NP-MRD: Showing NP-Card for (1r,2s,12r,21ar)-13-{[(2s,3r,4r,5r)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-1,12-dihydroxy-2,12-dimethyl-1h,2h,3h,13h,21ah-pyrrolo[1,2-a]azacyclononadecan-5-one (NP0290568)

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Record Information

Version

2.0

Created at

2022-09-09 21:18:38 UTC

Updated at

2022-09-09 21:18:38 UTC

NP-MRD ID

NP0290568

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,12r,21ar)-13-{[(2s,3r,4r,5r)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-1,12-dihydroxy-2,12-dimethyl-1h,2h,3h,13h,21ah-pyrrolo[1,2-a]azacyclononadecan-5-one

Description

Ciromicin A belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides. Based on a literature review very few articles have been published on Ciromicin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092223182D          

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M  END

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M  END


  Mrv1652309092223182D          

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  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  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  1  6  0  0  0
 13 15  1  1  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  1  0  0  0
 16 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35  4  1  6  0  0  0
 35 36  1  0  0  0  0
  2 36  1  0  0  0  0
 36 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0290568

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CN2[C@H](\C=C/C=C/C=C/C=C\C(O[C@@H]3OC[C@@H](O)[C@H](O)[C@H]3N)[C@](C)(O)\C=C\C=C\C=C\C2=O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H38N2O7/c1-19-17-30-20(25(19)33)13-9-5-3-4-6-10-14-22(37-27-24(29)26(34)21(31)18-36-27)28(2,35)16-12-8-7-11-15-23(30)32/h3-16,19-22,24-27,31,33-35H,17-18,29H2,1-2H3/b5-3+,6-4+,8-7+,13-9-,14-10-,15-11+,16-12+/t19-,20+,21+,22?,24+,25+,26-,27-,28+/m0/s1

> <INCHI_KEY>
BOXGALHYKYOYFJ-NTIGGAKHSA-N

> <FORMULA>
C28H38N2O7

> <MOLECULAR_WEIGHT>
514.619

> <EXACT_MASS>
514.267901572

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
54.0636014730749

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,12R,21aR)-13-{[(2S,3R,4R,5R)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-1,12-dihydroxy-2,12-dimethyl-1H,2H,3H,5H,12H,13H,21aH-pyrrolo[1,2-a]azacyclononadecan-5-one

> <JCHEM_LOGP>
0.5308065239999987

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.5806448433794

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.941682764792098

> <JCHEM_PKA_STRONGEST_BASIC>
8.12624297736225

> <JCHEM_POLAR_SURFACE_AREA>
145.71

> <JCHEM_REFRACTIVITY>
147.62250000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,12R,21aR)-13-{[(2S,3R,4R,5R)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-1,12-dihydroxy-2,12-dimethyl-1H,2H,3H,13H,21aH-pyrrolo[1,2-a]azacyclononadecan-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.713  -2.725   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.173  -2.720   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.272  -1.471   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.194  -1.941   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.689  -0.483   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.470   0.458   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.975   0.364   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.917   1.582   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.452   1.460   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.943   1.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.080   0.804   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.493   0.191   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.230  -1.161   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.172   0.057   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.724  -1.534   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.489  -2.679   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.029  -2.674   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.804  -4.005   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      14.344  -4.000   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      15.118  -5.331   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.353  -6.667   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      15.127  -7.998   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.813  -6.672   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.047  -8.009   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.038  -5.341   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      10.498  -5.347   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      10.241  -4.199   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.512  -5.556   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.104  -6.180   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.975  -7.227   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.481  -6.854   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.946  -6.986   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.654  -6.148   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.704  -4.936   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.199  -3.481   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.264  -3.962   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.735  -5.429   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   35                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17   27                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   18   26                                                  
CONECT   26   25                                                            
CONECT   27   16   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34    4   36                                                  
CONECT   36   35    2   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₈N₂O₇

Average Mass

514.6190 Da

Monoisotopic Mass

514.26790 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1CN2[C@H](\C=C/C=C/C=C/C=C\C(O[C@@H]3OC[C@@H](O)[C@H](O)[C@H]3N)[C@](C)(O)\C=C\C=C\C=C\C2=O)[C@@H]1O

InChI Identifier

InChI=1S/C28H38N2O7/c1-19-17-30-20(25(19)33)13-9-5-3-4-6-10-14-22(37-27-24(29)26(34)21(31)18-36-27)28(2,35)16-12-8-7-11-15-23(30)32/h3-16,19-22,24-27,31,33-35H,17-18,29H2,1-2H3/b5-3+,6-4+,8-7+,13-9-,14-10-,15-11+,16-12+/t19-,20+,21+,22?,24+,25+,26-,27-,28+/m0/s1

InChI Key

BOXGALHYKYOYFJ-NTIGGAKHSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolactams

Sub Class

Not Available

Direct Parent

Macrolactams

Alternative Parents

Substituents

Macrolactam
O-glycosyl compound
Glycosyl compound
Oxane
Monosaccharide
Tertiary carboxylic acid amide
Tertiary alcohol
Pyrrolidine
Secondary alcohol
Lactam
Carboxamide group
Amino acid or derivatives
1,2-aminoalcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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

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

146684660

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,12r,21ar)-13-{[(2s,3r,4r,5r)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-1,12-dihydroxy-2,12-dimethyl-1h,2h,3h,13h,21ah-pyrrolo[1,2-a]azacyclononadecan-5-one (NP0290568)

MOL for NP0290568 ((1r,2s,12r,21ar)-13-{[(2s,3r,4r,5r)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-1,12-dihydroxy-2,12-dimethyl-1h,2h,3h,13h,21ah-pyrrolo[1,2-a]azacyclononadecan-5-one)

3D MOL for NP0290568 ((1r,2s,12r,21ar)-13-{[(2s,3r,4r,5r)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-1,12-dihydroxy-2,12-dimethyl-1h,2h,3h,13h,21ah-pyrrolo[1,2-a]azacyclononadecan-5-one)

3D SDF for NP0290568 ((1r,2s,12r,21ar)-13-{[(2s,3r,4r,5r)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-1,12-dihydroxy-2,12-dimethyl-1h,2h,3h,13h,21ah-pyrrolo[1,2-a]azacyclononadecan-5-one)

3D-SDF for NP0290568 ((1r,2s,12r,21ar)-13-{[(2s,3r,4r,5r)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-1,12-dihydroxy-2,12-dimethyl-1h,2h,3h,13h,21ah-pyrrolo[1,2-a]azacyclononadecan-5-one)

PDB for NP0290568 ((1r,2s,12r,21ar)-13-{[(2s,3r,4r,5r)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-1,12-dihydroxy-2,12-dimethyl-1h,2h,3h,13h,21ah-pyrrolo[1,2-a]azacyclononadecan-5-one)

3D PDB for NP0290568 ((1r,2s,12r,21ar)-13-{[(2s,3r,4r,5r)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-1,12-dihydroxy-2,12-dimethyl-1h,2h,3h,13h,21ah-pyrrolo[1,2-a]azacyclononadecan-5-one)

SMILES for NP0290568 ((1r,2s,12r,21ar)-13-{[(2s,3r,4r,5r)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-1,12-dihydroxy-2,12-dimethyl-1h,2h,3h,13h,21ah-pyrrolo[1,2-a]azacyclononadecan-5-one)

INCHI for NP0290568 ((1r,2s,12r,21ar)-13-{[(2s,3r,4r,5r)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-1,12-dihydroxy-2,12-dimethyl-1h,2h,3h,13h,21ah-pyrrolo[1,2-a]azacyclononadecan-5-one)

Structure for NP0290568 ((1r,2s,12r,21ar)-13-{[(2s,3r,4r,5r)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-1,12-dihydroxy-2,12-dimethyl-1h,2h,3h,13h,21ah-pyrrolo[1,2-a]azacyclononadecan-5-one)

3D Structure for NP0290568 ((1r,2s,12r,21ar)-13-{[(2s,3r,4r,5r)-3-amino-4,5-dihydroxyoxan-2-yl]oxy}-1,12-dihydroxy-2,12-dimethyl-1h,2h,3h,13h,21ah-pyrrolo[1,2-a]azacyclononadecan-5-one)