NP-MRD: Showing NP-Card for 7,8-dehydrocerberin (NP0249897)

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Record Information

Version

2.0

Created at

2022-09-07 12:35:12 UTC

Updated at

2022-09-07 12:35:12 UTC

NP-MRD ID

NP0249897

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,8-dehydrocerberin

Description

7,8-Dehydrocerberin belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. 7,8-dehydrocerberin is found in Cerbera manghas. 7,8-dehydrocerberin was first documented in 2004 (PMID: 15305009). Based on a literature review very few articles have been published on 7,8-dehydrocerberin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072214352D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072214352D          

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    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2889   -1.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061   -2.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5793   -2.8729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0452   -1.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2351   -0.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8685    1.4085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0117    2.1096    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1996    1.9643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6678    2.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8557    2.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9481    3.3710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 19  1  1  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 25 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 19 34  1  0  0  0  0
 23 34  1  0  0  0  0
 34 35  1  1  0  0  0
 16 36  1  0  0  0  0
 11 36  1  0  0  0  0
  9 37  1  0  0  0  0
  3 37  1  0  0  0  0
 37 38  1  1  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0249897

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1[C@@H](O)[C@H](C)O[C@@H](O[C@H]2CC[C@@]3(C)[C@H](CC=C4[C@@H]3CC[C@]3(C)[C@H](CC[C@]43O)C3=CC(=O)OC3)C2)[C@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H46O9/c1-17-26(35)27(37-5)28(40-18(2)33)29(39-17)41-21-8-11-30(3)20(15-21)6-7-24-23(30)9-12-31(4)22(10-13-32(24,31)36)19-14-25(34)38-16-19/h7,14,17,20-23,26-29,35-36H,6,8-13,15-16H2,1-5H3/t17-,20+,21-,22+,23-,26-,27+,28-,29-,30-,31+,32-/m0/s1

> <INCHI_KEY>
MJWBKZJOFFGTCD-ZSCKLWMASA-N

> <FORMULA>
C32H46O9

> <MOLECULAR_WEIGHT>
574.711

> <EXACT_MASS>
574.314183061

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
62.96988772293493

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4R,5S,6S)-5-hydroxy-2-{[(1R,2S,5S,7R,11R,14R,15R)-11-hydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-yl]oxy}-4-methoxy-6-methyloxan-3-yl acetate

> <JCHEM_LOGP>
3.100055070666664

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.129833342058834

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.178452766207181

> <JCHEM_PKA_STRONGEST_BASIC>
-0.10954240124327697

> <JCHEM_POLAR_SURFACE_AREA>
120.75000000000003

> <JCHEM_REFRACTIVITY>
149.18589999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4R,5S,6S)-5-hydroxy-2-{[(1R,2S,5S,7R,11R,14R,15R)-11-hydroxy-2,15-dimethyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-yl]oxy}-4-methoxy-6-methyloxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      13.142   8.012   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.619   6.564   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      13.612   5.386   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.128   5.657   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      15.651   7.106   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      16.120   4.480   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.636   4.751   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      15.597   3.032   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      14.081   2.761   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.406  -2.959   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.131  -3.824   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.081  -5.363   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -0.084  -2.878   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.439  -1.430   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.355   2.629   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.089   3.938   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      11.573   3.667   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      10.580   4.844   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.064   4.573   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      11.103   6.292   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   37                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   36                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   20                                             
CONECT   15   14                                                            
CONECT   16   14   17   36                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   34                                                  
CONECT   20   19   14   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   34                                             
CONECT   24   23                                                            
CONECT   25   23   26   32                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   26                                                       
CONECT   32   25   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   19   23   35                                             
CONECT   35   34                                                            
CONECT   36   16   11                                                       
CONECT   37    9    3   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

View in JSmol

Synonyms

Value	Source
3beta-O-(2'-O-Acetyl-alpha-L-thevetosyl)-14beta-hydroxy-7-en-5beta-card-20(22)-enolide	ChEBI
3b-O-(2'-O-Acetyl-a-L-thevetosyl)-14b-hydroxy-7-en-5b-card-20(22)-enolide	Generator
3Β-O-(2'-O-acetyl-α-L-thevetosyl)-14β-hydroxy-7-en-5β-card-20(22)-enolide	Generator

Chemical Formula

C₃₂H₄₆O₉

Average Mass

574.7110 Da

Monoisotopic Mass

574.31418 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CO[C@@H]1[C@@H](O)[C@H](C)O[C@@H](O[C@H]2CC[C@@]3(C)[C@H](CC=C4[C@@H]3CC[C@]3(C)[C@H](CC[C@]43O)C3=CC(=O)OC3)C2)[C@H]1OC(C)=O

InChI Identifier

InChI=1S/C32H46O9/c1-17-26(35)27(37-5)28(40-18(2)33)29(39-17)41-21-8-11-30(3)20(15-21)6-7-24-23(30)9-12-31(4)22(10-13-32(24,31)36)19-14-25(34)38-16-19/h7,14,17,20-23,26-29,35-36H,6,8-13,15-16H2,1-5H3/t17-,20+,21-,22+,23-,26-,27+,28-,29-,30-,31+,32-/m0/s1

InChI Key

MJWBKZJOFFGTCD-ZSCKLWMASA-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
Cerbera manghas	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal glycosides

Alternative Parents

Substituents

Steroidal glycoside
Steroid lactone
Androstane-skeleton
14-hydroxysteroid
Hydroxysteroid
Delta-7-steroid
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
2-furanone
Oxane
Dicarboxylic acid or derivatives
Monosaccharide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Cyclic alcohol
Dihydrofuran
Carboxylic acid ester
Secondary alcohol
Lactone
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Ether
Acetal
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

acetate ester (CHEBI:65734 )
monosaccharide derivative (CHEBI:65734 )
cardenolide glycoside (CHEBI:65734 )

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

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

8229413

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10053853

PDB ID

Not Available

ChEBI ID

65734

Good Scents ID

Not Available

References

General References

Cheenpracha S, Karalai C, Rat-A-Pa Y, Ponglimanont C, Chantrapromma K: New cytotoxic cardenolide glycoside from the seeds of Cerbera manghas. Chem Pharm Bull (Tokyo). 2004 Aug;52(8):1023-5. doi: 10.1248/cpb.52.1023. [PubMed:15305009 ]
LOTUS database [Link]

Showing NP-Card for 7,8-dehydrocerberin (NP0249897)

MOL for NP0249897 (7,8-dehydrocerberin)

3D MOL for NP0249897 (7,8-dehydrocerberin)

3D SDF for NP0249897 (7,8-dehydrocerberin)

3D-SDF for NP0249897 (7,8-dehydrocerberin)

PDB for NP0249897 (7,8-dehydrocerberin)

3D PDB for NP0249897 (7,8-dehydrocerberin)

SMILES for NP0249897 (7,8-dehydrocerberin)

INCHI for NP0249897 (7,8-dehydrocerberin)

Structure for NP0249897 (7,8-dehydrocerberin)

3D Structure for NP0249897 (7,8-dehydrocerberin)