NP-MRD: Showing NP-Card for n-[2-(3-chloro-4-hydroxyphenyl)ethenyl]-2-ethoxy-3,9-dihydroxy-4-methoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid (NP0180497)

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Record Information

Version

2.0

Created at

2022-09-03 18:51:53 UTC

Updated at

2022-09-03 18:51:53 UTC

NP-MRD ID

NP0180497

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[2-(3-chloro-4-hydroxyphenyl)ethenyl]-2-ethoxy-3,9-dihydroxy-4-methoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid

Description

N-[2-(3-chloro-4-hydroxyphenyl)ethenyl]-2-ethoxy-3,9-dihydroxy-4-methoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. n-[2-(3-chloro-4-hydroxyphenyl)ethenyl]-2-ethoxy-3,9-dihydroxy-4-methoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid is found in Chondromyces crocatus. N-[2-(3-chloro-4-hydroxyphenyl)ethenyl]-2-ethoxy-3,9-dihydroxy-4-methoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161519122D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004161519122D          

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   19.2907  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762  -12.3750    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.8618  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -9.0750    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  4  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 27 26  1  4  0  0  0
 27 28  2  0  0  0  0
 28 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
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 29 36  1  0  0  0  0
 13 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0180497

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC(C)C(O)C(C)C(=O)C(C)=CC(OC)C(O)C(OCC)C(=O)NC=CC1=CC=C(O)C(Cl)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H42ClNO7/c1-7-9-10-17(3)24(32)19(5)25(33)18(4)15-23(36-6)26(34)27(37-8-2)28(35)30-14-13-20-11-12-22(31)21(29)16-20/h11-17,19,23-24,26-27,31-32,34H,7-10H2,1-6H3,(H,30,35)

> <INCHI_KEY>
BIBQKWSSQXEIHK-UHFFFAOYSA-N

> <FORMULA>
C28H42ClNO7

> <MOLECULAR_WEIGHT>
540.09

> <EXACT_MASS>
539.2649804

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
59.33886476574686

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[2-(3-chloro-4-hydroxyphenyl)ethenyl]-2-ethoxy-3,9-dihydroxy-4-methoxy-6,8,10-trimethyl-7-oxotetradec-5-enamide

> <ALOGPS_LOGP>
4.18

> <JCHEM_LOGP>
4.861871200333332

> <ALOGPS_LOGS>
-5.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.767503864888287

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.911869488896306

> <JCHEM_PKA_STRONGEST_BASIC>
-3.006488385715403

> <JCHEM_POLAR_SURFACE_AREA>
125.32000000000001

> <JCHEM_REFRACTIVITY>
145.81249999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.78e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[2-(3-chloro-4-hydroxyphenyl)ethenyl]-2-ethoxy-3,9-dihydroxy-4-methoxy-6,8,10-trimethyl-7-oxotetradec-5-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      10.669 -18.480   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003 -19.250   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.337 -18.480   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.670 -19.250   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.004 -18.480   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.004 -16.940   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.338 -19.250   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      17.338 -20.790   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      18.672 -18.480   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.672 -16.940   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.005 -19.250   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      20.005 -20.790   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      21.339 -18.480   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.673 -19.250   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.006 -18.480   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      24.006 -16.940   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      22.673 -16.170   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      25.340 -19.250   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      25.340 -20.790   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      26.674 -18.480   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      26.674 -16.940   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      25.340 -16.170   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      25.340 -14.630   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      28.007 -19.250   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      28.007 -20.790   0.000  0.00  0.00           O+0
HETATM   26  N   UNK     0      29.341 -18.480   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      30.675 -19.250   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      32.008 -18.480   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      33.342 -19.250   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      34.676 -18.480   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      36.009 -19.250   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      36.009 -20.790   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      37.343 -21.560   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      34.676 -21.560   0.000  0.00  0.00           C+0
HETATM   35 Cl   UNK     0      34.676 -23.100   0.000  0.00  0.00          Cl+0
HETATM   36  C   UNK     0      33.342 -20.790   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      21.339 -16.940   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   37                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   20   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   36                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   29                                                       
CONECT   37   13                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   74    0
END

View in JSmol

Synonyms

Value	Source
N-[2-(3-Chloro-4-hydroxyphenyl)ethenyl]-2-ethoxy-3,9-dihydroxy-4-methoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidate	Generator

Chemical Formula

C₂₈H₄₂ClNO₇

Average Mass

540.0900 Da

Monoisotopic Mass

539.26498 Da

IUPAC Name

N-[2-(3-chloro-4-hydroxyphenyl)ethenyl]-2-ethoxy-3,9-dihydroxy-4-methoxy-6,8,10-trimethyl-7-oxotetradec-5-enamide

Traditional Name

N-[2-(3-chloro-4-hydroxyphenyl)ethenyl]-2-ethoxy-3,9-dihydroxy-4-methoxy-6,8,10-trimethyl-7-oxotetradec-5-enamide

CAS Registry Number

Not Available

SMILES

CCCCC(C)C(O)C(C)C(=O)C(C)=CC(OC)C(O)C(OCC)C(=O)NC=CC1=CC=C(O)C(Cl)=C1

InChI Identifier

InChI=1S/C28H42ClNO7/c1-7-9-10-17(3)24(32)19(5)25(33)18(4)15-23(36-6)26(34)27(37-8-2)28(35)30-14-13-20-11-12-22(31)21(29)16-20/h11-17,19,23-24,26-27,31-32,34H,7-10H2,1-6H3,(H,30,35)

InChI Key

BIBQKWSSQXEIHK-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
Chondromyces crocatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Styrenes

Direct Parent

Styrenes

Alternative Parents

Substituents

2-chlorophenol
2-halophenol
Styrene
1-hydroxy-2-unsubstituted benzenoid
Halobenzene
Phenol
Chlorobenzene
B'-hydroxy-alpha,beta-unsaturated-ketone
Aryl chloride
Alpha-branched alpha,beta-unsaturated-ketone
Beta-hydroxy ketone
Aryl halide
Enone
Alpha,beta-unsaturated ketone
Acryloyl-group
Ketone
Secondary alcohol
Carboximidic acid
Carboximidic acid derivative
Organic 1,3-dipolar compound
Dialkyl ether
Propargyl-type 1,3-dipolar organic compound
Ether
Organic oxygen compound
Alcohol
Organic nitrogen compound
Carbonyl group
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	4.18	ALOGPS
logP	4.86	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	7.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.32 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	145.81 m³·mol⁻¹	ChemAxon
Polarizability	59.34 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

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

85400056

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-[2-(3-chloro-4-hydroxyphenyl)ethenyl]-2-ethoxy-3,9-dihydroxy-4-methoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid (NP0180497)

MOL for NP0180497 (n-[2-(3-chloro-4-hydroxyphenyl)ethenyl]-2-ethoxy-3,9-dihydroxy-4-methoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid)

3D MOL for NP0180497 (n-[2-(3-chloro-4-hydroxyphenyl)ethenyl]-2-ethoxy-3,9-dihydroxy-4-methoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid)

3D SDF for NP0180497 (n-[2-(3-chloro-4-hydroxyphenyl)ethenyl]-2-ethoxy-3,9-dihydroxy-4-methoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid)

3D-SDF for NP0180497 (n-[2-(3-chloro-4-hydroxyphenyl)ethenyl]-2-ethoxy-3,9-dihydroxy-4-methoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid)

PDB for NP0180497 (n-[2-(3-chloro-4-hydroxyphenyl)ethenyl]-2-ethoxy-3,9-dihydroxy-4-methoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid)

3D PDB for NP0180497 (n-[2-(3-chloro-4-hydroxyphenyl)ethenyl]-2-ethoxy-3,9-dihydroxy-4-methoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid)

SMILES for NP0180497 (n-[2-(3-chloro-4-hydroxyphenyl)ethenyl]-2-ethoxy-3,9-dihydroxy-4-methoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid)

INCHI for NP0180497 (n-[2-(3-chloro-4-hydroxyphenyl)ethenyl]-2-ethoxy-3,9-dihydroxy-4-methoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid)

Structure for NP0180497 (n-[2-(3-chloro-4-hydroxyphenyl)ethenyl]-2-ethoxy-3,9-dihydroxy-4-methoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid)

3D Structure for NP0180497 (n-[2-(3-chloro-4-hydroxyphenyl)ethenyl]-2-ethoxy-3,9-dihydroxy-4-methoxy-6,8,10-trimethyl-7-oxotetradec-5-enimidic acid)