NP-MRD: Showing NP-Card for cucurbitacin I (NP0031176)

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Record Information

Version

2.0

Created at

2021-06-19 22:19:49 UTC

Updated at

2021-08-20 00:00:23 UTC

NP-MRD ID

NP0031176

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cucurbitacin I

Provided By

JEOL Database JEOL Logo

Description

Cucurbitacin i belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. Thus, cucurbitacin I is considered to be a sterol. cucurbitacin I is found in Bryonia verrucosa, Citrullus colocynthis, Cucumis sativus, Cucurbita maxima, Cucurbita pepo, Elaeocarpus chinensis, Elaeocarpus hainanensis, Gyrinops walla, Hemsleya endecaphylla and Iberis umbellata. cucurbitacin I was first documented in 2009 (PMID: 19843642). Based on a literature review a significant number of articles have been published on Cucurbitacin i (PMID: 21062915) (PMID: 22328572) (PMID: 23478800) (PMID: 34220238) (PMID: 33987407).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100193D          

 79 82  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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   -6.7349   -0.0314   -2.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8313   -2.7950   -3.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0914   -2.6906   -2.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1563   -1.9873   -1.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8202    1.2137   -5.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4322    2.4752   -3.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1136    2.2239   -4.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4024   -0.8782   -1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2258   -1.4534   -1.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9736    2.1107   -1.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1992    1.3488   -0.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1264    2.5506   -0.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
 36 16  1  0
 21 20  2  0
 20 19  1  0
 19 18  1  0
 31 18  1  0
 28 21  1  0
 16 15  1  0
 15 13  1  0
 13 12  1  0
 12 36  1  0
 22 23  1  0
 16 17  1  1
 22 21  1  0
 28 30  1  1
 31 33  1  0
 31 32  1  6
 18 16  1  0
 36 37  1  6
 35 33  1  0
 13 14  1  0
 35 36  1  0
 12  9  1  0
  9  7  1  0
 24 25  1  0
  7  6  1  0
 24 26  1  0
  7  8  2  0
 26 27  2  0
  6  5  2  0
 24 23  2  0
  5  2  1  0
 33 34  2  0
  2  1  1  0
 26 28  1  0
  9 11  1  1
 28 29  1  0
  9 10  1  0
 22 31  1  0
  2  3  1  0
 22 63  1  1
  2  4  1  6
 25 65  1  0
 23 64  1  0
 20 62  1  0
 19 60  1  0
 19 61  1  0
 18 59  1  6
 35 75  1  0
 35 76  1  0
 29 66  1  0
 29 67  1  0
 29 68  1  0
 15 54  1  0
 15 55  1  0
 13 52  1  1
 12 51  1  6
 17 56  1  0
 17 57  1  0
 17 58  1  0
 30 69  1  0
 30 70  1  0
 30 71  1  0
 32 72  1  0
 32 73  1  0
 32 74  1  0
 37 77  1  0
 37 78  1  0
 37 79  1  0
 14 53  1  0
  6 46  1  0
  5 45  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
 11 50  1  0
 10 47  1  0
 10 48  1  0
 10 49  1  0
  3 41  1  0
  3 42  1  0
  3 43  1  0
  4 44  1  0
M  END


  Mrv1652306202100193D          

 79 82  0  0  0  0            999 V2000
   -0.5059   -2.9230    6.7269 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3447   -3.2826    5.5059 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3664   -4.3604    5.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5154   -3.8243    4.5032 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0465   -2.0609    4.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0511   -1.6586    3.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734   -0.4191    3.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3623    0.2767    4.1102 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8304   -0.0366    1.7685 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6611   -1.0944    1.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5659    1.1956    1.6865 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4091    0.1587    1.1696 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3689    1.2863    1.9164 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0799    0.7083    3.0059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3570    1.9146    0.9059 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3345    0.9608   -0.3118 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3232   -0.1929    0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7052    1.6156   -1.6814 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1306    2.1908   -1.7562 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1619    1.2775   -2.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9185    0.1278   -2.9929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4841   -0.3424   -3.2702 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3675   -0.9100   -4.6740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3910   -1.2075   -5.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1832   -1.6787   -6.7596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7974   -1.0769   -5.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6906   -1.2918   -5.8270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0438   -0.7943   -3.5130 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4661   -0.2065   -3.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0252   -2.1378   -2.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3706    0.7280   -2.9430 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1816    1.7111   -4.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0367   -0.0491   -2.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6786   -0.3404   -3.7184 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3577   -0.5576   -1.3704 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1917    0.5501   -0.3293 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1644    1.7060   -0.7259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1058   -2.5432    7.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2538   -2.1610    6.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0631   -3.7973    7.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649   -5.2675    6.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9509   -4.6586    4.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0610   -4.0219    6.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2622   -3.2085    4.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5976   -1.4748    5.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5406   -2.2222    2.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5624   -1.3419    1.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187   -0.7320    0.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1005   -2.0225    0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0511    1.2848    2.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1066   -0.7957    1.3293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2908    2.0618    2.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616    1.4435    3.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3601    2.0381    1.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0037    2.9115    0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2587   -1.0476   -0.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1712   -0.5948    1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3594    0.1593    0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748    2.5133   -1.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1201    3.0983   -2.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4615    2.5177   -0.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1807    1.6174   -2.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3044   -1.2097   -2.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3660   -1.0976   -5.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0827   -1.7864   -7.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2210   -0.8886   -3.7882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5630    0.7381   -3.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7349   -0.0314   -2.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8313   -2.7950   -3.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0914   -2.6906   -2.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1563   -1.9873   -1.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8202    1.2137   -5.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4322    2.4752   -3.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1136    2.2239   -4.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4024   -0.8782   -1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2258   -1.4534   -1.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9736    2.1107   -1.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1992    1.3488   -0.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1264    2.5506   -0.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
 36 16  1  0  0  0  0
 21 20  2  0  0  0  0
 20 19  1  0  0  0  0
 19 18  1  0  0  0  0
 31 18  1  0  0  0  0
 28 21  1  0  0  0  0
 16 15  1  0  0  0  0
 15 13  1  0  0  0  0
 13 12  1  0  0  0  0
 12 36  1  0  0  0  0
 22 23  1  0  0  0  0
 16 17  1  1  0  0  0
 22 21  1  0  0  0  0
 28 30  1  1  0  0  0
 31 33  1  0  0  0  0
 31 32  1  6  0  0  0
 18 16  1  0  0  0  0
 36 37  1  6  0  0  0
 35 33  1  0  0  0  0
 13 14  1  0  0  0  0
 35 36  1  0  0  0  0
 12  9  1  0  0  0  0
  9  7  1  0  0  0  0
 24 25  1  0  0  0  0
  7  6  1  0  0  0  0
 24 26  1  0  0  0  0
  7  8  2  0  0  0  0
 26 27  2  0  0  0  0
  6  5  2  0  0  0  0
 24 23  2  0  0  0  0
  5  2  1  0  0  0  0
 33 34  2  0  0  0  0
  2  1  1  0  0  0  0
 26 28  1  0  0  0  0
  9 11  1  1  0  0  0
 28 29  1  0  0  0  0
  9 10  1  0  0  0  0
 22 31  1  0  0  0  0
  2  3  1  0  0  0  0
 22 63  1  1  0  0  0
  2  4  1  6  0  0  0
 25 65  1  0  0  0  0
 23 64  1  0  0  0  0
 20 62  1  0  0  0  0
 19 60  1  0  0  0  0
 19 61  1  0  0  0  0
 18 59  1  6  0  0  0
 35 75  1  0  0  0  0
 35 76  1  0  0  0  0
 29 66  1  0  0  0  0
 29 67  1  0  0  0  0
 29 68  1  0  0  0  0
 15 54  1  0  0  0  0
 15 55  1  0  0  0  0
 13 52  1  1  0  0  0
 12 51  1  6  0  0  0
 17 56  1  0  0  0  0
 17 57  1  0  0  0  0
 17 58  1  0  0  0  0
 30 69  1  0  0  0  0
 30 70  1  0  0  0  0
 30 71  1  0  0  0  0
 32 72  1  0  0  0  0
 32 73  1  0  0  0  0
 32 74  1  0  0  0  0
 37 77  1  0  0  0  0
 37 78  1  0  0  0  0
 37 79  1  0  0  0  0
 14 53  1  0  0  0  0
  6 46  1  0  0  0  0
  5 45  1  0  0  0  0
  1 38  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
 11 50  1  0  0  0  0
 10 47  1  0  0  0  0
 10 48  1  0  0  0  0
 10 49  1  0  0  0  0
  3 41  1  0  0  0  0
  3 42  1  0  0  0  0
  3 43  1  0  0  0  0
  4 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031176

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])[C@]2([H])C(=C([H])C([H])([H])[C@@]3([H])[C@]4(C([H])([H])[H])C([H])([H])[C@@]([H])(O[H])[C@]([H])([C@@](O[H])(C(=O)C(\[H])=C(/[H])C(O[H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])[C@@]4(C([H])([H])[H])C([H])([H])C(=O)[C@@]23C([H])([H])[H])C(C1=O)(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,11-13,17,19-20,23,31-32,36-37H,10,14-15H2,1-8H3/b12-11+/t17-,19-,20+,23+,27+,28-,29+,30+/m1/s1

> <INCHI_KEY>
NISPVUDLMHQFRQ-MKIKIEMVSA-N

> <FORMULA>
C30H42O7

> <MOLECULAR_WEIGHT>
514.6503

> <EXACT_MASS>
514.293053698

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
56.51817177940234

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.33

> <JCHEM_LOGP>
3.0421913179999986

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.93902707742241

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.086396466932571

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8062198825595894

> <JCHEM_POLAR_SURFACE_AREA>
132.13

> <JCHEM_REFRACTIVITY>
143.4603

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.32e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 79 82  0  0  0  0  0  0  0  0999 V2000
   -0.5059   -2.9230    6.7269 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3447   -3.2826    5.5059 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3664   -4.3604    5.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5154   -3.8243    4.5032 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0465   -2.0609    4.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0511   -1.6586    3.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734   -0.4191    3.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3623    0.2767    4.1102 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8304   -0.0366    1.7685 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6611   -1.0944    1.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5659    1.1956    1.6865 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4091    0.1587    1.1696 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3689    1.2863    1.9164 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0799    0.7083    3.0059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3570    1.9146    0.9059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3345    0.9608   -0.3118 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3232   -0.1929    0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7052    1.6156   -1.6814 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1306    2.1908   -1.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1619    1.2775   -2.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9185    0.1278   -2.9929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4841   -0.3424   -3.2702 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3675   -0.9100   -4.6740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3910   -1.2075   -5.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0252   -2.1378   -2.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1816    1.7111   -4.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0367   -0.0491   -2.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6786   -0.3404   -3.7184 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1644    1.7060   -0.7259 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2538   -2.1610    6.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9509   -4.6586    4.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5624   -1.3419    1.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187   -0.7320    0.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1005   -2.0225    0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0511    1.2848    2.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1066   -0.7957    1.3293 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2908    2.0618    2.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616    1.4435    3.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3601    2.0381    1.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0037    2.9115    0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2587   -1.0476   -0.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1712   -0.5948    1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3594    0.1593    0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748    2.5133   -1.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1201    3.0983   -2.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4615    2.5177   -0.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1807    1.6174   -2.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3044   -1.2097   -2.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3660   -1.0976   -5.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0827   -1.7864   -7.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2210   -0.8886   -3.7882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5630    0.7381   -3.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7349   -0.0314   -2.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8313   -2.7950   -3.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0914   -2.6906   -2.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1563   -1.9873   -1.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8202    1.2137   -5.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4322    2.4752   -3.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1136    2.2239   -4.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4024   -0.8782   -1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2258   -1.4534   -1.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9736    2.1107   -1.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1992    1.3488   -0.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1264    2.5506   -0.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
 36 16  1  0
 21 20  2  0
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 19 18  1  0
 31 18  1  0
 28 21  1  0
 16 15  1  0
 15 13  1  0
 13 12  1  0
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 22 23  1  0
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 31 33  1  0
 31 32  1  6
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 12  9  1  0
  9  7  1  0
 24 25  1  0
  7  6  1  0
 24 26  1  0
  7  8  2  0
 26 27  2  0
  6  5  2  0
 24 23  2  0
  5  2  1  0
 33 34  2  0
  2  1  1  0
 26 28  1  0
  9 11  1  1
 28 29  1  0
  9 10  1  0
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  2  3  1  0
 22 63  1  1
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 30 69  1  0
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 37 77  1  0
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 37 79  1  0
 14 53  1  0
  6 46  1  0
  5 45  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
 11 50  1  0
 10 47  1  0
 10 48  1  0
 10 49  1  0
  3 41  1  0
  3 42  1  0
  3 43  1  0
  4 44  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.506  -2.923   6.727  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.345  -3.283   5.506  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.366  -4.360   5.867  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.515  -3.824   4.503  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.046  -2.061   4.967  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.051  -1.659   3.685  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.773  -0.419   3.276  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.362   0.277   4.110  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.830  -0.037   1.769  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.661  -1.094   1.042  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.566   1.196   1.687  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.409   0.159   1.170  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.369   1.286   1.916  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.080   0.708   3.006  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.357   1.915   0.906  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.335   0.961  -0.312  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.323  -0.193   0.048  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.705   1.616  -1.681  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.131   2.191  -1.756  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.162   1.278  -2.334  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.918   0.128  -2.993  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.484  -0.342  -3.270  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.368  -0.910  -4.674  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.391  -1.208  -5.479  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.183  -1.679  -6.760  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.797  -1.077  -5.004  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.691  -1.292  -5.827  0.00  0.00           O+0
HETATM   28  C   UNK     0      -5.044  -0.794  -3.513  0.00  0.00           C+0
HETATM   29  C   UNK     0      -6.466  -0.207  -3.378  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.025  -2.138  -2.758  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.371   0.728  -2.943  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.182   1.711  -4.137  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.037  -0.049  -2.755  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.679  -0.340  -3.718  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.358  -0.558  -1.370  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.192   0.550  -0.329  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.164   1.706  -0.726  0.00  0.00           C+0
HETATM   38  H   UNK     0       0.106  -2.543   7.553  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.254  -2.161   6.476  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.063  -3.797   7.083  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.865  -5.268   6.224  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.951  -4.659   4.988  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.061  -4.022   6.643  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.262  -3.208   4.404  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.598  -1.475   5.703  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.541  -2.222   2.915  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.562  -1.342   1.616  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.019  -0.732   0.074  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.100  -2.022   0.891  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.051   1.285   2.535  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.107  -0.796   1.329  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.291   2.062   2.320  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.462   1.444   3.519  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.360   2.038   1.329  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.004   2.912   0.618  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.259  -1.048  -0.621  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.171  -0.595   1.054  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.359   0.159   0.045  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.075   2.513  -1.739  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.120   3.098  -2.374  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.462   2.518  -0.764  0.00  0.00           H+0
HETATM   62  H   UNK     0      -5.181   1.617  -2.163  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.304  -1.210  -2.626  0.00  0.00           H+0
HETATM   64  H   UNK     0      -1.366  -1.098  -5.059  0.00  0.00           H+0
HETATM   65  H   UNK     0      -4.083  -1.786  -7.136  0.00  0.00           H+0
HETATM   66  H   UNK     0      -7.221  -0.889  -3.788  0.00  0.00           H+0
HETATM   67  H   UNK     0      -6.563   0.738  -3.926  0.00  0.00           H+0
HETATM   68  H   UNK     0      -6.735  -0.031  -2.330  0.00  0.00           H+0
HETATM   69  H   UNK     0      -5.831  -2.795  -3.106  0.00  0.00           H+0
HETATM   70  H   UNK     0      -4.091  -2.691  -2.908  0.00  0.00           H+0
HETATM   71  H   UNK     0      -5.156  -1.987  -1.680  0.00  0.00           H+0
HETATM   72  H   UNK     0      -0.820   1.214  -5.043  0.00  0.00           H+0
HETATM   73  H   UNK     0      -0.432   2.475  -3.898  0.00  0.00           H+0
HETATM   74  H   UNK     0      -2.114   2.224  -4.395  0.00  0.00           H+0
HETATM   75  H   UNK     0       1.402  -0.878  -1.430  0.00  0.00           H+0
HETATM   76  H   UNK     0      -0.226  -1.453  -1.143  0.00  0.00           H+0
HETATM   77  H   UNK     0       0.974   2.111  -1.723  0.00  0.00           H+0
HETATM   78  H   UNK     0       2.199   1.349  -0.757  0.00  0.00           H+0
HETATM   79  H   UNK     0       1.126   2.551  -0.032  0.00  0.00           H+0
CONECT    1    2   38   39   40                                             
CONECT    2    5    1    3    4                                             
CONECT    3    2   41   42   43                                             
CONECT    4    2   44                                                       
CONECT    5    6    2   45                                                  
CONECT    6    7    5   46                                                  
CONECT    7    9    6    8                                                  
CONECT    8    7                                                            
CONECT    9   12    7   11   10                                             
CONECT   10    9   47   48   49                                             
CONECT   11    9   50                                                       
CONECT   12   13   36    9   51                                             
CONECT   13   15   12   14   52                                             
CONECT   14   13   53                                                       
CONECT   15   16   13   54   55                                             
CONECT   16   36   15   17   18                                             
CONECT   17   16   56   57   58                                             
CONECT   18   19   31   16   59                                             
CONECT   19   20   18   60   61                                             
CONECT   20   21   19   62                                                  
CONECT   21   20   28   22                                                  
CONECT   22   23   21   31   63                                             
CONECT   23   22   24   64                                                  
CONECT   24   25   26   23                                                  
CONECT   25   24   65                                                       
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   21   30   26   29                                             
CONECT   29   28   66   67   68                                             
CONECT   30   28   69   70   71                                             
CONECT   31   18   33   32   22                                             
CONECT   32   31   72   73   74                                             
CONECT   33   31   35   34                                                  
CONECT   34   33                                                            
CONECT   35   33   36   75   76                                             
CONECT   36   16   12   37   35                                             
CONECT   37   36   77   78   79                                             
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    3                                                            
CONECT   42    3                                                            
CONECT   43    3                                                            
CONECT   44    4                                                            
CONECT   45    5                                                            
CONECT   46    6                                                            
CONECT   47   10                                                            
CONECT   48   10                                                            
CONECT   49   10                                                            
CONECT   50   11                                                            
CONECT   51   12                                                            
CONECT   52   13                                                            
CONECT   53   14                                                            
CONECT   54   15                                                            
CONECT   55   15                                                            
CONECT   56   17                                                            
CONECT   57   17                                                            
CONECT   58   17                                                            
CONECT   59   18                                                            
CONECT   60   19                                                            
CONECT   61   19                                                            
CONECT   62   20                                                            
CONECT   63   22                                                            
CONECT   64   23                                                            
CONECT   65   25                                                            
CONECT   66   29                                                            
CONECT   67   29                                                            
CONECT   68   29                                                            
CONECT   69   30                                                            
CONECT   70   30                                                            
CONECT   71   30                                                            
CONECT   72   32                                                            
CONECT   73   32                                                            
CONECT   74   32                                                            
CONECT   75   35                                                            
CONECT   76   35                                                            
CONECT   77   37                                                            
CONECT   78   37                                                            
CONECT   79   37                                                            
MASTER        0    0    0    0    0    0    0    0   79    0  164    0
END

RDKit          3D

79 82  0  0  0  0  0  0  0  0999 V2000
   -0.5059   -2.9230    6.7269 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3447   -3.2826    5.5059 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3664   -4.3604    5.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5154   -3.8243    4.5032 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0465   -2.0609    4.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0511   -1.6586    3.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734   -0.4191    3.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3623    0.2767    4.1102 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8304   -0.0366    1.7685 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6611   -1.0944    1.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5659    1.1956    1.6865 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4091    0.1587    1.1696 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3689    1.2863    1.9164 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0799    0.7083    3.0059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3570    1.9146    0.9059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3345    0.9608   -0.3118 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3232   -0.1929    0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7052    1.6156   -1.6814 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1306    2.1908   -1.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1619    1.2775   -2.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9185    0.1278   -2.9929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4841   -0.3424   -3.2702 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3675   -0.9100   -4.6740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3910   -1.2075   -5.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1832   -1.6787   -6.7596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7974   -1.0769   -5.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6906   -1.2918   -5.8270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0438   -0.7943   -3.5130 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4661   -0.2065   -3.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0252   -2.1378   -2.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3706    0.7280   -2.9430 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1816    1.7111   -4.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0367   -0.0491   -2.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6786   -0.3404   -3.7184 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3577   -0.5576   -1.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1917    0.5501   -0.3293 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1644    1.7060   -0.7259 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3601    2.0381    1.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0037    2.9115    0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2587   -1.0476   -0.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1712   -0.5948    1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3594    0.1593    0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748    2.5133   -1.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4615    2.5177   -0.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1807    1.6174   -2.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3044   -1.2097   -2.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3660   -1.0976   -5.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0827   -1.7864   -7.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2210   -0.8886   -3.7882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5630    0.7381   -3.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7349   -0.0314   -2.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8313   -2.7950   -3.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1563   -1.9873   -1.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8202    1.2137   -5.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1992    1.3488   -0.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1264    2.5506   -0.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol

Synonyms

Value	Source
JSI 124	MeSH
Elatericin b	MeSH

Chemical Formula

C₃₀H₄₂O₇

Average Mass

514.6503 Da

Monoisotopic Mass

514.29305 Da

IUPAC Name

(1R,2R,10S,11S,13R,14R,15R)-14-[(2R,4E)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-4,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7-diene-5,17-dione

Traditional Name

(1R,2R,10S,11S,13R,14R,15R)-14-[(2R,4E)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-4,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7-diene-5,17-dione

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])[C@]2([H])C(=C([H])C([H])([H])[C@@]3([H])[C@]4(C([H])([H])[H])C([H])([H])[C@@]([H])(O[H])[C@]([H])([C@@](O[H])(C(=O)C(\[H])=C(/[H])C(O[H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])[C@@]4(C([H])([H])[H])C([H])([H])C(=O)[C@@]23C([H])([H])[H])C(C1=O)(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C30H42O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,11-13,17,19-20,23,31-32,36-37H,10,14-15H2,1-8H3/b12-11+/t17-,19-,20+,23+,27+,28-,29+,30+/m1/s1

InChI Key

NISPVUDLMHQFRQ-MKIKIEMVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Begonia nantoensis	KNApSAcK Database	22123792
Bryonia alba	KNApSAcK Database	22123792
Bryonia dioica	KNApSAcK Database	22123792
Bryonia verrucosa	LOTUS Database	35616633
Citrullus colocynthis	JEOL database	Seger, C., et al, Magn. Reson. Chem. 43, 489 (2005)
Citrullus spp.	KNApSAcK Database	22123792
Cucumis sativus	LOTUS Database	35616633
Cucumis sativus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cucurbita maxima	LOTUS Database	35616633
Cucurbita pepo	LOTUS Database	35616633
Ecballium elaterium	KNApSAcK Database	22123792
Elaeocarpus chinensis	LOTUS Database	35616633
Elaeocarpus hainanensis	LOTUS Database	35616633
Gratiola officinalis	KNApSAcK Database	22123792
Gyrinops walla	LOTUS Database	35616633
Hemsleya endecaphylla	LOTUS Database	35616633
Iberis amara	KNApSAcK Database	22123792
Iberis umbellata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cucurbitacins

Direct Parent

Cucurbitacins

Alternative Parents

Substituents

Cucurbitacin skeleton
Triterpenoid
25-hydroxysteroid
22-oxosteroid
21-oxosteroid
20-hydroxysteroid
3-oxo-delta-1-steroid
2-hydroxysteroid
14-alpha-methylsteroid
Hydroxysteroid
11-oxosteroid
Oxosteroid
3-oxosteroid
16-alpha-hydroxysteroid
16-hydroxysteroid
Delta-1-steroid
Cyclohexenone
Acyloin
Alpha-hydroxy ketone
Tertiary alcohol
Alpha,beta-unsaturated ketone
Cyclic alcohol
Enone
Acryloyl-group
Cyclic ketone
Secondary alcohol
Ketone
Enol
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

cucurbitacin (CHEBI:3947 )
Cholesterol and derivatives (C08800 )
Cycloartane (C08800 )
Cholesterol and derivatives (LMST01010110 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	698.30 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	5.49 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.330 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	3.33	ALOGPS
logP	3.04	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	9.09	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	143.46 m³·mol⁻¹	ChemAxon
Polarizability	56.52 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003689

Chemspider ID

4444698

KEGG Compound ID

C08800

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

3947

Good Scents ID

rw1701371

References

General References

Lui VW, Yau DM, Wong EY, Ng YK, Lau CP, Ho Y, Chan JP, Hong B, Ho K, Cheung CS, Tsang CM, Tsao SW, Chan AT: Cucurbitacin I elicits anoikis sensitization, inhibits cellular invasion and in vivo tumor formation ability of nasopharyngeal carcinoma cells. Carcinogenesis. 2009 Dec;30(12):2085-94. doi: 10.1093/carcin/bgp253. [PubMed:19843642 ]
Chen YW, Chen KH, Huang PI, Chen YC, Chiou GY, Lo WL, Tseng LM, Hsu HS, Chang KW, Chiou SH: Cucurbitacin I suppressed stem-like property and enhanced radiation-induced apoptosis in head and neck squamous carcinoma--derived CD44(+)ALDH1(+) cells. Mol Cancer Ther. 2010 Nov;9(11):2879-92. doi: 10.1158/1535-7163.MCT-10-0504. Epub 2010 Nov 9. [PubMed:21062915 ]
Tseng LM, Huang PI, Chen YR, Chen YC, Chou YC, Chen YW, Chang YL, Hsu HS, Lan YT, Chen KH, Chi CW, Chiou SH, Yang DM, Lee CH: Targeting signal transducer and activator of transcription 3 pathway by cucurbitacin I diminishes self-renewing and radiochemoresistant abilities in thyroid cancer-derived CD133+ cells. J Pharmacol Exp Ther. 2012 May;341(2):410-23. doi: 10.1124/jpet.111.188730. Epub 2012 Feb 10. [PubMed:22328572 ]
Lopez-Haber C, Kazanietz MG: Cucurbitacin I inhibits Rac1 activation in breast cancer cells by a reactive oxygen species-mediated mechanism and independently of Janus tyrosine kinase 2 and P-Rex1. Mol Pharmacol. 2013 May;83(5):1141-54. doi: 10.1124/mol.112.084293. Epub 2013 Mar 11. [PubMed:23478800 ]
Patel SB, Ghane SG: Phyto-constituents profiling of Luffa echinata and in vitro assessment of antioxidant, anti-diabetic, anticancer and anti-acetylcholine esterase activities. Saudi J Biol Sci. 2021 Jul;28(7):3835-3846. doi: 10.1016/j.sjbs.2021.03.050. Epub 2021 Mar 27. [PubMed:34220238 ]
Zhang X, Zhu M, Hong Z, Chen C: Co-culturing polarized M2 Thp-1-derived macrophages enhance stemness of lung adenocarcinoma A549 cells. Ann Transl Med. 2021 Apr;9(8):709. doi: 10.21037/atm-21-1256. [PubMed:33987407 ]
Seger, C., et al. (2005). Seger, C., et al, Magn. Reson. Chem. 43, 489 (2005). Mag. Reson. Chem..

Showing NP-Card for cucurbitacin I (NP0031176)

MOL for NP0031176 (cucurbitacin I)

3D MOL for NP0031176 (cucurbitacin I)

3D SDF for NP0031176 (cucurbitacin I)

3D-SDF for NP0031176 (cucurbitacin I)

PDB for NP0031176 (cucurbitacin I)

3D PDB for NP0031176 (cucurbitacin I)

SMILES for NP0031176 (cucurbitacin I)

INCHI for NP0031176 (cucurbitacin I)

Structure for NP0031176 (cucurbitacin I)

3D Structure for NP0031176 (cucurbitacin I)