NP-MRD: Showing NP-Card for (5s,6s)-5,16-dihydroxy-6-(2-hydroxypropan-2-yl)-7,11,19-trioxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-20-one (NP0193513)

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Record Information

Version

2.0

Created at

2022-09-04 10:58:23 UTC

Updated at

2022-09-04 10:58:24 UTC

NP-MRD ID

NP0193513

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5s,6s)-5,16-dihydroxy-6-(2-hydroxypropan-2-yl)-7,11,19-trioxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-20-one

Description

CHEMBL3577249 belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. (5s,6s)-5,16-dihydroxy-6-(2-hydroxypropan-2-yl)-7,11,19-trioxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-20-one is found in Cullen corylifolium. Based on a literature review very few articles have been published on CHEMBL3577249.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042212582D          

 27 31  0  0  1  0            999 V2000
   -1.2944   -4.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4700   -4.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4410   -5.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4989   -3.7150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3545   -4.5105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8157   -3.8264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6088   -4.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3083   -3.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0369   -4.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8120   -3.7211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3201   -4.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1431   -4.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6043   -3.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4273   -3.8018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7891   -4.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6121   -4.6006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3279   -5.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5049   -5.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0438   -5.8540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208   -5.7966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7596   -6.4807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8589   -5.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0658   -4.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3663   -5.2653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6378   -4.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8626   -5.1605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6354   -5.9536    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
  2  4  1  0  0  0  0
  5  2  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 11 22  2  0  0  0  0
 22 23  1  0  0  0  0
  9 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  6  0  0  0
M  END

     RDKit          3D

 43 47  0  0  0  0  0  0  0  0999 V2000
   -5.2825    1.8392    0.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5903    0.5417    0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6019    0.2993    1.6146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5123   -0.5212    0.5440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9331    0.4723   -0.8604 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9766    1.4761   -1.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7045    0.9627   -0.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4736    1.6266   -0.6632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6870    0.9314   -0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9571    1.2835   -0.2444 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6769    0.1917   -0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0229   -0.0486    0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8755    1.0214    0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2124    0.7735    0.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7326   -0.4960    0.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1054   -0.6988    0.8675 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5096   -1.3330    0.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6688   -2.3534    0.2104 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3848   -2.1761   -0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6229   -3.1728   -0.0899 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8559   -0.9138   -0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5941   -0.4430   -0.3889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5951   -1.1152   -0.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7790   -0.4003   -0.7840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1790   -0.8316   -0.9957 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3115   -1.3083   -2.3067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7460    2.4303    1.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4257    2.4516   -0.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2809    1.6222    1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0094    0.6748    2.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4271   -0.7815    1.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6540    0.8610    1.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3097   -0.3491    0.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7142    0.5602   -1.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4441    2.6991   -0.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4676    2.0113    0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8798    1.6445    0.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4766   -0.7342    1.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2147   -2.5886    0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6694   -2.1836   -0.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5084   -1.5868   -0.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6849   -0.7708   -2.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 23 22  1  0
 22 11  2  0
 11 10  1  0
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 12 13  2  0
 13 14  1  0
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 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 26  5  1  0
 20 22  1  0
 25  7  1  0
 18 12  1  0
 10  9  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  5 35  1  6
  8 36  1  0
 24 41  1  0
 26 42  1  1
 27 43  1  0
 13 37  1  0
 14 38  1  0
 16 39  1  0
 17 40  1  0
M  END


  Mrv1652309042212582D          

 27 31  0  0  1  0            999 V2000
   -1.2944   -4.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4700   -4.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4410   -5.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4989   -3.7150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3545   -4.5105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8157   -3.8264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6088   -4.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3083   -3.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0369   -4.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8120   -3.7211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3201   -4.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1431   -4.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6043   -3.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4273   -3.8018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7891   -4.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6121   -4.6006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3279   -5.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5049   -5.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0438   -5.8540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208   -5.7966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7596   -6.4807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8589   -5.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0658   -4.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3663   -5.2653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6378   -4.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8626   -5.1605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6354   -5.9536    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
  2  4  1  0  0  0  0
  5  2  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 11 22  2  0  0  0  0
 22 23  1  0  0  0  0
  9 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0193513

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)[C@H]1OC2=CC3=C(C=C2[C@@H]1O)C1=C(O3)C2=CC=C(O)C=C2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O7/c1-20(2,24)18-16(22)11-6-10-13(7-14(11)26-18)25-17-9-4-3-8(21)5-12(9)27-19(23)15(10)17/h3-7,16,18,21-22,24H,1-2H3/t16-,18-/m0/s1

> <INCHI_KEY>
ZJBOZZWXWWQLRJ-WMZOPIPTSA-N

> <FORMULA>
C20H16O7

> <MOLECULAR_WEIGHT>
368.341

> <EXACT_MASS>
368.089602855

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
37.624403371367904

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6S)-5,16-dihydroxy-6-(2-hydroxypropan-2-yl)-7,11,19-trioxapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-1(12),2(10),3,8,13,15,17-heptaen-20-one

> <JCHEM_LOGP>
1.7309244886666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.975336360218588

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.1150326061325

> <JCHEM_PKA_STRONGEST_BASIC>
-3.052734147248945

> <JCHEM_POLAR_SURFACE_AREA>
109.36

> <JCHEM_REFRACTIVITY>
93.63839999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6S)-5,16-dihydroxy-6-(2-hydroxypropan-2-yl)-7,11,19-trioxapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-1(12),2(10),3,8,13,15,17-heptaen-20-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.416  -8.528   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.877  -8.474   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.823 -10.013   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.931  -6.935   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.662  -8.420   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.523  -7.143   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.003  -7.567   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.309  -6.750   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.669  -7.473   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.116  -6.946   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.064  -8.159   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.600  -8.267   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.461  -6.990   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.998  -7.097   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.673  -8.481   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.209  -8.588   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.812  -9.758   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.276  -9.651   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.415 -10.927   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.879 -10.820   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.018 -12.097   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.203  -9.436   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.723  -9.012   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.417  -9.829   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.057  -9.106   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.610  -9.633   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.186 -11.113   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   25                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   23                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   11   23                                                  
CONECT   23   22    9   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24    7   26                                                  
CONECT   26   25    5   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₆O₇

Average Mass

368.3410 Da

Monoisotopic Mass

368.08960 Da

IUPAC Name

(5S,6S)-5,16-dihydroxy-6-(2-hydroxypropan-2-yl)-7,11,19-trioxapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-1(12),2(10),3,8,13,15,17-heptaen-20-one

Traditional Name

(5S,6S)-5,16-dihydroxy-6-(2-hydroxypropan-2-yl)-7,11,19-trioxapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-1(12),2(10),3,8,13,15,17-heptaen-20-one

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@H]1OC2=CC3=C(C=C2[C@@H]1O)C1=C(O3)C2=CC=C(O)C=C2OC1=O

InChI Identifier

InChI=1S/C20H16O7/c1-20(2,24)18-16(22)11-6-10-13(7-14(11)26-18)25-17-9-4-3-8(21)5-12(9)27-19(23)15(10)17/h3-7,16,18,21-22,24H,1-2H3/t16-,18-/m0/s1

InChI Key

ZJBOZZWXWWQLRJ-WMZOPIPTSA-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
Cullen corylifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Substituents

Coumestan
Angular furanocoumarin
Furanocoumarin
Coumarin
Benzopyran
1-benzopyran
Benzofuran
Coumaran
Furopyran
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Furan
Heteroaromatic compound
Tertiary alcohol
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Ether
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	1.73	ChemAxon
pKa (Strongest Acidic)	7.12	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.36 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	93.64 m³·mol⁻¹	ChemAxon
Polarizability	37.62 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

Not Available

Chemspider ID

59004894

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122177580

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5s,6s)-5,16-dihydroxy-6-(2-hydroxypropan-2-yl)-7,11,19-trioxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-20-one (NP0193513)

MOL for NP0193513 ((5s,6s)-5,16-dihydroxy-6-(2-hydroxypropan-2-yl)-7,11,19-trioxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-20-one)

3D MOL for NP0193513 ((5s,6s)-5,16-dihydroxy-6-(2-hydroxypropan-2-yl)-7,11,19-trioxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-20-one)

3D SDF for NP0193513 ((5s,6s)-5,16-dihydroxy-6-(2-hydroxypropan-2-yl)-7,11,19-trioxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-20-one)

3D-SDF for NP0193513 ((5s,6s)-5,16-dihydroxy-6-(2-hydroxypropan-2-yl)-7,11,19-trioxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-20-one)

PDB for NP0193513 ((5s,6s)-5,16-dihydroxy-6-(2-hydroxypropan-2-yl)-7,11,19-trioxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-20-one)

3D PDB for NP0193513 ((5s,6s)-5,16-dihydroxy-6-(2-hydroxypropan-2-yl)-7,11,19-trioxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-20-one)

SMILES for NP0193513 ((5s,6s)-5,16-dihydroxy-6-(2-hydroxypropan-2-yl)-7,11,19-trioxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-20-one)

INCHI for NP0193513 ((5s,6s)-5,16-dihydroxy-6-(2-hydroxypropan-2-yl)-7,11,19-trioxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-20-one)

Structure for NP0193513 ((5s,6s)-5,16-dihydroxy-6-(2-hydroxypropan-2-yl)-7,11,19-trioxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-20-one)

3D Structure for NP0193513 ((5s,6s)-5,16-dihydroxy-6-(2-hydroxypropan-2-yl)-7,11,19-trioxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-1(12),2(10),3,8,13(18),14,16-heptaen-20-one)