NP-MRD: Showing NP-Card for (19s)-19-ethyl-7-methoxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl hexanoate (NP0237416)

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Record Information

Version

2.0

Created at

2022-09-06 20:32:49 UTC

Updated at

2022-09-06 20:32:49 UTC

NP-MRD ID

NP0237416

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(19s)-19-ethyl-7-methoxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl hexanoate

Description

(19S)-19-ethyl-7-methoxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]Henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-19-yl hexanoate belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring). (19s)-19-ethyl-7-methoxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl hexanoate is found in Camptotheca acuminata. Based on a literature review very few articles have been published on (19S)-19-ethyl-7-methoxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]Henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-19-yl hexanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062222322D          

 35 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309062222322D          

 35 39  0  0  1  0            999 V2000
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 24 35  2  0  0  0  0
 19 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0237416

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC(=O)O[C@]1(CC)C(=O)OCC2=C1C=C1N(CC3=C1N=C1C=CC(OC)=CC1=C3)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H28N2O6/c1-4-6-7-8-23(30)35-27(5-2)20-13-22-24-17(11-16-12-18(33-3)9-10-21(16)28-24)14-29(22)25(31)19(20)15-34-26(27)32/h9-13H,4-8,14-15H2,1-3H3/t27-/m0/s1

> <INCHI_KEY>
FHNISFXQFOJLCB-MHZLTWQESA-N

> <FORMULA>
C27H28N2O6

> <MOLECULAR_WEIGHT>
476.529

> <EXACT_MASS>
476.19473663

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
52.26754331243593

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(19S)-19-ethyl-7-methoxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-19-yl hexanoate

> <JCHEM_LOGP>
3.537939224666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.1564530329064624

> <JCHEM_POLAR_SURFACE_AREA>
95.03000000000002

> <JCHEM_REFRACTIVITY>
128.53709999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(19S)-19-ethyl-7-methoxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-19-yl hexanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       7.313   2.392   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.646   3.162   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.980   2.392   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.314   3.162   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.647   2.392   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.981   3.162   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.981   4.702   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      15.315   2.392   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      16.648   3.162   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.658   4.342   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.185   5.789   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.638   4.342   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      17.111   5.789   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      19.155   4.074   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      19.682   2.627   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.692   1.448   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.175   1.715   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.185   0.535   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.712  -0.912   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      18.228  -1.179   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      19.218   0.001   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      20.735  -0.267   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      18.443  -2.704   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.059  -3.379   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.634  -4.860   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.140  -5.232   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.715  -6.713   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.221  -7.085   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.797  -8.565   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      11.302  -8.938   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.151  -5.977   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.576  -4.497   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.070  -4.124   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      14.495  -2.644   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0      15.989  -2.272   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                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   12   17                                             
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16    9   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   35                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   16   22                                                  
CONECT   22   21                                                            
CONECT   23   20   24                                                       
CONECT   24   23   25   35                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   26   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   24   19                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
(19S)-19-Ethyl-7-methoxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0,.0,.0,]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-19-yl hexanoic acid	Generator

Chemical Formula

C₂₇H₂₈N₂O₆

Average Mass

476.5290 Da

Monoisotopic Mass

476.19474 Da

IUPAC Name

(19S)-19-ethyl-7-methoxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-19-yl hexanoate

Traditional Name

(19S)-19-ethyl-7-methoxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-19-yl hexanoate

CAS Registry Number

Not Available

SMILES

CCCCCC(=O)O[C@]1(CC)C(=O)OCC2=C1C=C1N(CC3=C1N=C1C=CC(OC)=CC1=C3)C2=O

InChI Identifier

InChI=1S/C27H28N2O6/c1-4-6-7-8-23(30)35-27(5-2)20-13-22-24-17(11-16-12-18(33-3)9-10-21(16)28-24)14-29(22)25(31)19(20)15-34-26(27)32/h9-13H,4-8,14-15H2,1-3H3/t27-/m0/s1

InChI Key

FHNISFXQFOJLCB-MHZLTWQESA-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
Camptotheca acuminata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring).

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Camptothecins

Sub Class

Not Available

Direct Parent

Camptothecins

Alternative Parents

Substituents

Camptothecin
Pyranopyridine
Quinoline
Anisole
Phenol ether
Alkyl aryl ether
Fatty acid ester
Pyridinone
Dicarboxylic acid or derivatives
Pyridine
Fatty acyl
Benzenoid
Heteroaromatic compound
Lactone
Lactam
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Azacycle
Carboxylic acid derivative
Ether
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Organooxygen compound
Organic oxide
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	3.54	ChemAxon
pKa (Strongest Basic)	3.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	95.03 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	128.54 m³·mol⁻¹	ChemAxon
Polarizability	52.27 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

8402925

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10227435

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (19s)-19-ethyl-7-methoxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl hexanoate (NP0237416)

MOL for NP0237416 ((19s)-19-ethyl-7-methoxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl hexanoate)

3D MOL for NP0237416 ((19s)-19-ethyl-7-methoxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl hexanoate)

3D SDF for NP0237416 ((19s)-19-ethyl-7-methoxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl hexanoate)

3D-SDF for NP0237416 ((19s)-19-ethyl-7-methoxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl hexanoate)

PDB for NP0237416 ((19s)-19-ethyl-7-methoxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl hexanoate)

3D PDB for NP0237416 ((19s)-19-ethyl-7-methoxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl hexanoate)

SMILES for NP0237416 ((19s)-19-ethyl-7-methoxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl hexanoate)

INCHI for NP0237416 ((19s)-19-ethyl-7-methoxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl hexanoate)

Structure for NP0237416 ((19s)-19-ethyl-7-methoxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl hexanoate)

3D Structure for NP0237416 ((19s)-19-ethyl-7-methoxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-19-yl hexanoate)