NP-MRD: Showing NP-Card for (2z)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]-3-(4-methoxyphenyl)prop-2-en-1-one (NP0156297)

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Record Information

Version

2.0

Created at

2022-09-02 13:29:12 UTC

Updated at

2022-09-02 13:29:12 UTC

NP-MRD ID

NP0156297

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(S)-Isoverbasikrine belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides. Based on a literature review very few articles have been published on (S)-Isoverbasikrine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022215292D          

 36 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309022215292D          

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  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
M  END
> <DATABASE_ID>
NP0156297

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(\C=C/C(=O)N2CCCCNCCCN[C@@H](CC(O)=NCCC2)C2=CC=CC=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H40N4O3/c1-36-26-14-11-24(12-15-26)13-16-29(35)33-21-6-5-17-30-18-7-19-31-27(25-9-3-2-4-10-25)23-28(34)32-20-8-22-33/h2-4,9-16,27,30-31H,5-8,17-23H2,1H3,(H,32,34)/b16-13-/t27-/m0/s1

> <INCHI_KEY>
XHTALCPRDZVQLY-LAGAIYJSSA-N

> <FORMULA>
C29H40N4O3

> <MOLECULAR_WEIGHT>
492.664

> <EXACT_MASS>
492.310041164

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.3404261440225

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.66

> <JCHEM_LOGP>
0.6299502498364618

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6200578096216542

> <JCHEM_PKA_STRONGEST_BASIC>
9.395396606830369

> <JCHEM_POLAR_SURFACE_AREA>
86.19

> <JCHEM_REFRACTIVITY>
146.16669999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.68e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-1-[(8S)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]-3-(4-methoxyphenyl)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      -4.557  -0.051   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.223  -0.821   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.223  -2.361   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.890  -3.131   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.890  -4.671   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.223  -5.441   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.223  -6.981   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.557  -7.751   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.891  -6.981   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.891  -5.441   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -7.224  -7.751   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -6.049  -8.746   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.632 -10.172   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.168 -10.057   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -9.544 -11.031   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0     -10.969 -10.448   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0     -12.187 -11.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -13.612 -10.807   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -13.820  -9.282   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0     -15.245  -8.699   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0     -15.453  -7.173   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -16.878  -6.590   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -18.096  -7.533   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -19.521  -6.950   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -19.729  -5.424   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -18.512  -4.481   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -17.086  -5.064   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -14.235  -6.230   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -12.810  -6.813   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -12.602  -8.339   0.000  0.00  0.00           O+0
HETATM   31  N   UNK     0     -11.593  -5.870   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0     -10.167  -6.453   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -8.950  -5.510   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -7.524  -6.093   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.557  -4.671   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.557  -3.131   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                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₀N₄O₃

Average Mass

492.6640 Da

Monoisotopic Mass

492.31004 Da

IUPAC Name

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

Traditional Name

(2Z)-1-[(8S)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]-3-(4-methoxyphenyl)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=C1

InChI Identifier

InChI=1S/C29H40N4O3/c1-36-26-14-11-24(12-15-26)13-16-29(35)33-21-6-5-17-30-18-7-19-31-27(25-9-3-2-4-10-25)23-28(34)32-20-8-22-33/h2-4,9-16,27,30-31H,5-8,17-23H2,1H3,(H,32,34)/b16-13-/t27-/m0/s1

InChI Key

XHTALCPRDZVQLY-LAGAIYJSSA-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 macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolactams

Sub Class

Not Available

Direct Parent

Macrolactams

Alternative Parents

Substituents

Macrolactam
Cinnamic acid or derivatives
Beta amino acid or derivatives
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Lactam
Secondary carboxylic acid amide
Organoheterocyclic compound
Ether
Secondary aliphatic amine
Azacycle
Carboxylic acid derivative
Secondary amine
Organic nitrogen compound
Amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic oxygen 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	2.66	ALOGPS
logP	0.63	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	3.62	ChemAxon
pKa (Strongest Basic)	9.4	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.19 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	146.17 m³·mol⁻¹	ChemAxon
Polarizability	55.34 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

101043950

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2z)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]-3-(4-methoxyphenyl)prop-2-en-1-one (NP0156297)

MOL for NP0156297 ((2z)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]-3-(4-methoxyphenyl)prop-2-en-1-one)

3D MOL for NP0156297 ((2z)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]-3-(4-methoxyphenyl)prop-2-en-1-one)

3D SDF for NP0156297 ((2z)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]-3-(4-methoxyphenyl)prop-2-en-1-one)

3D-SDF for NP0156297 ((2z)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]-3-(4-methoxyphenyl)prop-2-en-1-one)

PDB for NP0156297 ((2z)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]-3-(4-methoxyphenyl)prop-2-en-1-one)

3D PDB for NP0156297 ((2z)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]-3-(4-methoxyphenyl)prop-2-en-1-one)

SMILES for NP0156297 ((2z)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]-3-(4-methoxyphenyl)prop-2-en-1-one)

INCHI for NP0156297 ((2z)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]-3-(4-methoxyphenyl)prop-2-en-1-one)

Structure for NP0156297 ((2z)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]-3-(4-methoxyphenyl)prop-2-en-1-one)

3D Structure for NP0156297 ((2z)-1-[(8s)-6-hydroxy-8-phenyl-1,5,9,13-tetraazacycloheptadec-5-en-1-yl]-3-(4-methoxyphenyl)prop-2-en-1-one)