NP-MRD: Showing NP-Card for (-)-Alisamycin (NP0061658)

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Record Information

Version

2.0

Created at

2022-04-28 06:24:24 UTC

Updated at

2022-04-28 06:24:24 UTC

NP-MRD ID

NP0061658

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Alisamycin

Description

Alisamycin belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. (-)-Alisamycin is found in Streptomyces actuosus and Streptomyces sp. HIL Y-8831582. Based on a literature review very few articles have been published on Alisamycin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282208242D          

 38 41  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1652304282208242D          

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 20 25  1  0  0  0  0
  1 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 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  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 33 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0061658

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C(NC(=O)\C=C\C=C\C=C\[C@@]2(O)C=C(NC(=O)\C=C\C=C\C3CCCCC3)C(=O)[C@@H]3O[C@H]23)C(=O)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C29H32N2O7/c32-21-15-16-22(33)25(21)31-24(35)13-6-1-2-9-17-29(37)18-20(26(36)27-28(29)38-27)30-23(34)14-8-7-12-19-10-4-3-5-11-19/h1-2,6-9,12-14,17-19,27-28,32,37H,3-5,10-11,15-16H2,(H,30,34)(H,31,35)/b2-1+,12-7+,13-6+,14-8+,17-9+/t27-,28-,29+/m0/s1

> <INCHI_KEY>
JNNCGBMBOYDZEW-BSHZQBLZSA-N

> <FORMULA>
C29H32N2O7

> <MOLECULAR_WEIGHT>
520.582

> <EXACT_MASS>
520.220951378

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
57.03033485620266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4E,6E)-7-[(1S,2R,6R)-4-[(2E,4E)-5-cyclohexylpenta-2,4-dienamido]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]-N-(2-hydroxy-5-oxocyclopent-1-en-1-yl)hepta-2,4,6-trienamide

> <ALOGPS_LOGP>
3.82

> <JCHEM_LOGP>
1.954111906333332

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.600035444108876

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.044304696804438

> <JCHEM_PKA_STRONGEST_BASIC>
-3.344784735369491

> <JCHEM_POLAR_SURFACE_AREA>
145.32999999999998

> <JCHEM_REFRACTIVITY>
148.96679999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.89e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6E)-7-[(1S,2R,6R)-4-[(2E,4E)-5-cyclohexylpenta-2,4-dienamido]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]-N-(2-hydroxy-5-oxocyclopent-1-en-1-yl)hepta-2,4,6-trienamide

> <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       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.724  -0.590   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.278  -0.590   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.739  -0.643   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.016  -2.003   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.523  -2.057   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.246  -3.417   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.785  -3.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.508  -4.830   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.692  -6.136   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      -5.047  -4.884   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -5.770  -6.244   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.095  -7.628   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.203  -8.698   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.563  -7.975   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -7.295  -6.458   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -8.365  -5.350   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -3.578  -7.895   0.000  0.00  0.00           O+0
HETATM   26  N   UNK     0       6.668   3.850   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002   7.700   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.336  10.010   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.669  12.320   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.003  13.090   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.337  12.320   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.337  10.780   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      12.003  10.010   0.000  0.00  0.00           C+0
CONECT    1    2    6   26                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    9   10                                             
CONECT    4    3    5    8                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    4                                                       
CONECT    9    3                                                            
CONECT   10    3   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   19   24                                                  
CONECT   24   23                                                            
CONECT   25   20                                                            
CONECT   26    1   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   33                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₂N₂O₇

Average Mass

520.5820 Da

Monoisotopic Mass

520.22095 Da

IUPAC Name

(2E,4E,6E)-7-[(1S,2R,6R)-4-[(2E,4E)-5-cyclohexylpenta-2,4-dienamido]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]-N-(2-hydroxy-5-oxocyclopent-1-en-1-yl)hepta-2,4,6-trienamide

Traditional Name

(2E,4E,6E)-7-[(1S,2R,6R)-4-[(2E,4E)-5-cyclohexylpenta-2,4-dienamido]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]-N-(2-hydroxy-5-oxocyclopent-1-en-1-yl)hepta-2,4,6-trienamide

CAS Registry Number

Not Available

SMILES

OC1=C(NC(=O)\C=C\C=C\C=C\[C@@]2(O)C=C(NC(=O)\C=C\C=C\C3CCCCC3)C(=O)[C@@H]3O[C@H]23)C(=O)CC1

InChI Identifier

InChI=1S/C29H32N2O7/c32-21-15-16-22(33)25(21)31-24(35)13-6-1-2-9-17-29(37)18-20(26(36)27-28(29)38-27)30-23(34)14-8-7-12-19-10-4-3-5-11-19/h1-2,6-9,12-14,17-19,27-28,32,37H,3-5,10-11,15-16H2,(H,30,34)(H,31,35)/b2-1+,12-7+,13-6+,14-8+,17-9+/t27-,28-,29+/m0/s1

InChI Key

JNNCGBMBOYDZEW-BSHZQBLZSA-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 actuosus	LOTUS Database	35616633
Streptomyces sp. HIL Y-8831582	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
N-acyl-amine
Tertiary alcohol
Vinylogous acid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Alcohol
Organic oxide
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
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
logP	3.82	ALOGPS
logP	1.95	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	9.04	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	145.33 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	148.97 m³·mol⁻¹	ChemAxon
Polarizability	57.03 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00017197

Chemspider ID

9181026

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11005836

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Alisamycin (NP0061658)

MOL for NP0061658 ((-)-Alisamycin)

3D MOL for NP0061658 ((-)-Alisamycin)

3D SDF for NP0061658 ((-)-Alisamycin)

3D-SDF for NP0061658 ((-)-Alisamycin)

PDB for NP0061658 ((-)-Alisamycin)

3D PDB for NP0061658 ((-)-Alisamycin)

SMILES for NP0061658 ((-)-Alisamycin)

INCHI for NP0061658 ((-)-Alisamycin)

Structure for NP0061658 ((-)-Alisamycin)

3D Structure for NP0061658 ((-)-Alisamycin)