NP-MRD: Showing NP-Card for Ammosamide B (NP0008154)

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Record Information

Version

2.0

Created at

2020-12-09 05:48:22 UTC

Updated at

2021-07-15 16:59:34 UTC

NP-MRD ID

NP0008154

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ammosamide B

Provided By

NPAtlas

Description

Ammosamide B is found in Streptomyces. Ammosamide B was first documented in 2010 (PMID: 20515072). Based on a literature review very few articles have been published on Ammosamide B (PMID: 22515470) (PMID: 23764772) (PMID: 22206487) (PMID: 20131899).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106073D          

 30 32  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242106073D          

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M  END
> <DATABASE_ID>
NP0008154

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N([H])C(=O)C1=NC2=C(N([H])[H])C(Cl)=C(N([H])[H])C3=C2C(=C1[H])C(=O)N3C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H10ClN5O2/c1-18-10-5-3(12(18)20)2-4(11(16)19)17-9(5)7(14)6(13)8(10)15/h2H,14-15H2,1H3,(H2,16,19)

> <INCHI_KEY>
HWRGTOQGZGTNID-UHFFFAOYSA-N

> <FORMULA>
C12H10ClN5O2

> <MOLECULAR_WEIGHT>
291.693

> <EXACT_MASS>
291.052302296

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
28.13688695964867

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9,11-diamino-10-chloro-2-methyl-3-oxo-2,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-1(12),4,6,8,10-pentaene-6-carboxamide

> <ALOGPS_LOGP>
0.39

> <JCHEM_LOGP>
-0.703711082

> <ALOGPS_LOGS>
-2.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.098718633518704

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.949905209544799

> <JCHEM_PKA_STRONGEST_BASIC>
0.980265918044936

> <JCHEM_POLAR_SURFACE_AREA>
128.32999999999998

> <JCHEM_REFRACTIVITY>
75.48270000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.72e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9,11-diamino-10-chloro-2-methyl-3-oxo-2,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-1(12),4,6,8,10-pentaene-6-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
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 18 30  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.531  -1.438  -0.471  0.00  0.00           C+0
HETATM    2  N   UNK     0      -2.106  -1.299  -0.380  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.067  -2.277  -0.555  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.260  -3.470  -0.830  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.194  -1.580  -0.345  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.545  -1.908  -0.362  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.473  -0.920  -0.101  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.880  -1.306  -0.128  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.871  -0.337   0.132  0.00  0.00           N+0
HETATM   10  O   UNK     0       4.263  -2.469  -0.372  0.00  0.00           O+0
HETATM   11  N   UNK     0       2.134   0.374   0.175  0.00  0.00           N+0
HETATM   12  C   UNK     0       0.824   0.691   0.190  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.337   1.947   0.451  0.00  0.00           C+0
HETATM   14  N   UNK     0       1.251   2.991   0.723  0.00  0.00           N+0
HETATM   15  C   UNK     0      -1.030   2.201   0.450  0.00  0.00           C+0
HETATM   16 Cl   UNK     0      -1.644   3.824   0.787  0.00  0.00          Cl+0
HETATM   17  C   UNK     0      -1.975   1.221   0.190  0.00  0.00           C+0
HETATM   18  N   UNK     0      -3.369   1.464   0.186  0.00  0.00           N+0
HETATM   19  C   UNK     0      -1.473  -0.043  -0.072  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.119  -0.276  -0.066  0.00  0.00           C+0
HETATM   21  H   UNK     0      -3.875  -2.476  -0.463  0.00  0.00           H+0
HETATM   22  H   UNK     0      -4.045  -0.912   0.357  0.00  0.00           H+0
HETATM   23  H   UNK     0      -3.874  -0.932  -1.415  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.763  -2.931  -0.581  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.760   0.633  -0.193  0.00  0.00           H+0
HETATM   26  H   UNK     0       5.721  -0.605   0.654  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.692   3.527  -0.070  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.456   3.190   1.728  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.925   1.441  -0.692  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.869   1.675   1.074  0.00  0.00           H+0
CONECT    1    2   21   22   23                                             
CONECT    2    1    3   19                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   20                                                  
CONECT    6    5    7   24                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   25   26                                                  
CONECT   10    8                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13   27   28                                                  
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17   29   30                                                  
CONECT   19   17   20    2                                                  
CONECT   20   19    5   12                                                  
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    6                                                            
CONECT   25    9                                                            
CONECT   26    9                                                            
CONECT   27   14                                                            
CONECT   28   14                                                            
CONECT   29   18                                                            
CONECT   30   18                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

RDKit          3D

30 32  0  0  0  0  0  0  0  0999 V2000
   -3.5312   -1.4378   -0.4713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1064   -1.2990   -0.3798 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0666   -2.2774   -0.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2602   -3.4704   -0.8304 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1940   -1.5802   -0.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5448   -1.9081   -0.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4727   -0.9201   -0.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8798   -1.3055   -0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8713   -0.3365    0.1315 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2626   -2.4685   -0.3720 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1336    0.3742    0.1747 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8239    0.6910    0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371    1.9473    0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2514    2.9907    0.7234 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0305    2.2012    0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6437    3.8237    0.7872 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.9749    1.2207    0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3689    1.4644    0.1857 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4727   -0.0429   -0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1194   -0.2756   -0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8747   -2.4756   -0.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0454   -0.9118    0.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8743   -0.9320   -1.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7629   -2.9312   -0.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7604    0.6326   -0.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7205   -0.6053    0.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6916    3.5266   -0.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4560    3.1901    1.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9246    1.4408   -0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8688    1.6745    1.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  7 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 19  2  1  0
 20  5  1  0
 20 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  6 24  1  0
  9 25  1  0
  9 26  1  0
 14 27  1  0
 14 28  1  0
 18 29  1  0
 18 30  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₂H₁₀ClN₅O₂

Average Mass

291.6930 Da

Monoisotopic Mass

291.05230 Da

IUPAC Name

9,11-diamino-10-chloro-2-methyl-3-oxo-2,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-1(12),4,6,8,10-pentaene-6-carboxamide

Traditional Name

9,11-diamino-10-chloro-2-methyl-3-oxo-2,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-1(12),4,6,8,10-pentaene-6-carboxamide

CAS Registry Number

Not Available

SMILES

CN1C(=O)C2=CC(=NC3=C2C1=C(N)C(Cl)=C3N)C(N)=O

InChI Identifier

InChI=1S/C12H10ClN5O2/c1-18-10-5-3(12(18)20)2-4(11(16)19)17-9(5)7(14)6(13)8(10)15/h2H,14-15H2,1H3,(H2,16,19)

InChI Key

HWRGTOQGZGTNID-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	NPAtlas	19090514

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as quinoline carboxamides. These are quinolines in which the quinoline ring system is substituted by one or more carboxamide groups.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinoline carboxamides

Direct Parent

Quinoline carboxamides

Alternative Parents

Substituents

Quinoline-2-carboxamide
Aminoquinoline
Haloquinoline
Chloroquinoline
Indole or derivatives
Pyridine carboxylic acid or derivatives
2-heteroaryl carboxamide
Aryl chloride
Pyridine
Aryl halide
Benzenoid
Tertiary carboxylic acid amide
Heteroaromatic compound
Primary carboxylic acid amide
Amino acid or derivatives
Lactam
Carboxamide group
Azacycle
Carboxylic acid derivative
Organohalogen compound
Organooxygen compound
Primary amine
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organochloride
Organonitrogen 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	0.39	ALOGPS
logP	-0.7	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	14.95	ChemAxon
pKa (Strongest Basic)	0.98	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	128.33 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.48 m³·mol⁻¹	ChemAxon
Polarizability	28.14 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA002004

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

27024038

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25113669

PDB ID

UXH

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pan E, Jamison M, Yousufuddin M, MacMillan JB: Ammosamide D, an oxidatively ring opened ammosamide analog from a marine-derived Streptomyces variabilis. Org Lett. 2012 May 4;14(9):2390-3. doi: 10.1021/ol300806e. Epub 2012 Apr 20. [PubMed:22515470 ]
Takayama Y, Yamada T, Tatekabe S, Nagasawa K: A tandem Friedel-Crafts based method for the construction of a tricyclic pyrroloquinoline skeleton and its application in the synthesis of ammosamide B. Chem Commun (Camb). 2013 Jul 25;49(58):6519-21. doi: 10.1039/c3cc42463d. Epub 2013 Jun 14. [PubMed:23764772 ]
Reddy PV, Jensen KC, Mesecar AD, Fanwick PE, Cushman M: Design, synthesis, and biological evaluation of potent quinoline and pyrroloquinoline ammosamide analogues as inhibitors of quinone reductase 2. J Med Chem. 2012 Jan 12;55(1):367-77. doi: 10.1021/jm201251c. Epub 2011 Dec 29. [PubMed:22206487 ]
Reddy PV, Banerjee B, Cushman M: Efficient total synthesis of ammosamide B. Org Lett. 2010 Jul 2;12(13):3112-4. doi: 10.1021/ol101215x. [PubMed:20515072 ]
Hughes CC, Fenical W: Total synthesis of the ammosamides. J Am Chem Soc. 2010 Mar 3;132(8):2528-9. doi: 10.1021/ja9106572. [PubMed:20131899 ]

Showing NP-Card for Ammosamide B (NP0008154)

MOL for NP0008154 (Ammosamide B)

3D MOL for NP0008154 (Ammosamide B)

3D SDF for NP0008154 (Ammosamide B)

3D-SDF for NP0008154 (Ammosamide B)

PDB for NP0008154 (Ammosamide B)

3D PDB for NP0008154 (Ammosamide B)

SMILES for NP0008154 (Ammosamide B)

INCHI for NP0008154 (Ammosamide B)

Structure for NP0008154 (Ammosamide B)

3D Structure for NP0008154 (Ammosamide B)