NP-MRD: Showing NP-Card for Antibiotic 81-484 (NP0062201)

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Record Information

Version

2.0

Created at

2022-04-28 06:51:33 UTC

Updated at

2022-04-28 06:51:33 UTC

NP-MRD ID

NP0062201

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Antibiotic 81-484

Description

Kazusamycin A, also known as hydroxyelactocin, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Antibiotic 81-484 is found in Actinomycete ATCC 39366 and Streptomyces sp. No.81-484. Antibiotic 81-484 was first documented in 2004 (PMID: 15330629). Based on a literature review very few articles have been published on Kazusamycin A (PMID: 16617017).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282208512D          

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M  END

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M  END


  Mrv1652304282208512D          

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   -8.4780    3.5566    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.2881    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8282    3.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6383    3.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1784    2.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9886    2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9084    1.8416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5582    2.3093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2079    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2079    4.9598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8577    3.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5075    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0476    3.0889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1573    4.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4568    5.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1634    6.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1066    7.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3766    4.1802    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  8  1  6  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 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
 16 17  2  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  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
 25 30  1  0  0  0  0
 23 31  1  1  0  0  0
 22 32  1  1  0  0  0
 21 33  1  1  0  0  0
 18 34  1  0  0  0  0
 34 35  1  0  0  0  0
 16 36  1  0  0  0  0
 12 37  1  6  0  0  0
 10 38  1  0  0  0  0
 38 39  1  0  0  0  0
  3 40  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0062201

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C33H48O7/c1-8-27(13-14-29-24(5)12-15-31(37)40-29)17-21(2)10-9-11-22(3)18-28(20-34)33(39)26(7)32(38)25(6)16-23(4)19-30(35)36/h9,11-15,17-19,21,24-26,28-29,32,34,38H,8,10,16,20H2,1-7H3,(H,35,36)/b11-9+,14-13+,22-18+,23-19+,27-17-/t21-,24+,25+,26+,28+,29+,32-/m1/s1

> <INCHI_KEY>
KZMHNEBMQDBQND-LBNZKSCFSA-N

> <FORMULA>
C33H48O7

> <MOLECULAR_WEIGHT>
556.74

> <EXACT_MASS>
556.340003886

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
62.702492928293736

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,5S,6R,7S,9S,10E,12E,15R,16Z,18E)-17-ethyl-6-hydroxy-9-(hydroxymethyl)-3,5,7,11,15-pentamethyl-19-[(2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-8-oxononadeca-2,10,12,16,18-pentaenoic acid

> <ALOGPS_LOGP>
4.70

> <JCHEM_LOGP>
6.294633913000001

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.0747175833359

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.568903950588611

> <JCHEM_PKA_STRONGEST_BASIC>
-2.678795669570837

> <JCHEM_POLAR_SURFACE_AREA>
121.13000000000001

> <JCHEM_REFRACTIVITY>
164.25270000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.03e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,5S,6R,7S,9S,10E,12E,15R,16Z,18E)-17-ethyl-6-hydroxy-9-(hydroxymethyl)-3,5,7,11,15-pentamethyl-19-[(2S,3S)-3-methyl-6-oxo-2,3-dihydropyran-2-yl]-8-oxononadeca-2,10,12,16,18-pentaenoic acid

> <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       2.826   5.766   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.313   6.057   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.809   7.512   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.817   8.676   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.330   8.385   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.834   6.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.346   6.639   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.313  10.131   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.199  10.422   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.703  11.878   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.215  12.169   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.223  11.004   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.736  11.295   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.744  10.131   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.256  10.422   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.264   9.258   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.777   9.549   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -10.785   8.385   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -12.297   8.676   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0     -12.801  10.131   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0     -13.305   7.512   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -14.817   7.803   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -15.826   6.639   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -17.338   6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -18.346   5.766   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -19.858   6.057   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -20.866   4.893   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -22.379   5.184   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0     -20.362   3.438   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0     -17.842   4.311   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -15.321   5.184   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0     -15.321   9.258   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0     -12.801   6.057   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -10.281   6.930   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0     -11.289   5.766   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -7.760   7.803   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.719   9.549   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.305  13.042   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.199  14.497   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.703   7.803   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   40                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   38                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   37                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   36                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   34                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   33                                                  
CONECT   22   21   23   32                                                  
CONECT   23   22   24   31                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25                                                            
CONECT   31   23                                                            
CONECT   32   22                                                            
CONECT   33   21                                                            
CONECT   34   18   35                                                       
CONECT   35   34                                                            
CONECT   36   16                                                            
CONECT   37   12                                                            
CONECT   38   10   39                                                       
CONECT   39   38                                                            
CONECT   40    3                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   80    0
END

View in JSmol

Synonyms

Value	Source
16-Hydroxyleptomycin b	MeSH
Hydroxyelactocin	MeSH
Kazusamycin	MeSH

Chemical Formula

C₃₃H₄₈O₇

Average Mass

556.7400 Da

Monoisotopic Mass

556.34000 Da

IUPAC Name

(2E,5S,6R,7S,9S,10E,12E,15R,16Z,18E)-17-ethyl-6-hydroxy-9-(hydroxymethyl)-3,5,7,11,15-pentamethyl-19-[(2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-8-oxononadeca-2,10,12,16,18-pentaenoic acid

Traditional Name

(2E,5S,6R,7S,9S,10E,12E,15R,16Z,18E)-17-ethyl-6-hydroxy-9-(hydroxymethyl)-3,5,7,11,15-pentamethyl-19-[(2S,3S)-3-methyl-6-oxo-2,3-dihydropyran-2-yl]-8-oxononadeca-2,10,12,16,18-pentaenoic acid

CAS Registry Number

Not Available

SMILES

CC\C(\C=C\[C@@H]1OC(=O)C=C[C@@H]1C)=C\[C@H](C)C\C=C\C(\C)=C\[C@@H](CO)C(=O)[C@@H](C)[C@H](O)[C@@H](C)C\C(C)=C\C(O)=O

InChI Identifier

InChI=1S/C33H48O7/c1-8-27(13-14-29-24(5)12-15-31(37)40-29)17-21(2)10-9-11-22(3)18-28(20-34)33(39)26(7)32(38)25(6)16-23(4)19-30(35)36/h9,11-15,17-19,21,24-26,28-29,32,34,38H,8,10,16,20H2,1-7H3,(H,35,36)/b11-9+,14-13+,22-18+,23-19+,27-17-/t21-,24+,25+,26+,28+,29+,32-/m1/s1

InChI Key

KZMHNEBMQDBQND-LBNZKSCFSA-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
Actinomycete ATCC 39366	-	KNApSAcK
Streptomyces sp. No.81-484	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very long-chain fatty acids

Alternative Parents

Substituents

Very long-chain fatty acid
Diterpene lactone
Diterpenoid
Branched fatty acid
Dihydropyranone
Methyl-branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Beta-hydroxy ketone
Dicarboxylic acid or derivatives
Unsaturated fatty acid
Pyran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Ketone
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Carbonyl group
Primary alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	4.7	ALOGPS
logP	6.29	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.57	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	164.25 m³·mol⁻¹	ChemAxon
Polarizability	62.7 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00018590

Chemspider ID

9447925

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11272917

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ando R, Amano Y, Nakamura H, Arai N, Kuwajima I: Design, synthesis, and evaluation of novel kazusamycin A derivatives as potent antitumor agents. Bioorg Med Chem Lett. 2006 Jun 15;16(12):3315-8. doi: 10.1016/j.bmcl.2006.03.056. Epub 2006 Apr 17. [PubMed:16617017 ]
Arai N, Chikaraishi N, Omura S, Kuwajima I: First total synthesis of the antitumor compound (-)-kazusamycin A and absolute structure determination. Org Lett. 2004 Aug 19;6(17):2845-8. doi: 10.1021/ol049219z. [PubMed:15330629 ]

Showing NP-Card for Antibiotic 81-484 (NP0062201)

MOL for NP0062201 (Antibiotic 81-484)

3D MOL for NP0062201 (Antibiotic 81-484)

3D SDF for NP0062201 (Antibiotic 81-484)

3D-SDF for NP0062201 (Antibiotic 81-484)

PDB for NP0062201 (Antibiotic 81-484)

3D PDB for NP0062201 (Antibiotic 81-484)

SMILES for NP0062201 (Antibiotic 81-484)

INCHI for NP0062201 (Antibiotic 81-484)

Structure for NP0062201 (Antibiotic 81-484)

3D Structure for NP0062201 (Antibiotic 81-484)