NP-MRD: Showing NP-Card for Cremeomycin (NP0022342)

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Record Information

Version

2.0

Created at

2021-01-06 07:32:35 UTC

Updated at

2021-07-15 17:38:47 UTC

NP-MRD ID

NP0022342

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cremeomycin

Provided By

NPAtlas

Description

Cremeomycin is found in Streptomyces cremeus and Streptomyces cremeus NRRL 3241. Cremeomycin was first documented in 1995 (PMID: 7622439).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105353D          

 20 20  0  0  0  0            999 V2000
   -3.2241   -0.8980    0.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5732    0.3218   -0.0484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1744    0.3064   -0.1043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5135   -0.6490   -0.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9360   -0.7271   -0.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404    0.1809   -0.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1867    0.0909   -0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8901    0.9667    0.1512 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7890   -0.9409   -1.0662 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0816    1.2708    0.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8110    2.1490    0.9764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3704    1.3428    0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9473    2.2781    1.1500 N   0  3  0  0  0  4  0  0  0  0  0  0
   -1.4289    2.8960    2.1203 N   0  5  0  0  0  2  0  0  0  0  0  0
   -2.9086   -1.2617    1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9694   -1.7099   -0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3255   -0.7306    0.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1112   -1.4346   -1.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4386   -1.5285   -1.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6733   -1.9232   -0.8362 H   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  2  0  0  0  0
 12  3  1  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  4 18  1  0  0  0  0
  5 19  1  0  0  0  0
  9 20  1  0  0  0  0
M  CHG  2  13   1  14  -1
M  END
> <DATABASE_ID>
NP0022342

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])C([H])=C(OC([H])([H])[H])C(=[N+]=[N-])C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H6N2O4/c1-14-5-3-2-4(8(12)13)7(11)6(5)10-9/h2-3H,1H3,(H,12,13)

> <INCHI_KEY>
HTCPEWKHGGGJBI-UHFFFAOYSA-N

> <FORMULA>
C8H6N2O4

> <MOLECULAR_WEIGHT>
194.146

> <EXACT_MASS>
194.032756681

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
17.199417124182105

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(-lambda4,-lambda2-diazynylidene)-4-methoxy-6-oxocyclohexa-1,3-diene-1-carboxylic acid

> <ALOGPS_LOGP>
1.34

> <JCHEM_LOGP>
-0.9984355892092788

> <ALOGPS_LOGS>
-2.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.51949895327998

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6148388330355363

> <JCHEM_PKA_STRONGEST_BASIC>
-4.987911841438677

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
46.671900000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.86e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(-lambda4,-lambda2-diazynylidene)-4-methoxy-6-oxocyclohexa-1,3-diene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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      -3.224  -0.898   0.289  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.573   0.322  -0.048  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.174   0.306  -0.104  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.514  -0.649  -0.738  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.936  -0.727  -0.835  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.740   0.181  -0.281  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.187   0.091  -0.386  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.890   0.967   0.151  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.789  -0.941  -1.066  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.082   1.271   0.439  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.811   2.149   0.976  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.370   1.343   0.532  0.00  0.00           C+0
HETATM   13  N   UNK     0      -0.947   2.278   1.150  0.00  0.00           N+1
HETATM   14  N   UNK     0      -1.429   2.896   2.120  0.00  0.00           N-1
HETATM   15  H   UNK     0      -2.909  -1.262   1.302  0.00  0.00           H+0
HETATM   16  H   UNK     0      -2.969  -1.710  -0.425  0.00  0.00           H+0
HETATM   17  H   UNK     0      -4.325  -0.731   0.346  0.00  0.00           H+0
HETATM   18  H   UNK     0      -1.111  -1.435  -1.220  0.00  0.00           H+0
HETATM   19  H   UNK     0       1.439  -1.529  -1.365  0.00  0.00           H+0
HETATM   20  H   UNK     0       3.673  -1.923  -0.836  0.00  0.00           H+0
CONECT    1    2   15   16   17                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   20                                                       
CONECT   10    6   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13    3                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    1                                                            
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    4                                                            
CONECT   19    5                                                            
CONECT   20    9                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
6-Carboxy-2-(diazyn-1-ium-1-yl)-3-methoxybenzen-1-olic acid	Generator

Chemical Formula

C₈H₆N₂O₄

Average Mass

194.1460 Da

Monoisotopic Mass

194.03276 Da

IUPAC Name

5-(-lambda4,-lambda2-diazynylidene)-4-methoxy-6-oxocyclohexa-1,3-diene-1-carboxylic acid

Traditional Name

5-(-lambda4,-lambda2-diazynylidene)-4-methoxy-6-oxocyclohexa-1,3-diene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C(O)=O)C(=O)C1=[N+]=[N-]

InChI Identifier

InChI=1S/C8H6N2O4/c1-14-5-3-2-4(8(12)13)7(11)6(5)10-9/h2-3H,1H3,(H,12,13)

InChI Key

HTCPEWKHGGGJBI-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 cremeus	NPAtlas	7622439
Streptomyces cremeus NRRL 3241	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diazo compounds. These are organic compounds having the divalent diazo group, =N+=N-, attached to a carbon atom.

Kingdom

Organic compounds

Super Class

Organic 1,3-dipolar compounds

Class

Propargyl-type 1,3-dipolar organic compounds

Sub Class

Diazo compounds

Direct Parent

Diazo compounds

Alternative Parents

Substituents

Ketone
Cyclic ketone
Diazo compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxide
Hydrocarbon derivative
Organic zwitterion
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	1.34	ALOGPS
logP	-1	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.61	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	46.67 m³·mol⁻¹	ChemAxon
Polarizability	17.2 Å³	ChemAxon
Number of Rings	1	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

NPA006413

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28285805

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

McGuire JN, Wilson SR, Rinehart KL: Cremeomycin, a novel cytotoxic antibiotic from Streptomyces cremeus. Structure elucidation and biological activity. J Antibiot (Tokyo). 1995 Jun;48(6):516-9. doi: 10.7164/antibiotics.48.516. [PubMed:7622439 ]

Showing NP-Card for Cremeomycin (NP0022342)

MOL for NP0022342 (Cremeomycin)

3D MOL for NP0022342 (Cremeomycin)

3D SDF for NP0022342 (Cremeomycin)

3D-SDF for NP0022342 (Cremeomycin)

PDB for NP0022342 (Cremeomycin)

3D PDB for NP0022342 (Cremeomycin)

SMILES for NP0022342 (Cremeomycin)

INCHI for NP0022342 (Cremeomycin)

Structure for NP0022342 (Cremeomycin)

3D Structure for NP0022342 (Cremeomycin)