NP-MRD: Showing NP-Card for Chaboside (NP0071014)

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Record Information

Version

2.0

Created at

2022-04-28 16:25:00 UTC

Updated at

2022-04-28 16:25:00 UTC

NP-MRD ID

NP0071014

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chaboside

Description

SCHEMBL8320251 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). Chaboside is found in Ophiorrhiza pumila. Based on a literature review very few articles have been published on SCHEMBL8320251.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218252D          

 40 45  0  0  1  0            999 V2000
    3.7054    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575    0.7556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9604   -0.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2929   -1.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6255   -0.6422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282218252D          

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 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 19 22  1  1  0  0  0
  4 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
  3 26  1  0  0  0  0
 24 27  1  0  0  0  0
 28 27  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 28 33  1  0  0  0  0
 32 34  1  1  0  0  0
 34 35  1  0  0  0  0
 31 36  1  6  0  0  0
 30 37  1  1  0  0  0
 29 38  1  6  0  0  0
 23 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0071014

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]1(O)C(=O)OCC2=C1C=C1N(CC3=C1N=C1C=CC(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)=C(OC)C1=C3)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H28N2O11/c1-3-27(36)14-7-16-19-11(8-29(16)24(34)13(14)10-38-26(27)35)6-12-15(28-19)4-5-17(23(12)37-2)39-25-22(33)21(32)20(31)18(9-30)40-25/h4-7,18,20-22,25,30-33,36H,3,8-10H2,1-2H3/t18-,20-,21+,22-,25-,27+/m1/s1

> <INCHI_KEY>
IKXVTCBCZXAVDP-JGPVVIQESA-N

> <FORMULA>
C27H28N2O11

> <MOLECULAR_WEIGHT>
556.524

> <EXACT_MASS>
556.16930973

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
56.44956838176313

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(19S)-19-ethyl-19-hydroxy-8-methoxy-7-{[(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

> <ALOGPS_LOGP>
0.50

> <JCHEM_LOGP>
-1.5090614426666658

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.239564392968983

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.57031283428488

> <JCHEM_PKA_STRONGEST_BASIC>
3.849190204276838

> <JCHEM_POLAR_SURFACE_AREA>
188.33999999999997

> <JCHEM_REFRACTIVITY>
135.08099999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.70e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(19S)-19-ethyl-19-hydroxy-8-methoxy-7-{[(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                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.917   0.266   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       7.947   1.410   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       9.454   1.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.930  -0.374   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.899  -1.519   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.393  -1.199   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.147  -2.104   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       4.901  -1.199   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       5.377   0.266   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.346   1.410   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.395  -1.519   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.919  -2.984   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.173   0.450   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.727   3.059   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.542   3.751   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.722   4.741   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.917   3.304   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      11.436  -0.695   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.466   0.450   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.990   1.914   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.484   2.235   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.973   0.130   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      15.003   1.274   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.527   2.739   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.558   3.883   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      17.064   3.563   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.540   2.098   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      16.509   0.954   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      19.046   1.778   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      20.077   2.923   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      18.095   4.707   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      15.082   5.348   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      13.021   3.059   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      11.912  -2.159   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      13.418  -2.479   0.000  0.00  0.00           C+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5   23                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8    1   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   11   20   22                                             
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19                                                            
CONECT   23    4   24   39                                                  
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25    3                                                       
CONECT   27   24   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30   38                                                  
CONECT   30   29   31   37                                                  
CONECT   31   30   32   36                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32   28                                                       
CONECT   34   32   35                                                       
CONECT   35   34                                                            
CONECT   36   31                                                            
CONECT   37   30                                                            
CONECT   38   29                                                            
CONECT   39   23   40                                                       
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₈N₂O₁₁

Average Mass

556.5240 Da

Monoisotopic Mass

556.16931 Da

IUPAC Name

(19S)-19-ethyl-19-hydroxy-8-methoxy-7-{[(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(=O)OCC2=C1C=C1N(CC3=C1N=C1C=CC(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)=C(OC)C1=C3)C2=O

InChI Identifier

InChI=1S/C27H28N2O11/c1-3-27(36)14-7-16-19-11(8-29(16)24(34)13(14)10-38-26(27)35)6-12-15(28-19)4-5-17(23(12)37-2)39-25-22(33)21(32)20(31)18(9-30)40-25/h4-7,18,20-22,25,30-33,36H,3,8-10H2,1-2H3/t18-,20-,21+,22-,25-,27+/m1/s1

InChI Key

IKXVTCBCZXAVDP-JGPVVIQESA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Ophiorrhiza pumila	Plant	KNApSAcK

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
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Pyranopyridine
Quinoline
Anisole
Alkyl aryl ether
Pyridinone
Monosaccharide
Oxane
Pyridine
Benzenoid
Tertiary alcohol
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Lactone
Lactam
Azacycle
Oxacycle
Polyol
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Monocarboxylic acid or derivatives
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organopnictogen compound
Alcohol
Primary alcohol
Organic nitrogen 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	0.5	ALOGPS
logP	-1.5	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.57	ChemAxon
pKa (Strongest Basic)	3.85	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	188.34 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	135.08 m³·mol⁻¹	ChemAxon
Polarizability	56.45 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	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

9203269

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11028089

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Chaboside (NP0071014)

MOL for NP0071014 (Chaboside)

3D MOL for NP0071014 (Chaboside)

3D SDF for NP0071014 (Chaboside)

3D-SDF for NP0071014 (Chaboside)

PDB for NP0071014 (Chaboside)

3D PDB for NP0071014 (Chaboside)

SMILES for NP0071014 (Chaboside)

INCHI for NP0071014 (Chaboside)

Structure for NP0071014 (Chaboside)

3D Structure for NP0071014 (Chaboside)