NP-MRD: Showing NP-Card for 1,1,1-trichloro-4-hydroxy-11-methyltrideca-3,5,7,9-tetraen-2-one (NP0312580)

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Record Information

Version

2.0

Created at

2022-09-11 09:29:01 UTC

Updated at

2022-09-11 09:29:02 UTC

NP-MRD ID

NP0312580

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,1,1-trichloro-4-hydroxy-11-methyltrideca-3,5,7,9-tetraen-2-one

Description

1,1,1-Trichloro-4-hydroxy-11-methyltrideca-3,5,7,9-tetraen-2-one belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'. 1,1,1-trichloro-4-hydroxy-11-methyltrideca-3,5,7,9-tetraen-2-one is found in Streptomyces carzinostaticus. 1,1,1-Trichloro-4-hydroxy-11-methyltrideca-3,5,7,9-tetraen-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 35  0  0  0  0  0  0  0  0999 V2000
   -3.5255    3.2345    0.9903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8812    2.2887    2.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4088    0.8573    1.9133 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8934    0.1528    3.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9592    0.7252    1.7163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5020    0.0697    0.6506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1168   -0.1248    0.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3438   -0.7660   -0.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8213   -1.4308   -1.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1298   -1.5929   -2.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1570   -1.0346   -1.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6969   -0.3215   -0.0733 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4490   -1.0430   -1.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4437   -1.5522   -2.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6936   -1.2473   -1.9257 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2752   -2.3778   -3.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9596   -2.7030   -4.0591 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.3844   -1.4953   -4.6693 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5090   -3.9057   -3.0324 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.4482    3.8008    0.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0923    2.7833    0.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8237    4.0508    1.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5449    2.7003    3.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9940    2.2186    2.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9549    0.4267    1.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6050   -0.8997    3.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9921    0.2919    3.2755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3541    0.6104    4.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2820    1.1710    2.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2218   -0.3543   -0.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5803    0.3236    1.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9746   -0.9364   -1.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2161   -1.9756   -2.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3656   -2.1475   -2.9472 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5920    0.6756   -0.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9570   -0.4727   -0.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  6
  4 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 12 35  1  0
 13 36  1  0
M  END


  Mrv1533004251504492D          

 19 18  0  0  0  0            999 V2000
    6.1875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    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
    1.2375   -0.7145    0.0000 O   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
  3  4  1  0  0  0  0
  5  3  1  4  0  0  0
  5  6  2  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  9  8  1  4  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  4  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
 11 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0312580

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H17Cl3O2/c1-3-11(2)8-6-4-5-7-9-12(18)10-13(19)14(15,16)17/h4-11,18H,3H2,1-2H3

> <INCHI_KEY>
XOJPDOWNAJBCPS-UHFFFAOYSA-N

> <FORMULA>
C14H17Cl3O2

> <MOLECULAR_WEIGHT>
323.64

> <EXACT_MASS>
322.0294129

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
32.94419499613966

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,1,1-trichloro-4-hydroxy-11-methyltrideca-3,5,7,9-tetraen-2-one

> <ALOGPS_LOGP>
5.19

> <JCHEM_LOGP>
5.088552782666666

> <ALOGPS_LOGS>
-6.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.598464904638488

> <JCHEM_PKA_STRONGEST_BASIC>
-5.5988314507111285

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
88.6293

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.91e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,1,1-trichloro-4-hydroxy-11-methyltrideca-3,5,7,9-tetraen-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.780   5.335   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.470   6.668   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.470   4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+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
HETATM   19  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19   11                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₇Cl₃O₂

Average Mass

323.6400 Da

Monoisotopic Mass

322.02941 Da

IUPAC Name

1,1,1-trichloro-4-hydroxy-11-methyltrideca-3,5,7,9-tetraen-2-one

Traditional Name

1,1,1-trichloro-4-hydroxy-11-methyltrideca-3,5,7,9-tetraen-2-one

CAS Registry Number

Not Available

SMILES

CCC(C)C=CC=CC=CC(O)=CC(=O)C(Cl)(Cl)Cl

InChI Identifier

InChI=1S/C14H17Cl3O2/c1-3-11(2)8-6-4-5-7-9-12(18)10-13(19)14(15,16)17/h4-11,18H,3H2,1-2H3

InChI Key

XOJPDOWNAJBCPS-UHFFFAOYSA-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	5.19	ALOGPS
logP	5.09	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	8.6	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	7	ChemAxon
Refractivity	88.63 m³·mol⁻¹	ChemAxon
Polarizability	32.94 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,1,1-trichloro-4-hydroxy-11-methyltrideca-3,5,7,9-tetraen-2-one (NP0312580)

MOL for NP0312580 (1,1,1-trichloro-4-hydroxy-11-methyltrideca-3,5,7,9-tetraen-2-one)

3D MOL for NP0312580 (1,1,1-trichloro-4-hydroxy-11-methyltrideca-3,5,7,9-tetraen-2-one)

3D SDF for NP0312580 (1,1,1-trichloro-4-hydroxy-11-methyltrideca-3,5,7,9-tetraen-2-one)

3D-SDF for NP0312580 (1,1,1-trichloro-4-hydroxy-11-methyltrideca-3,5,7,9-tetraen-2-one)

PDB for NP0312580 (1,1,1-trichloro-4-hydroxy-11-methyltrideca-3,5,7,9-tetraen-2-one)

3D PDB for NP0312580 (1,1,1-trichloro-4-hydroxy-11-methyltrideca-3,5,7,9-tetraen-2-one)

SMILES for NP0312580 (1,1,1-trichloro-4-hydroxy-11-methyltrideca-3,5,7,9-tetraen-2-one)

INCHI for NP0312580 (1,1,1-trichloro-4-hydroxy-11-methyltrideca-3,5,7,9-tetraen-2-one)

Structure for NP0312580 (1,1,1-trichloro-4-hydroxy-11-methyltrideca-3,5,7,9-tetraen-2-one)

3D Structure for NP0312580 (1,1,1-trichloro-4-hydroxy-11-methyltrideca-3,5,7,9-tetraen-2-one)