NP-MRD: Showing NP-Card for (7aS,10R,10aR)-7a,9,10,10a-Tetrahydro-10-hydroxy-9,9-dimethyl-2-phenyl-4H-furo[3',2':4,5]furo[2,3-h]-1-benzopyran-4-one (NP0059859)

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Record Information

Version

2.0

Created at

2022-04-28 05:01:12 UTC

Updated at

2022-04-28 05:01:12 UTC

NP-MRD ID

NP0059859

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(7aS,10R,10aR)-7a,9,10,10a-Tetrahydro-10-hydroxy-9,9-dimethyl-2-phenyl-4H-furo[3',2':4,5]furo[2,3-h]-1-benzopyran-4-one

Description

Semiglabrinol belongs to the class of organic compounds known as 8-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 8-position. Thus, semiglabrinol is considered to be a flavonoid. (7aS,10R,10aR)-7a,9,10,10a-Tetrahydro-10-hydroxy-9,9-dimethyl-2-phenyl-4H-furo[3',2':4,5]furo[2,3-h]-1-benzopyran-4-one is found in Tephrosia apollinea , Tephrosia semiglabra and Tephrosia semiglabrata. (7aS,10R,10aR)-7a,9,10,10a-Tetrahydro-10-hydroxy-9,9-dimethyl-2-phenyl-4H-furo[3',2':4,5]furo[2,3-h]-1-benzopyran-4-one was first documented in 2006 (PMID: 17127656). Based on a literature review very few articles have been published on Semiglabrinol (PMID: 34959438).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207012D          

 26 30  0  0  1  0            999 V2000
    0.6114   -0.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0107   -0.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7910   -0.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9493   -1.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273   -2.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4530   -1.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7683   -1.6023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1161   -0.8542    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5121   -0.2922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8600    0.4559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6789    0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8372   -0.4534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8720    1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4650    0.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4592    1.1770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1477    0.3844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9280    0.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5500    0.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -0.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0137   -1.2414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0863    1.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4643    2.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6226    2.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4030    3.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250    2.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667    1.7295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  4  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9  3  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 10 15  1  6  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
  1 19  1  0  0  0  0
 19 20  2  0  0  0  0
 17 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
M  END

     RDKit          3D

 44 48  0  0  0  0  0  0  0  0999 V2000
   -4.0749    0.7523   -0.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4264    0.8601    0.6171 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7974    2.1648    1.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7562   -0.2324    1.3902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0736   -1.3058    0.8726 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7218   -2.1872    1.8935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3231   -2.2337    1.9987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5641   -2.9653    2.8993 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7992   -2.8712    2.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3966   -2.0646    1.8934 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7873   -1.9629    1.8213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4718   -2.6140    2.6231 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2984   -1.1304    0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5169   -0.4168   -0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0925    0.4530   -1.0524 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4412    0.6214   -1.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9607    1.4694   -2.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1207    2.1557   -3.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7632    1.9806   -2.8880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2530    1.1408   -1.9034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2107   -0.5522    0.0809 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6555   -1.3354    0.9965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7373   -1.4286    1.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7933   -0.7937    0.2626 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9083    0.6936    0.4877 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5170    1.4350   -0.6238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2933   -0.2974   -1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0478    1.2878   -0.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4488    1.2596   -1.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3299    2.0365    2.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9104    2.8445    1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5122    2.7580    0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6713   -1.8669    0.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0076   -3.6100    3.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4629   -3.4201    3.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3790   -1.0466    0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1607    0.1274   -0.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0195    1.6060   -2.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5396    2.8100   -3.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1161    2.5296   -3.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1837    1.0146   -1.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7708   -1.0656   -0.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4225    1.0163    1.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5214    2.3838   -0.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 25  2  1  0
 20 15  1  0
 24  5  1  0
 23  7  1  0
 22 10  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  6
  8 34  1  0
  9 35  1  0
 13 36  1  0
 24 42  1  6
 25 43  1  1
 26 44  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  0
M  END


  Mrv1652304282207012D          

 26 30  0  0  1  0            999 V2000
    0.6114   -0.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0107   -0.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7910   -0.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9493   -1.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273   -2.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4530   -1.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7683   -1.6023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1161   -0.8542    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5121   -0.2922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8600    0.4559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6789    0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8372   -0.4534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8720    1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4650    0.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4592    1.1770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1477    0.3844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9280    0.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5500    0.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -0.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0137   -1.2414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0863    1.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4643    2.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6226    2.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4030    3.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250    2.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667    1.7295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  4  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9  3  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 10 15  1  6  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
  1 19  1  0  0  0  0
 19 20  2  0  0  0  0
 17 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0059859

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)O[C@@H]2OC3=CC=C4C(=O)C=C(OC4=C3[C@@H]2[C@H]1O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H18O5/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/h3-10,17,19-20,23H,1-2H3/t17-,19-,20+/m1/s1

> <INCHI_KEY>
XBKLVCYSINXGAW-RLLQIKCJSA-N

> <FORMULA>
C21H18O5

> <MOLECULAR_WEIGHT>
350.37

> <EXACT_MASS>
350.11542368

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
36.51805051069083

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(12S,15R,16R)-15-hydroxy-14,14-dimethyl-4-phenyl-3,11,13-trioxatetracyclo[8.6.0.0^{2,7}.0^{12,16}]hexadeca-1,4,7,9-tetraen-6-one

> <ALOGPS_LOGP>
3.12

> <JCHEM_LOGP>
2.7889213486666664

> <ALOGPS_LOGS>
-3.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.780259809083624

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.415307762358722

> <JCHEM_PKA_STRONGEST_BASIC>
-3.491092522281309

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
95.378

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.90e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(12S,15R,16R)-15-hydroxy-14,14-dimethyl-4-phenyl-3,11,13-trioxatetracyclo[8.6.0.0^{2,7}.0^{12,16}]hexadeca-1,4,7,9-tetraen-6-one

> <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       1.141  -1.805   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.020  -0.794   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.477  -1.294   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.772  -2.805   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.611  -3.817   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.846  -3.317   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.301  -2.991   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.950  -1.595   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.823  -0.546   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.472   0.851   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.001   0.665   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.296  -0.846   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.361   2.162   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.468   1.132   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.724   2.197   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.276   0.718   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.732   1.217   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.893   0.206   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.598  -1.306   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.759  -2.317   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.028   2.729   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.867   3.740   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.162   5.252   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.619   5.751   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.780   4.740   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.484   3.228   0.000  0.00  0.00           C+0
CONECT    1    2    6   19                                                  
CONECT    2    1    3   16                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12   13   14                                             
CONECT   12   11    8                                                       
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15   10                                                            
CONECT   16    2   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18    1   20                                                  
CONECT   20   19                                                            
CONECT   21   17   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₁₈O₅

Average Mass

350.3700 Da

Monoisotopic Mass

350.11542 Da

IUPAC Name

(12S,15R,16R)-15-hydroxy-14,14-dimethyl-4-phenyl-3,11,13-trioxatetracyclo[8.6.0.0^{2,7}.0^{12,16}]hexadeca-1,4,7,9-tetraen-6-one

Traditional Name

(12S,15R,16R)-15-hydroxy-14,14-dimethyl-4-phenyl-3,11,13-trioxatetracyclo[8.6.0.0^{2,7}.0^{12,16}]hexadeca-1,4,7,9-tetraen-6-one

CAS Registry Number

Not Available

SMILES

CC1(C)O[C@@H]2OC3=CC=C4C(=O)C=C(OC4=C3[C@@H]2[C@H]1O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C21H18O5/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/h3-10,17,19-20,23H,1-2H3/t17-,19-,20+/m1/s1

InChI Key

XBKLVCYSINXGAW-RLLQIKCJSA-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
Tephrosia apollinea	Plant	KNApSAcK
Tephrosia semiglabra	Plant	KNApSAcK
Tephrosia semiglabrata	Plant	KNApSAcK

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

8-prenylated flavones

Alternative Parents

Substituents

8-prenylated flavone
Chromone
Benzopyran
1-benzopyran
Coumaran
Pyranone
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Pyran
Heteroaromatic compound
Oxolane
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12110015 )

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	3.12	ALOGPS
logP	2.79	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.42	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	95.38 m³·mol⁻¹	ChemAxon
Polarizability	36.52 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

C00013465

Chemspider ID

9210668

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11035494

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shafie A, Khan S, Zehra, Mohammad T, Anjum F, Hasan GM, Yadav DK, Hassan MI: Identification of Phytoconstituents as Potent Inhibitors of Casein Kinase-1 Alpha Using Virtual Screening and Molecular Dynamics Simulations. Pharmaceutics. 2021 Dec 15;13(12). pii: pharmaceutics13122157. doi: 10.3390/pharmaceutics13122157. [PubMed:34959438 ]
Hisham A, John S, Al-Shuaily W, Asai T, Fujimoto Y: (+)-Apollineanin: a new flavanone from Tephrosia apollinea. Nat Prod Res. 2006 Oct;20(12):1046-52. doi: 10.1080/14786410500399714. [PubMed:17127656 ]

Showing NP-Card for (7aS,10R,10aR)-7a,9,10,10a-Tetrahydro-10-hydroxy-9,9-dimethyl-2-phenyl-4H-furo[3',2':4,5]furo[2,3-h]-1-benzopyran-4-one (NP0059859)

MOL for NP0059859 ((7aS,10R,10aR)-7a,9,10,10a-Tetrahydro-10-hydroxy-9,9-dimethyl-2-phenyl-4H-furo[3',2':4,5]furo[2,3-h]-1-benzopyran-4-one)

3D MOL for NP0059859 ((7aS,10R,10aR)-7a,9,10,10a-Tetrahydro-10-hydroxy-9,9-dimethyl-2-phenyl-4H-furo[3',2':4,5]furo[2,3-h]-1-benzopyran-4-one)

3D SDF for NP0059859 ((7aS,10R,10aR)-7a,9,10,10a-Tetrahydro-10-hydroxy-9,9-dimethyl-2-phenyl-4H-furo[3',2':4,5]furo[2,3-h]-1-benzopyran-4-one)

3D-SDF for NP0059859 ((7aS,10R,10aR)-7a,9,10,10a-Tetrahydro-10-hydroxy-9,9-dimethyl-2-phenyl-4H-furo[3',2':4,5]furo[2,3-h]-1-benzopyran-4-one)

PDB for NP0059859 ((7aS,10R,10aR)-7a,9,10,10a-Tetrahydro-10-hydroxy-9,9-dimethyl-2-phenyl-4H-furo[3',2':4,5]furo[2,3-h]-1-benzopyran-4-one)

3D PDB for NP0059859 ((7aS,10R,10aR)-7a,9,10,10a-Tetrahydro-10-hydroxy-9,9-dimethyl-2-phenyl-4H-furo[3',2':4,5]furo[2,3-h]-1-benzopyran-4-one)

SMILES for NP0059859 ((7aS,10R,10aR)-7a,9,10,10a-Tetrahydro-10-hydroxy-9,9-dimethyl-2-phenyl-4H-furo[3',2':4,5]furo[2,3-h]-1-benzopyran-4-one)

INCHI for NP0059859 ((7aS,10R,10aR)-7a,9,10,10a-Tetrahydro-10-hydroxy-9,9-dimethyl-2-phenyl-4H-furo[3',2':4,5]furo[2,3-h]-1-benzopyran-4-one)

Structure for NP0059859 ((7aS,10R,10aR)-7a,9,10,10a-Tetrahydro-10-hydroxy-9,9-dimethyl-2-phenyl-4H-furo[3',2':4,5]furo[2,3-h]-1-benzopyran-4-one)

3D Structure for NP0059859 ((7aS,10R,10aR)-7a,9,10,10a-Tetrahydro-10-hydroxy-9,9-dimethyl-2-phenyl-4H-furo[3',2':4,5]furo[2,3-h]-1-benzopyran-4-one)