NP-MRD: Showing NP-Card for Psorospermin (NP0051707)

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Record Information

Version

2.0

Created at

2022-04-27 22:58:21 UTC

Updated at

2022-04-27 22:58:21 UTC

NP-MRD ID

NP0051707

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Psorospermin

Description

Psorospermin belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. Psorospermin 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. Psorospermin is found in psorospermum febrifugum and Psorospermum spp.. Psorospermin was first documented in 2005 (PMID: 16275994). Based on a literature review a significant number of articles have been published on psorospermin (PMID: 33935707) (PMID: 21885273) (PMID: 19926174) (PMID: 19594412) (PMID: 19191562) (PMID: 19149484).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200582D          

 25 29  0  0  1  0            999 V2000
    4.2442   -0.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9947   -1.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1889   -1.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6327   -0.6290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8822    0.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6880    0.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0956    1.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9037    0.8856    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9956    0.0658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5130    1.4419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2758    1.7562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1666    0.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0711    2.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3260    0.7666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5202    0.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2707   -0.1968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8269   -0.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5774   -1.5924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649   -0.3739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0913    0.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1582    1.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9640    1.1989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2136    1.9852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9394   -2.0247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1336   -2.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  8 10  1  6  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  1  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  2  0  0  0  0
 16 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 15 22  2  0  0  0  0
 22 23  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END

     RDKit          3D

 41 45  0  0  0  0  0  0  0  0999 V2000
   -0.5135    4.5521    1.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0232    3.2653    1.0950 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4356    2.2578    0.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7653    2.4066   -0.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3296    1.3684   -1.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6501    0.1673   -1.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5582    0.0052   -0.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1923   -1.1401   -0.4417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3479   -1.3555    0.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9776   -2.5811    0.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3477   -3.5623   -0.6364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1721   -2.8414    0.7486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7813   -1.8502    1.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1479   -0.6101    1.5646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9532   -0.3623    0.9256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3086    0.8572    0.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8291    1.7930    1.6522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1085    1.0419    0.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4584   -0.7584   -1.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8278   -0.0945   -1.8675 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6107   -0.5926   -0.6936 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0776   -2.0246   -0.8047 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0830    0.2156    0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8048   -0.3839    0.5423 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4996    1.2606   -1.8075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3842    5.2351    1.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1243    4.8965    0.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1931    4.6636    2.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2693    3.3508   -0.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7762   -4.4664   -0.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6207   -3.8387    0.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7159   -2.0592    1.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6120    0.1772    2.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0767   -0.8506   -2.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4721   -1.7428   -1.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3382   -0.3189   -2.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4032   -2.7014   -0.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1217   -2.1400   -0.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0341   -2.3884   -1.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0106    1.3192    0.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9042   -0.1696    1.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 18  2  0
 18 16  1  0
 16 17  2  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
 12 10  1  0
 10 11  1  0
 10  9  2  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6 19  1  0
 19 20  1  0
 20 25  1  0
 25  5  1  0
  5  4  2  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
  4  3  1  0
 24 21  1  0
  7 18  1  0
  5  6  1  0
  9 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 14 33  1  0
 13 32  1  0
 12 31  1  0
 11 30  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  6
  4 29  1  0
 22 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  1  0
 23 41  1  0
M  END


  Mrv1652304282200582D          

 25 29  0  0  1  0            999 V2000
    4.2442   -0.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9947   -1.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1889   -1.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6327   -0.6290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8822    0.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6880    0.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0956    1.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9037    0.8856    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9956    0.0658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5130    1.4419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2758    1.7562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1666    0.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0711    2.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3260    0.7666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5202    0.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2707   -0.1968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8269   -0.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5774   -1.5924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649   -0.3739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0913    0.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1582    1.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9640    1.1989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2136    1.9852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9394   -2.0247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1336   -2.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  8 10  1  6  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  1  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  2  0  0  0  0
 16 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 15 22  2  0  0  0  0
 22 23  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051707

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C(=O)C3=CC=CC(O)=C3OC2=C2C[C@@H](OC2=C1)[C@@]1(C)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C19H16O6/c1-19(8-23-19)14-6-10-12(24-14)7-13(22-2)15-16(21)9-4-3-5-11(20)17(9)25-18(10)15/h3-5,7,14,20H,6,8H2,1-2H3/t14-,19-/m1/s1

> <INCHI_KEY>
BBNDPXOGORGETN-AUUYWEPGSA-N

> <FORMULA>
C19H16O6

> <MOLECULAR_WEIGHT>
340.331

> <EXACT_MASS>
340.094688235

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
34.45865695697759

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-10-hydroxy-5-methoxy-2-[(2R)-2-methyloxiran-2-yl]-1H,2H,6H-furo[2,3-c]xanthen-6-one

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
2.5622312303333326

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.8810279329576165

> <JCHEM_PKA_STRONGEST_BASIC>
-3.618565819718517

> <JCHEM_POLAR_SURFACE_AREA>
77.52000000000001

> <JCHEM_REFRACTIVITY>
88.08630000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
psorospermin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       7.923  -0.513   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.457  -1.981   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.953  -2.312   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.914  -1.174   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.380   0.294   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.884   0.624   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.645   1.963   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.154   1.653   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.325   0.123   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.291   2.691   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.715   3.278   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      11.511   1.752   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.466   3.992   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.342   1.431   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.838   1.100   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.372  -0.367   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.410  -1.505   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.944  -2.973   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.868  -0.698   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.170   0.440   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.295   1.907   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.800   2.238   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.265   3.706   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.487  -3.779   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.983  -4.110   0.000  0.00  0.00           C+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6   14                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8    1                                                       
CONECT   10    8   11   12   13                                             
CONECT   11   10   12                                                       
CONECT   12   11   10                                                       
CONECT   13   10                                                            
CONECT   14    5   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16    4   18                                                  
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   15   23                                                  
CONECT   23   22                                                            
CONECT   24    3   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Value	Source
Psorospermine	MeSH

Chemical Formula

C₁₉H₁₆O₆

Average Mass

340.3310 Da

Monoisotopic Mass

340.09469 Da

IUPAC Name

(2R)-10-hydroxy-5-methoxy-2-[(2R)-2-methyloxiran-2-yl]-1H,2H,6H-furo[2,3-c]xanthen-6-one

Traditional Name

psorospermin

CAS Registry Number

Not Available

SMILES

COC1=C2C(=O)C3=CC=CC(O)=C3OC2=C2C[C@@H](OC2=C1)[C@@]1(C)CO1

InChI Identifier

InChI=1S/C19H16O6/c1-19(8-23-19)14-6-10-12(24-14)7-13(22-2)15-16(21)9-4-3-5-11(20)17(9)25-18(10)15/h3-5,7,14,20H,6,8H2,1-2H3/t14-,19-/m1/s1

InChI Key

BBNDPXOGORGETN-AUUYWEPGSA-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
Psorospermum febrifugum	-	KNApSAcK
Psorospermum spp.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Xanthone
Chromone
Coumaran
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous ester
Dialkyl ether
Oxirane
Ether
Oxacycle
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotetracyclic compound (CHEBI:8617 )
epoxide (CHEBI:8617 )
xanthones (CHEBI:8617 )
xanthenes (C10090 )

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	2.98	ALOGPS
logP	2.56	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.88	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.52 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	88.09 m³·mol⁻¹	ChemAxon
Polarizability	34.46 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00002972

Chemspider ID

112368

KEGG Compound ID

C10090

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

126451

PDB ID

Not Available

ChEBI ID

8617

Good Scents ID

Not Available

References

General References

Anywar G, Kakudidi E, Byamukama R, Mukonzo J, Schubert A, Oryem-Origa H, Jassoy C: A Review of the Toxicity and Phytochemistry of Medicinal Plant Species Used by Herbalists in Treating People Living With HIV/AIDS in Uganda. Front Pharmacol. 2021 Apr 15;12:615147. doi: 10.3389/fphar.2021.615147. eCollection 2021. [PubMed:33935707 ]
Kang JA, Yang Z, Lee JY, De U, Kim TH, Park JY, Lee HJ, Park YJ, Chun P, Kim HS, Jeong LS, Moon HR: Design, synthesis and anticancer activity of novel dihydrobenzofuro[4,5-b][1,8]naphthyridin-6-one derivatives. Bioorg Med Chem Lett. 2011 Oct 1;21(19):5730-4. doi: 10.1016/j.bmcl.2011.08.016. Epub 2011 Aug 18. [PubMed:21885273 ]
Boutefnouchet S, Minh NT, Putrus R, Pfeiffer B, Leonce S, Pierre A, Michel S, Tillequin F, Lallemand MC: Synthesis and cytotoxic activity of psorospermin and acronycine analogues in the 3-propyloxy-acridin-9(10H)-one and -benzo[b]acridin-125H-one series. Eur J Med Chem. 2010 Feb;45(2):581-7. doi: 10.1016/j.ejmech.2009.10.045. Epub 2009 Nov 4. [PubMed:19926174 ]
Nguyen QC, Nguyen TT, Yougnia R, Gaslonde T, Dufat H, Michel S, Tillequin F: Acronycine derivatives: a promising series of anticancer agents. Anticancer Agents Med Chem. 2009 Sep;9(7):804-15. doi: 10.2174/187152009789056921. Epub 2009 Sep 1. [PubMed:19594412 ]
Nguyen HT, Lallemand MC, Boutefnouchet S, Michel S, Tillequin F: Antitumor psoropermum xanthones and sarcomelicope acridones: privileged structures implied in DNA alkylation. J Nat Prod. 2009 Mar 27;72(3):527-39. doi: 10.1021/np800644y. [PubMed:19191562 ]
Pouli N, Marakos P: Fused xanthone derivatives as antiproliferative agents. Anticancer Agents Med Chem. 2009 Jan;9(1):77-98. doi: 10.2174/187152009787047699. [PubMed:19149484 ]
Carey SS, Gleason-Guzman M, Gokhale V, Hurley LH: Psorospermin structural requirements for P-glycoprotein resistance reversal. Mol Cancer Ther. 2008 Nov;7(11):3617-23. doi: 10.1158/1535-7163.MCT-08-0519. [PubMed:19001443 ]
Boutefnouchet S, Gaboriaud-Kolar N, Nguyen TM, Depauw S, David-Cordonnier MH, Pfeiffer B, Leonce S, Pierre A, Tillequin F, Lallemand MC, Michel S: Synthesis, cytotoxic activity, and mechanism of action of furo[2,3-c]acridin-6-one and benzo[b]furo[3,2-h]acridin-6-one analogues of psorospermin and acronycine. J Med Chem. 2008 Nov 27;51(22):7287-97. doi: 10.1021/jm8009487. [PubMed:18947222 ]
Fellows IM, Schwaebe M, Dexheimer TS, Vankayalapati H, Gleason-Guzman M, Whitten JP, Hurley LH: Determination of the importance of the stereochemistry of psorospermin in topoisomerase II-induced alkylation of DNA and in vitro and in vivo biological activity. Mol Cancer Ther. 2005 Nov;4(11):1729-39. doi: 10.1158/1535-7163.MCT-05-0183. [PubMed:16275994 ]
Pinto MM, Sousa ME, Nascimento MS: Xanthone derivatives: new insights in biological activities. Curr Med Chem. 2005;12(21):2517-38. doi: 10.2174/092986705774370691. [PubMed:16250875 ]

Showing NP-Card for Psorospermin (NP0051707)

MOL for NP0051707 (Psorospermin)

3D MOL for NP0051707 (Psorospermin)

3D SDF for NP0051707 (Psorospermin)

3D-SDF for NP0051707 (Psorospermin)

PDB for NP0051707 (Psorospermin)

3D PDB for NP0051707 (Psorospermin)

SMILES for NP0051707 (Psorospermin)

INCHI for NP0051707 (Psorospermin)

Structure for NP0051707 (Psorospermin)

3D Structure for NP0051707 (Psorospermin)