NP-MRD: Showing NP-Card for (2e)-3-(3,4-dimethoxyphenyl)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]prop-2-en-1-one (NP0159031)

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Record Information

Version

2.0

Created at

2022-09-02 16:42:56 UTC

Updated at

2022-09-02 16:42:56 UTC

NP-MRD ID

NP0159031

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-3-(3,4-dimethoxyphenyl)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]prop-2-en-1-one

Description

Verbasitrine belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid. Based on a literature review very few articles have been published on Verbasitrine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022218422D          

 38 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309022218422D          

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   -1.6367   -4.1454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7480   -3.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5116   -3.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6229   -2.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6483    1.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6483    2.0975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3627    2.5100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3627    3.3350    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  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  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  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
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 31 32  1  4  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 11 34  1  0  0  0  0
  6 35  1  0  0  0  0
 35 36  2  0  0  0  0
  3 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0159031

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(\C=C\C(=O)N2CCCCNCCCN[C@@H](CC(O)=NCCC2)C2=CC=CC=C2)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C30H42N4O4/c1-37-27-14-12-24(22-28(27)38-2)13-15-30(36)34-20-7-6-16-31-17-8-18-32-26(25-10-4-3-5-11-25)23-29(35)33-19-9-21-34/h3-5,10-15,22,26,31-32H,6-9,16-21,23H2,1-2H3,(H,33,35)/b15-13+/t26-/m0/s1

> <INCHI_KEY>
KHXMIZBSBCSMPA-PUESRJFGSA-N

> <FORMULA>
C30H42N4O4

> <MOLECULAR_WEIGHT>
522.69

> <EXACT_MASS>
522.320605848

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
59.53065876576625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-(3,4-dimethoxyphenyl)-1-[(8S)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]prop-2-en-1-one

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
0.4727194378558856

> <ALOGPS_LOGS>
-5.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.59689230554459

> <JCHEM_PKA_STRONGEST_BASIC>
9.395315780325218

> <JCHEM_POLAR_SURFACE_AREA>
95.42

> <JCHEM_REFRACTIVITY>
152.62989999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.72e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(3,4-dimethoxyphenyl)-1-[(8S)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]prop-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.943   6.995   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.610   6.225   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.610   4.685   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.276   3.915   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.276   2.375   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.610   1.605   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.610   0.065   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.943  -0.705   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.943  -2.245   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -6.277  -3.015   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -3.610  -3.015   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -3.336  -1.499   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.810  -1.291   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.141  -2.678   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.390  -3.383   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       0.598  -4.909   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       2.023  -5.492   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.231  -7.018   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.013  -7.961   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       1.221  -9.487   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       0.003 -10.430   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.211 -11.956   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.637 -12.539   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.845 -14.065   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.627 -15.008   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.798 -14.425   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.006 -12.899   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.422  -9.847   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.630  -8.321   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.412  -7.378   0.000  0.00  0.00           O+0
HETATM   31  N   UNK     0      -3.055  -7.738   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0      -3.263  -6.212   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.688  -5.629   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.896  -4.103   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.943   2.375   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.943   3.915   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -6.277   4.685   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -6.277   6.225   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   35                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   34                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   21   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   11                                                       
CONECT   35    6   36                                                       
CONECT   36   35    3   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₂N₄O₄

Average Mass

522.6900 Da

Monoisotopic Mass

522.32061 Da

IUPAC Name

(2E)-3-(3,4-dimethoxyphenyl)-1-[(8S)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]prop-2-en-1-one

Traditional Name

(2E)-3-(3,4-dimethoxyphenyl)-1-[(8S)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]prop-2-en-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C(\C=C\C(=O)N2CCCCNCCCN[C@@H](CC(O)=NCCC2)C2=CC=CC=C2)C=C1OC

InChI Identifier

InChI=1S/C30H42N4O4/c1-37-27-14-12-24(22-28(27)38-2)13-15-30(36)34-20-7-6-16-31-17-8-18-32-26(25-10-4-3-5-11-25)23-29(35)33-19-9-21-34/h3-5,10-15,22,26,31-32H,6-9,16-21,23H2,1-2H3,(H,33,35)/b15-13+/t26-/m0/s1

InChI Key

KHXMIZBSBCSMPA-PUESRJFGSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Not Available

Direct Parent

Cinnamic acids and derivatives

Alternative Parents

Substituents

Cinnamic acid or derivatives
O-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Anisole
Phenol ether
Styrene
Methoxybenzene
Alkyl aryl ether
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Cyclic carboximidic acid
Amino acid or derivatives
Carboxamide group
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organoheterocyclic compound
Carboxylic acid derivative
Secondary aliphatic amine
Ether
Secondary amine
Azacycle
Organic oxide
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Amine
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	2.68	ALOGPS
logP	0.47	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	5.6	ChemAxon
pKa (Strongest Basic)	9.4	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.42 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	152.63 m³·mol⁻¹	ChemAxon
Polarizability	59.53 Å³	ChemAxon
Number of Rings	3	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

15860020

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-3-(3,4-dimethoxyphenyl)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]prop-2-en-1-one (NP0159031)

MOL for NP0159031 ((2e)-3-(3,4-dimethoxyphenyl)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]prop-2-en-1-one)

3D MOL for NP0159031 ((2e)-3-(3,4-dimethoxyphenyl)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]prop-2-en-1-one)

3D SDF for NP0159031 ((2e)-3-(3,4-dimethoxyphenyl)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]prop-2-en-1-one)

3D-SDF for NP0159031 ((2e)-3-(3,4-dimethoxyphenyl)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]prop-2-en-1-one)

PDB for NP0159031 ((2e)-3-(3,4-dimethoxyphenyl)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]prop-2-en-1-one)

3D PDB for NP0159031 ((2e)-3-(3,4-dimethoxyphenyl)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]prop-2-en-1-one)

SMILES for NP0159031 ((2e)-3-(3,4-dimethoxyphenyl)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]prop-2-en-1-one)

INCHI for NP0159031 ((2e)-3-(3,4-dimethoxyphenyl)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]prop-2-en-1-one)

Structure for NP0159031 ((2e)-3-(3,4-dimethoxyphenyl)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]prop-2-en-1-one)

3D Structure for NP0159031 ((2e)-3-(3,4-dimethoxyphenyl)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]prop-2-en-1-one)