NP-MRD: Showing NP-Card for (+)-Schweinfurthin A (NP0083196)

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Record Information

Version

2.0

Created at

2022-04-29 04:14:34 UTC

Updated at

2022-04-29 04:14:34 UTC

NP-MRD ID

NP0083196

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Schweinfurthin A

Description

Schweinfurthin A belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring. (+)-Schweinfurthin A is found in Macaranga schweinfurthii. (+)-Schweinfurthin A was first documented in 2002 (PMID: 12375907). Based on a literature review a significant number of articles have been published on Schweinfurthin A (PMID: 20000454) (PMID: 31813476) (PMID: 24515854) (PMID: 21822274) (PMID: 21226493) (PMID: 20442305).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206142D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292206142D          

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   -2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  4 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  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  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 28 35  1  0  0  0  0
 21 36  1  0  0  0  0
 13 37  1  0  0  0  0
  4 38  1  6  0  0  0
  2 39  1  6  0  0  0
  1 40  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0083196

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\CC1=C(O)C=C(\C=C\C2=CC3=C(O[C@]4(C)C[C@@H](O)[C@@H](O)C(C)(C)[C@H]4C3)C(O)=C2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C34H44O6/c1-20(2)8-7-9-21(3)10-13-25-26(35)15-23(16-27(25)36)12-11-22-14-24-18-30-33(4,5)32(39)29(38)19-34(30,6)40-31(24)28(37)17-22/h8,10-12,14-17,29-30,32,35-39H,7,9,13,18-19H2,1-6H3/b12-11+,21-10+/t29-,30-,32-,34-/m1/s1

> <INCHI_KEY>
HSDZWMOBUPRZEU-LXYWBZBZSA-N

> <FORMULA>
C34H44O6

> <MOLECULAR_WEIGHT>
548.72

> <EXACT_MASS>
548.313789137

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
64.4040459795856

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4aR,9aR)-7-[(E)-2-{4-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3,5-dihydroxyphenyl}ethenyl]-1,1,4a-trimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthene-2,3,5-triol

> <ALOGPS_LOGP>
5.76

> <JCHEM_LOGP>
6.891505279333334

> <ALOGPS_LOGS>
-5.52

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.340865059661803

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.415853763536479

> <JCHEM_PKA_STRONGEST_BASIC>
-3.193168952938845

> <JCHEM_POLAR_SURFACE_AREA>
110.38000000000001

> <JCHEM_REFRACTIVITY>
162.5832000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.65e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
schweinfurthin A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.945   3.670   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.391   3.670   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -5.335   6.160   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -9.336   8.470   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -8.002  10.780   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.668  13.090   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -10.669   6.160   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6   40                                                  
CONECT    2    1    3   39                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12   38                                             
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7    8                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    4                                                       
CONECT   13   11   14   37                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15   10                                                       
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   36                                                  
CONECT   22   21   23   26                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   19                                                       
CONECT   25   23                                                            
CONECT   26   22   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   35                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   28                                                            
CONECT   36   21                                                            
CONECT   37   13                                                            
CONECT   38    4                                                            
CONECT   39    2                                                            
CONECT   40    1                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₄₄O₆

Average Mass

548.7200 Da

Monoisotopic Mass

548.31379 Da

IUPAC Name

(2S,3R,4aR,9aR)-7-[(E)-2-{4-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3,5-dihydroxyphenyl}ethenyl]-1,1,4a-trimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthene-2,3,5-triol

Traditional Name

schweinfurthin A

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC1=C(O)C=C(\C=C\C2=CC3=C(O[C@]4(C)C[C@@H](O)[C@@H](O)C(C)(C)[C@H]4C3)C(O)=C2)C=C1O

InChI Identifier

InChI=1S/C34H44O6/c1-20(2)8-7-9-21(3)10-13-25-26(35)15-23(16-27(25)36)12-11-22-14-24-18-30-33(4,5)32(39)29(38)19-34(30,6)40-31(24)28(37)17-22/h8,10-12,14-17,29-30,32,35-39H,7,9,13,18-19H2,1-6H3/b12-11+,21-10+/t29-,30-,32-,34-/m1/s1

InChI Key

HSDZWMOBUPRZEU-LXYWBZBZSA-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
Macaranga schweinfurthii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthenes

Alternative Parents

Substituents

Xanthene
Stilbene
Aromatic monoterpenoid
Monoterpenoid
Styrene
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Cyclic alcohol
1,2-diol
Secondary alcohol
Oxacycle
Ether
Polyol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen 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	5.76	ALOGPS
logP	6.89	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	8.42	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	162.58 m³·mol⁻¹	ChemAxon
Polarizability	64.4 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00050220

Chemspider ID

558606

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

643462

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Klausmeyer P, Van QN, Jato J, McCloud TG, Beutler JA: Schweinfurthins I and J from Macaranga schweinfurthii. J Nat Prod. 2010 Mar 26;73(3):479-81. doi: 10.1021/np9006348. [PubMed:20000454 ]
Treadwell EM, Neighbors JD, Wiemer DF: A cascade cyclization approach to schweinfurthin B. Org Lett. 2002 Oct 17;4(21):3639-42. doi: 10.1021/ol0266368. [PubMed:12375907 ]
Moosavi B, Gao M, Zhu XL, Yang GF: The anti-cancer compound Schweinfurthin A targets Osh2 and disrupts lipid metabolism in the yeast model. Bioorg Chem. 2020 Jan;94:103471. doi: 10.1016/j.bioorg.2019.103471. Epub 2019 Nov 25. [PubMed:31813476 ]
Lockett S, Verma C, Brafman A, Gudla P, Nandy K, Mimaki Y, Fuchs PL, Jaja J, Reilly KM, Beutler J, Turbyville TJ: Quantitative analysis of F-actin redistribution in astrocytoma cells treated with candidate pharmaceuticals. Cytometry A. 2014 Jun;85(6):512-21. doi: 10.1002/cyto.a.22442. Epub 2014 Feb 11. [PubMed:24515854 ]
Burgett AW, Poulsen TB, Wangkanont K, Anderson DR, Kikuchi C, Shimada K, Okubo S, Fortner KC, Mimaki Y, Kuroda M, Murphy JP, Schwalb DJ, Petrella EC, Cornella-Taracido I, Schirle M, Tallarico JA, Shair MD: Natural products reveal cancer cell dependence on oxysterol-binding proteins. Nat Chem Biol. 2011 Aug 7;7(9):639-47. doi: 10.1038/nchembio.625. [PubMed:21822274 ]
Topczewski JJ, Kodet JG, Wiemer DF: Exploration of cascade cyclizations terminated by tandem aromatic substitution: total synthesis of (+)-schweinfurthin A. J Org Chem. 2011 Feb 4;76(3):909-19. doi: 10.1021/jo1022102. Epub 2011 Jan 12. [PubMed:21226493 ]
Turbyville TJ, Gursel DB, Tuskan RG, Walrath JC, Lipschultz CA, Lockett SJ, Wiemer DF, Beutler JA, Reilly KM: Schweinfurthin A selectively inhibits proliferation and Rho signaling in glioma and neurofibromatosis type 1 tumor cells in a NF1-GRD-dependent manner. Mol Cancer Ther. 2010 May;9(5):1234-43. doi: 10.1158/1535-7163.MCT-09-0834. Epub 2010 May 4. [PubMed:20442305 ]
Cui C, JaJa J, Turbyville T, Beutler J, Gudla P, Nandy K, Lockett S: Quantifying the astrocytoma cell response to candidate pharmaceutical from F-ACTIN image analysis. Annu Int Conf IEEE Eng Med Biol Soc. 2009;2009:5768-71. doi: 10.1109/IEMBS.2009.5332528. [PubMed:19963655 ]

Showing NP-Card for (+)-Schweinfurthin A (NP0083196)

MOL for NP0083196 ((+)-Schweinfurthin A)

3D MOL for NP0083196 ((+)-Schweinfurthin A)

3D SDF for NP0083196 ((+)-Schweinfurthin A)

3D-SDF for NP0083196 ((+)-Schweinfurthin A)

PDB for NP0083196 ((+)-Schweinfurthin A)

3D PDB for NP0083196 ((+)-Schweinfurthin A)

SMILES for NP0083196 ((+)-Schweinfurthin A)

INCHI for NP0083196 ((+)-Schweinfurthin A)

Structure for NP0083196 ((+)-Schweinfurthin A)

3D Structure for NP0083196 ((+)-Schweinfurthin A)