NP-MRD: Showing NP-Card for (3z,5e,7e,9e)-1,1,1-trichloro-4-hydroxy-11-methyldodeca-3,5,7,9-tetraen-2-one (NP0294899)

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Record Information

Version

1.0

Created at

2022-09-10 03:38:45 UTC

Updated at

2022-09-10 03:38:45 UTC

NP-MRD ID

NP0294899

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3z,5e,7e,9e)-1,1,1-trichloro-4-hydroxy-11-methyldodeca-3,5,7,9-tetraen-2-one

Description

Neocarzilin B belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'. (3z,5e,7e,9e)-1,1,1-trichloro-4-hydroxy-11-methyldodeca-3,5,7,9-tetraen-2-one is found in Streptomyces carzinostaticus. It was first documented in 2004 (PMID: 15328113). Based on a literature review very few articles have been published on Neocarzilin B (PMID: 31403069).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 32  0  0  0  0  0  0  0  0999 V2000
   -5.6748   -0.7733   -1.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8922    0.2897   -0.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1162    0.3011    0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4466    0.2336   -0.9628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4724    0.1981   -0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0594    0.1432   -0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0761    0.1072    0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3338    0.0526   -0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2627    0.0188    0.8942 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6799   -0.0362    0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9922   -0.0497   -0.8922 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6452   -0.0722    1.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0503   -0.1266    1.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8305   -0.1559    2.0605 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6941   -0.1522   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4866   -0.2418   -0.0428 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.2877   -1.5685   -1.2601 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.3694    1.3878   -1.1271 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.6886   -1.6849   -0.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1547   -1.0173   -2.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6712   -0.3846   -1.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2544    1.2827   -1.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1839    0.5914    1.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8887   -0.6800    1.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5174    1.1345    1.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1916    0.2219   -2.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7328    0.2100    0.9568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8171    0.1320   -1.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3420    0.1194    1.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6469    0.0381   -1.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0512    0.0287    1.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5492    0.5102   -1.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3003   -0.0576    2.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
M  END


  Mrv1652309102205382D          

 18 17  0  0  0  0            999 V2000
    5.7750    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -2.1434    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.8414    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.0164    0.0000 Cl  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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0294899

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)\C=C\C=C\C=C\C(\O)=C\C(=O)C(Cl)(Cl)Cl

> <INCHI_IDENTIFIER>
InChI=1S/C13H15Cl3O2/c1-10(2)7-5-3-4-6-8-11(17)9-12(18)13(14,15)16/h3-10,17H,1-2H3/b4-3+,7-5+,8-6+,11-9-

> <INCHI_KEY>
AMLVEWQRORIQBK-DSCOCKGISA-N

> <FORMULA>
C13H15Cl3O2

> <MOLECULAR_WEIGHT>
309.61

> <EXACT_MASS>
308.0137628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
31.474707108807984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3Z,5E,7E,9E)-1,1,1-trichloro-4-hydroxy-11-methyldodeca-3,5,7,9-tetraen-2-one

> <JCHEM_LOGP>
4.643984117666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.655249884976262

> <JCHEM_PKA_STRONGEST_BASIC>
-5.573993700311385

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
84.02829999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3Z,5E,7E,9E)-1,1,1-trichloro-4-hydroxy-11-methyldodeca-3,5,7,9-tetraen-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      10.780   5.335   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.470   6.668   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.470   4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000  -2.667   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0       0.770  -4.001   0.000  0.00  0.00          Cl+0
HETATM   17 Cl   UNK     0      -1.334  -3.437   0.000  0.00  0.00          Cl+0
HETATM   18 Cl   UNK     0       1.334  -1.897   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₅Cl₃O₂

Average Mass

309.6100 Da

Monoisotopic Mass

308.01376 Da

IUPAC Name

(3Z,5E,7E,9E)-1,1,1-trichloro-4-hydroxy-11-methyldodeca-3,5,7,9-tetraen-2-one

Traditional Name

(3Z,5E,7E,9E)-1,1,1-trichloro-4-hydroxy-11-methyldodeca-3,5,7,9-tetraen-2-one

CAS Registry Number

Not Available

SMILES

CC(C)\C=C\C=C\C=C\C(\O)=C\C(=O)C(Cl)(Cl)Cl

InChI Identifier

InChI=1S/C13H15Cl3O2/c1-10(2)7-5-3-4-6-8-11(17)9-12(18)13(14,15)16/h3-10,17H,1-2H3/b4-3+,7-5+,8-6+,11-9-

InChI Key

AMLVEWQRORIQBK-DSCOCKGISA-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

Species Name	Source	Reference
Streptomyces carzinostaticus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Enones

Alternative Parents

Substituents

Alpha-haloketone
Alpha-chloroketone
Vinylogous acid
Enone
Acryloyl-group
Ketone
Enol
Organic oxide
Hydrocarbon derivative
Organochloride
Organohalogen compound
Alkyl halide
Alkyl chloride
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	4.64	ChemAxon
pKa (Strongest Acidic)	8.66	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	84.03 m³·mol⁻¹	ChemAxon
Polarizability	31.47 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

78434587

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14620605

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gleissner CM, Pyka CL, Heydenreuter W, Gronauer TF, Atzberger C, Korotkov VS, Cheng W, Hacker SM, Vollmar AM, Braig S, Sieber SA: Neocarzilin A Is a Potent Inhibitor of Cancer Cell Motility Targeting VAT-1 Controlled Pathways. ACS Cent Sci. 2019 Jul 24;5(7):1170-1178. doi: 10.1021/acscentsci.9b00266. Epub 2019 Jun 18. [PubMed:31403069 ]
Otsuka M, Ichinose K, Fujii I, Ebizuka Y: Cloning, sequencing, and functional analysis of an iterative type I polyketide synthase gene cluster for biosynthesis of the antitumor chlorinated polyenone neocarzilin in "Streptomyces carzinostaticus". Antimicrob Agents Chemother. 2004 Sep;48(9):3468-76. doi: 10.1128/AAC.48.9.3468-3476.2004. [PubMed:15328113 ]
LOTUS database [Link]

Showing NP-Card for (3z,5e,7e,9e)-1,1,1-trichloro-4-hydroxy-11-methyldodeca-3,5,7,9-tetraen-2-one (NP0294899)

MOL for NP0294899 ((3z,5e,7e,9e)-1,1,1-trichloro-4-hydroxy-11-methyldodeca-3,5,7,9-tetraen-2-one)

3D MOL for NP0294899 ((3z,5e,7e,9e)-1,1,1-trichloro-4-hydroxy-11-methyldodeca-3,5,7,9-tetraen-2-one)

3D SDF for NP0294899 ((3z,5e,7e,9e)-1,1,1-trichloro-4-hydroxy-11-methyldodeca-3,5,7,9-tetraen-2-one)

3D-SDF for NP0294899 ((3z,5e,7e,9e)-1,1,1-trichloro-4-hydroxy-11-methyldodeca-3,5,7,9-tetraen-2-one)

PDB for NP0294899 ((3z,5e,7e,9e)-1,1,1-trichloro-4-hydroxy-11-methyldodeca-3,5,7,9-tetraen-2-one)

3D PDB for NP0294899 ((3z,5e,7e,9e)-1,1,1-trichloro-4-hydroxy-11-methyldodeca-3,5,7,9-tetraen-2-one)

SMILES for NP0294899 ((3z,5e,7e,9e)-1,1,1-trichloro-4-hydroxy-11-methyldodeca-3,5,7,9-tetraen-2-one)

INCHI for NP0294899 ((3z,5e,7e,9e)-1,1,1-trichloro-4-hydroxy-11-methyldodeca-3,5,7,9-tetraen-2-one)

Structure for NP0294899 ((3z,5e,7e,9e)-1,1,1-trichloro-4-hydroxy-11-methyldodeca-3,5,7,9-tetraen-2-one)

3D Structure for NP0294899 ((3z,5e,7e,9e)-1,1,1-trichloro-4-hydroxy-11-methyldodeca-3,5,7,9-tetraen-2-one)