NP-MRD: Showing NP-Card for Bufalin (NP0078365)

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Record Information

Version

2.0

Created at

2022-04-28 23:27:41 UTC

Updated at

2022-04-28 23:27:41 UTC

NP-MRD ID

NP0078365

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bufalin

Description

Bufalin belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. Thus, bufalin is considered to be a sterol. Bufalin is found in Apis cerana, Bufo bankorensis, Bufo bufo, Bufo gargarizans, Cunninghamella blakesleana, Cunninghamella blakesleeana, Duttaphrynus melanostictus, Bryophyllum pinnatum and Phrynoidis asper. Bufalin was first documented in 2022 (PMID: 35409366). Based on a literature review a small amount of articles have been published on bufalin (PMID: 35345394) (PMID: 35241510) (PMID: 35235052) (PMID: 35153791).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201272D          

 28 32  0  0  1  0            999 V2000
    2.6190   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1111   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3066   -2.0955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -2.7469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4893   -2.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9830   -1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3228   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4850    1.4085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  7 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 10 16  2  0  0  0  0
  5 17  1  6  0  0  0
  4 18  1  6  0  0  0
  3 19  1  1  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 25 27  1  6  0  0  0
 22 28  1  6  0  0  0
M  END

     RDKit          3D

 62 66  0  0  0  0  0  0  0  0999 V2000
    2.6234   -1.9723    0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4658   -0.7559    0.0230 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0916   -1.0417   -1.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6049   -1.2267   -1.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2561    0.0541   -0.7126 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1182   -0.1078    0.3744 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1909    1.0257   -0.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    0.3961    0.6532 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2815    1.5028    1.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1557    0.9517    1.9371 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3458    0.0307    1.1005 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0194   -0.3729   -0.1840 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1967   -1.5249   -0.7370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1221   -0.9829   -1.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8606   -0.2209   -0.0895 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6018   -1.2287    0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7981    0.7847   -0.7423 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2291    0.4471   -0.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8962    0.4965    0.6413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2463    0.1664    0.7078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9342   -0.2135   -0.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1731   -0.5203   -0.3841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2605   -0.2467   -1.5472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9890    0.0553   -1.6590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4449    2.1349   -0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9704    1.9485    0.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9939    0.5954    0.8022 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6668    0.7363    2.0386 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6524   -1.9236    1.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6234   -2.9261    0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195   -2.0222    1.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9339   -0.2546   -2.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7377   -2.0002   -1.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8350   -2.0080   -0.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9939   -1.5170   -2.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8460    0.4988   -1.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1581    0.7900    0.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6348    1.8875    0.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6371    1.4566   -1.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7737    0.0567    1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9016    2.2364    1.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121    2.0227    0.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5030    1.7663    2.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6252    0.4228    2.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1907   -0.9131    1.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038    0.4250   -0.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7049   -1.9403   -1.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0693   -2.3307    0.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0241   -0.3404   -2.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7743   -1.8411   -1.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7176   -0.9143    1.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9364   -2.1370    0.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5435   -1.5221    0.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5450    0.8051   -1.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3600    0.7950    1.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7846    0.2011    1.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4688    0.0116   -2.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4810    2.9164   -1.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    2.4703    0.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6690    2.7227    0.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4034    2.0170   -0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2461    0.1775    2.7310 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  1
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  1
 11 27  1  0
 27 28  1  1
 27 26  1  0
 26 25  1  0
 25 17  1  0
 17 18  1  0
 18 24  2  0
 24 23  1  0
 23 21  1  0
 21 22  2  0
 21 20  1  0
 20 19  2  0
 27 15  1  0
 19 18  1  0
 17 15  1  0
  2 12  1  0
  2  8  1  0
 16 51  1  0
 16 52  1  0
 16 53  1  0
 14 49  1  0
 14 50  1  0
 13 47  1  0
 13 48  1  0
 12 46  1  6
 11 45  1  1
 10 43  1  0
 10 44  1  0
  9 41  1  0
  9 42  1  0
  8 40  1  1
  7 38  1  0
  7 39  1  0
  5 36  1  6
  6 37  1  0
  4 34  1  0
  4 35  1  0
  3 32  1  0
  3 33  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 28 62  1  0
 26 60  1  0
 26 61  1  0
 25 58  1  0
 25 59  1  0
 17 54  1  6
 24 57  1  0
 20 56  1  0
 19 55  1  0
M  END


  Mrv1652304292201272D          

 28 32  0  0  1  0            999 V2000
    2.6190   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1111   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3066   -2.0955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -2.7469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4893   -2.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9830   -1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3228   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4850    1.4085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  7 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 10 16  2  0  0  0  0
  5 17  1  6  0  0  0
  4 18  1  6  0  0  0
  3 19  1  1  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 25 27  1  6  0  0  0
 22 28  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0078365

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@@H](O)CC[C@]34C)[C@@]1(O)CC[C@@H]2C1=COC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O4/c1-22-10-7-17(25)13-16(22)4-5-20-19(22)8-11-23(2)18(9-12-24(20,23)27)15-3-6-21(26)28-14-15/h3,6,14,16-20,25,27H,4-5,7-13H2,1-2H3/t16-,17+,18-,19+,20-,22+,23-,24+/m1/s1

> <INCHI_KEY>
QEEBRPGZBVVINN-BMPKRDENSA-N

> <FORMULA>
C24H34O4

> <MOLECULAR_WEIGHT>
386.532

> <EXACT_MASS>
386.245709575

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
43.255521938520914

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(1S,2S,5S,7R,10R,11S,14S,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2H-pyran-2-one

> <ALOGPS_LOGP>
3.25

> <JCHEM_LOGP>
3.276761503666667

> <ALOGPS_LOGS>
-4.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.29639631666254

> <JCHEM_PKA_STRONGEST_BASIC>
0.2791948967908412

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
108.48869999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(1S,2S,5S,7R,10R,11S,14S,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.407  -1.269   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.353  -2.485   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.772  -3.912   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.717  -5.127   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      10.247  -4.122   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.302  -2.907   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.505   2.629   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   22                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5    9   18                                             
CONECT    5    4    6    7   17                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    7   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   10                                                       
CONECT   17    5                                                            
CONECT   18    4                                                            
CONECT   19    3   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21    2   23   28                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25   21                                                       
CONECT   27   25                                                            
CONECT   28   22                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Value	Source
3,14-Dihydroxy-bufa-20,22-dienolide	ChEBI
3-beta,14-Dihydroxy-5-beta-bufa-20,22-dienolide	ChEBI
3beta,14beta-Dihydroxy-5beta-bufa-20,22-dienolide	ChEBI
(3beta,5beta)-3,14-Dihydroxybufa-20,22-dienolide	Kegg
3-b,14-Dihydroxy-5-b-bufa-20,22-dienolide	Generator
3-Β,14-dihydroxy-5-β-bufa-20,22-dienolide	Generator
3b,14b-Dihydroxy-5b-bufa-20,22-dienolide	Generator
3Β,14β-dihydroxy-5β-bufa-20,22-dienolide	Generator
(3b,5b)-3,14-Dihydroxybufa-20,22-dienolide	Generator
(3Β,5β)-3,14-dihydroxybufa-20,22-dienolide	Generator
Bufalin, (3alpha,5beta)-isomer	MeSH

Chemical Formula

C₂₄H₃₄O₄

Average Mass

386.5320 Da

Monoisotopic Mass

386.24571 Da

IUPAC Name

5-[(1S,2S,5S,7R,10R,11S,14S,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2H-pyran-2-one

Traditional Name

5-[(1S,2S,5S,7R,10R,11S,14S,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pyran-2-one

CAS Registry Number

Not Available

SMILES

C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@@H](O)CC[C@]34C)[C@@]1(O)CC[C@@H]2C1=COC(=O)C=C1

InChI Identifier

InChI=1S/C24H34O4/c1-22-10-7-17(25)13-16(22)4-5-20-19(22)8-11-23(2)18(9-12-24(20,23)27)15-3-6-21(26)28-14-15/h3,6,14,16-20,25,27H,4-5,7-13H2,1-2H3/t16-,17+,18-,19+,20-,22+,23-,24+/m1/s1

InChI Key

QEEBRPGZBVVINN-BMPKRDENSA-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
Apis cerana	LOTUS Database	35616633
Bufo bankorensis	LOTUS Database	35616633
Bufo bufo	LOTUS Database	35616633
Bufo gargarizans	LOTUS Database	35616633
Cunninghamella blakesleana	Fungi	KNApSAcK
Cunninghamella blakesleeana	LOTUS Database	35616633
Duttaphrynus melanostictus	LOTUS Database	35616633
Kalanchoe pinnata	Plant	KNApSAcK
Phrynoidis asper	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Bufanolides and derivatives

Alternative Parents

Substituents

Bufanolide-skeleton
3-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
3-beta-hydroxysteroid
Pyranone
Pyran
Tertiary alcohol
Heteroaromatic compound
Cyclic alcohol
Secondary alcohol
Lactone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:517248 )
14beta-hydroxy steroid (CHEBI:517248 )
Bufanolides and derivatives (C16922 )
Bufanolide and derivatives [Fig] (C16922 )
Bufotoxins (C16922 )
Bufanolides and derivatives (LMST01130001 )

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	3.25	ALOGPS
logP	3.28	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	0.28	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	108.49 m³·mol⁻¹	ChemAxon
Polarizability	43.26 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

C00042323

Chemspider ID

7826155

KEGG Compound ID

C16922

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bufalin

METLIN ID

Not Available

PubChem Compound

9547215

PDB ID

Not Available

ChEBI ID

517248

Good Scents ID

Not Available

References

General References

Sampath V, Horesh N, Sasi B, Zannadeh H, Pogodin I, Singh SV, Deutsch J, Lichtstein D: Synthesis and Biological Evaluation of Novel Bufalin Derivatives. Int J Mol Sci. 2022 Apr 4;23(7):4007. doi: 10.3390/ijms23074007. [PubMed:35409366 ]
Jiang HY, Zheng HM, Xia C, Li X, Wang G, Zhao T, Cui XN, Wang RY, Liu Y: The Research Progress of Bufalin in the Treatment of Hepatocellular Carcinoma. Onco Targets Ther. 2022 Mar 22;15:291-298. doi: 10.2147/OTT.S333233. eCollection 2022. [PubMed:35345394 ]
Kuo JY, Liao CL, Ma YS, Kuo CL, Chen JC, Huang YP, Huang WW, Peng SF, Chung JG: Combination Treatment of Sorafenib and Bufalin Induces Apoptosis in NCI-H292 Human Lung Cancer Cells In Vitro. In Vivo. 2022 Mar-Apr;36(2):582-595. doi: 10.21873/invivo.12741. [PubMed:35241510 ]
Kreutzer FP, Meinecke A, Mitzka S, Hunkler HJ, Hobuss L, Abbas N, Geffers R, Weusthoff J, Xiao K, Jonigk DD, Fiedler J, Thum T: Development and characterization of anti-fibrotic natural compound similars with improved effectivity. Basic Res Cardiol. 2022 Mar 2;117(1):9. doi: 10.1007/s00395-022-00919-6. [PubMed:35235052 ]
Yu CC, Li Y, Cheng ZJ, Wang X, Mao W, Zhang YW: Active Components of Traditional Chinese Medicinal Material for Multiple Myeloma: Current Evidence and Future Directions. Front Pharmacol. 2022 Jan 27;13:818179. doi: 10.3389/fphar.2022.818179. eCollection 2022. [PubMed:35153791 ]

Showing NP-Card for Bufalin (NP0078365)

MOL for NP0078365 (Bufalin)

3D MOL for NP0078365 (Bufalin)

3D SDF for NP0078365 (Bufalin)

3D-SDF for NP0078365 (Bufalin)

PDB for NP0078365 (Bufalin)

3D PDB for NP0078365 (Bufalin)

SMILES for NP0078365 (Bufalin)

INCHI for NP0078365 (Bufalin)

Structure for NP0078365 (Bufalin)

3D Structure for NP0078365 (Bufalin)