NP-MRD: Showing NP-Card for (+)-5''-deacetylpurpurin (NP0043593)

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Record Information

Version

2.0

Created at

2021-06-21 00:57:25 UTC

Updated at

2021-06-30 00:19:21 UTC

NP-MRD ID

NP0043593

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-5''-deacetylpurpurin

Provided By

JEOL Database JEOL Logo

Description

2Alpha-Phenyl-10beta-hydroxy-11,11-dimethyl-8,9-(epoxyethano)-8alpha,9alpha-dihydro-2H-furo[2,3-h][1]benzopyran-4(3H)-one belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position. (+)-5''-deacetylpurpurin is found in Indigofera spicata. (+)-5''-deacetylpurpurin was first documented in 2013 (Perez, L. B., et al.). Based on a literature review very few articles have been published on 2alpha-Phenyl-10beta-hydroxy-11,11-dimethyl-8,9-(epoxyethano)-8alpha,9alpha-dihydro-2H-furo[2,3-h][1]benzopyran-4(3H)-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102573D          

 46 50  0  0  0  0            999 V2000
    2.4252    2.9323   -1.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2103    1.4220   -1.0551 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3683    0.7718   -0.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2049    0.9020   -2.3999 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3563   -0.2575   -2.4219 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4651   -0.2345   -3.5607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7867   -0.4084   -3.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9330   -0.5192   -3.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1541   -0.6708   -3.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1942   -0.6851   -1.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0252   -0.5401   -0.9813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8234   -0.4323   -1.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5486   -0.2821   -1.1188 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8275    1.0693   -0.4919 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7887    1.0124    0.9279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9915   -0.5036    0.3834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2502   -0.1077    0.9588 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1132   -0.1575    2.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6288    0.8836    3.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5208    0.8424    4.6462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9009   -0.2396    5.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3896   -1.2830    4.4991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4966   -1.2445    3.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3821   -1.0065    0.4796 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4702   -0.8854   -1.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5267   -0.9975   -1.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3860    3.1691   -1.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033    3.3869   -0.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6561    3.4095   -1.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3197    0.9538   -0.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4479    1.1620    0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2559   -0.3164   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9942   -1.1450   -2.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8279   -1.1263   -0.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9210    1.6555    5.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8166   -0.2699    6.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0911   -2.0696    2.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3357   -0.6941    0.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2067   -2.0613    0.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  2  0  0  0  0
 11 10  2  0  0  0  0
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  9 10  1  0  0  0  0
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  2  3  1  0  0  0  0
 11 12  1  0  0  0  0
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 23 44  1  0  0  0  0
 14 37  1  6  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
 15 38  1  0  0  0  0
M  END

     RDKit          3D

 46 50  0  0  0  0  0  0  0  0999 V2000
    2.4252    2.9323   -1.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2103    1.4220   -1.0551 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3683    0.7718   -0.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2049    0.9020   -2.3999 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3563   -0.2575   -2.4219 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4651   -0.2345   -3.5607 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3896   -1.2830    4.4991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4966   -1.2445    3.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3821   -1.0065    0.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4702   -0.8854   -1.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5267   -0.9975   -1.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3860    3.1691   -1.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033    3.3869   -0.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6561    3.4095   -1.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3197    0.9538   -0.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4479    1.1620    0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2559   -0.3164   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9942   -1.1450   -2.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8834   -0.4941   -4.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0718   -0.7798   -3.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8279   -1.1263   -0.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306212102573D          

 46 50  0  0  0  0            999 V2000
    2.4252    2.9323   -1.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2103    1.4220   -1.0551 C   0  0  2  0  0  0  0  0  0  0  0  0
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 14 15  1  0  0  0  0
  8 34  1  0  0  0  0
  9 35  1  0  0  0  0
 24 45  1  0  0  0  0
 24 46  1  0  0  0  0
 17 39  1  1  0  0  0
 19 40  1  0  0  0  0
 20 41  1  0  0  0  0
 21 42  1  0  0  0  0
 22 43  1  0  0  0  0
 23 44  1  0  0  0  0
 14 37  1  6  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
 15 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043593

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])[C@@]2([H])C3=C(O[C@@]2([H])OC1(C([H])([H])[H])C([H])([H])[H])C([H])=C([H])C1=C3O[C@]([H])(C2=C([H])C([H])=C([H])C([H])=C2[H])C([H])([H])C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O5/c1-21(2)19(23)17-16-14(25-20(17)26-21)9-8-12-13(22)10-15(24-18(12)16)11-6-4-3-5-7-11/h3-9,15,17,19-20,23H,10H2,1-2H3/t15-,17+,19+,20-/m0/s1

> <INCHI_KEY>
CHMTWRQIIYWNMW-ZSXHRAQDSA-N

> <FORMULA>
C21H20O5

> <MOLECULAR_WEIGHT>
352.386

> <EXACT_MASS>
352.131073744

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
37.32728508120579

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,12S,15R,16R)-15-hydroxy-14,14-dimethyl-4-phenyl-3,11,13-trioxatetracyclo[8.6.0.0^{2,7}.0^{12,16}]hexadeca-1(10),2(7),8-trien-6-one

> <ALOGPS_LOGP>
2.84

> <JCHEM_LOGP>
2.917340265333334

> <ALOGPS_LOGS>
-3.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.564286590615044

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.392510768085149

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4870931101101315

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
93.7539

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,12S,15R,16R)-15-hydroxy-14,14-dimethyl-4-phenyl-3,11,13-trioxatetracyclo[8.6.0.0^{2,7}.0^{12,16}]hexadeca-1(10),2(7),8-trien-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 46 50  0  0  0  0  0  0  0  0999 V2000
    2.4252    2.9323   -1.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2103    1.4220   -1.0551 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3683    0.7718   -0.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2049    0.9020   -2.3999 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3563   -0.2575   -2.4219 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4651   -0.2345   -3.5607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7867   -0.4084   -3.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9330   -0.5192   -3.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1541   -0.6708   -3.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1942   -0.6851   -1.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0252   -0.5401   -0.9813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8234   -0.4323   -1.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5486   -0.2821   -1.1188 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8275    1.0693   -0.4919 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7887    1.0124    0.9279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9915   -0.5036    0.3834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2502   -0.1077    0.9588 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1132   -0.1575    2.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6288    0.8836    3.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5208    0.8424    4.6462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9009   -0.2396    5.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3896   -1.2830    4.4991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4966   -1.2445    3.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3821   -1.0065    0.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4702   -0.8854   -1.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5267   -0.9975   -1.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3860    3.1691   -1.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033    3.3869   -0.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6561    3.4095   -1.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3197    0.9538   -0.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4479    1.1620    0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2559   -0.3164   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9942   -1.1450   -2.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8834   -0.4941   -4.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0718   -0.7798   -3.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8279   -1.1263   -0.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0879    1.8137   -0.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0915    0.6735    1.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4313    0.9355    0.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1196    1.7379    2.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9210    1.6555    5.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8166   -0.2699    6.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9063   -2.1276    4.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0911   -2.0696    2.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3357   -0.6941    0.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2067   -2.0613    0.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  2  0
 11 10  2  0
 21 22  1  0
 11 16  1  0
 22 23  2  0
 23 18  1  0
  7 12  2  0
 10 25  1  0
 25 24  1  0
 24 17  1  0
 12 13  1  0
  5  6  1  0
  6  7  1  0
  5 13  1  0
 17 16  1  0
  7  8  1  0
 25 26  2  0
 17 18  1  0
 13 14  1  0
 14  2  1  0
  2  4  1  0
  4  5  1  0
  8  9  2  0
  5 33  1  6
 18 19  2  0
 13 36  1  1
  9 10  1  0
  2  1  1  6
 19 20  1  0
  2  3  1  0
 11 12  1  0
 14 15  1  0
  8 34  1  0
  9 35  1  0
 24 45  1  0
 24 46  1  0
 17 39  1  1
 19 40  1  0
 20 41  1  0
 21 42  1  0
 22 43  1  0
 23 44  1  0
 14 37  1  6
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
 15 38  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       2.425   2.932  -1.122  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.210   1.422  -1.055  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.368   0.772  -0.287  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.205   0.902  -2.400  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.356  -0.258  -2.422  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.465  -0.235  -3.561  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.787  -0.408  -3.038  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.933  -0.519  -3.802  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.154  -0.671  -3.139  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.194  -0.685  -1.733  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.025  -0.540  -0.981  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.823  -0.432  -1.655  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.549  -0.282  -1.119  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.828   1.069  -0.492  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.789   1.012   0.928  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.992  -0.504   0.383  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.250  -0.108   0.959  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.113  -0.158   2.468  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.629   0.884   3.255  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.521   0.842   4.646  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.901  -0.240   5.267  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.390  -1.283   4.499  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.497  -1.244   3.108  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.382  -1.006   0.480  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.470  -0.885  -1.016  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.527  -0.998  -1.628  0.00  0.00           O+0
HETATM   27  H   UNK     0       3.386   3.169  -1.593  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.403   3.387  -0.126  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.656   3.410  -1.740  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.320   0.954  -0.800  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.448   1.162   0.733  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.256  -0.316  -0.232  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.994  -1.145  -2.513  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.883  -0.494  -4.886  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.072  -0.780  -3.714  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.828  -1.126  -0.479  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.088   1.814  -0.815  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.092   0.674   1.182  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.431   0.936   0.660  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.120   1.738   2.793  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.921   1.656   5.247  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.817  -0.270   6.351  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.906  -2.128   4.984  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.091  -2.070   2.526  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.336  -0.694   0.919  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.207  -2.061   0.721  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2   14    4    1    3                                             
CONECT    3    2   30   31   32                                             
CONECT    4    2    5                                                       
CONECT    5    6   13    4   33                                             
CONECT    6    5    7                                                       
CONECT    7   12    6    8                                                  
CONECT    8    7    9   34                                                  
CONECT    9    8   10   35                                                  
CONECT   10   11   25    9                                                  
CONECT   11   10   16   12                                                  
CONECT   12    7   13   11                                                  
CONECT   13   12    5   14   36                                             
CONECT   14   13    2   15   37                                             
CONECT   15   14   38                                                       
CONECT   16   11   17                                                       
CONECT   17   24   16   18   39                                             
CONECT   18   23   17   19                                                  
CONECT   19   18   20   40                                                  
CONECT   20   21   19   41                                                  
CONECT   21   20   22   42                                                  
CONECT   22   21   23   43                                                  
CONECT   23   22   18   44                                                  
CONECT   24   25   17   45   46                                             
CONECT   25   10   24   26                                                  
CONECT   26   25                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    3                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    5                                                            
CONECT   34    8                                                            
CONECT   35    9                                                            
CONECT   36   13                                                            
CONECT   37   14                                                            
CONECT   38   15                                                            
CONECT   39   17                                                            
CONECT   40   19                                                            
CONECT   41   20                                                            
CONECT   42   21                                                            
CONECT   43   22                                                            
CONECT   44   23                                                            
CONECT   45   24                                                            
CONECT   46   24                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  100    0
END

RDKit          3D

46 50  0  0  0  0  0  0  0  0999 V2000
    2.4252    2.9323   -1.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2103    1.4220   -1.0551 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3683    0.7718   -0.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2049    0.9020   -2.3999 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3563   -0.2575   -2.4219 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4651   -0.2345   -3.5607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7867   -0.4084   -3.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9330   -0.5192   -3.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1541   -0.6708   -3.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1942   -0.6851   -1.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0252   -0.5401   -0.9813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8234   -0.4323   -1.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5486   -0.2821   -1.1188 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8275    1.0693   -0.4919 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7887    1.0124    0.9279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9915   -0.5036    0.3834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2502   -0.1077    0.9588 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1132   -0.1575    2.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6288    0.8836    3.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5208    0.8424    4.6462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9009   -0.2396    5.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3896   -1.2830    4.4991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4966   -1.2445    3.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3821   -1.0065    0.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4702   -0.8854   -1.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5267   -0.9975   -1.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3860    3.1691   -1.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033    3.3869   -0.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6561    3.4095   -1.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3197    0.9538   -0.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4479    1.1620    0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2559   -0.3164   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9942   -1.1450   -2.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8834   -0.4941   -4.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0718   -0.7798   -3.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8279   -1.1263   -0.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0879    1.8137   -0.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0915    0.6735    1.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4313    0.9355    0.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1196    1.7379    2.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9210    1.6555    5.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8166   -0.2699    6.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9063   -2.1276    4.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0911   -2.0696    2.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3357   -0.6941    0.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2067   -2.0613    0.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  2  0
 11 10  2  0
 21 22  1  0
 11 16  1  0
 22 23  2  0
 23 18  1  0
  7 12  2  0
 10 25  1  0
 25 24  1  0
 24 17  1  0
 12 13  1  0
  5  6  1  0
  6  7  1  0
  5 13  1  0
 17 16  1  0
  7  8  1  0
 25 26  2  0
 17 18  1  0
 13 14  1  0
 14  2  1  0
  2  4  1  0
  4  5  1  0
  8  9  2  0
  5 33  1  6
 18 19  2  0
 13 36  1  1
  9 10  1  0
  2  1  1  6
 19 20  1  0
  2  3  1  0
 11 12  1  0
 14 15  1  0
  8 34  1  0
  9 35  1  0
 24 45  1  0
 24 46  1  0
 17 39  1  1
 19 40  1  0
 20 41  1  0
 21 42  1  0
 22 43  1  0
 23 44  1  0
 14 37  1  6
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
 15 38  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
2a-Phenyl-10b-hydroxy-11,11-dimethyl-8,9-(epoxyethano)-8a,9a-dihydro-2H-furo[2,3-H][1]benzopyran-4(3H)-one	Generator
2Α-phenyl-10β-hydroxy-11,11-dimethyl-8,9-(epoxyethano)-8α,9α-dihydro-2H-furo[2,3-H][1]benzopyran-4(3H)-one	Generator

Chemical Formula

C₂₁H₂₀O₅

Average Mass

352.3860 Da

Monoisotopic Mass

352.13107 Da

IUPAC Name

(4S,12S,15R,16R)-15-hydroxy-14,14-dimethyl-4-phenyl-3,11,13-trioxatetracyclo[8.6.0.0^{2,7}.0^{12,16}]hexadeca-1(10),2(7),8-trien-6-one

Traditional Name

(4S,12S,15R,16R)-15-hydroxy-14,14-dimethyl-4-phenyl-3,11,13-trioxatetracyclo[8.6.0.0^{2,7}.0^{12,16}]hexadeca-1(10),2(7),8-trien-6-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])[C@@]2([H])C3=C(O[C@@]2([H])OC1(C([H])([H])[H])C([H])([H])[H])C([H])=C([H])C1=C3O[C@]([H])(C2=C([H])C([H])=C([H])C([H])=C2[H])C([H])([H])C1=O

InChI Identifier

InChI=1S/C21H20O5/c1-21(2)19(23)17-16-14(25-20(17)26-21)9-8-12-13(22)10-15(24-18(12)16)11-6-4-3-5-7-11/h3-9,15,17,19-20,23H,10H2,1-2H3/t15-,17+,19+,20-/m0/s1

InChI Key

CHMTWRQIIYWNMW-ZSXHRAQDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Indigofera spicata	JEOL database	Perez, L. B., et al, J. Nat. Prod. 76, 1498 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

8-prenylated flavanones

Alternative Parents

Substituents

8-prenylated flavanone
Flavanone
Chromone
Chromane
Benzopyran
1-benzopyran
Coumaran
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Oxolane
Secondary alcohol
Ketone
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aldehyde
Organooxygen 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	2.84	ALOGPS
logP	2.92	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	13.39	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	93.75 m³·mol⁻¹	ChemAxon
Polarizability	37.33 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72189185

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Perez, L. B., et al. (2013). Perez, L. B., et al, J. Nat. Prod. 76, 1498 (2013). J. Nat. Prod..

Showing NP-Card for (+)-5''-deacetylpurpurin (NP0043593)

MOL for NP0043593 ((+)-5''-deacetylpurpurin)

3D MOL for NP0043593 ((+)-5''-deacetylpurpurin)

3D SDF for NP0043593 ((+)-5''-deacetylpurpurin)

3D-SDF for NP0043593 ((+)-5''-deacetylpurpurin)

PDB for NP0043593 ((+)-5''-deacetylpurpurin)

3D PDB for NP0043593 ((+)-5''-deacetylpurpurin)

SMILES for NP0043593 ((+)-5''-deacetylpurpurin)

INCHI for NP0043593 ((+)-5''-deacetylpurpurin)

Structure for NP0043593 ((+)-5''-deacetylpurpurin)

3D Structure for NP0043593 ((+)-5''-deacetylpurpurin)