NP-MRD: Showing NP-Card for 3-Chloro-4-hydroxy-5((2E,6E)-3,7,11-trimethyl-10-methylenedodeca-2,6-dienyl)benzamide (NP0332456)

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Record Information

Version

2.0

Created at

2024-01-30 08:21:32 UTC

Updated at

2024-09-03 04:19:17 UTC

NP-MRD ID

NP0332456

Natural Product DOI

https://doi.org/10.57994/1699

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Chloro-4-hydroxy-5((2E,6E)-3,7,11-trimethyl-10-methylenedodeca-2,6-dienyl)benzamide

Description

3-Chloro-4-hydroxy-5((2E,6E)-3,7,11-trimethyl-10-methylenedodeca-2,6-dienyl)benzamide belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review very few articles have been published on 3-Chloro-4-hydroxy-5((2E,6E)-3,7,11-trimethyl-10-methylenedodeca-2,6-dienyl)benzamide.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01302408212D          

 27 27  0  0  0  0            999 V2000
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -8.6625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 18 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
  4 27  2  0  0  0  0
M  END


  Mrv2104 01302408212D          

 27 27  0  0  0  0            999 V2000
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -8.6625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 18 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
  4 27  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332456

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=C)CC\C(C)=C\CC\C(C)=C\CC1=CC(=CC(Cl)=C1O)C(N)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H32ClNO2/c1-15(2)18(5)11-9-16(3)7-6-8-17(4)10-12-19-13-20(23(25)27)14-21(24)22(19)26/h7,10,13-15,26H,5-6,8-9,11-12H2,1-4H3,(H2,25,27)/b16-7+,17-10+

> <INCHI_KEY>
SPCCTOBMYIUWKU-CHGLLVKUSA-N

> <FORMULA>
C23H32ClNO2

> <MOLECULAR_WEIGHT>
389.96

> <EXACT_MASS>
389.212157

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
45.47952310231277

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-chloro-4-hydroxy-5-[(2E,6E)-3,7,11-trimethyl-10-methylidenedodeca-2,6-dien-1-yl]benzamide

> <JCHEM_LOGP>
6.517313781

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.058843461574767

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.799254308234151

> <JCHEM_PKA_STRONGEST_BASIC>
-0.2714301831556966

> <JCHEM_POLAR_SURFACE_AREA>
63.32000000000001

> <JCHEM_REFRACTIVITY>
117.24619999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-chloro-4-hydroxy-5-[(2E,6E)-3,7,11-trimethyl-10-methylidenedodeca-2,6-dien-1-yl]benzamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-JAN-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JAN-24         0                                  
HETATM    1  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.672 -12.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.005 -11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.339 -12.320   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.673 -11.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.006 -12.320   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.340 -11.550   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      25.340 -10.010   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      26.674 -12.320   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      24.006 -13.860   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      22.673 -14.630   0.000  0.00  0.00           C+0
HETATM   24 Cl   UNK     0      22.673 -16.170   0.000  0.00  0.00          Cl+0
HETATM   25  C   UNK     0      21.339 -13.860   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      20.005 -14.630   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   27                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   18   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16   26                                                  
CONECT   26   25                                                            
CONECT   27    4                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₂ClNO₂

Average Mass

389.9600 Da

Monoisotopic Mass

389.21216 Da

IUPAC Name

3-chloro-4-hydroxy-5-[(2E,6E)-3,7,11-trimethyl-10-methylidenedodeca-2,6-dien-1-yl]benzamide

Traditional Name

3-chloro-4-hydroxy-5-[(2E,6E)-3,7,11-trimethyl-10-methylidenedodeca-2,6-dien-1-yl]benzamide

CAS Registry Number

Not Available

SMILES

CC(C)C(=C)CC\C(C)=C\CC\C(C)=C\CC1=CC(=CC(Cl)=C1O)C(N)=O

InChI Identifier

InChI=1S/C23H32ClNO2/c1-15(2)18(5)11-9-16(3)7-6-8-17(4)10-12-19-13-20(23(25)27)14-21(24)22(19)26/h7,10,13-15,26H,5-6,8-9,11-12H2,1-4H3,(H2,25,27)/b16-7+,17-10+

InChI Key

SPCCTOBMYIUWKU-CHGLLVKUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	jittra.kor@biotec.or.th	Not Available	Jittra Kornsakulkarn	2024-05-02	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	jittra.kor@biotec.or.th	Not Available	Jittra Kornsakulkarn	2024-05-02	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, C3D6O, experimental)	jittra.kor@biotec.or.th	Not Available	Jittra Kornsakulkarn	2024-05-02	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, C3D6O, experimental)	jittra.kor@biotec.or.th	Not Available	Jittra Kornsakulkarn	2024-05-02	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	jittra.kor@biotec.or.th	Not Available	Jittra Kornsakulkarn	2024-05-02	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	jittra.kor@biotec.or.th	Not Available	Jittra Kornsakulkarn	2024-05-02	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C3D6O, experimental)	jittra.kor@biotec.or.th	Not Available	Jittra Kornsakulkarn	2024-05-02	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
xtbgensis TBRC-BCC 18687		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Halobenzoic acid or derivatives
3-halobenzoic acid or derivatives
Benzoic acid or derivatives
Benzamide
2-chlorophenol
2-halophenol
Benzoyl
Phenol
Halobenzene
Chlorobenzene
Benzenoid
Monocyclic benzene moiety
Carboxamide group
Chloroalkene
Haloalkene
Vinyl halide
Vinyl chloride
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	6.52	ChemAxon
pKa (Strongest Acidic)	6.8	ChemAxon
pKa (Strongest Basic)	-0.27	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	117.25 m³·mol⁻¹	ChemAxon
Polarizability	45.48 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	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

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

Not Available

Showing NP-Card for 3-Chloro-4-hydroxy-5((2E,6E)-3,7,11-trimethyl-10-methylenedodeca-2,6-dienyl)benzamide (NP0332456)

MOL for NP0332456 (3-Chloro-4-hydroxy-5((2E,6E)-3,7,11-trimethyl-10-methylenedodeca-2,6-dienyl)benzamide)

3D MOL for NP0332456 (3-Chloro-4-hydroxy-5((2E,6E)-3,7,11-trimethyl-10-methylenedodeca-2,6-dienyl)benzamide)

3D SDF for NP0332456 (3-Chloro-4-hydroxy-5((2E,6E)-3,7,11-trimethyl-10-methylenedodeca-2,6-dienyl)benzamide)

3D-SDF for NP0332456 (3-Chloro-4-hydroxy-5((2E,6E)-3,7,11-trimethyl-10-methylenedodeca-2,6-dienyl)benzamide)

PDB for NP0332456 (3-Chloro-4-hydroxy-5((2E,6E)-3,7,11-trimethyl-10-methylenedodeca-2,6-dienyl)benzamide)

3D PDB for NP0332456 (3-Chloro-4-hydroxy-5((2E,6E)-3,7,11-trimethyl-10-methylenedodeca-2,6-dienyl)benzamide)

SMILES for NP0332456 (3-Chloro-4-hydroxy-5((2E,6E)-3,7,11-trimethyl-10-methylenedodeca-2,6-dienyl)benzamide)

INCHI for NP0332456 (3-Chloro-4-hydroxy-5((2E,6E)-3,7,11-trimethyl-10-methylenedodeca-2,6-dienyl)benzamide)

Structure for NP0332456 (3-Chloro-4-hydroxy-5((2E,6E)-3,7,11-trimethyl-10-methylenedodeca-2,6-dienyl)benzamide)

3D Structure for NP0332456 (3-Chloro-4-hydroxy-5((2E,6E)-3,7,11-trimethyl-10-methylenedodeca-2,6-dienyl)benzamide)