NP-MRD: Showing NP-Card for NSC 177499 (NP0062305)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 06:59:45 UTC

Updated at

2022-04-28 06:59:46 UTC

NP-MRD ID

NP0062305

Secondary Accession Numbers

None

Natural Product Identification

Common Name

NSC 177499

Description

(E)-tomaymycin belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine. NSC 177499 is found in Streptomyces achromogenes var. tomaymyceticus No. A-2127. Based on a literature review very few articles have been published on (E)-tomaymycin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
   -4.0567    3.1375   -0.9391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2815    2.9697    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5009    1.9118    0.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3342    0.8534   -0.6125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7216   -0.2310    0.2495 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2738   -1.4242   -0.4631 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2397   -1.6847   -1.4632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9181   -2.8542   -1.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0016   -1.4393   -1.0781 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3043   -1.1106   -0.5695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3323   -1.6988   -1.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6398   -1.4714   -0.9010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7055   -2.0603   -1.6114 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8678   -0.6581    0.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1902   -0.4414    0.5525 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5504    0.3726    1.6477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8423   -0.0605    0.9096 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5616   -0.2988    0.5164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5302    0.3809    1.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9828    0.8776    2.4158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8402    0.5154    1.0547 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6431    1.5760    1.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5406    2.8045   -1.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0568    2.6548   -0.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2471    4.2348   -1.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3625    3.7214    1.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2601    0.5547   -1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5983    1.1758   -1.3704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5735   -0.5502    0.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3608   -2.3009    0.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6486   -3.0161   -2.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3591   -2.8350   -0.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2234   -3.7352   -1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0372   -1.7410   -2.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1133   -2.3320   -2.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6429   -1.8597   -1.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6315    0.1468    1.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9130    0.2090    2.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5372    1.4518    1.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0249    0.5795    1.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0506    2.4482    1.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3177    1.2274    2.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22  3  1  0
  3  4  1  0
  4  5  1  0
  3  2  2  0
  2  1  1  0
  5  6  1  0
 18 10  1  0
  5 21  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  6 30  1  1
  9 34  1  0
 11 35  1  0
 13 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 22 41  1  0
 22 42  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  2 26  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
M  END


  Mrv1652304282208592D          

 22 24  0  0  1  0            999 V2000
    5.8459    0.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6713    1.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8857    1.8368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2747    1.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4493    0.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2349    0.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9277   -0.1631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1028   -0.1539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5956    0.4969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7882    1.2991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5354    1.6487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5447    2.4737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0847    1.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4574    1.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6552    1.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0874    0.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7732    0.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7365   -0.8931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9132   -0.9456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2823    2.1392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1077    2.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6314    0.5265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
  9 17  1  0  0  0  0
  8 18  1  6  0  0  0
 18 19  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
  1 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0062305

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1NC2=CC(O)=C(OC)C=C2C(=O)N2C\C(C[C@@H]12)=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C16H20N2O4/c1-4-9-5-12-15(22-3)17-11-7-13(19)14(21-2)6-10(11)16(20)18(12)8-9/h4,6-7,12,15,17,19H,5,8H2,1-3H3/b9-4+/t12-,15+/m0/s1

> <INCHI_KEY>
UQVNRKBFAXNOGA-LWTNMJDUSA-N

> <FORMULA>
C16H20N2O4

> <MOLECULAR_WEIGHT>
304.346

> <EXACT_MASS>
304.142307132

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
32.62605248012736

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5E,7S,8R)-5-ethylidene-12-hydroxy-8,13-dimethoxy-3,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(14),10,12-trien-2-one

> <ALOGPS_LOGP>
1.95

> <JCHEM_LOGP>
1.9876376769999995

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.81583384459005

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.090936188024095

> <JCHEM_PKA_STRONGEST_BASIC>
-0.12616840546177066

> <JCHEM_POLAR_SURFACE_AREA>
71.03000000000002

> <JCHEM_REFRACTIVITY>
84.43660000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.85e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5E,7S,8R)-5-ethylidene-12-hydroxy-8,13-dimethoxy-3,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(14),10,12-trien-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      10.912   1.453   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.586   2.958   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.120   3.429   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.979   2.394   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.305   0.889   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.772   0.418   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       7.332  -0.304   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.792  -0.287   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.845   0.927   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       5.205   2.425   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       6.599   3.078   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.617   4.617   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.892   3.230   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.721   2.229   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.223   2.589   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.163   1.472   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.310   0.807   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.108  -1.667   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.571  -1.765   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.727   3.993   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      11.401   5.498   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.379   0.983   0.000  0.00  0.00           O+0
CONECT    1    2    6   22                                                  
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10    4   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14    9                                                       
CONECT   18    8   19                                                       
CONECT   19   18                                                            
CONECT   20    2   21                                                       
CONECT   21   20                                                            
CONECT   22    1                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₀N₂O₄

Average Mass

304.3460 Da

Monoisotopic Mass

304.14231 Da

IUPAC Name

(5E,7S,8R)-5-ethylidene-12-hydroxy-8,13-dimethoxy-3,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(14),10,12-trien-2-one

Traditional Name

(5E,7S,8R)-5-ethylidene-12-hydroxy-8,13-dimethoxy-3,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(14),10,12-trien-2-one

CAS Registry Number

Not Available

SMILES

CO[C@H]1NC2=CC(O)=C(OC)C=C2C(=O)N2C\C(C[C@@H]12)=C\C

InChI Identifier

InChI=1S/C16H20N2O4/c1-4-9-5-12-15(22-3)17-11-7-13(19)14(21-2)6-10(11)16(20)18(12)8-9/h4,6-7,12,15,17,19H,5,8H2,1-3H3/b9-4+/t12-,15+/m0/s1

InChI Key

UQVNRKBFAXNOGA-LWTNMJDUSA-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 achromogenes var. tomaymyceticus No. A-2127	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,4-benzodiazepines

Alternative Parents

Substituents

1,4-benzodiazepine
Anisole
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Vinylogous amide
Tertiary carboxylic acid amide
Pyrrolidine
Carboxamide group
Lactam
Carboxylic acid derivative
Ether
Azacycle
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Organonitrogen compound
Organooxygen 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	1.95	ALOGPS
logP	1.99	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	9.09	ChemAxon
pKa (Strongest Basic)	-0.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	71.03 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	84.44 m³·mol⁻¹	ChemAxon
Polarizability	32.63 Å³	ChemAxon
Number of Rings	3	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

13076951

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12444381

PDB ID

Not Available

ChEBI ID

167317

Good Scents ID

Not Available

References

General References

Showing NP-Card for NSC 177499 (NP0062305)

MOL for NP0062305 (NSC 177499)

3D MOL for NP0062305 (NSC 177499)

3D SDF for NP0062305 (NSC 177499)

3D-SDF for NP0062305 (NSC 177499)

PDB for NP0062305 (NSC 177499)

3D PDB for NP0062305 (NSC 177499)

SMILES for NP0062305 (NSC 177499)

INCHI for NP0062305 (NSC 177499)

Structure for NP0062305 (NSC 177499)

3D Structure for NP0062305 (NSC 177499)