NP-MRD: Showing NP-Card for 5-acetyl-9-hydroperoxy-18-hydroxy-16-(1h-indol-3-ylmethyl)-6,13,14-trimethyl-12-oxa-17-azapentacyclo[8.8.0.0¹,¹⁵.0⁴,⁸.0¹¹,¹³]octadec-17-en-2-one (NP0282053)

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Record Information

Version

2.0

Created at

2022-09-09 08:44:24 UTC

Updated at

2022-09-09 08:44:24 UTC

NP-MRD ID

NP0282053

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-acetyl-9-hydroperoxy-18-hydroxy-16-(1h-indol-3-ylmethyl)-6,13,14-trimethyl-12-oxa-17-azapentacyclo[8.8.0.0¹,¹⁵.0⁴,⁸.0¹¹,¹³]octadec-17-en-2-one

Description

5-Acetyl-9-hydroperoxy-18-hydroxy-16-[(1H-indol-3-yl)methyl]-6,13,14-trimethyl-12-oxa-17-azapentacyclo[8.8.0.0¹,¹⁵.0⁴,⁸.0¹¹,¹³]Octadec-17-en-2-one belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. Based on a literature review very few articles have been published on 5-acetyl-9-hydroperoxy-18-hydroxy-16-[(1H-indol-3-yl)methyl]-6,13,14-trimethyl-12-oxa-17-azapentacyclo[8.8.0.0¹,¹⁵.0⁴,⁸.0¹¹,¹³]Octadec-17-en-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092210442D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309092210442D          

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    0.1034    0.8939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9795    1.6644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6661    1.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3527    0.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0581    1.2082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8433    2.0048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4258    2.5890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  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  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  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
 19 27  1  0  0  0  0
 22 27  1  0  0  0  0
 17 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 13 35  1  0  0  0  0
 35 36  1  0  0  0  0
  8 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0282053

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2C(CC(=O)C34C(C(CC5=CNC6=CC=CC=C56)N=C3O)C(C)C3(C)OC3C4C2OO)C1C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H36N2O6/c1-13-9-19-18(23(13)15(3)33)11-22(34)30-24(14(2)29(4)27(37-29)25(30)26(19)38-36)21(32-28(30)35)10-16-12-31-20-8-6-5-7-17(16)20/h5-8,12-14,18-19,21,23-27,31,36H,9-11H2,1-4H3,(H,32,35)

> <INCHI_KEY>
RKJMPHAHDKAJNT-UHFFFAOYSA-N

> <FORMULA>
C30H36N2O6

> <MOLECULAR_WEIGHT>
520.626

> <EXACT_MASS>
520.257336887

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
56.565501582605954

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-acetyl-9-hydroperoxy-18-hydroxy-16-[(1H-indol-3-yl)methyl]-6,13,14-trimethyl-12-oxa-17-azapentacyclo[8.8.0.0^{1,15}.0^{4,8}.0^{11,13}]octadec-17-en-2-one

> <JCHEM_LOGP>
2.677854673130066

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.727610207285482

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.692080212900146

> <JCHEM_PKA_STRONGEST_BASIC>
5.328402263341322

> <JCHEM_POLAR_SURFACE_AREA>
124.51000000000002

> <JCHEM_REFRACTIVITY>
138.72660000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-acetyl-9-hydroperoxy-18-hydroxy-16-(1H-indol-3-ylmethyl)-6,13,14-trimethyl-12-oxa-17-azapentacyclo[8.8.0.0^{1,15}.0^{4,8}.0^{11,13}]octadec-17-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      12.377   1.643   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.041   0.877   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.036  -0.663   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       9.710   1.651   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.554   3.183   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.701   4.210   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.048   3.508   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.274   2.177   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.301   1.030   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.505  -0.318   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.928  -0.008   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.016   1.529   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.293  -0.138   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.369  -1.239   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.893  -1.016   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       4.654  -2.603   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       3.136  -2.344   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.034  -3.420   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.415  -4.913   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.847  -5.481   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       3.748  -7.018   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       2.256  -7.399   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.541  -8.763   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.002  -8.826   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.821  -7.524   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.106  -6.161   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.432  -6.098   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.913  -0.821   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.631   0.033   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.251  -0.650   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.730   1.570   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.193   1.669   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.828   3.107   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.110   2.253   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.392   1.399   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.708   2.255   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.307   3.742   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       6.395   4.833   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   36                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   28   35                                             
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   19   22                                                  
CONECT   28   17   13   29                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   31   35                                                  
CONECT   35   34   13   36                                                  
CONECT   36   35    8   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₆N₂O₆

Average Mass

520.6260 Da

Monoisotopic Mass

520.25734 Da

IUPAC Name

5-acetyl-9-hydroperoxy-18-hydroxy-16-[(1H-indol-3-yl)methyl]-6,13,14-trimethyl-12-oxa-17-azapentacyclo[8.8.0.0^{1,15}.0^{4,8}.0^{11,13}]octadec-17-en-2-one

Traditional Name

5-acetyl-9-hydroperoxy-18-hydroxy-16-(1H-indol-3-ylmethyl)-6,13,14-trimethyl-12-oxa-17-azapentacyclo[8.8.0.0^{1,15}.0^{4,8}.0^{11,13}]octadec-17-en-2-one

CAS Registry Number

Not Available

SMILES

CC1CC2C(CC(=O)C34C(C(CC5=CNC6=CC=CC=C56)N=C3O)C(C)C3(C)OC3C4C2OO)C1C(C)=O

InChI Identifier

InChI=1S/C30H36N2O6/c1-13-9-19-18(23(13)15(3)33)11-22(34)30-24(14(2)29(4)27(37-29)25(30)26(19)38-36)21(32-28(30)35)10-16-12-31-20-8-6-5-7-17(16)20/h5-8,12-14,18-19,21,23-27,31,36H,9-11H2,1-4H3,(H,32,35)

InChI Key

RKJMPHAHDKAJNT-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

3-alkylindole
11-noriridane monoterpenoid
Aromatic monoterpenoid
Isoindole or derivatives
Indole or derivatives
Indole
Oxepane
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Cyclic carboximidic acid
Pyrroline
Pyrrole
Hydroperoxide
Ketone
Alkyl hydroperoxide
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Peroxol
Ether
Oxirane
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	ChemAxon
pKa (Strongest Acidic)	2.69	ChemAxon
pKa (Strongest Basic)	5.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	124.51 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	138.73 m³·mol⁻¹	ChemAxon
Polarizability	56.57 Å³	ChemAxon
Number of Rings	7	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

162915907

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-acetyl-9-hydroperoxy-18-hydroxy-16-(1h-indol-3-ylmethyl)-6,13,14-trimethyl-12-oxa-17-azapentacyclo[8.8.0.0¹,¹⁵.0⁴,⁸.0¹¹,¹³]octadec-17-en-2-one (NP0282053)

MOL for NP0282053 (5-acetyl-9-hydroperoxy-18-hydroxy-16-(1h-indol-3-ylmethyl)-6,13,14-trimethyl-12-oxa-17-azapentacyclo[8.8.0.0¹,¹⁵.0⁴,⁸.0¹¹,¹³]octadec-17-en-2-one)

3D MOL for NP0282053 (5-acetyl-9-hydroperoxy-18-hydroxy-16-(1h-indol-3-ylmethyl)-6,13,14-trimethyl-12-oxa-17-azapentacyclo[8.8.0.0¹,¹⁵.0⁴,⁸.0¹¹,¹³]octadec-17-en-2-one)

3D SDF for NP0282053 (5-acetyl-9-hydroperoxy-18-hydroxy-16-(1h-indol-3-ylmethyl)-6,13,14-trimethyl-12-oxa-17-azapentacyclo[8.8.0.0¹,¹⁵.0⁴,⁸.0¹¹,¹³]octadec-17-en-2-one)

3D-SDF for NP0282053 (5-acetyl-9-hydroperoxy-18-hydroxy-16-(1h-indol-3-ylmethyl)-6,13,14-trimethyl-12-oxa-17-azapentacyclo[8.8.0.0¹,¹⁵.0⁴,⁸.0¹¹,¹³]octadec-17-en-2-one)

PDB for NP0282053 (5-acetyl-9-hydroperoxy-18-hydroxy-16-(1h-indol-3-ylmethyl)-6,13,14-trimethyl-12-oxa-17-azapentacyclo[8.8.0.0¹,¹⁵.0⁴,⁸.0¹¹,¹³]octadec-17-en-2-one)

3D PDB for NP0282053 (5-acetyl-9-hydroperoxy-18-hydroxy-16-(1h-indol-3-ylmethyl)-6,13,14-trimethyl-12-oxa-17-azapentacyclo[8.8.0.0¹,¹⁵.0⁴,⁸.0¹¹,¹³]octadec-17-en-2-one)

SMILES for NP0282053 (5-acetyl-9-hydroperoxy-18-hydroxy-16-(1h-indol-3-ylmethyl)-6,13,14-trimethyl-12-oxa-17-azapentacyclo[8.8.0.0¹,¹⁵.0⁴,⁸.0¹¹,¹³]octadec-17-en-2-one)

INCHI for NP0282053 (5-acetyl-9-hydroperoxy-18-hydroxy-16-(1h-indol-3-ylmethyl)-6,13,14-trimethyl-12-oxa-17-azapentacyclo[8.8.0.0¹,¹⁵.0⁴,⁸.0¹¹,¹³]octadec-17-en-2-one)

Structure for NP0282053 (5-acetyl-9-hydroperoxy-18-hydroxy-16-(1h-indol-3-ylmethyl)-6,13,14-trimethyl-12-oxa-17-azapentacyclo[8.8.0.0¹,¹⁵.0⁴,⁸.0¹¹,¹³]octadec-17-en-2-one)

3D Structure for NP0282053 (5-acetyl-9-hydroperoxy-18-hydroxy-16-(1h-indol-3-ylmethyl)-6,13,14-trimethyl-12-oxa-17-azapentacyclo[8.8.0.0¹,¹⁵.0⁴,⁸.0¹¹,¹³]octadec-17-en-2-one)