NP-MRD: Showing NP-Card for Cucurbitacin B (NP0026813)

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Record Information

Version

2.0

Created at

2021-06-19 18:36:44 UTC

Updated at

2021-08-20 00:00:10 UTC

NP-MRD ID

NP0026813

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cucurbitacin B

Provided By

JEOL Database JEOL Logo

Description

Cucurbitacin B is found in Acanthosicyos horridus, Begonia heracleifolia, Begonia nantoensis, Begonia parviflora, Begonia plebeja, Bolbostemma paniculatum, Bryonia cretica, Bryonia verrucosa, Chrysosplenium flagelliferum, Citrullus colocynthis , Cogniauxia podolaena, Cucumis prophetarum, Cucumis sativus, Cucurbita foetidissima, Cucurbita maxima, Cucurbita pepo, Datisca glomerata, Ecballium elaterium, Hemsleya endecaphylla, Iberis umbellata, Ipomopsis aggregata, Luffa operculata, Marah fabacea, Morierina montana, Picrorhiza kurrooa, Trichosanthes hupehensis, Trichosanthes kirilowii, Trichosanthes multiloba, Trichosanthes tricuspidata and Wilbrandia ebracteata. Cucurbitacin B was first documented in 2008 (PMID: 18309509). Based on a literature review a small amount of articles have been published on Cucurbitacin b (PMID: 18442812) (PMID: 18561312) (PMID: 19700240) (PMID: 20153103).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120363D          

 86 89  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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    0.6947   -0.2498    2.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7127   -1.5504    1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6336   -0.4492    1.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5709    2.4978   -0.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4215    3.5191    1.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0446    1.9496    2.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3659    2.3522    3.9683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0770    1.0371    0.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3178    2.9647   -0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6757    4.0172    1.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4521    1.5687    1.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5365    3.6455    2.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6106    3.1988    5.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3334    4.4766    0.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3724    2.1151   -2.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4867    0.8111   -3.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
 39 40  1  6
 25 68  1  6
 12 13  1  0
 31 32  1  1
 27 29  1  0
 29 30  2  0
 25 34  1  0
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 24 23  2  0
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 19 20  1  1
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 15 12  1  0
 27 28  1  0
 34 36  1  0
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 38 36  1  0
 10  9  1  0
 39 19  1  0
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 31 24  1  0
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 25 26  1  0
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 25 24  1  0
  5  7  1  0
 19 18  1  0
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 18 16  1  0
  4  2  1  0
 16 15  1  0
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 15 39  1  0
  2  3  2  0
 13 52  1  0
 13 53  1  0
 13 54  1  0
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 23 67  1  0
 22 65  1  0
 22 66  1  0
 38 82  1  0
 38 83  1  0
 18 59  1  0
 18 60  1  0
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 40 84  1  0
 40 85  1  0
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 32 73  1  0
 32 74  1  0
 32 75  1  0
 33 76  1  0
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 17 58  1  0
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  1 41  1  0
  1 42  1  0
  1 43  1  0
M  END


  Mrv1652306192120363D          

 86 89  0  0  0  0            999 V2000
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    0.2992   -6.4172   -0.5393 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5218   -8.0131   -1.9541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4734   -7.2355    0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5791   -3.3998   -2.5111 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6979   -3.6440   -2.9746 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9545   -1.9866   -2.7006 C   0  0  2  0  0  0  0  0  0  0  0  0
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 10  9  1  0  0  0  0
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 29 31  1  0  0  0  0
  9  8  2  0  0  0  0
 31 24  1  0  0  0  0
  8  5  1  0  0  0  0
 25 26  1  0  0  0  0
  5  6  1  0  0  0  0
 25 24  1  0  0  0  0
  5  7  1  0  0  0  0
 19 18  1  0  0  0  0
  5  4  1  1  0  0  0
 18 16  1  0  0  0  0
  4  2  1  0  0  0  0
 16 15  1  0  0  0  0
  2  1  1  0  0  0  0
 15 39  1  0  0  0  0
  2  3  2  0  0  0  0
 13 52  1  0  0  0  0
 13 53  1  0  0  0  0
 13 54  1  0  0  0  0
 27 71  1  6  0  0  0
 26 69  1  0  0  0  0
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 22 65  1  0  0  0  0
 22 66  1  0  0  0  0
 38 82  1  0  0  0  0
 38 83  1  0  0  0  0
 18 59  1  0  0  0  0
 18 60  1  0  0  0  0
 16 57  1  6  0  0  0
 15 56  1  1  0  0  0
 40 84  1  0  0  0  0
 40 85  1  0  0  0  0
 40 86  1  0  0  0  0
 32 73  1  0  0  0  0
 32 74  1  0  0  0  0
 32 75  1  0  0  0  0
 33 76  1  0  0  0  0
 33 77  1  0  0  0  0
 33 78  1  0  0  0  0
 20 61  1  0  0  0  0
 20 62  1  0  0  0  0
 20 63  1  0  0  0  0
 35 79  1  0  0  0  0
 35 80  1  0  0  0  0
 35 81  1  0  0  0  0
 28 72  1  0  0  0  0
 17 58  1  0  0  0  0
  9 51  1  0  0  0  0
 14 55  1  0  0  0  0
  8 50  1  0  0  0  0
  6 44  1  0  0  0  0
  6 45  1  0  0  0  0
  6 46  1  0  0  0  0
  7 47  1  0  0  0  0
  7 48  1  0  0  0  0
  7 49  1  0  0  0  0
  1 41  1  0  0  0  0
  1 42  1  0  0  0  0
  1 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0026813

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@]3([H])C([H])([H])C([H])=C4[C@@]([H])(C([H])([H])[C@]([H])(O[H])C(=O)C4(C([H])([H])[H])C([H])([H])[H])[C@@]3(C(=O)C([H])([H])[C@]2(C([H])([H])[H])[C@@]1([H])[C@@](O[H])(C(=O)C(\[H])=C(/[H])C(OC(=O)C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12+/t19-,20+,21-,22+,25+,29+,30-,31+,32+/m1/s1

> <INCHI_KEY>
IXQKXEUSCPEQRD-DKRGWESNSA-N

> <FORMULA>
C32H46O8

> <MOLECULAR_WEIGHT>
558.712

> <EXACT_MASS>
558.319268441

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
60.803293894609176

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E,6R)-6-[(1R,2R,4S,10S,11S,13R,14R,15R)-4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate

> <ALOGPS_LOGP>
3.70

> <JCHEM_LOGP>
3.1330849993333327

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.490311222689868

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.802778313685344

> <JCHEM_PKA_STRONGEST_BASIC>
-2.883865598695122

> <JCHEM_POLAR_SURFACE_AREA>
138.20000000000002

> <JCHEM_REFRACTIVITY>
151.04330000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.56e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E,6R)-6-[(1R,2R,4S,10S,11S,13R,14R,15R)-4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 86 89  0  0  0  0  0  0  0  0999 V2000
   -1.8241   -6.5469    0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5395   -7.2573    0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3110   -8.4157    0.4313 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2992   -6.4172   -0.5393 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6176   -6.8610   -0.9450 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5218   -8.0131   -1.9541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4734   -7.2355    0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2959   -5.6896   -1.6421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7871   -4.4584   -1.8174 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5791   -3.3998   -2.5111 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6979   -3.6440   -2.9746 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9545   -1.9866   -2.7006 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7440   -2.1191   -3.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9274   -1.1975   -3.4051 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6259   -1.3210   -1.3347 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9083   -1.1611   -0.4616 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0624   -2.3289    0.3366 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7051    0.0781    0.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2094    0.4379    0.2847 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4480   -0.4951    1.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8560    1.9383    0.5359 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1580    2.4546    1.9538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0392    2.3100    2.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2508    2.0832    2.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7101    2.0529    1.1567 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9435    2.9745    1.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0810    2.5711    1.9309 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1622    3.4806    1.7461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5987    2.5892    3.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2746    3.1617    4.2379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3243    1.7864    3.6960 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8918    2.1423    5.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6812    0.2878    3.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5930    2.3499    0.0737 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5221    3.8656   -0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0337    1.6076   -1.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8850    2.0905   -1.9748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5151    0.2028   -1.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9850    0.1037   -1.2432 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7031    1.0781   -2.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4960   -7.2239    0.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3069   -6.2417   -0.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6272   -5.6787    1.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5005   -8.2621   -2.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8420   -7.7572   -2.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4586   -6.4346    1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2991   -5.8951   -2.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1213   -2.5468   -3.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9764   -2.7703   -4.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4592   -1.1563   -4.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5884   -1.8284   -3.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9395   -2.0151   -0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8177   -1.0396   -1.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9238   -2.2586    0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9894   -0.1139    1.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3351    0.8999    0.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6947   -0.2498    2.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7127   -1.5504    1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6336   -0.4492    1.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5709    2.4978   -0.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4215    3.5191    1.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0446    1.9496    2.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3659    2.3522    3.9683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0770    1.0371    0.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3178    2.9647   -0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6757    4.0172    1.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4521    1.5687    1.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5365    3.6455    2.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7057    1.9705    5.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6106    3.1988    5.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0473    1.5302    5.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8093   -0.3288    3.9293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0550   -0.0476    2.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4680    0.0651    4.4125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3334    4.4766    0.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4391    4.2365   -0.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7274   -0.0032   -2.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1021   -0.5154   -0.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7899    1.0802   -2.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3724    2.1151   -2.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4867    0.8111   -3.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
 39 40  1  6
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 12 13  1  0
 31 32  1  1
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 31 33  1  0
 24 23  2  0
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 19 20  1  1
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 34 36  1  0
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 19 18  1  0
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M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.824  -6.547   0.422  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.540  -7.257   0.120  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.311  -8.416   0.431  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.299  -6.417  -0.539  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.618  -6.861  -0.945  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.522  -8.013  -1.954  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.473  -7.236   0.273  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.296  -5.690  -1.642  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.787  -4.458  -1.817  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.579  -3.400  -2.511  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.698  -3.644  -2.975  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.954  -1.987  -2.701  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.744  -2.119  -3.625  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.927  -1.198  -3.405  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.626  -1.321  -1.335  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.908  -1.161  -0.462  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.062  -2.329   0.337  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.705   0.078   0.439  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.209   0.438   0.285  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.448  -0.495   1.277  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.856   1.938   0.536  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.158   2.455   1.954  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.039   2.310   2.932  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.251   2.083   2.620  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.710   2.053   1.157  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.943   2.974   1.009  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.081   2.571   1.931  0.00  0.00           C+0
HETATM   28  O   UNK     0      -5.162   3.481   1.746  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.599   2.589   3.377  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.275   3.162   4.238  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.324   1.786   3.696  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.892   2.142   5.137  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.681   0.288   3.682  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.593   2.350   0.074  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.522   3.866  -0.273  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.034   1.608  -1.222  0.00  0.00           C+0
HETATM   37  O   UNK     0      -1.885   2.091  -1.975  0.00  0.00           O+0
HETATM   38  C   UNK     0      -0.515   0.203  -1.518  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.985   0.104  -1.243  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.703   1.078  -2.228  0.00  0.00           C+0
HETATM   41  H   UNK     0      -2.496  -7.224   0.958  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.307  -6.242  -0.509  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.627  -5.679   1.057  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.128  -8.926  -1.497  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.501  -8.262  -2.380  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.842  -7.757  -2.776  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.516  -7.428  -0.008  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.103  -8.136   0.772  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.459  -6.435   1.021  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.299  -5.895  -2.019  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.802  -4.192  -1.457  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.121  -2.547  -3.109  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.976  -2.770  -4.477  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.459  -1.156  -4.059  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.588  -1.828  -3.764  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.940  -2.015  -0.835  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.818  -1.040  -1.059  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.924  -2.259   0.787  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.989  -0.114   1.480  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.335   0.900   0.079  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.695  -0.250   2.315  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.713  -1.550   1.171  0.00  0.00           H+0
HETATM   63  H   UNK     0      -0.634  -0.449   1.170  0.00  0.00           H+0
HETATM   64  H   UNK     0       1.571   2.498  -0.082  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.422   3.519   1.910  0.00  0.00           H+0
HETATM   66  H   UNK     0       2.045   1.950   2.353  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.366   2.352   3.968  0.00  0.00           H+0
HETATM   68  H   UNK     0      -2.077   1.037   0.966  0.00  0.00           H+0
HETATM   69  H   UNK     0      -3.318   2.965  -0.021  0.00  0.00           H+0
HETATM   70  H   UNK     0      -2.676   4.017   1.227  0.00  0.00           H+0
HETATM   71  H   UNK     0      -4.452   1.569   1.696  0.00  0.00           H+0
HETATM   72  H   UNK     0      -5.537   3.646   2.636  0.00  0.00           H+0
HETATM   73  H   UNK     0      -2.706   1.970   5.852  0.00  0.00           H+0
HETATM   74  H   UNK     0      -1.611   3.199   5.220  0.00  0.00           H+0
HETATM   75  H   UNK     0      -1.047   1.530   5.474  0.00  0.00           H+0
HETATM   76  H   UNK     0      -1.809  -0.329   3.929  0.00  0.00           H+0
HETATM   77  H   UNK     0      -3.055  -0.048   2.709  0.00  0.00           H+0
HETATM   78  H   UNK     0      -3.468   0.065   4.412  0.00  0.00           H+0
HETATM   79  H   UNK     0      -0.333   4.477   0.616  0.00  0.00           H+0
HETATM   80  H   UNK     0       0.279   4.067  -0.995  0.00  0.00           H+0
HETATM   81  H   UNK     0      -1.439   4.237  -0.743  0.00  0.00           H+0
HETATM   82  H   UNK     0      -0.727  -0.003  -2.571  0.00  0.00           H+0
HETATM   83  H   UNK     0      -1.102  -0.515  -0.939  0.00  0.00           H+0
HETATM   84  H   UNK     0       2.790   1.080  -2.105  0.00  0.00           H+0
HETATM   85  H   UNK     0       1.372   2.115  -2.129  0.00  0.00           H+0
HETATM   86  H   UNK     0       1.487   0.811  -3.268  0.00  0.00           H+0
CONECT    1    2   41   42   43                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5    8    6    7    4                                             
CONECT    6    5   44   45   46                                             
CONECT    7    5   47   48   49                                             
CONECT    8    9    5   50                                                  
CONECT    9   10    8   51                                                  
CONECT   10   12    9   11                                                  
CONECT   11   10                                                            
CONECT   12   13   15   10   14                                             
CONECT   13   12   52   53   54                                             
CONECT   14   12   55                                                       
CONECT   15   12   16   39   56                                             
CONECT   16   17   18   15   57                                             
CONECT   17   16   58                                                       
CONECT   18   19   16   59   60                                             
CONECT   19   20   21   39   18                                             
CONECT   20   19   61   62   63                                             
CONECT   21   22   34   64   19                                             
CONECT   22   23   21   65   66                                             
CONECT   23   24   22   67                                                  
CONECT   24   23   31   25                                                  
CONECT   25   68   34   26   24                                             
CONECT   26   27   25   69   70                                             
CONECT   27   29   28   26   71                                             
CONECT   28   27   72                                                       
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   32   33   29   24                                             
CONECT   32   31   73   74   75                                             
CONECT   33   31   76   77   78                                             
CONECT   34   25   21   35   36                                             
CONECT   35   34   79   80   81                                             
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   39   36   82   83                                             
CONECT   39   40   38   19   15                                             
CONECT   40   39   84   85   86                                             
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    1                                                            
CONECT   44    6                                                            
CONECT   45    6                                                            
CONECT   46    6                                                            
CONECT   47    7                                                            
CONECT   48    7                                                            
CONECT   49    7                                                            
CONECT   50    8                                                            
CONECT   51    9                                                            
CONECT   52   13                                                            
CONECT   53   13                                                            
CONECT   54   13                                                            
CONECT   55   14                                                            
CONECT   56   15                                                            
CONECT   57   16                                                            
CONECT   58   17                                                            
CONECT   59   18                                                            
CONECT   60   18                                                            
CONECT   61   20                                                            
CONECT   62   20                                                            
CONECT   63   20                                                            
CONECT   64   21                                                            
CONECT   65   22                                                            
CONECT   66   22                                                            
CONECT   67   23                                                            
CONECT   68   25                                                            
CONECT   69   26                                                            
CONECT   70   26                                                            
CONECT   71   27                                                            
CONECT   72   28                                                            
CONECT   73   32                                                            
CONECT   74   32                                                            
CONECT   75   32                                                            
CONECT   76   33                                                            
CONECT   77   33                                                            
CONECT   78   33                                                            
CONECT   79   35                                                            
CONECT   80   35                                                            
CONECT   81   35                                                            
CONECT   82   38                                                            
CONECT   83   38                                                            
CONECT   84   40                                                            
CONECT   85   40                                                            
CONECT   86   40                                                            
MASTER        0    0    0    0    0    0    0    0   86    0  178    0
END

RDKit          3D

86 89  0  0  0  0  0  0  0  0999 V2000
   -1.8241   -6.5469    0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
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  6 45  1  0
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  1 41  1  0
  1 42  1  0
  1 43  1  0
M  END

View in JSmol

Synonyms

Value	Source
1,2-Dihydro-alpha-elaterin	ChEBI
2beta,16alpha,20,25-Tetrahydroxy-9-methyl-19-nor-9beta,10alpha-lanosta-5,23-diene-3,11,22-trione, 25-acetate	ChEBI
2beta,16alpha,20,25-Tetrahydroxy-9-methyl-3,11,22-trioxo-19-nor-9beta,10alpha-lanosta-5,23-dien-25-yl acetate	ChEBI
1,2-Dihydro-a-elaterin	Generator
1,2-Dihydro-α-elaterin	Generator
2b,16a,20,25-Tetrahydroxy-9-methyl-19-nor-9b,10a-lanosta-5,23-diene-3,11,22-trione, 25-acetate	Generator
2b,16a,20,25-Tetrahydroxy-9-methyl-19-nor-9b,10a-lanosta-5,23-diene-3,11,22-trione, 25-acetic acid	Generator
2beta,16alpha,20,25-Tetrahydroxy-9-methyl-19-nor-9beta,10alpha-lanosta-5,23-diene-3,11,22-trione, 25-acetic acid	Generator
2Β,16α,20,25-tetrahydroxy-9-methyl-19-nor-9β,10α-lanosta-5,23-diene-3,11,22-trione, 25-acetate	Generator
2Β,16α,20,25-tetrahydroxy-9-methyl-19-nor-9β,10α-lanosta-5,23-diene-3,11,22-trione, 25-acetic acid	Generator
2b,16a,20,25-Tetrahydroxy-9-methyl-3,11,22-trioxo-19-nor-9b,10a-lanosta-5,23-dien-25-yl acetate	Generator
2b,16a,20,25-Tetrahydroxy-9-methyl-3,11,22-trioxo-19-nor-9b,10a-lanosta-5,23-dien-25-yl acetic acid	Generator
2beta,16alpha,20,25-Tetrahydroxy-9-methyl-3,11,22-trioxo-19-nor-9beta,10alpha-lanosta-5,23-dien-25-yl acetic acid	Generator
2Β,16α,20,25-tetrahydroxy-9-methyl-3,11,22-trioxo-19-nor-9β,10α-lanosta-5,23-dien-25-yl acetate	Generator
2Β,16α,20,25-tetrahydroxy-9-methyl-3,11,22-trioxo-19-nor-9β,10α-lanosta-5,23-dien-25-yl acetic acid	Generator
Cucurbitacin b 2-sulfate	MeSH

Chemical Formula

C₃₂H₄₆O₈

Average Mass

558.7120 Da

Monoisotopic Mass

558.31927 Da

IUPAC Name

(3E,6R)-6-[(1R,2R,4S,10S,11S,13R,14R,15R)-4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate

Traditional Name

(3E,6R)-6-[(1R,2R,4S,10S,11S,13R,14R,15R)-4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@]3([H])C([H])([H])C([H])=C4[C@@]([H])(C([H])([H])[C@]([H])(O[H])C(=O)C4(C([H])([H])[H])C([H])([H])[H])[C@@]3(C(=O)C([H])([H])[C@]2(C([H])([H])[H])[C@@]1([H])[C@@](O[H])(C(=O)C(\[H])=C(/[H])C(OC(=O)C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12+/t19-,20+,21-,22+,25+,29+,30-,31+,32+/m1/s1

InChI Key

IXQKXEUSCPEQRD-DKRGWESNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acanthosicyos horridus	LOTUS Database	35616633
Anagallis arvensis	KNApSAcK Database	22123792
Begonia heracleifolia	LOTUS Database	35616633
Begonia nantoensis	JEOL database	Wu, P.-L., et al, Chem. Pharm. Bull. 52, 345 (2004)
Begonia parviflora	LOTUS Database	35616633
Begonia plebeja	LOTUS Database	35616633
Bolbostemma paniculatum	LOTUS Database	35616633
Bryonia alba	KNApSAcK Database	22123792
Bryonia cretica	LOTUS Database	35616633
Bryonia dioica	KNApSAcK Database	22123792
Bryonia verrucosa	LOTUS Database	35616633
Casearia arborea	KNApSAcK Database	22123792
Chrysosplenium flagelliferum	LOTUS Database	35616633
Citrullus colocynthis	Plant	KNApSAcK
Citrullus lanatus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cogniauxia podolaena	LOTUS Database	35616633
Cucumis africanus	KNApSAcK Database	22123792
Cucumis melo	KNApSAcK Database	22123792
Cucumis prophetarum	LOTUS Database	35616633
Cucumis sativus	LOTUS Database	35616633
Cucumis sativus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cucurbita foetidissima	LOTUS Database	35616633
Cucurbita maxima	LOTUS Database	35616633
Cucurbita pepo	LOTUS Database	35616633
Datisca glomerata	LOTUS Database	35616633
Ecballium elaterium	LOTUS Database	35616633
Hemsleya endecaphylla	LOTUS Database	35616633
Iberis spp.	KNApSAcK Database	22123792
Iberis umbellata	LOTUS Database	35616633
Ipomopsis aggregata	LOTUS Database	35616633
Lagenaria siceraria	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Licania intrapetiolaris	KNApSAcK Database	22123792
Luffa aegyptiaca	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Luffa operculata	LOTUS Database	35616633
Marah fabacea	LOTUS Database	35616633
Momordica charantia	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Morierina montana	LOTUS Database	35616633
Picrorhiza kurrooa	LOTUS Database	35616633
Trichosanthes hupehensis	LOTUS Database	35616633
Trichosanthes kirilowii	LOTUS Database	35616633
Trichosanthes multiloba	LOTUS Database	35616633
Trichosanthes tricuspidata	LOTUS Database	35616633
Wilbrandia ebracteata	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Diabrotica undecimpunctata howardi	KNApSAcK Database	22123792
Leucopaxillus gentianeus	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.38 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.7	ALOGPS
logP	3.13	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	12.8	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	138.2 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	151.04 m³·mol⁻¹	ChemAxon
Polarizability	60.8 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003683

Chemspider ID

4444693

KEGG Compound ID

C08794

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

3941

Good Scents ID

rw1846421

References

General References

Liu T, Zhang M, Zhang H, Sun C, Deng Y: Inhibitory effects of cucurbitacin B on laryngeal squamous cell carcinoma. Eur Arch Otorhinolaryngol. 2008 Oct;265(10):1225-32. doi: 10.1007/s00405-008-0625-9. Epub 2008 Feb 29. [PubMed:18309509 ]
Liu T, Zhang M, Zhang H, Sun C, Yang X, Deng Y, Ji W: Combined antitumor activity of cucurbitacin B and docetaxel in laryngeal cancer. Eur J Pharmacol. 2008 Jun 10;587(1-3):78-84. doi: 10.1016/j.ejphar.2008.03.032. Epub 2008 Apr 1. [PubMed:18442812 ]
Yin D, Wakimoto N, Xing H, Lu D, Huynh T, Wang X, Black KL, Koeffler HP: Cucurbitacin B markedly inhibits growth and rapidly affects the cytoskeleton in glioblastoma multiforme. Int J Cancer. 2008 Sep 15;123(6):1364-75. doi: 10.1002/ijc.23648. [PubMed:18561312 ]
Chan KT, Li K, Liu SL, Chu KH, Toh M, Xie WD: Cucurbitacin B inhibits STAT3 and the Raf/MEK/ERK pathway in leukemia cell line K562. Cancer Lett. 2010 Mar 1;289(1):46-52. doi: 10.1016/j.canlet.2009.07.015. Epub 2009 Aug 22. [PubMed:19700240 ]
Chan KT, Meng FY, Li Q, Ho CY, Lam TS, To Y, Lee WH, Li M, Chu KH, Toh M: Cucurbitacin B induces apoptosis and S phase cell cycle arrest in BEL-7402 human hepatocellular carcinoma cells and is effective via oral administration. Cancer Lett. 2010 Aug 1;294(1):118-24. doi: 10.1016/j.canlet.2010.01.029. Epub 2010 Feb 11. [PubMed:20153103 ]
Wu, P.-L., et al. (2004). Wu, P.-L., et al, Chem. Pharm. Bull. 52, 345 (2004). Chem. Pharm. Bull..

Showing NP-Card for Cucurbitacin B (NP0026813)

MOL for NP0026813 (Cucurbitacin B)

3D MOL for NP0026813 (Cucurbitacin B)

3D SDF for NP0026813 (Cucurbitacin B)

3D-SDF for NP0026813 (Cucurbitacin B)

PDB for NP0026813 (Cucurbitacin B)

3D PDB for NP0026813 (Cucurbitacin B)

SMILES for NP0026813 (Cucurbitacin B)

INCHI for NP0026813 (Cucurbitacin B)

Structure for NP0026813 (Cucurbitacin B)

3D Structure for NP0026813 (Cucurbitacin B)