NP-MRD: Showing NP-Card for caerulomycin c (NP0195335)

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Record Information

Version

2.0

Created at

2022-09-04 13:10:31 UTC

Updated at

2022-09-04 13:10:31 UTC

NP-MRD ID

NP0195335

Secondary Accession Numbers

None

Natural Product Identification

Common Name

caerulomycin c

Description

Caerulomycin C belongs to the class of organic compounds known as bipyridines and oligopyridines. These are organic compounds containing two pyridine rings linked to each other. Caerulomycin C is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. caerulomycin c is found in Actinoalloteichus cyanogriseus. caerulomycin c was first documented in 1996 (PMID: 11667035). Based on a literature review a small amount of articles have been published on caerulomycin C (PMID: 12098253) (PMID: 12003535).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
    3.2781   -2.8967   -0.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9141   -2.5356   -0.3770 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4937   -1.2321   -0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3258   -0.1927    0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8124    1.0781    0.3444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6954    2.2046    0.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2173    3.3852    0.8658 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9682    4.4828    1.1844 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5118    1.2925    0.2233 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3770    0.2907   -0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7685    0.7302   -0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7909   -0.0847   -0.5760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1155    0.4016   -0.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3024    1.7303   -0.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2636    2.5542   -0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0357    2.0534    0.0340 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1175   -0.9560   -0.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7273   -2.0130   -0.5914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2115   -2.8813    0.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4594   -3.1589    0.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9647   -2.1149   -0.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3844   -3.8461   -0.8740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3892   -0.3639    0.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7595    2.0613    0.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417    4.8271    0.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6672   -1.1185   -0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8973   -0.2797   -1.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3248    2.1101   -0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4536    3.6123    0.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7149   -2.2078    1.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9823   -3.5421    0.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4005   -3.3904    0.9631 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
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  5  9  2  0
  9 10  1  0
 10 17  2  0
 17 18  1  0
 18 19  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 17  3  1  0
 16 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  8 25  1  0
 19 30  1  0
 19 31  1  0
 19 32  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
M  END


  Mrv1652309042215102D          

 19 20  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   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 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    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
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  5  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 10 17  2  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0195335

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=N\O)=NC(=C1OC)C1=CC=CC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C13H13N3O3/c1-18-11-7-9(8-15-17)16-12(13(11)19-2)10-5-3-4-6-14-10/h3-8,17H,1-2H3/b15-8+

> <INCHI_KEY>
WZBOHQZLZFLYKP-OVCLIPMQSA-N

> <FORMULA>
C13H13N3O3

> <MOLECULAR_WEIGHT>
259.265

> <EXACT_MASS>
259.095691291

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
26.509697067977502

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(E)-N-({3,4-dimethoxy-[2,2'-bipyridine]-6-yl}methylidene)hydroxylamine

> <JCHEM_LOGP>
2.0380096836666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.906407407472654

> <JCHEM_PKA_STRONGEST_BASIC>
2.5686981786376357

> <JCHEM_POLAR_SURFACE_AREA>
76.83

> <JCHEM_REFRACTIVITY>
69.08330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(E)-N-({3,4-dimethoxy-[2,2'-bipyridine]-6-yl}methylidene)hydroxylamine

> <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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       4.001  -6.930   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       1.334  -5.390   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -2.667  -4.620   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   10    3   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₃N₃O₃

Average Mass

259.2650 Da

Monoisotopic Mass

259.09569 Da

IUPAC Name

(E)-N-({3,4-dimethoxy-[2,2'-bipyridine]-6-yl}methylidene)hydroxylamine

Traditional Name

(E)-N-({3,4-dimethoxy-[2,2'-bipyridine]-6-yl}methylidene)hydroxylamine

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=N\O)=NC(=C1OC)C1=CC=CC=N1

InChI Identifier

InChI=1S/C13H13N3O3/c1-18-11-7-9(8-15-17)16-12(13(11)19-2)10-5-3-4-6-14-10/h3-8,17H,1-2H3/b15-8+

InChI Key

WZBOHQZLZFLYKP-OVCLIPMQSA-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
Actinoalloteichus cyanogriseus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bipyridines and oligopyridines. These are organic compounds containing two pyridine rings linked to each other.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Bipyridines and oligopyridines

Direct Parent

Bipyridines and oligopyridines

Alternative Parents

Substituents

Bipyridine
Alkyl aryl ether
Heteroaromatic compound
Aldoxime
Azacycle
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ether (CHEBI:69232 )
pyridine alkaloid (CHEBI:69232 )
bipyridines (CHEBI:69232 )
aldoxime (CHEBI:69232 )

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	2.04	ChemAxon
pKa (Strongest Acidic)	8.91	ChemAxon
pKa (Strongest Basic)	2.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	69.08 m³·mol⁻¹	ChemAxon
Polarizability	26.51 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

26618626

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135503530

PDB ID

Not Available

ChEBI ID

69232

Good Scents ID

Not Available

References

General References

Sammakia T, Stangeland EL, Whitcomb MC: Total synthesis of caerulomycin C via the halogen dance reaction. Org Lett. 2002 Jul 11;4(14):2385-8. doi: 10.1021/ol026135m. [PubMed:12098253 ]
Mongin F, Trecourt F, Gervais B, Mongin O, Queguiner G: First synthesis of caerulomycin B. A new synthesis of caerulomycin C. J Org Chem. 2002 May 17;67(10):3272-6. doi: 10.1021/jo010913r. [PubMed:12003535 ]
Trecourt F, Gervais B, Mallet M, Queguiner G: First Synthesis of Caerulomycin C. J Org Chem. 1996 Mar 8;61(5):1673-1676. doi: 10.1021/jo950823k. [PubMed:11667035 ]
LOTUS database [Link]

Showing NP-Card for caerulomycin c (NP0195335)

MOL for NP0195335 (caerulomycin c)

3D MOL for NP0195335 (caerulomycin c)

3D SDF for NP0195335 (caerulomycin c)

3D-SDF for NP0195335 (caerulomycin c)

PDB for NP0195335 (caerulomycin c)

3D PDB for NP0195335 (caerulomycin c)

SMILES for NP0195335 (caerulomycin c)

INCHI for NP0195335 (caerulomycin c)

Structure for NP0195335 (caerulomycin c)

3D Structure for NP0195335 (caerulomycin c)