NP-MRD: Showing NP-Card for (19s)-19-ethyl-19-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione (NP0211568)

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Record Information

Version

2.0

Created at

2022-09-05 09:54:14 UTC

Updated at

2022-09-05 09:54:14 UTC

NP-MRD ID

NP0211568

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(19s)-19-ethyl-19-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione

Description

20-O-Glucosylcamptothecin 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-19-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione is found in Mostuea brunonis. Based on a literature review very few articles have been published on 20-O-Glucosylcamptothecin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052211542D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309052211542D          

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 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 30 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 28 37  2  0  0  0  0
 23 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0211568

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]1(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(=O)OCC2=C1C=C1N(CC3=C1N=C1C=CC=CC1=C3)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H26N2O9/c1-2-26(37-24-22(32)21(31)20(30)18(10-29)36-24)15-8-17-19-13(7-12-5-3-4-6-16(12)27-19)9-28(17)23(33)14(15)11-35-25(26)34/h3-8,18,20-22,24,29-32H,2,9-11H2,1H3/t18-,20-,21+,22-,24+,26+/m1/s1

> <INCHI_KEY>
PWBVJDZNUOVIOE-FATQUBODSA-N

> <FORMULA>
C26H26N2O9

> <MOLECULAR_WEIGHT>
510.499

> <EXACT_MASS>
510.163830425

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
51.230189833212364

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(19S)-19-ethyl-19-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-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)-heptaene-14,18-dione

> <JCHEM_LOGP>
-0.550592407666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.199382145677411

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.20873728996578

> <JCHEM_PKA_STRONGEST_BASIC>
3.073194757320142

> <JCHEM_POLAR_SURFACE_AREA>
158.88

> <JCHEM_REFRACTIVITY>
126.9058

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(19S)-19-ethyl-19-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-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)-heptaene-14,18-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       7.818   2.328   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.178   3.051   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.484   2.235   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      11.061   3.662   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.113   4.876   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.690   6.304   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.742   7.517   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.319   8.945   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.370  10.159   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.217   7.303   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.269   8.517   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.640   5.875   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.115   5.661   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.588   4.662   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.011   3.234   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.990   1.914   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      13.021   3.059   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      12.466   0.450   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.436  -0.695   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.930  -0.374   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.454   1.090   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.947   1.410   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.917   0.266   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       7.393  -1.199   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       8.899  -1.519   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.375  -2.984   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.147  -2.104   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.901  -1.199   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.395  -1.519   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.173   0.450   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0       4.346   1.410   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0       5.377   0.266   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16   21                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    5   15                                                  
CONECT   15   14                                                            
CONECT   16    3   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20    3   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   37                                                  
CONECT   24   23   25   27                                                  
CONECT   25   24   20   26                                                  
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29   37                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   30   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   28   23                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₆N₂O₉

Average Mass

510.4990 Da

Monoisotopic Mass

510.16383 Da

IUPAC Name

(19S)-19-ethyl-19-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-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)-heptaene-14,18-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@@]1(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(=O)OCC2=C1C=C1N(CC3=C1N=C1C=CC=CC1=C3)C2=O

InChI Identifier

InChI=1S/C26H26N2O9/c1-2-26(37-24-22(32)21(31)20(30)18(10-29)36-24)15-8-17-19-13(7-12-5-3-4-6-16(12)27-19)9-28(17)23(33)14(15)11-35-25(26)34/h3-8,18,20-22,24,29-32H,2,9-11H2,1H3/t18-,20-,21+,22-,24+,26+/m1/s1

InChI Key

PWBVJDZNUOVIOE-FATQUBODSA-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
Mostuea brunonis	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
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Pyranopyridine
Quinoline
Pyridinone
Monosaccharide
Oxane
Pyridine
Fatty acyl
Benzenoid
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Lactam
Lactone
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Oxacycle
Polyol
Monocarboxylic acid or derivatives
Acetal
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Carbonyl group
Organic nitrogen compound
Alcohol
Organonitrogen compound
Organooxygen compound
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	-0.55	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	3.07	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	158.88 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	126.91 m³·mol⁻¹	ChemAxon
Polarizability	51.23 Å³	ChemAxon
Number of Rings	6	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

8990864

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10815559

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-19-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione (NP0211568)

MOL for NP0211568 ((19s)-19-ethyl-19-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione)

3D MOL for NP0211568 ((19s)-19-ethyl-19-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione)

3D SDF for NP0211568 ((19s)-19-ethyl-19-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione)

3D-SDF for NP0211568 ((19s)-19-ethyl-19-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione)

PDB for NP0211568 ((19s)-19-ethyl-19-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione)

3D PDB for NP0211568 ((19s)-19-ethyl-19-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione)

SMILES for NP0211568 ((19s)-19-ethyl-19-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione)

INCHI for NP0211568 ((19s)-19-ethyl-19-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione)

Structure for NP0211568 ((19s)-19-ethyl-19-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione)

3D Structure for NP0211568 ((19s)-19-ethyl-19-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione)