607

> <JCHEM_POLAR_SURFACE_AREA>
182.21999999999997

> <JCHEM_REFRACTIVITY>
127.72359999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4-bis(acetyloxy)-5-cyano-1,7-dihydroxy-3-methyl-6,11-dioxo-1H,2H,4H-benzo[b]carbazol-3-yl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       0.047  -5.609   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.537  -5.220   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.619  -6.316   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.945  -3.735   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.864  -2.639   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.436  -3.346   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.517  -4.442   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.250  -5.317   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.159  -5.842   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.268  -7.098   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.910  -8.498   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.443  -8.642   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.018  -9.754   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.693  -5.986   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.334  -7.386   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.584  -4.730   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.942  -3.331   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.409  -3.186   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.767  -1.787   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.234  -1.643   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.342  -2.898   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.592  -0.243   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       8.075  -2.288   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       7.897  -0.758   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       7.719   0.772   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       9.417  -3.043   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.876  -2.551   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.180  -1.041   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.032  -3.569   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.491  -3.077   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.795  -1.567   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      14.647  -4.094   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.344  -5.604   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.884  -6.096   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.729  -5.078   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.269  -5.570   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       9.966  -7.080   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       9.114  -4.553   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9   18                                             
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   38                                                  
CONECT   17   16   18   23                                                  
CONECT   18   17    7   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   17   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   38                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   35                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   29   36                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   16   26                                                  
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
2,4-Bis(acetyloxy)-5-cyano-1,7-dihydroxy-3-methyl-6,11-dioxo-1H,2H,3H,4H,5H,6H,11H-benzo[b]carbazol-3-yl 2-methylpropanoic acid	Generator

Chemical Formula

C₂₆H₂₄N₂O₁₀

Average Mass

524.4820 Da

Monoisotopic Mass

524.14309 Da

IUPAC Name

2,4-bis(acetyloxy)-5-cyano-1,7-dihydroxy-3-methyl-6,11-dioxo-1H,2H,3H,4H,5H,6H,11H-benzo[b]carbazol-3-yl 2-methylpropanoate

Traditional Name

2,4-bis(acetyloxy)-5-cyano-1,7-dihydroxy-3-methyl-6,11-dioxo-1H,2H,4H-benzo[b]carbazol-3-yl 2-methylpropanoate

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)OC1(C)C(OC(C)=O)C(O)C2=C(C1OC(C)=O)N(C#N)C1=C2C(=O)C2=CC=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C26H24N2O10/c1-10(2)25(35)38-26(5)23(36-11(3)29)19-17(22(34)24(26)37-12(4)30)16-18(28(19)9-27)21(33)15-13(20(16)32)7-6-8-14(15)31/h6-8,10,22-24,31,34H,1-5H3

InChI Key

MLTKYZACIJTYFJ-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 chattanoogensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
Naphthalene
Tricarboxylic acid or derivatives
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Vinylogous acid
Vinylogous amide
Secondary alcohol
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
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	2.01	ALOGPS
logP	2.39	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	7.74	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	182.22 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	127.72 m³·mol⁻¹	ChemAxon
Polarizability	51.93 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

85142551

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,4-bis(acetyloxy)-5-cyano-1,7-dihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-3-yl 2-methylpropanoate (NP0241750)

MOL for NP0241750 (2,4-bis(acetyloxy)-5-cyano-1,7-dihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-3-yl 2-methylpropanoate)

3D MOL for NP0241750 (2,4-bis(acetyloxy)-5-cyano-1,7-dihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-3-yl 2-methylpropanoate)

3D SDF for NP0241750 (2,4-bis(acetyloxy)-5-cyano-1,7-dihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-3-yl 2-methylpropanoate)

3D-SDF for NP0241750 (2,4-bis(acetyloxy)-5-cyano-1,7-dihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-3-yl 2-methylpropanoate)

PDB for NP0241750 (2,4-bis(acetyloxy)-5-cyano-1,7-dihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-3-yl 2-methylpropanoate)

3D PDB for NP0241750 (2,4-bis(acetyloxy)-5-cyano-1,7-dihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-3-yl 2-methylpropanoate)

SMILES for NP0241750 (2,4-bis(acetyloxy)-5-cyano-1,7-dihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-3-yl 2-methylpropanoate)

INCHI for NP0241750 (2,4-bis(acetyloxy)-5-cyano-1,7-dihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-3-yl 2-methylpropanoate)

Structure for NP0241750 (2,4-bis(acetyloxy)-5-cyano-1,7-dihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-3-yl 2-methylpropanoate)

3D Structure for NP0241750 (2,4-bis(acetyloxy)-5-cyano-1,7-dihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-3-yl 2-methylpropanoate)