NP-MRD: Showing NP-Card for simalikalactone d (NP0330944)

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Record Information

Version

2.0

Created at

2022-09-12 16:47:15 UTC

Updated at

2022-09-12 16:47:16 UTC

NP-MRD ID

NP0330944

Secondary Accession Numbers

None

Natural Product Identification

Common Name

simalikalactone d

Description

Simalikalactone D is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. simalikalactone d is found in Leitneria floridana, Quassia africana, Quassia amara, Simaba guianensis and Simaba orinocensis. simalikalactone d was first documented in 1985 (PMID: 17340534). Based on a literature review a small amount of articles have been published on simalikalactone D (PMID: 11141127) (PMID: 11842321) (PMID: 16730421) (PMID: 8289064).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122218472D          

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M  END

     RDKit          2D

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M  END


  Mrv1652309122218472D          

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M  END
> <DATABASE_ID>
NP0330944

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](C)C(=O)O[C@@H]1[C@H]2[C@@]3(C)OC[C@]22[C@@H](C[C@H]4C(C)=CC(=O)[C@@H](O)[C@]4(C)[C@H]2[C@@H](O)[C@@H]3O)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O9/c1-6-10(2)21(30)34-16-18-24(5)20(29)15(27)17-23(4)12(11(3)7-13(26)19(23)28)8-14(33-22(16)31)25(17,18)9-32-24/h7,10,12,14-20,27-29H,6,8-9H2,1-5H3/t10-,12+,14-,15-,16-,17-,18+,19-,20+,23+,24-,25-/m1/s1

> <INCHI_KEY>
OKIKYYZNNZCZRX-ZPUVFWQWSA-N

> <FORMULA>
C25H34O9

> <MOLECULAR_WEIGHT>
478.538

> <EXACT_MASS>
478.220282675

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
48.58881144878348

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,3R,6R,8S,12S,13S,14R,15R,16S,17R)-12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-9-en-3-yl (2R)-2-methylbutanoate

> <JCHEM_LOGP>
0.5388179093333324

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.257162559532738

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.66032395199369

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3139924370582197

> <JCHEM_POLAR_SURFACE_AREA>
139.59

> <JCHEM_REFRACTIVITY>
117.23200000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3R,6R,8S,12S,13S,14R,15R,16S,17R)-12,15,16-trihydroxy-9,13,17-trimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-9-en-3-yl (2R)-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.574   9.007   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.162   7.584   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.224   6.363   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.303   6.565   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.812   4.940   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.338   4.737   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.127   3.719   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.654   3.921   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.299   5.303   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.878   6.784   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.837   5.378   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.675   4.083   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.204   4.411   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.220   3.260   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.740   3.509   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.284   4.949   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.715   2.317   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.171   0.876   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.146  -0.315   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.651   0.627   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.107  -0.813   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.676   1.819   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.114   0.385   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.143   1.605   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.832   0.108   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.978  -0.920   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.385  -0.362   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.964  -1.844   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.372   0.831   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.446  -0.400   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.035   1.432   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.831   2.794   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.884   2.676   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.763   2.606   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   34                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   33                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   14   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25   33                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31   34                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   12   24   34                                             
CONECT   34   33    8   29                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
(+)-Simalikalactone	ChEBI

Chemical Formula

C₂₅H₃₄O₉

Average Mass

478.5380 Da

Monoisotopic Mass

478.22028 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC[C@@H](C)C(=O)O[C@@H]1[C@H]2[C@@]3(C)OC[C@]22[C@@H](C[C@H]4C(C)=CC(=O)[C@@H](O)[C@]4(C)[C@H]2[C@@H](O)[C@@H]3O)OC1=O

InChI Identifier

InChI=1S/C25H34O9/c1-6-10(2)21(30)34-16-18-24(5)20(29)15(27)17-23(4)12(11(3)7-13(26)19(23)28)8-14(33-22(16)31)25(17,18)9-32-24/h7,10,12,14-20,27-29H,6,8-9H2,1-5H3/t10-,12+,14-,15-,16-,17-,18+,19-,20+,23+,24-,25-/m1/s1

InChI Key

OKIKYYZNNZCZRX-ZPUVFWQWSA-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
Leitneria floridana	LOTUS Database	35616633
Quassia africana	LOTUS Database	35616633
Quassia amara	LOTUS Database	35616633
Simaba guianensis	LOTUS Database	35616633
Simaba orinocensis	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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

C00003731

Chemspider ID

23327078

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15161842

PDB ID

Not Available

ChEBI ID

66486

Good Scents ID

Not Available

References

General References

Xu Z, Chang FR, Wang HK, Kashiwada Y, McPhail AT, Bastow KF, Tachibana Y, Cosentino M, Lee KH: Anti-HIV agents 45(1) and antitumor agents 205.(2) two new sesquiterpenes, leitneridanins A and B, and the cytotoxic and anti-HIV principles from Leitneria floridana. J Nat Prod. 2000 Dec;63(12):1712-5. doi: 10.1021/np000260u. [PubMed:11141127 ]
Apers S, Cimanga K, Vanden Berghe D, Van Meenen E, Longanga AO, Foriers A, Vlietinck A, Pieters L: Antiviral activity of simalikalactone D, a quassinoid from Quassia africana. Planta Med. 2002 Jan;68(1):20-4. doi: 10.1055/s-2002-19870. [PubMed:11842321 ]
Bertani S, Houel E, Stien D, Chevolot L, Jullian V, Garavito G, Bourdy G, Deharo E: Simalikalactone D is responsible for the antimalarial properties of an Amazonian traditional remedy made with Quassia amara L. (Simaroubaceae). J Ethnopharmacol. 2006 Nov 3;108(1):155-7. doi: 10.1016/j.jep.2006.04.017. Epub 2006 Apr 27. [PubMed:16730421 ]
Arisawa M, Fujita A, Morita N, Kinghorn AD, Cordell GA, Farnsworth NR: Plant Anticancer Agents XXXV. Further Constituents of Simaba multiflora1,2. Planta Med. 1985 Aug;51(4):348-9. doi: 10.1055/s-2007-969512. [PubMed:17340534 ]
Cabral JA, McChesney JD, Milhous WK: A new antimalarial quassinoid from Simaba guianensis. J Nat Prod. 1993 Nov;56(11):1954-61. doi: 10.1021/np50101a014. [PubMed:8289064 ]
LOTUS database [Link]

Showing NP-Card for simalikalactone d (NP0330944)

MOL for NP0330944 (simalikalactone d)

3D MOL for NP0330944 (simalikalactone d)

3D SDF for NP0330944 (simalikalactone d)

3D-SDF for NP0330944 (simalikalactone d)

PDB for NP0330944 (simalikalactone d)

3D PDB for NP0330944 (simalikalactone d)

SMILES for NP0330944 (simalikalactone d)

INCHI for NP0330944 (simalikalactone d)

Structure for NP0330944 (simalikalactone d)

3D Structure for NP0330944 (simalikalactone d)