NP-MRD: Showing NP-Card for 7,8,19-trihydroxy-2,10-dimethyl-17-(octa-2,4-dien-1-yl)-16-azatetracyclo[12.6.0.0⁴,⁹.0¹⁶,²⁰]icosa-2,5,10,12-tetraen-15-one (NP0298041)

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Record Information

Version

2.0

Created at

2022-09-10 08:56:18 UTC

Updated at

2022-09-10 08:56:18 UTC

NP-MRD ID

NP0298041

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,8,19-trihydroxy-2,10-dimethyl-17-(octa-2,4-dien-1-yl)-16-azatetracyclo[12.6.0.0⁴,⁹.0¹⁶,²⁰]icosa-2,5,10,12-tetraen-15-one

Description

7,8,19-Trihydroxy-2,10-dimethyl-17-(octa-2,4-dien-1-yl)-16-azatetracyclo[12.6.0.0⁴,⁹.0¹⁶,²⁰]Icosa-2,5,10,12-tetraen-15-one belongs to the class of organic compounds known as pyrrolizidinones. Pyrrolizidinones are compounds containing a pyrrolizidine moiety which bears a ketone. Pyrrolizidine is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom. Based on a literature review very few articles have been published on 7,8,19-trihydroxy-2,10-dimethyl-17-(octa-2,4-dien-1-yl)-16-azatetracyclo[12.6.0.0⁴,⁹.0¹⁶,²⁰]Icosa-2,5,10,12-tetraen-15-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102210562D          

 34 37  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309102210562D          

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 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  4  0  0  0
 29 30  2  0  0  0  0
 30 31  1  4  0  0  0
 14 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
  9 34  1  0  0  0  0
 13 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0298041

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC=CC=CCC1CC(O)C2C3C(C=CC=C(C)C4C(O)C(O)C=CC4C=C3C)C(=O)N12

> <INCHI_IDENTIFIER>
InChI=1S/C29H39NO4/c1-4-5-6-7-8-9-12-21-17-24(32)27-26-19(3)16-20-14-15-23(31)28(33)25(20)18(2)11-10-13-22(26)29(34)30(21)27/h6-11,13-16,20-28,31-33H,4-5,12,17H2,1-3H3

> <INCHI_KEY>
APYNVIXJDXCVNV-UHFFFAOYSA-N

> <FORMULA>
C29H39NO4

> <MOLECULAR_WEIGHT>
465.634

> <EXACT_MASS>
465.28790874

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
55.161944316309224

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7,8,19-trihydroxy-2,10-dimethyl-17-(octa-2,4-dien-1-yl)-16-azatetracyclo[12.6.0.0^{4,9}.0^{16,20}]icosa-2,5,10,12-tetraen-15-one

> <JCHEM_LOGP>
2.7669695720000007

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.413466447520367

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.469965853090397

> <JCHEM_PKA_STRONGEST_BASIC>
0.04403522358368506

> <JCHEM_POLAR_SURFACE_AREA>
80.99999999999999

> <JCHEM_REFRACTIVITY>
141.64300000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
7,8,19-trihydroxy-2,10-dimethyl-17-(octa-2,4-dien-1-yl)-16-azatetracyclo[12.6.0.0^{4,9}.0^{16,20}]icosa-2,5,10,12-tetraen-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.139   5.197   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.841   4.009   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.302   2.566   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.282   1.379   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.744  -0.064   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.724  -1.252   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.185  -2.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.166  -3.883   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.684  -3.628   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.371  -2.249   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.894  -2.476   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.973  -1.377   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.149  -3.995   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.248  -5.074   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.785  -4.979   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.718  -6.517   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.471  -3.600   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.008  -3.506   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.695  -2.127   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.232  -2.032   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.083  -3.316   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      15.620  -3.221   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      13.396  -4.695   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      14.247  -5.978   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      11.859  -4.789   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.173  -6.168   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.023  -7.452   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.635  -6.263   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.949  -7.641   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.412  -7.736   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.561  -6.452   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.038  -6.225   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.959  -7.324   0.000  0.00  0.00           O+0
HETATM   34  N   UNK     0       4.783  -4.707   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   34                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   34                                                  
CONECT   14   13   15   31                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   18   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   14   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    9   13                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₉NO₄

Average Mass

465.6340 Da

Monoisotopic Mass

465.28791 Da

IUPAC Name

7,8,19-trihydroxy-2,10-dimethyl-17-(octa-2,4-dien-1-yl)-16-azatetracyclo[12.6.0.0^{4,9}.0^{16,20}]icosa-2,5,10,12-tetraen-15-one

Traditional Name

7,8,19-trihydroxy-2,10-dimethyl-17-(octa-2,4-dien-1-yl)-16-azatetracyclo[12.6.0.0^{4,9}.0^{16,20}]icosa-2,5,10,12-tetraen-15-one

CAS Registry Number

Not Available

SMILES

CCCC=CC=CCC1CC(O)C2C3C(C=CC=C(C)C4C(O)C(O)C=CC4C=C3C)C(=O)N12

InChI Identifier

InChI=1S/C29H39NO4/c1-4-5-6-7-8-9-12-21-17-24(32)27-26-19(3)16-20-14-15-23(31)28(33)25(20)18(2)11-10-13-22(26)29(34)30(21)27/h6-11,13-16,20-28,31-33H,4-5,12,17H2,1-3H3

InChI Key

APYNVIXJDXCVNV-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 pyrrolizidinones. Pyrrolizidinones are compounds containing a pyrrolizidine moiety which bears a ketone. Pyrrolizidine is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolizidines

Sub Class

Pyrrolizidinones

Direct Parent

Pyrrolizidinones

Alternative Parents

Substituents

Pyrrolizidinone
Pyrrolidone
2-pyrrolidone
N-alkylpyrrolidine
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Secondary alcohol
Polyol
Carboxylic acid derivative
Azacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.77	ChemAxon
pKa (Strongest Acidic)	13.47	ChemAxon
pKa (Strongest Basic)	0.044	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	81 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	141.64 m³·mol⁻¹	ChemAxon
Polarizability	55.16 Å³	ChemAxon
Number of Rings	4	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

75295561

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7,8,19-trihydroxy-2,10-dimethyl-17-(octa-2,4-dien-1-yl)-16-azatetracyclo[12.6.0.0⁴,⁹.0¹⁶,²⁰]icosa-2,5,10,12-tetraen-15-one (NP0298041)

MOL for NP0298041 (7,8,19-trihydroxy-2,10-dimethyl-17-(octa-2,4-dien-1-yl)-16-azatetracyclo[12.6.0.0⁴,⁹.0¹⁶,²⁰]icosa-2,5,10,12-tetraen-15-one)

3D MOL for NP0298041 (7,8,19-trihydroxy-2,10-dimethyl-17-(octa-2,4-dien-1-yl)-16-azatetracyclo[12.6.0.0⁴,⁹.0¹⁶,²⁰]icosa-2,5,10,12-tetraen-15-one)

3D SDF for NP0298041 (7,8,19-trihydroxy-2,10-dimethyl-17-(octa-2,4-dien-1-yl)-16-azatetracyclo[12.6.0.0⁴,⁹.0¹⁶,²⁰]icosa-2,5,10,12-tetraen-15-one)

3D-SDF for NP0298041 (7,8,19-trihydroxy-2,10-dimethyl-17-(octa-2,4-dien-1-yl)-16-azatetracyclo[12.6.0.0⁴,⁹.0¹⁶,²⁰]icosa-2,5,10,12-tetraen-15-one)

PDB for NP0298041 (7,8,19-trihydroxy-2,10-dimethyl-17-(octa-2,4-dien-1-yl)-16-azatetracyclo[12.6.0.0⁴,⁹.0¹⁶,²⁰]icosa-2,5,10,12-tetraen-15-one)

3D PDB for NP0298041 (7,8,19-trihydroxy-2,10-dimethyl-17-(octa-2,4-dien-1-yl)-16-azatetracyclo[12.6.0.0⁴,⁹.0¹⁶,²⁰]icosa-2,5,10,12-tetraen-15-one)

SMILES for NP0298041 (7,8,19-trihydroxy-2,10-dimethyl-17-(octa-2,4-dien-1-yl)-16-azatetracyclo[12.6.0.0⁴,⁹.0¹⁶,²⁰]icosa-2,5,10,12-tetraen-15-one)

INCHI for NP0298041 (7,8,19-trihydroxy-2,10-dimethyl-17-(octa-2,4-dien-1-yl)-16-azatetracyclo[12.6.0.0⁴,⁹.0¹⁶,²⁰]icosa-2,5,10,12-tetraen-15-one)

Structure for NP0298041 (7,8,19-trihydroxy-2,10-dimethyl-17-(octa-2,4-dien-1-yl)-16-azatetracyclo[12.6.0.0⁴,⁹.0¹⁶,²⁰]icosa-2,5,10,12-tetraen-15-one)

3D Structure for NP0298041 (7,8,19-trihydroxy-2,10-dimethyl-17-(octa-2,4-dien-1-yl)-16-azatetracyclo[12.6.0.0⁴,⁹.0¹⁶,²⁰]icosa-2,5,10,12-tetraen-15-one)