NP-MRD: Showing NP-Card for (+)-Schweinfurthin F (NP0077139)

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Record Information

Version

2.0

Created at

2022-04-28 22:17:51 UTC

Updated at

2022-04-28 22:17:51 UTC

NP-MRD ID

NP0077139

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Schweinfurthin F

Description

Schweinfurthin F 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 F 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 F is found in Macaranga alnifolia. (+)-Schweinfurthin F was first documented in 2007 (PMID: 17236766). Based on a literature review a small amount of articles have been published on schweinfurthin F (PMID: 34714084) (PMID: 20869871) (PMID: 20116262).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200172D          

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M  END

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 30 31  1  0  0  0  0
 25 31  1  0  0  0  0
 29 32  1  6  0  0  0
 28 33  1  0  0  0  0
 28 34  1  0  0  0  0
 25 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0077139

> <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)CC[C@@H](O)C(C)(C)[C@H]1C2

> <INCHI_IDENTIFIER>
InChI=1S/C30H38O5/c1-18(2)7-10-22-23(31)14-20(15-24(22)32)9-8-19-13-21-17-26-29(3,4)27(33)11-12-30(26,5)35-28(21)25(16-19)34-6/h7-9,13-16,26-27,31-33H,10-12,17H2,1-6H3/b9-8+/t26-,27-,30-/m1/s1

> <INCHI_KEY>
BUFNPAYKUGAAAO-HLULBIOLSA-N

> <FORMULA>
C30H38O5

> <MOLECULAR_WEIGHT>
478.629

> <EXACT_MASS>
478.271924324

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
56.18133845199956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
6.19

> <JCHEM_LOGP>
6.525382673333332

> <ALOGPS_LOGS>
-5.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.914638880035058

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.461811277828204

> <JCHEM_PKA_STRONGEST_BASIC>
-2.92940373229317

> <JCHEM_POLAR_SURFACE_AREA>
79.15

> <JCHEM_REFRACTIVITY>
141.945

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.03e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(E)-2-[(7R,8aR,10aR)-7-hydroxy-4-methoxy-8,8,10a-trimethyl-6,7,8a,9-tetrahydro-5H-xanthen-2-yl]ethenyl]-2-(3-methylbut-2-en-1-yl)benzene-1,3-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  -0.770   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.057  -2.130   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.611  -2.130   0.000  0.00  0.00           C+0
HETATM   35  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   35                                             
CONECT   26   25   27   28                                                  
CONECT   27   26    1                                                       
CONECT   28   26   29   33   34                                             
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30   25                                                       
CONECT   32   29                                                            
CONECT   33   28                                                            
CONECT   34   28                                                            
CONECT   35   25                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
(S,S,S)-Schweinfurthin F	MeSH
(R,R,R)-Schweinfurthin F	MeSH

Chemical Formula

C₃₀H₃₈O₅

Average Mass

478.6290 Da

Monoisotopic Mass

478.27192 Da

IUPAC Name

5-[(E)-2-[(2R,4aR,9aR)-2-hydroxy-5-methoxy-1,1,4a-trimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthen-7-yl]ethenyl]-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol

Traditional Name

5-[(E)-2-[(7R,8aR,10aR)-7-hydroxy-4-methoxy-8,8,10a-trimethyl-6,7,8a,9-tetrahydro-5H-xanthen-2-yl]ethenyl]-2-(3-methylbut-2-en-1-yl)benzene-1,3-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)CC[C@@H](O)C(C)(C)[C@H]1C2

InChI Identifier

InChI=1S/C30H38O5/c1-18(2)7-10-22-23(31)14-20(15-24(22)32)9-8-19-13-21-17-26-29(3,4)27(33)11-12-30(26,5)35-28(21)25(16-19)34-6/h7-9,13-16,26-27,31-33H,10-12,17H2,1-6H3/b9-8+/t26-,27-,30-/m1/s1

InChI Key

BUFNPAYKUGAAAO-HLULBIOLSA-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
Styrene
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Cyclic alcohol
Secondary alcohol
Ether
Oxacycle
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:66436 )
resorcinols (CHEBI:66436 )
cyclic ether (CHEBI:66436 )
stilbenoid (CHEBI:66436 )

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	6.19	ALOGPS
logP	6.53	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	8.46	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.15 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	141.94 m³·mol⁻¹	ChemAxon
Polarizability	56.18 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

C00040259

Chemspider ID

17625380

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16721018

PDB ID

Not Available

ChEBI ID

66436

Good Scents ID

Not Available

References

General References

Schroeder CM, Dey PN, Beutler JA, Wiemer DF: Synthesis of a Coumarin-Based Analogue of Schweinfurthin F. J Org Chem. 2021 Dec 3;86(23):16824-16833. doi: 10.1021/acs.joc.1c02046. Epub 2021 Oct 29. [PubMed:34714084 ]
Ulrich NC, Kuder CH, Hohl RJ, Wiemer DF: Biologically active biotin derivatives of schweinfurthin F. Bioorg Med Chem Lett. 2010 Nov 15;20(22):6716-20. doi: 10.1016/j.bmcl.2010.08.143. Epub 2010 Sep 6. [PubMed:20869871 ]
Ulrich NC, Kodet JG, Mente NR, Kuder CH, Beutler JA, Hohl RJ, Wiemer DF: Structural analogues of schweinfurthin F: probing the steric, electronic, and hydrophobic properties of the D-ring substructure. Bioorg Med Chem. 2010 Feb 15;18(4):1676-83. doi: 10.1016/j.bmc.2009.12.063. Epub 2010 Jan 4. [PubMed:20116262 ]
Mente NR, Wiemer AJ, Neighbors JD, Beutler JA, Hohl RJ, Wiemer DF: Total synthesis of (R,R,R)- and (S,S,S)-schweinfurthin F: differences of bioactivity in the enantiomeric series. Bioorg Med Chem Lett. 2007 Feb 15;17(4):911-5. doi: 10.1016/j.bmcl.2006.11.096. Epub 2006 Dec 12. [PubMed:17236766 ]

Showing NP-Card for (+)-Schweinfurthin F (NP0077139)

MOL for NP0077139 ((+)-Schweinfurthin F)

3D MOL for NP0077139 ((+)-Schweinfurthin F)

3D SDF for NP0077139 ((+)-Schweinfurthin F)

3D-SDF for NP0077139 ((+)-Schweinfurthin F)

PDB for NP0077139 ((+)-Schweinfurthin F)

3D PDB for NP0077139 ((+)-Schweinfurthin F)

SMILES for NP0077139 ((+)-Schweinfurthin F)

INCHI for NP0077139 ((+)-Schweinfurthin F)

Structure for NP0077139 ((+)-Schweinfurthin F)

3D Structure for NP0077139 ((+)-Schweinfurthin F)