NP-MRD: Showing NP-Card for Antiostatin B3 (NP0061597)

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Record Information

Version

2.0

Created at

2022-04-28 06:21:35 UTC

Updated at

2022-04-28 06:21:35 UTC

NP-MRD ID

NP0061597

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Antiostatin B3

Description

1-({[3-Hydroxy-2-methyl-1-(5-methylhexyl)-9H-carbazol-4-yl]-C-hydroxycarbonimidoyl}amino)-N-(2-methylpropyl)methanimidic acid 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. Antiostatin B3 is found in Streptomyces cyaneus 2007-SV1. 1-({[3-Hydroxy-2-methyl-1-(5-methylhexyl)-9H-carbazol-4-yl]-C-hydroxycarbonimidoyl}amino)-N-(2-methylpropyl)methanimidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251506292D          

 33 35  0  0  0  0            999 V2000
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   -4.7062   -0.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9918   -0.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2773   -0.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004251506292D          

 33 35  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0061597

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CCCCC1=C(C)C(O)=C(NC(=O)NC(=O)NCC(C)C)C2=C1NC1=C2C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H36N4O3/c1-15(2)10-6-7-11-18-17(5)24(31)23(29-26(33)30-25(32)27-14-16(3)4)21-19-12-8-9-13-20(19)28-22(18)21/h8-9,12-13,15-16,28,31H,6-7,10-11,14H2,1-5H3,(H3,27,29,30,32,33)

> <INCHI_KEY>
JFQYWYPWQFAAHW-UHFFFAOYSA-N

> <FORMULA>
C26H36N4O3

> <MOLECULAR_WEIGHT>
452.599

> <EXACT_MASS>
452.278741035

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.53693064829006

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-({[3-hydroxy-2-methyl-1-(5-methylhexyl)-9H-carbazol-4-yl]carbamoyl}amino)-N-(2-methylpropyl)formamide

> <ALOGPS_LOGP>
5.23

> <JCHEM_LOGP>
6.351232415

> <ALOGPS_LOGS>
-5.40

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.092774851942803

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.272466296978049

> <JCHEM_PKA_STRONGEST_BASIC>
-6.253413671443217

> <JCHEM_POLAR_SURFACE_AREA>
106.25

> <JCHEM_REFRACTIVITY>
133.5123

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.79e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-({[3-hydroxy-2-methyl-1-(5-methylhexyl)-9H-carbazol-4-yl]carbamoyl}amino)-N-(2-methylpropyl)formamide

> <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     -12.786  -1.051   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.452  -0.281   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -11.452   1.259   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.119  -1.051   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.785  -0.281   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.451  -1.051   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.118  -0.281   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.784  -1.051   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.450  -0.281   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.450   1.259   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.117  -1.051   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.783  -0.281   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.117  -2.591   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -0.783  -3.361   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       0.551  -2.591   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.551  -1.051   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       1.884  -3.361   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       3.218  -2.591   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.218  -1.051   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0       4.552  -3.361   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       5.886  -2.591   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.219  -3.361   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.553  -2.591   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.219  -4.901   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.450  -3.361   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.770  -4.868   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.865  -6.113   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.492  -7.520   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.023  -7.681   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.928  -6.435   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.302  -5.029   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0      -5.928  -3.622   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0      -4.784  -2.591   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   33                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   25                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   13   26   33                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   26   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32    8   25                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
1-({[3-hydroxy-2-methyl-1-(5-methylhexyl)-9H-carbazol-4-yl]-C-hydroxycarbonimidoyl}amino)-N-(2-methylpropyl)methanimidate	Generator

Chemical Formula

C₂₆H₃₆N₄O₃

Average Mass

452.5990 Da

Monoisotopic Mass

452.27874 Da

IUPAC Name

1-({[3-hydroxy-2-methyl-1-(5-methylhexyl)-9H-carbazol-4-yl]carbamoyl}amino)-N-(2-methylpropyl)formamide

Traditional Name

1-({[3-hydroxy-2-methyl-1-(5-methylhexyl)-9H-carbazol-4-yl]carbamoyl}amino)-N-(2-methylpropyl)formamide

CAS Registry Number

Not Available

SMILES

CC(C)CCCCC1=C(C)C(O)=C(NC(=O)NC(=O)NCC(C)C)C2=C1NC1=C2C=CC=C1

InChI Identifier

InChI=1S/C26H36N4O3/c1-15(2)10-6-7-11-18-17(5)24(31)23(29-26(33)30-25(32)27-14-16(3)4)21-19-12-8-9-13-20(19)28-22(18)21/h8-9,12-13,15-16,28,31H,6-7,10-11,14H2,1-5H3,(H3,27,29,30,32,33)

InChI Key

JFQYWYPWQFAAHW-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 cyaneus 2007-SV1	Bacteria	KNApSAcK

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
Hydroxyindole
Indole
Phenol
Benzenoid
Pyrrole
Heteroaromatic compound
Urea
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic oxygen 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	5.23	ALOGPS
logP	6.35	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	8.27	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	106.25 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	133.51 m³·mol⁻¹	ChemAxon
Polarizability	52.54 Å³	ChemAxon
Number of Rings	3	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

14805053

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Antiostatin B3 (NP0061597)

MOL for NP0061597 (Antiostatin B3)

3D MOL for NP0061597 (Antiostatin B3)

3D SDF for NP0061597 (Antiostatin B3)

3D-SDF for NP0061597 (Antiostatin B3)

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3D PDB for NP0061597 (Antiostatin B3)

SMILES for NP0061597 (Antiostatin B3)

INCHI for NP0061597 (Antiostatin B3)

Structure for NP0061597 (Antiostatin B3)

3D Structure for NP0061597 (Antiostatin B3)