NP-MRD: Showing NP-Card for Miroestrol (NP0052168)

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Record Information

Version

2.0

Created at

2022-04-27 23:19:25 UTC

Updated at

2022-04-27 23:19:25 UTC

NP-MRD ID

NP0052168

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Miroestrol

Description

Miroestrol belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Miroestrol is found in Pueraria candollei var. mirifica and Pueraria mirifica . Miroestrol was first documented in 2020 (PMID: 32434998). Based on a literature review a small amount of articles have been published on Miroestrol (PMID: 34382493) (PMID: 34106388) (PMID: 33790074) (PMID: 33582859).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201192D          

 26 30  0  0  1  0            999 V2000
    5.7616   -0.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0794   -0.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5790    0.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7608    0.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4429   -0.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9433   -1.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6247   -0.5055    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1243    0.1504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4421    0.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2604    1.0171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2650    0.1029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0396   -0.6890    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3791   -1.3746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2661   -1.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0049   -1.6377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -2.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5076   -1.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8756   -0.7344    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2139   -1.1643    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0575   -1.9743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8084    0.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5529    0.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5834    1.3845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0998   -1.0150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4753    0.9006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8977   -0.0840    0.0000 O   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
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  1  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 24  1  1  0  0  0
 11 25  1  6  0  0  0
  2 26  1  0  0  0  0
M  END

     RDKit          3D

 48 52  0  0  0  0  0  0  0  0999 V2000
    0.6749    1.3349   -1.5479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1589    1.3281   -0.1361 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1849    2.7074    0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9183    0.3973    0.7710 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0961   -0.7911    1.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4835   -2.0340    1.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7541   -2.3319    0.5435 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6212   -1.3268    0.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661   -1.6859   -0.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7876   -0.7440   -0.7078 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0535   -1.1294   -1.1903 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4280    0.5743   -0.6165 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1863    0.9080   -0.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2408    0.0062    0.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2896   -0.5941    1.6714 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1795   -0.4717    3.0542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1010   -1.7802    1.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2659   -2.6315    2.2100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7563   -1.9955    0.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0236   -0.5973   -0.4850 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0608   -0.6323   -1.3770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7209   -0.0959   -1.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3209    1.0101   -0.1908 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9048    0.6756    1.1399 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3279    0.2814    0.7028 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0750    1.3902    0.3873 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1728    2.2944   -1.8250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3383    0.4521   -1.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1563    1.2310   -2.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7192    3.2908    0.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1712    2.5522    1.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0357    3.3252    0.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1243    0.8922    1.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1738   -2.8802    1.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1869   -2.7281   -0.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7854   -1.2167   -0.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1459    1.3484   -0.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721    1.9633   -0.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3132   -0.0436    3.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1091   -2.5547   -0.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7221   -2.4969    0.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7233   -1.3288   -1.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9665   -0.8906   -1.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0149    0.3014   -2.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8715    1.9282   -0.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9184    1.4994    1.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7865   -0.3142    1.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8859    1.6032   -0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  2 23  1  0
 23 22  1  0
 22 20  1  0
 20 21  1  6
 20 19  1  0
 19 17  1  0
 17 18  2  0
 17 15  1  0
 15 16  1  1
 15 24  1  0
 24 25  1  0
 25 26  1  0
 15  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14  4  1  0
  4  2  1  0
 24 23  1  0
  4  5  1  0
 25 20  1  0
 14  8  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
 23 45  1  6
 22 43  1  0
 22 44  1  0
 21 42  1  0
 19 40  1  0
 19 41  1  0
 16 39  1  0
 24 46  1  1
 25 47  1  1
 26 48  1  0
  6 34  1  0
  9 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
  4 33  1  1
M  END


  Mrv1652304282201192D          

 26 30  0  0  1  0            999 V2000
    5.7616   -0.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0794   -0.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5790    0.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7608    0.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4429   -0.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9433   -1.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6247   -0.5055    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1243    0.1504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4421    0.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2604    1.0171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2650    0.1029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0396   -0.6890    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3791   -1.3746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2661   -1.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0049   -1.6377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -2.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5076   -1.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8756   -0.7344    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2139   -1.1643    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0575   -1.9743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8084    0.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5529    0.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5834    1.3845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0998   -1.0150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4753    0.9006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8977   -0.0840    0.0000 O   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
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  1  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 24  1  1  0  0  0
 11 25  1  6  0  0  0
  2 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052168

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@H]2C[C@@]3(O)CC(=O)[C@](O)([C@@H]2[C@H]3O)C2=COC3=CC(O)=CC=C3[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O6/c1-18(2)11-6-19(24)7-14(22)20(25,16(11)17(19)23)12-8-26-13-5-9(21)3-4-10(13)15(12)18/h3-5,8,11,15-17,21,23-25H,6-7H2,1-2H3/t11-,15+,16-,17+,19+,20-/m0/s1

> <INCHI_KEY>
RJKLDOLOCIQYFS-PRTISISMSA-N

> <FORMULA>
C20H22O6

> <MOLECULAR_WEIGHT>
358.39

> <EXACT_MASS>
358.141638428

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.164647789455145

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3R,13S,16R,17R,18S)-7,13,16,17-tetrahydroxy-2,2-dimethyl-10-oxapentacyclo[14.2.1.0^{3,12}.0^{4,9}.0^{13,18}]nonadeca-4,6,8,11-tetraen-14-one

> <ALOGPS_LOGP>
0.61

> <JCHEM_LOGP>
0.43112812033333353

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.672648847692756

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.372820527632419

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3890265781735884

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
91.73199999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,13S,16R,17R,18S)-7,13,16,17-tetrahydroxy-2,2-dimethyl-10-oxapentacyclo[14.2.1.0^{3,12}.0^{4,9}.0^{13,18}]nonadeca-4,6,8,11-tetraen-14-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      10.755  -1.775   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.348  -0.353   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.414   0.871   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.887   0.674   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.293  -0.747   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.228  -1.971   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.766  -0.944   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.832   0.281   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.425   1.702   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.953   1.899   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.228   0.192   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.807  -1.286   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.441  -2.566   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.097  -2.372   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.476  -3.057   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.311  -3.897   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.814  -3.028   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.635  -1.371   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.266  -2.173   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.974  -3.685   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.509   0.292   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.899   1.046   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.956   2.584   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.186  -1.895   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.621   1.681   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      12.876  -0.157   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   22   25                                             
CONECT   12   11   13   19                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13    7   15   16                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18                                                       
CONECT   18   17   19   21   24                                             
CONECT   19   18   12   20                                                  
CONECT   20   19                                                            
CONECT   21   18   22                                                       
CONECT   22   21   11   23                                                  
CONECT   23   22                                                            
CONECT   24   18                                                            
CONECT   25   11                                                            
CONECT   26    2                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂O₆

Average Mass

358.3900 Da

Monoisotopic Mass

358.14164 Da

IUPAC Name

(1S,3R,13S,16R,17R,18S)-7,13,16,17-tetrahydroxy-2,2-dimethyl-10-oxapentacyclo[14.2.1.0^{3,12}.0^{4,9}.0^{13,18}]nonadeca-4,6,8,11-tetraen-14-one

Traditional Name

(1S,3R,13S,16R,17R,18S)-7,13,16,17-tetrahydroxy-2,2-dimethyl-10-oxapentacyclo[14.2.1.0^{3,12}.0^{4,9}.0^{13,18}]nonadeca-4,6,8,11-tetraen-14-one

CAS Registry Number

Not Available

SMILES

CC1(C)[C@H]2C[C@@]3(O)CC(=O)[C@](O)([C@@H]2[C@H]3O)C2=COC3=CC(O)=CC=C3[C@@H]12

InChI Identifier

InChI=1S/C20H22O6/c1-18(2)11-6-19(24)7-14(22)20(25,16(11)17(19)23)12-8-26-13-5-9(21)3-4-10(13)15(12)18/h3-5,8,11,15-17,21,23-25H,6-7H2,1-2H3/t11-,15+,16-,17+,19+,20-/m0/s1

InChI Key

RJKLDOLOCIQYFS-PRTISISMSA-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
Pueraria candollei var. mirifica	Plant	KNApSAcK
Pueraria mirifica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Benzopyran
Naphthalene
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyran
Cyclic alcohol
Tertiary alcohol
Ketone
Secondary alcohol
Oxacycle
Polyol
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:6949 )
organooxygen compound (CHEBI:6949 )
Steroids (C08831 )

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	0.61	ALOGPS
logP	0.43	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	9.37	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	91.73 m³·mol⁻¹	ChemAxon
Polarizability	36.16 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

C00003662

Chemspider ID

144658

KEGG Compound ID

C08831

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Miroestrol

METLIN ID

Not Available

PubChem Compound

165001

PDB ID

Not Available

ChEBI ID

6949

Good Scents ID

Not Available

References

General References

Jaipakdee N, Jarukamjorn K, Putalun W, Limpongsa E: Permeation, stability and acute dermal irritation of miroestrol and deoxymiroestrol from Pueraria candollei var. mirifica crude extract loaded transdermal gels. Pharm Dev Technol. 2021 Nov;26(9):967-977. doi: 10.1080/10837450.2021.1967982. Epub 2021 Aug 23. [PubMed:34382493 ]
Sae-Foo W, Krittanai S, Juengsanguanpornsuk W, Yusakul G, Sakamoto S, Putalun W: Fragment antigen-binding (Fab) antibody-based lateral flow immunoassay for rapid and sensitive detection of potent phytoestrogen, deoxymiroestrol. J Nat Med. 2021 Sep;75(4):1043-1049. doi: 10.1007/s11418-021-01539-5. Epub 2021 Jun 9. [PubMed:34106388 ]
Masada S, Hosoe J, Arai R, Demizu Y, Hakamatsuka T, Goda Y, Uchiyama N: Miroestrol Quantification in Pueraria mirifica Crude Drugs and Products by Single-Reference UPLC/PDA/MS Using Relative Molar Sensitivities to Kwakhurin. Chem Pharm Bull (Tokyo). 2021 Jun 1;69(6):573-580. doi: 10.1248/cpb.c21-00160. Epub 2021 Mar 30. [PubMed:33790074 ]
Rattanapisit K, Kitisripanya T, Konyanee A, Sae-Foo W, Burapapiruin A, Putalun W, Sakamoto S, Phoolcharoen W, Yusakul G: Plant-made antibody against miroestrol: a new platform for expression of full-length immunoglobulin G against small-molecule targets in immunoassays. Plant Cell Rep. 2021 Apr;40(4):723-733. doi: 10.1007/s00299-021-02670-z. Epub 2021 Feb 13. [PubMed:33582859 ]
Tsuji G, Yusa M, Masada S, Yokoo H, Hosoe J, Hakamatsuka T, Demizu Y, Uchiyama N: Facile Synthesis of Kwakhurin, a Marker Compound of Pueraria mirifica and Its Quantitative NMR Analysis for Standardization as a Reagent. Chem Pharm Bull (Tokyo). 2020 Aug 1;68(8):797-801. doi: 10.1248/cpb.c20-00346. Epub 2020 May 21. [PubMed:32434998 ]

Showing NP-Card for Miroestrol (NP0052168)

MOL for NP0052168 (Miroestrol)

3D MOL for NP0052168 (Miroestrol)

3D SDF for NP0052168 (Miroestrol)

3D-SDF for NP0052168 (Miroestrol)

PDB for NP0052168 (Miroestrol)

3D PDB for NP0052168 (Miroestrol)

SMILES for NP0052168 (Miroestrol)

INCHI for NP0052168 (Miroestrol)

Structure for NP0052168 (Miroestrol)

3D Structure for NP0052168 (Miroestrol)