NP-MRD: Showing NP-Card for (+)-Schweinfurthin E (NP0077138)

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Record Information

Version

2.0

Created at

2022-04-28 22:17:48 UTC

Updated at

2022-04-28 22:17:48 UTC

NP-MRD ID

NP0077138

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Schweinfurthin E

Description

Schweinfurthin E 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 E 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. (+)-Schweinfurthin E is found in Macaranga alnifolia. (+)-Schweinfurthin E was first documented in 2007 (PMID: 17326683). Based on a literature review a small amount of articles have been published on schweinfurthin E (PMID: 31496281) (PMID: 19697910).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200172D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292200172D          

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  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
  1 27  1  0  0  0  0
 26 28  1  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
 25 31  1  0  0  0  0
 30 32  1  6  0  0  0
 29 33  1  6  0  0  0
 28 34  1  0  0  0  0
 28 35  1  0  0  0  0
 25 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0077138

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C2=CC(O)=C(CC=C(C)C)C(O)=C2)=CC2=C1O[C@]1(C)C[C@@H](O)[C@@H](O)C(C)(C)[C@H]1C2

> <INCHI_IDENTIFIER>
InChI=1S/C30H38O6/c1-17(2)7-10-21-22(31)12-19(13-23(21)32)9-8-18-11-20-15-26-29(3,4)28(34)24(33)16-30(26,5)36-27(20)25(14-18)35-6/h7-9,11-14,24,26,28,31-34H,10,15-16H2,1-6H3/b9-8+/t24-,26-,28-,30-/m1/s1

> <INCHI_KEY>
IYHZCJNEODJYKB-DMCZWXATSA-N

> <FORMULA>
C30H38O6

> <MOLECULAR_WEIGHT>
494.628

> <EXACT_MASS>
494.266838944

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
57.08563972399475

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4aR,9aR)-7-[(E)-2-[3,5-dihydroxy-4-(3-methylbut-2-en-1-yl)phenyl]ethenyl]-5-methoxy-1,1,4a-trimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthene-2,3-diol

> <ALOGPS_LOGP>
5.15

> <JCHEM_LOGP>
5.377685060333333

> <ALOGPS_LOGS>
-5.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.914558929423094

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.461808354169468

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1931689536838705

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
143.2629

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.14e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4aR,9aR)-7-[(E)-2-[3,5-dihydroxy-4-(3-methylbut-2-en-1-yl)phenyl]ethenyl]-5-methoxy-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthene-2,3-diol

> <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       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.672  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.338  -6.930   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      16.004   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.057  -2.130   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.611  -2.130   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
CONECT    1    2    6   27                                                  
CONECT    2    1    3   24                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   21                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    9                                                       
CONECT   15   13                                                            
CONECT   16   12   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   11                                                            
CONECT   22    3   23                                                       
CONECT   23   22                                                            
CONECT   24    2   25                                                       
CONECT   25   24   26   31   36                                             
CONECT   26   25   27   28                                                  
CONECT   27   26    1                                                       
CONECT   28   26   29   34   35                                             
CONECT   29   28   30   33                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30   25                                                       
CONECT   32   30                                                            
CONECT   33   29                                                            
CONECT   34   28                                                            
CONECT   35   28                                                            
CONECT   36   25                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
5-O-Methylvedelianin	ChEBI

Chemical Formula

C₃₀H₃₈O₆

Average Mass

494.6280 Da

Monoisotopic Mass

494.26684 Da

IUPAC Name

(2S,3R,4aR,9aR)-7-[(E)-2-[3,5-dihydroxy-4-(3-methylbut-2-en-1-yl)phenyl]ethenyl]-5-methoxy-1,1,4a-trimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthene-2,3-diol

Traditional Name

(2S,3R,4aR,9aR)-7-[(E)-2-[3,5-dihydroxy-4-(3-methylbut-2-en-1-yl)phenyl]ethenyl]-5-methoxy-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthene-2,3-diol

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C2=CC(O)=C(CC=C(C)C)C(O)=C2)=CC2=C1O[C@]1(C)C[C@@H](O)[C@@H](O)C(C)(C)[C@H]1C2

InChI Identifier

InChI=1S/C30H38O6/c1-17(2)7-10-21-22(31)12-19(13-23(21)32)9-8-18-11-20-15-26-29(3,4)28(34)24(33)16-30(26,5)36-27(20)25(14-18)35-6/h7-9,11-14,24,26,28,31-34H,10,15-16H2,1-6H3/b9-8+/t24-,26-,28-,30-/m1/s1

InChI Key

IYHZCJNEODJYKB-DMCZWXATSA-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 alnifolia	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
Anisole
Resorcinol
Styrene
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
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:66435 )
resorcinols (CHEBI:66435 )
cyclic ether (CHEBI:66435 )
stilbenoid (CHEBI:66435 )

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	5.15	ALOGPS
logP	5.38	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	8.46	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	143.26 m³·mol⁻¹	ChemAxon
Polarizability	57.09 Å³	ChemAxon
Number of Rings	4	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

C00040258

Chemspider ID

17273700

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16116472

PDB ID

Not Available

ChEBI ID

66435

Good Scents ID

Not Available

References

General References

Yoder BJ, Cao S, Norris A, Miller JS, Ratovoson F, Razafitsalama J, Andriantsiferana R, Rasamison VE, Kingston DG: Antiproliferative prenylated stilbenes and flavonoids from Macaranga alnifolia from the Madagascar rainforest. J Nat Prod. 2007 Mar;70(3):342-6. doi: 10.1021/np060484y. Epub 2007 Feb 28. [PubMed:17326683 ]
Vu LTN, Anh LT, Cuc NT, Nhiem NX, Tai BH, Van Kiem P, Litaudon M, Thach TD, Van Minh C, Mai HDT, Van Cuong P: Prenylated flavonoids and other constituents from Macaranga indica. Nat Prod Res. 2021 Jul;35(13):2123-2130. doi: 10.1080/14786419.2019.1662007. Epub 2019 Sep 9. [PubMed:31496281 ]
Topczewski JJ, Neighbors JD, Wiemer DF: Total synthesis of (+)-schweinfurthins B and E. J Org Chem. 2009 Sep 18;74(18):6965-72. doi: 10.1021/jo901161m. [PubMed:19697910 ]

Showing NP-Card for (+)-Schweinfurthin E (NP0077138)

MOL for NP0077138 ((+)-Schweinfurthin E)

3D MOL for NP0077138 ((+)-Schweinfurthin E)

3D SDF for NP0077138 ((+)-Schweinfurthin E)

3D-SDF for NP0077138 ((+)-Schweinfurthin E)

PDB for NP0077138 ((+)-Schweinfurthin E)

3D PDB for NP0077138 ((+)-Schweinfurthin E)

SMILES for NP0077138 ((+)-Schweinfurthin E)

INCHI for NP0077138 ((+)-Schweinfurthin E)

Structure for NP0077138 ((+)-Schweinfurthin E)

3D Structure for NP0077138 ((+)-Schweinfurthin E)