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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:52 UTC

Update Date

2022-03-07 02:49:15 UTC

HMDB ID

HMDB0002398

Secondary Accession Numbers

HMDB02398

Metabolite Identification

Common Name

Crocin

Description

Crocin is a water-soluble carotenoid pigment of saffron (Crocus sativus L.) that has been used as a spice for flavoring and coloring food preparations, and in Chinese traditional medicine as an anodyne or tranquilizer. Saffron is now used worldwide in folk medicine and is reputed to be useful in treating various human disorders such as heart and blood disorders. Stroke and heart attack are involved in reputed folkloric uses of saffron. Saffron is orally administrated as a decoction. Saffron extract exerts a protective effect on renal ischemia reperfusion induced oxidative damage in rats. Crocin suppresses tumor necrosis factor (TNF)alpha-induced apoptosis of pheochromocytoma (PC12) cells by modulating mRNA expressions of Bcl-2 family proteins, which trigger downstream signals culminating in caspase-3 activation followed by cell death. Depriving cultured PC12 cells of serum/glucose causes a rapid increase in cellular ceramide levels, followed by an increase in the risk of cell death. The accumulation of ceramide was found to depend on the activation of neutral sphingomyelinase (nSMase). Crocin prevented the activation of nSMase by enhancing the transcription of gamma-glutamylcysteinyl synthase, which contributes to a stable glutathione supply that blocks the activity of nSMase. (PMID: 17215084 ). Crocetin esters present in saffron stigmas and in Gardenia jasminoides Ellis fruit are the compounds responsible for their color. (PMID: 16448211 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv1652301212022263D          

 68 71  0  0  0  0            999 V2000
   -3.1923    3.3913   -1.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5475   -1.2278    0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1287   -2.1026   -0.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4747   -2.6780    0.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9374    1.8081   -0.7759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083    0.8923   -0.5356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5491    0.5108   -0.8819 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5088   -0.7211    0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2943    1.4624   -0.7665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4234    1.0895   -0.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8945    1.7139   -0.9040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6728    0.2577   -0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9282    0.2085   -0.9340 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9206   -0.4192    0.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.7810    4.2526   -0.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1270    3.2555   -1.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2692   -1.0110   -1.7376 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6650   -1.7449   -0.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4761    1.5748   -0.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2473    0.0593   -0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2599   -1.0915   -0.9163 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8813   -1.2610    0.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.4523    2.9003   -0.3690 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.0876    1.9312   -0.5754 C   0  0  2  0  0  0  0  0  0  0  0  0
  -13.0869   -2.0027   -1.8239 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.7044   -0.9343    0.2452 C   0  0  2  0  0  0  0  0  0  0  0  0
  -16.6074    2.6989    0.5894 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.4249    1.4814   -0.0862 C   0  0  2  0  0  0  0  0  0  0  0  0
  -13.2286   -3.0812   -0.8250 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.2882   -0.6080    1.6329 C   0  0  2  0  0  0  0  0  0  0  0  0
  -16.3588    1.6104    1.5886 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.9305    0.1994   -0.6571 C   0  0  1  0  0  0  0  0  0  0  0  0
  -12.6488   -2.7711    0.5352 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.4453   -1.2476    2.7325 C   0  0  1  0  0  0  0  0  0  0  0  0
  -15.9305    0.3396    0.9132 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.9168   -0.7306   -1.2075 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.5354   -1.7828    0.5183 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0279   -0.7783    2.6178 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.5884   -1.6096   -0.9240 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2661   -0.8467    0.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.1553    0.6222   -0.3610 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.5264   -0.2559   -0.7658 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.0169   -1.7216   -0.9260 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.6429   -1.0336    1.1390 C   0  0  1  0  0  0  0  0  0  0  0  0
  -14.2338    4.3177    1.1370 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7850    4.1912   -0.5379 O   0  0  0  0  0  0  0  0  0  0  0  0
  -17.7904    2.5099   -0.1451 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4995    1.5100    1.3215 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7723   -4.3308   -1.2887 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3011    0.7411    1.8906 O   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3520    2.0110    2.4714 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9783    0.4288   -1.5941 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6197   -2.5512    1.4991 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4902   -2.6306    2.5875 O   0  0  0  0  0  0  0  0  0  0  0  0
  -17.0140   -0.4785    0.6817 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1274   -2.0680   -0.9917 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4868   -2.1559    1.3857 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8777    0.5804    2.9264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6896   -2.8953   -0.9221 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5440    0.3587    0.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1965   -0.3301   -0.5425 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6153   -1.0811   -1.2322 O   0  0  0  0  0  0  0  0  0  0  0  0
  -14.5300    1.8885   -0.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4369    1.0401   -1.4031 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9631   -1.2394   -1.7460 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5873   -1.8121    0.5271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8060   -0.9614   -0.9316 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3615   -1.5916    1.1383 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  2 20  1  0  0  0  0
  3 21  1  0  0  0  0
  4 22  1  0  0  0  0
  5  6  2  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  2  0  0  0  0
  7 13  1  0  0  0  0
  8 12  2  0  0  0  0
  8 14  1  0  0  0  0
  9 19  2  0  0  0  0
 10 20  2  0  0  0  0
 11 19  1  0  0  0  0
 12 20  1  0  0  0  0
 13 21  2  0  0  0  0
 14 22  2  0  0  0  0
 23 15  1  1  0  0  0
 15 45  1  0  0  0  0
 24 16  1  6  0  0  0
 16 46  1  0  0  0  0
 25 17  1  1  0  0  0
 17 61  1  0  0  0  0
 26 18  1  6  0  0  0
 18 62  1  0  0  0  0
 21 39  1  0  0  0  0
 22 40  1  0  0  0  0
 23 27  1  0  0  0  0
 23 63  1  0  0  0  0
 24 28  1  0  0  0  0
 24 64  1  0  0  0  0
 25 29  1  0  0  0  0
 25 65  1  0  0  0  0
 26 30  1  0  0  0  0
 26 66  1  0  0  0  0
 27 31  1  0  0  0  0
 27 47  1  6  0  0  0
 28 32  1  0  0  0  0
 28 48  1  1  0  0  0
 29 33  1  0  0  0  0
 29 49  1  6  0  0  0
 30 34  1  0  0  0  0
 30 50  1  1  0  0  0
 31 35  1  0  0  0  0
 31 51  1  1  0  0  0
 32 36  1  0  0  0  0
 32 52  1  6  0  0  0
 33 37  1  0  0  0  0
 33 53  1  1  0  0  0
 34 38  1  0  0  0  0
 34 54  1  6  0  0  0
 35 41  1  0  0  0  0
 35 55  1  6  0  0  0
 36 42  1  0  0  0  0
 36 56  1  1  0  0  0
 37 43  1  0  0  0  0
 37 57  1  1  0  0  0
 38 44  1  0  0  0  0
 38 58  1  6  0  0  0
 39 59  2  0  0  0  0
 39 67  1  0  0  0  0
 40 60  2  0  0  0  0
 40 68  1  0  0  0  0
 41 61  1  1  0  0  0
 41 63  1  0  0  0  0
 42 62  1  6  0  0  0
 42 64  1  0  0  0  0
 43 65  1  0  0  0  0
 43 67  1  1  0  0  0
 44 66  1  0  0  0  0
 44 68  1  1  0  0  0
M  END

HMDB0002398
     RDKit          3D
Crocin
132135  0  0  0  0  0  0  0  0999 V2000
    2.5197   -3.6286    0.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6128   -2.9219   -0.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9110   -2.4780   -0.8800 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0731   -2.9100   -0.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3672   -2.4454   -0.9272 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4696   -3.0391   -0.5398 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3965   -4.2370    0.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7726   -2.4431   -0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8580   -3.0437   -0.6010 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8832   -1.1183   -1.2863 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1782   -0.5634   -1.5269 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6261   -0.0738   -0.2270 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8738    0.4832   -0.5431 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.9295    0.1685    0.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0982    0.8347    0.1350 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1862    0.4357    0.9304 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.5631    1.4393    1.7729 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6684    2.1692    1.4242 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.5141    3.5271    2.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5379    4.4021    1.8348 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7927    2.3995   -0.0561 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.0702    2.9592   -0.2873 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7338    1.1168   -0.8564 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.8245    1.2502   -1.9070 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3322   -0.0056    0.0782 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.4081   -0.3535    0.8665 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6047    1.8922   -0.9182 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.7074    2.6828   -1.1382 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7167    1.8538   -2.1575 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.6594    2.7465   -1.9779 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1504    0.5106   -2.4990 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8486    0.0698   -3.6539 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4954   -2.5048   -0.9805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1552   -2.6459   -0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8383   -2.2559   -1.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1937   -2.3607   -0.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2875   -2.0848   -1.4631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0737   -1.6595   -2.8568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6055   -2.0221   -0.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6762   -1.8273   -1.6220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0071   -1.7479   -1.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0742   -1.6216   -1.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9780   -1.5668   -3.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3722   -1.3735   -1.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4204   -1.3451   -1.6953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3888   -1.1535    0.3030 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5671   -0.8799    1.0605 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.4514    0.5806    1.1520 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6584    0.9481    1.8228 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.9726    2.3325    1.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0811    2.9395    1.8558 O   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2980    2.3558    1.6588 C   0  0  2  0  0  0  0  0  0  0  0  0
  -14.9760    3.0196    0.5758 O   0  0  0  0  0  0  0  0  0  0  0  0
  -15.9602    2.1956    0.1078 C   0  0  2  0  0  0  0  0  0  0  0  0
  -17.0260    2.9757   -0.6669 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.0461    2.1184   -1.0851 O   0  0  0  0  0  0  0  0  0  0  0  0
  -16.5733    1.2463    1.0635 C   0  0  1  0  0  0  0  0  0  0  0  0
  -16.1805   -0.0992    0.8143 O   0  0  0  0  0  0  0  0  0  0  0  0
  -16.4256    1.5797    2.5167 C   0  0  2  0  0  0  0  0  0  0  0  0
  -17.6188    2.1549    3.0111 O   0  0  0  0  0  0  0  0  0  0  0  0
  -15.2451    2.4681    2.7967 C   0  0  1  0  0  0  0  0  0  0  0  0
  -14.6707    2.2846    4.0300 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3732    0.7244    3.2658 C   0  0  1  0  0  0  0  0  0  0  0  0
  -12.4408    0.2003    3.9831 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2436   -0.3056    3.3939 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.0319    0.2723    2.9932 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4985   -1.4405    2.4162 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.6206   -2.1669    2.8079 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4522   -3.5939    1.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7277   -3.0803    1.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1522   -4.6753    0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9395   -1.6955   -1.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0549   -3.7069    0.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4608   -1.5870   -1.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8474   -3.9699    1.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4015   -4.5968    0.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7870   -4.9799   -0.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8893   -1.3954   -1.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1791   -0.0225   -1.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1123   -0.9333    0.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6253    0.4634    1.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.8752   -0.4298    1.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.6417    1.7357    1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.5101    3.8876    1.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

  Mrv1652301212022263D          

 68 71  0  0  0  0            999 V2000
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    1.5475   -1.2278    0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
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 43 67  1  1  0  0  0
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 44 68  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0002398

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C44H64O24/c1-19(11-7-13-21(3)39(59)67-43-37(57)33(53)29(49)25(65-43)17-61-41-35(55)31(51)27(47)23(15-45)63-41)9-5-6-10-20(2)12-8-14-22(4)40(60)68-44-38(58)34(54)30(50)26(66-44)18-62-42-36(56)32(52)28(48)24(16-46)64-42/h5-14,23-38,41-58H,15-18H2,1-4H3/b6-5+,11-7+,12-8+,19-9+,20-10+,21-13+,22-14+/t23-,24-,25-,26-,27-,28-,29-,30-,31+,32+,33+,34+,35-,36-,37-,38-,41-,42-,43+,44+/m1/s1

> <INCHI_KEY>
SEBIKDIMAPSUBY-RTJKDTQDSA-N

> <FORMULA>
C44H64O24

> <MOLECULAR_WEIGHT>
976.972

> <EXACT_MASS>
976.378752941

> <JCHEM_ACCEPTOR_COUNT>
22

> <JCHEM_ATOM_COUNT>
132

> <JCHEM_AVERAGE_POLARIZABILITY>
100.06898038130447

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
bis[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl] (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate

> <ALOGPS_LOGP>
-0.02

> <JCHEM_LOGP>
-3.210937580666667

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.088030392139236

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.668685014311508

> <JCHEM_PKA_STRONGEST_BASIC>
-3.678613072130494

> <JCHEM_POLAR_SURFACE_AREA>
391.20000000000005

> <JCHEM_REFRACTIVITY>
233.48580000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
saffron

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002398
     RDKit          3D
Crocin
132135  0  0  0  0  0  0  0  0999 V2000
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M  END

HEADER    PROTEIN                                 21-JAN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JAN-20         0                                  
HETATM    1  C   UNK     0      -3.192   3.391  -1.128  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.548  -1.228   0.068  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.129  -2.103  -0.850  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.475  -2.678   0.952  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.937   1.808  -0.776  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.008   0.892  -0.536  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.549   0.511  -0.882  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.509  -0.721   0.241  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.294   1.462  -0.767  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.423   1.089  -0.503  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.894   1.714  -0.904  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.673   0.258  -0.068  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.928   0.209  -0.934  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.921  -0.419   0.357  0.00  0.00           C+0
HETATM   15  C   UNK     0     -14.781   4.253  -0.140  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.127   3.256  -1.333  0.00  0.00           C+0
HETATM   17  C   UNK     0     -14.269  -1.011  -1.738  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.665  -1.745  -0.580  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.476   1.575  -0.829  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.247   0.059  -0.199  0.00  0.00           C+0
HETATM   21  C   UNK     0      -7.260  -1.091  -0.916  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.881  -1.261   0.680  0.00  0.00           C+0
HETATM   23  C   UNK     0     -15.452   2.900  -0.369  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.088   1.931  -0.575  0.00  0.00           C+0
HETATM   25  C   UNK     0     -13.087  -2.003  -1.824  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.704  -0.934   0.245  0.00  0.00           C+0
HETATM   27  C   UNK     0     -16.607   2.699   0.589  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.425   1.481  -0.086  0.00  0.00           C+0
HETATM   29  C   UNK     0     -13.229  -3.081  -0.825  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.288  -0.608   1.633  0.00  0.00           C+0
HETATM   31  C   UNK     0     -16.359   1.610   1.589  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.930   0.199  -0.657  0.00  0.00           C+0
HETATM   33  C   UNK     0     -12.649  -2.771   0.535  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.445  -1.248   2.732  0.00  0.00           C+0
HETATM   35  C   UNK     0     -15.931   0.340   0.913  0.00  0.00           C+0
HETATM   36  C   UNK     0      16.917  -0.731  -1.208  0.00  0.00           C+0
HETATM   37  C   UNK     0     -11.535  -1.783   0.518  0.00  0.00           C+0
HETATM   38  C   UNK     0      11.028  -0.778   2.618  0.00  0.00           C+0
HETATM   39  C   UNK     0      -8.588  -1.610  -0.924  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.266  -0.847   0.741  0.00  0.00           C+0
HETATM   41  C   UNK     0     -15.155   0.622  -0.361  0.00  0.00           C+0
HETATM   42  C   UNK     0      15.526  -0.256  -0.766  0.00  0.00           C+0
HETATM   43  C   UNK     0     -11.017  -1.722  -0.926  0.00  0.00           C+0
HETATM   44  C   UNK     0      10.643  -1.034   1.139  0.00  0.00           C+0
HETATM   45  O   UNK     0     -14.234   4.318   1.137  0.00  0.00           O+0
HETATM   46  O   UNK     0      16.785   4.191  -0.538  0.00  0.00           O+0
HETATM   47  O   UNK     0     -17.790   2.510  -0.145  0.00  0.00           O+0
HETATM   48  O   UNK     0      17.500   1.510   1.321  0.00  0.00           O+0
HETATM   49  O   UNK     0     -12.772  -4.331  -1.289  0.00  0.00           O+0
HETATM   50  O   UNK     0      13.301   0.741   1.891  0.00  0.00           O+0
HETATM   51  O   UNK     0     -15.352   2.011   2.471  0.00  0.00           O+0
HETATM   52  O   UNK     0      18.978   0.429  -1.594  0.00  0.00           O+0
HETATM   53  O   UNK     0     -13.620  -2.551   1.499  0.00  0.00           O+0
HETATM   54  O   UNK     0      12.490  -2.631   2.587  0.00  0.00           O+0
HETATM   55  O   UNK     0     -17.014  -0.479   0.682  0.00  0.00           O+0
HETATM   56  O   UNK     0      17.127  -2.068  -0.992  0.00  0.00           O+0
HETATM   57  O   UNK     0     -10.487  -2.156   1.386  0.00  0.00           O+0
HETATM   58  O   UNK     0      10.878   0.580   2.926  0.00  0.00           O+0
HETATM   59  O   UNK     0      -8.690  -2.895  -0.922  0.00  0.00           O+0
HETATM   60  O   UNK     0       8.544   0.359   0.396  0.00  0.00           O+0
HETATM   61  O   UNK     0     -14.197  -0.330  -0.543  0.00  0.00           O+0
HETATM   62  O   UNK     0      14.615  -1.081  -1.232  0.00  0.00           O+0
HETATM   63  O   UNK     0     -14.530   1.889  -0.223  0.00  0.00           O+0
HETATM   64  O   UNK     0      15.437   1.040  -1.403  0.00  0.00           O+0
HETATM   65  O   UNK     0     -11.963  -1.239  -1.746  0.00  0.00           O+0
HETATM   66  O   UNK     0      11.587  -1.812   0.527  0.00  0.00           O+0
HETATM   67  O   UNK     0      -9.806  -0.961  -0.932  0.00  0.00           O+0
HETATM   68  O   UNK     0       9.361  -1.592   1.138  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7   11   13                                                       
CONECT    8   12   14                                                       
CONECT    9    5   19                                                       
CONECT   10    6   20                                                       
CONECT   11    7   19                                                       
CONECT   12    8   20                                                       
CONECT   13    7   21                                                       
CONECT   14    8   22                                                       
CONECT   15   23   45                                                       
CONECT   16   24   46                                                       
CONECT   17   25   61                                                       
CONECT   18   26   62                                                       
CONECT   19    1    9   11                                                  
CONECT   20    2   10   12                                                  
CONECT   21    3   13   39                                                  
CONECT   22    4   14   40                                                  
CONECT   23   15   27   63                                                  
CONECT   24   16   28   64                                                  
CONECT   25   17   29   65                                                  
CONECT   26   18   30   66                                                  
CONECT   27   23   31   47                                                  
CONECT   28   24   32   48                                                  
CONECT   29   25   33   49                                                  
CONECT   30   26   34   50                                                  
CONECT   31   27   35   51                                                  
CONECT   32   28   36   52                                                  
CONECT   33   29   37   53                                                  
CONECT   34   30   38   54                                                  
CONECT   35   31   41   55                                                  
CONECT   36   32   42   56                                                  
CONECT   37   33   43   57                                                  
CONECT   38   34   44   58                                                  
CONECT   39   21   59   67                                                  
CONECT   40   22   60   68                                                  
CONECT   41   35   61   63                                                  
CONECT   42   36   62   64                                                  
CONECT   43   37   65   67                                                  
CONECT   44   38   66   68                                                  
CONECT   45   15                                                            
CONECT   46   16                                                            
CONECT   47   27                                                            
CONECT   48   28                                                            
CONECT   49   29                                                            
CONECT   50   30                                                            
CONECT   51   31                                                            
CONECT   52   32                                                            
CONECT   53   33                                                            
CONECT   54   34                                                            
CONECT   55   35                                                            
CONECT   56   36                                                            
CONECT   57   37                                                            
CONECT   58   38                                                            
CONECT   59   39                                                            
CONECT   60   40                                                            
CONECT   61   17   41                                                       
CONECT   62   18   42                                                       
CONECT   63   23   41                                                       
CONECT   64   24   42                                                       
CONECT   65   25   43                                                       
CONECT   66   26   44                                                       
CONECT   67   39   43                                                       
CONECT   68   40   44                                                       
MASTER        0    0    0    0    0    0    0    0   68    0  142    0
END

COMPND    HMDB0002398
HETATM    1  C1  UNL     1       2.520  -3.629   0.876  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.613  -2.922  -0.411  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.911  -2.478  -0.880  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.073  -2.910  -0.477  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.367  -2.445  -0.927  1.00  0.00           C  
HETATM    6  C6  UNL     1       7.470  -3.039  -0.540  1.00  0.00           C  
HETATM    7  C7  UNL     1       7.397  -4.237   0.365  1.00  0.00           C  
HETATM    8  C8  UNL     1       8.773  -2.443  -0.803  1.00  0.00           C  
HETATM    9  O1  UNL     1       9.858  -3.044  -0.601  1.00  0.00           O  
HETATM   10  O2  UNL     1       8.883  -1.118  -1.286  1.00  0.00           O  
HETATM   11  C9  UNL     1      10.178  -0.563  -1.527  1.00  0.00           C  
HETATM   12  O3  UNL     1      10.626  -0.074  -0.227  1.00  0.00           O  
HETATM   13  C10 UNL     1      11.874   0.483  -0.543  1.00  0.00           C  
HETATM   14  C11 UNL     1      12.929   0.168   0.439  1.00  0.00           C  
HETATM   15  O4  UNL     1      14.098   0.835   0.135  1.00  0.00           O  
HETATM   16  C12 UNL     1      15.186   0.436   0.930  1.00  0.00           C  
HETATM   17  O5  UNL     1      15.563   1.439   1.773  1.00  0.00           O  
HETATM   18  C13 UNL     1      16.668   2.169   1.424  1.00  0.00           C  
HETATM   19  C14 UNL     1      16.514   3.527   2.103  1.00  0.00           C  
HETATM   20  O6  UNL     1      17.538   4.402   1.835  1.00  0.00           O  
HETATM   21  C15 UNL     1      16.793   2.400  -0.056  1.00  0.00           C  
HETATM   22  O7  UNL     1      18.070   2.959  -0.287  1.00  0.00           O  
HETATM   23  C16 UNL     1      16.734   1.117  -0.856  1.00  0.00           C  
HETATM   24  O8  UNL     1      15.825   1.250  -1.907  1.00  0.00           O  
HETATM   25  C17 UNL     1      16.332  -0.006   0.078  1.00  0.00           C  
HETATM   26  O9  UNL     1      17.408  -0.353   0.866  1.00  0.00           O  
HETATM   27  C18 UNL     1      11.605   1.892  -0.918  1.00  0.00           C  
HETATM   28  O10 UNL     1      12.707   2.683  -1.138  1.00  0.00           O  
HETATM   29  C19 UNL     1      10.717   1.854  -2.158  1.00  0.00           C  
HETATM   30  O11 UNL     1       9.659   2.746  -1.978  1.00  0.00           O  
HETATM   31  C20 UNL     1      10.150   0.511  -2.499  1.00  0.00           C  
HETATM   32  O12 UNL     1      10.849   0.070  -3.654  1.00  0.00           O  
HETATM   33  C21 UNL     1       1.495  -2.505  -0.980  1.00  0.00           C  
HETATM   34  C22 UNL     1       0.155  -2.646  -0.460  1.00  0.00           C  
HETATM   35  C23 UNL     1      -0.838  -2.256  -1.262  1.00  0.00           C  
HETATM   36  C24 UNL     1      -2.194  -2.361  -0.764  1.00  0.00           C  
HETATM   37  C25 UNL     1      -3.287  -2.085  -1.463  1.00  0.00           C  
HETATM   38  C26 UNL     1      -3.074  -1.659  -2.857  1.00  0.00           C  
HETATM   39  C27 UNL     1      -4.606  -2.022  -0.882  1.00  0.00           C  
HETATM   40  C28 UNL     1      -5.676  -1.827  -1.622  1.00  0.00           C  
HETATM   41  C29 UNL     1      -7.007  -1.748  -1.006  1.00  0.00           C  
HETATM   42  C30 UNL     1      -8.074  -1.622  -1.736  1.00  0.00           C  
HETATM   43  C31 UNL     1      -7.978  -1.567  -3.212  1.00  0.00           C  
HETATM   44  C32 UNL     1      -9.372  -1.373  -1.058  1.00  0.00           C  
HETATM   45  O13 UNL     1     -10.420  -1.345  -1.695  1.00  0.00           O  
HETATM   46  O14 UNL     1      -9.389  -1.154   0.303  1.00  0.00           O  
HETATM   47  C33 UNL     1     -10.567  -0.880   1.060  1.00  0.00           C  
HETATM   48  O15 UNL     1     -10.451   0.581   1.152  1.00  0.00           O  
HETATM   49  C34 UNL     1     -11.658   0.948   1.823  1.00  0.00           C  
HETATM   50  C35 UNL     1     -11.973   2.333   1.391  1.00  0.00           C  
HETATM   51  O16 UNL     1     -13.081   2.940   1.856  1.00  0.00           O  
HETATM   52  C36 UNL     1     -14.298   2.356   1.659  1.00  0.00           C  
HETATM   53  O17 UNL     1     -14.976   3.020   0.576  1.00  0.00           O  
HETATM   54  C37 UNL     1     -15.960   2.196   0.108  1.00  0.00           C  
HETATM   55  C38 UNL     1     -17.026   2.976  -0.667  1.00  0.00           C  
HETATM   56  O18 UNL     1     -18.046   2.118  -1.085  1.00  0.00           O  
HETATM   57  C39 UNL     1     -16.573   1.246   1.064  1.00  0.00           C  
HETATM   58  O19 UNL     1     -16.181  -0.099   0.814  1.00  0.00           O  
HETATM   59  C40 UNL     1     -16.426   1.580   2.517  1.00  0.00           C  
HETATM   60  O20 UNL     1     -17.619   2.155   3.011  1.00  0.00           O  
HETATM   61  C41 UNL     1     -15.245   2.468   2.797  1.00  0.00           C  
HETATM   62  O21 UNL     1     -14.671   2.285   4.030  1.00  0.00           O  
HETATM   63  C42 UNL     1     -11.373   0.724   3.266  1.00  0.00           C  
HETATM   64  O22 UNL     1     -12.441   0.200   3.983  1.00  0.00           O  
HETATM   65  C43 UNL     1     -10.244  -0.306   3.394  1.00  0.00           C  
HETATM   66  O23 UNL     1      -9.032   0.272   2.993  1.00  0.00           O  
HETATM   67  C44 UNL     1     -10.499  -1.441   2.416  1.00  0.00           C  
HETATM   68  O24 UNL     1     -11.621  -2.167   2.808  1.00  0.00           O  
HETATM   69  H1  UNL     1       3.452  -3.594   1.489  1.00  0.00           H  
HETATM   70  H2  UNL     1       1.728  -3.080   1.466  1.00  0.00           H  
HETATM   71  H3  UNL     1       2.152  -4.675   0.792  1.00  0.00           H  
HETATM   72  H4  UNL     1       3.940  -1.696  -1.648  1.00  0.00           H  
HETATM   73  H5  UNL     1       5.055  -3.707   0.284  1.00  0.00           H  
HETATM   74  H6  UNL     1       6.461  -1.587  -1.597  1.00  0.00           H  
HETATM   75  H7  UNL     1       6.847  -3.970   1.277  1.00  0.00           H  
HETATM   76  H8  UNL     1       8.402  -4.597   0.575  1.00  0.00           H  
HETATM   77  H9  UNL     1       6.787  -4.980  -0.214  1.00  0.00           H  
HETATM   78  H10 UNL     1      10.889  -1.395  -1.630  1.00  0.00           H  
HETATM   79  H11 UNL     1      12.179  -0.022  -1.530  1.00  0.00           H  
HETATM   80  H12 UNL     1      13.112  -0.933   0.378  1.00  0.00           H  
HETATM   81  H13 UNL     1      12.625   0.463   1.481  1.00  0.00           H  
HETATM   82  H14 UNL     1      14.875  -0.430   1.590  1.00  0.00           H  
HETATM   83  H15 UNL     1      17.642   1.736   1.762  1.00  0.00           H  
HETATM   84  H16 UNL     1      15.510   3.888   1.820  1.00  0.00           H  
HETATM   85  H17 UNL     1      16.478   3.287   3.206  1.00  0.00           H  
HETATM   86  H18 UNL     1      18.412   3.987   1.762  1.00  0.00           H  
HETATM   87  H19 UNL     1      16.075   3.154  -0.429  1.00  0.00           H  
HETATM   88  H20 UNL     1      18.273   2.988  -1.255  1.00  0.00           H  
HETATM   89  H21 UNL     1      17.717   0.892  -1.311  1.00  0.00           H  
HETATM   90  H22 UNL     1      15.377   2.134  -1.882  1.00  0.00           H  
HETATM   91  H23 UNL     1      16.063  -0.933  -0.518  1.00  0.00           H  
HETATM   92  H24 UNL     1      17.682  -1.302   0.750  1.00  0.00           H  
HETATM   93  H25 UNL     1      10.962   2.343  -0.110  1.00  0.00           H  
HETATM   94  H26 UNL     1      12.738   3.377  -0.427  1.00  0.00           H  
HETATM   95  H27 UNL     1      11.384   2.240  -2.997  1.00  0.00           H  
HETATM   96  H28 UNL     1       9.805   3.506  -2.607  1.00  0.00           H  
HETATM   97  H29 UNL     1       9.091   0.672  -2.901  1.00  0.00           H  
HETATM   98  H30 UNL     1      10.568   0.719  -4.374  1.00  0.00           H  
HETATM   99  H31 UNL     1       1.672  -2.005  -1.960  1.00  0.00           H  
HETATM  100  H32 UNL     1      -0.033  -3.033   0.514  1.00  0.00           H  
HETATM  101  H33 UNL     1      -0.663  -1.880  -2.254  1.00  0.00           H  
HETATM  102  H34 UNL     1      -2.390  -2.687   0.268  1.00  0.00           H  
HETATM  103  H35 UNL     1      -2.286  -0.840  -2.873  1.00  0.00           H  
HETATM  104  H36 UNL     1      -2.610  -2.477  -3.480  1.00  0.00           H  
HETATM  105  H37 UNL     1      -3.922  -1.256  -3.386  1.00  0.00           H  
HETATM  106  H38 UNL     1      -4.695  -2.137   0.197  1.00  0.00           H  
HETATM  107  H39 UNL     1      -5.622  -1.725  -2.705  1.00  0.00           H  
HETATM  108  H40 UNL     1      -7.075  -1.793   0.063  1.00  0.00           H  
HETATM  109  H41 UNL     1      -8.936  -1.239  -3.680  1.00  0.00           H  
HETATM  110  H42 UNL     1      -7.237  -0.791  -3.486  1.00  0.00           H  
HETATM  111  H43 UNL     1      -7.650  -2.515  -3.669  1.00  0.00           H  
HETATM  112  H44 UNL     1     -11.498  -0.989   0.484  1.00  0.00           H  
HETATM  113  H45 UNL     1     -12.435   0.274   1.413  1.00  0.00           H  
HETATM  114  H46 UNL     1     -12.024   2.315   0.255  1.00  0.00           H  
HETATM  115  H47 UNL     1     -11.088   3.029   1.618  1.00  0.00           H  
HETATM  116  H48 UNL     1     -14.174   1.346   1.261  1.00  0.00           H  
HETATM  117  H49 UNL     1     -15.468   1.564  -0.697  1.00  0.00           H  
HETATM  118  H50 UNL     1     -17.423   3.752  -0.017  1.00  0.00           H  
HETATM  119  H51 UNL     1     -16.582   3.378  -1.610  1.00  0.00           H  
HETATM  120  H52 UNL     1     -17.795   1.540  -1.845  1.00  0.00           H  
HETATM  121  H53 UNL     1     -17.683   1.220   0.845  1.00  0.00           H  
HETATM  122  H54 UNL     1     -16.601  -0.331  -0.054  1.00  0.00           H  
HETATM  123  H55 UNL     1     -16.278   0.636   3.080  1.00  0.00           H  
HETATM  124  H56 UNL     1     -17.703   3.095   2.710  1.00  0.00           H  
HETATM  125  H57 UNL     1     -15.632   3.549   2.783  1.00  0.00           H  
HETATM  126  H58 UNL     1     -14.181   3.129   4.245  1.00  0.00           H  
HETATM  127  H59 UNL     1     -10.999   1.672   3.701  1.00  0.00           H  
HETATM  128  H60 UNL     1     -13.151  -0.110   3.365  1.00  0.00           H  
HETATM  129  H61 UNL     1     -10.205  -0.729   4.408  1.00  0.00           H  
HETATM  130  H62 UNL     1      -8.832   1.089   3.511  1.00  0.00           H  
HETATM  131  H63 UNL     1      -9.625  -2.137   2.541  1.00  0.00           H  
HETATM  132  H64 UNL     1     -12.119  -2.415   2.000  1.00  0.00           H  
CONECT    1    2   69   70   71
CONECT    2    3   33   33
CONECT    3    4    4   72
CONECT    4    5   73
CONECT    5    6    6   74
CONECT    6    7    8
CONECT    7   75   76   77
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   31   78
CONECT   12   13
CONECT   13   14   27   79
CONECT   14   15   80   81
CONECT   15   16
CONECT   16   17   25   82
CONECT   17   18
CONECT   18   19   21   83
CONECT   19   20   84   85
CONECT   20   86
CONECT   21   22   23   87
CONECT   22   88
CONECT   23   24   25   89
CONECT   24   90
CONECT   25   26   91
CONECT   26   92
CONECT   27   28   29   93
CONECT   28   94
CONECT   29   30   31   95
CONECT   30   96
CONECT   31   32   97
CONECT   32   98
CONECT   33   34   99
CONECT   34   35   35  100
CONECT   35   36  101
CONECT   36   37   37  102
CONECT   37   38   39
CONECT   38  103  104  105
CONECT   39   40   40  106
CONECT   40   41  107
CONECT   41   42   42  108
CONECT   42   43   44
CONECT   43  109  110  111
CONECT   44   45   45   46
CONECT   46   47
CONECT   47   48   67  112
CONECT   48   49
CONECT   49   50   63  113
CONECT   50   51  114  115
CONECT   51   52
CONECT   52   53   61  116
CONECT   53   54
CONECT   54   55   57  117
CONECT   55   56  118  119
CONECT   56  120
CONECT   57   58   59  121
CONECT   58  122
CONECT   59   60   61  123
CONECT   60  124
CONECT   61   62  125
CONECT   62  126
CONECT   63   64   65  127
CONECT   64  128
CONECT   65   66   67  129
CONECT   66  130
CONECT   67   68  131
CONECT   68  132
END

HMDB0002398
     RDKit          3D
Crocin
132135  0  0  0  0  0  0  0  0999 V2000
    2.5197   -3.6286    0.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6128   -2.9219   -0.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9110   -2.4780   -0.8800 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0731   -2.9100   -0.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3672   -2.4454   -0.9272 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4696   -3.0391   -0.5398 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3965   -4.2370    0.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7726   -2.4431   -0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8580   -3.0437   -0.6010 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8832   -1.1183   -1.2863 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1782   -0.5634   -1.5269 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6261   -0.0738   -0.2270 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8738    0.4832   -0.5431 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.9295    0.1685    0.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0982    0.8347    0.1350 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1862    0.4357    0.9304 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.5631    1.4393    1.7729 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6684    2.1692    1.4242 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.5141    3.5271    2.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5379    4.4021    1.8348 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7927    2.3995   -0.0561 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.0702    2.9592   -0.2873 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7338    1.1168   -0.8564 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.8245    1.2502   -1.9070 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3322   -0.0056    0.0782 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.4081   -0.3535    0.8665 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6047    1.8922   -0.9182 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.7074    2.6828   -1.1382 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7167    1.8538   -2.1575 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.6594    2.7465   -1.9779 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1504    0.5106   -2.4990 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8486    0.0698   -3.6539 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4954   -2.5048   -0.9805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1552   -2.6459   -0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8383   -2.2559   -1.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1937   -2.3607   -0.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2875   -2.0848   -1.4631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0737   -1.6595   -2.8568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6055   -2.0221   -0.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6762   -1.8273   -1.6220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0071   -1.7479   -1.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0742   -1.6216   -1.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9780   -1.5668   -3.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3722   -1.3735   -1.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4204   -1.3451   -1.6953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3888   -1.1535    0.3030 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5671   -0.8799    1.0605 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.4514    0.5806    1.1520 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6584    0.9481    1.8228 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.9726    2.3325    1.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0811    2.9395    1.8558 O   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2980    2.3558    1.6588 C   0  0  2  0  0  0  0  0  0  0  0  0
  -14.9760    3.0196    0.5758 O   0  0  0  0  0  0  0  0  0  0  0  0
  -15.9602    2.1956    0.1078 C   0  0  2  0  0  0  0  0  0  0  0  0
  -17.0260    2.9757   -0.6669 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.0461    2.1184   -1.0851 O   0  0  0  0  0  0  0  0  0  0  0  0
  -16.5733    1.2463    1.0635 C   0  0  1  0  0  0  0  0  0  0  0  0
  -16.1805   -0.0992    0.8143 O   0  0  0  0  0  0  0  0  0  0  0  0
  -16.4256    1.5797    2.5167 C   0  0  2  0  0  0  0  0  0  0  0  0
  -17.6188    2.1549    3.0111 O   0  0  0  0  0  0  0  0  0  0  0  0
  -15.2451    2.4681    2.7967 C   0  0  1  0  0  0  0  0  0  0  0  0
  -14.6707    2.2846    4.0300 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3732    0.7244    3.2658 C   0  0  1  0  0  0  0  0  0  0  0  0
  -12.4408    0.2003    3.9831 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2436   -0.3056    3.3939 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.0319    0.2723    2.9932 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4985   -1.4405    2.4162 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.6206   -2.1669    2.8079 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4522   -3.5939    1.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7277   -3.0803    1.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1522   -4.6753    0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9395   -1.6955   -1.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0549   -3.7069    0.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4608   -1.5870   -1.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8474   -3.9699    1.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4015   -4.5968    0.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7870   -4.9799   -0.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8893   -1.3954   -1.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1791   -0.0225   -1.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1123   -0.9333    0.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6253    0.4634    1.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.8752   -0.4298    1.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.6417    1.7357    1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.5101    3.8876    1.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.4777    3.2866    3.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.4121    3.9865    1.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.0747    3.1545   -0.4290 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.2726    2.9878   -1.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.7175    0.8918   -1.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3771    2.1338   -1.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.0635   -0.9331   -0.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.6818   -1.3021    0.7498 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9617    2.3428   -0.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7377    3.3770   -0.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3841    2.2403   -2.9973 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8050    3.5058   -2.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0909    0.6724   -2.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
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 68132  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
alpha-Crocin	ChEBI
Bis(beta-D-gentiobiosyl) crocetin	ChEBI
C.I. 75100	ChEBI
Crocetin di-beta-D-gentiobiose ester	ChEBI
Crocetin di-gentiobiose ester	ChEBI
Crocetin digentiobioside	ChEBI
Crocine	ChEBI
Natural red 1	ChEBI
Natural yellow 19	ChEBI
Natural yellow 6	ChEBI
Saffron	ChEBI
trans-Crocetin bis(beta-D-gentiobiosyl) ester	ChEBI
a-Crocin	Generator
Α-crocin	Generator
Bis(b-D-gentiobiosyl) crocetin	Generator
Bis(β-D-gentiobiosyl) crocetin	Generator
Crocetin di-b-D-gentiobiose ester	Generator
Crocetin di-β-D-gentiobiose ester	Generator
trans-Crocetin bis(b-D-gentiobiosyl) ester	Generator
trans-Crocetin bis(β-D-gentiobiosyl) ester	Generator
all-trans-Crocetin di-beta-D-gentiobiosyl ester	HMDB
all-trans-Crocetin di-beta-delta-gentiobiosyl ester	HMDB
Crocetin bis(gentiobiosyl) ester	HMDB
Crocetin digentiobiose ester	HMDB
Crocin 1	HMDB
Gardenia yellow	HMDB
Saffron (JP15)	HMDB
Crocin	MeSH

Chemical Formula

C₄₄H₆₄O₂₄

Average Molecular Weight

976.972

Monoisotopic Molecular Weight

976.378752941

IUPAC Name

bis[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl] (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate

Traditional Name

saffron

CAS Registry Number

42553-65-1

SMILES

C\C(\C=C\C=C(/C)C(=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O)=C/C=C/C=C(\C)/C=C/C=C(\C)C(=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C44H64O24/c1-19(11-7-13-21(3)39(59)67-43-37(57)33(53)29(49)25(65-43)17-61-41-35(55)31(51)27(47)23(15-45)63-41)9-5-6-10-20(2)12-8-14-22(4)40(60)68-44-38(58)34(54)30(50)26(66-44)18-62-42-36(56)32(52)28(48)24(16-46)64-42/h5-14,23-38,41-58H,15-18H2,1-4H3/b6-5+,11-7+,12-8+,19-9+,20-10+,21-13+,22-14+/t23-,24-,25-,26-,27-,28-,29-,30-,31+,32+,33+,34+,35-,36-,37-,38-,41-,42-,43+,44+/m1/s1

InChI Key

SEBIKDIMAPSUBY-RTJKDTQDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Disaccharide
Glycosyl compound
O-glycosyl compound
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

diester (CHEBI:79068 )
disaccharide derivative (CHEBI:79068 )
diterpenoid (CHEBI:79068 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0002398)
Membrane (HMDB: HMDB0002398)

Source

Exogenous

Exogenous (HMDB: HMDB0002398)

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Herb and spice

Spice

Saffron (FooDB: FOOD00063)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	186 °C	Not Available
Boiling Point	1169.04 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	3688 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-4.742 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.57 g/L	ALOGPS
logP	-0.02	ALOGPS
logP	-3.2	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	11.67	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	22	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	391.2 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	233.49 m³·mol⁻¹	ChemAxon
Polarizability	100.07 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	291.717	30932474
DeepCCS	[M-H]-	289.994	30932474
DeepCCS	[M-2H]-	324.026	30932474
DeepCCS	[M+Na]+	297.951	30932474
AllCCS	[M+H]+	294.2	32859911
AllCCS	[M+H-H2O]+	294.6	32859911
AllCCS	[M+NH4]+	293.8	32859911
AllCCS	[M+Na]+	293.7	32859911
AllCCS	[M-H]-	308.6	32859911
AllCCS	[M+Na-2H]-	315.1	32859911
AllCCS	[M+HCOO]-	322.2	32859911

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Crocin 10V, Negative-QTOF	splash10-0fb9-0000008009-3b75a0bb1954441908e5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Crocin 20V, Negative-QTOF	splash10-0udi-0002009000-9e622eb534e813be910c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Crocin 40V, Negative-QTOF	splash10-0059-1259001000-27e1be6013a6ff14a567	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crocin 10V, Positive-QTOF	splash10-0570-0107109005-8d4ac227319c8db4f8a8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crocin 20V, Positive-QTOF	splash10-01p9-0316529102-33fcee1955a03eb2acbe	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crocin 40V, Positive-QTOF	splash10-03mr-1948544002-585ea2a4ab28ee86f4ac	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crocin 10V, Negative-QTOF	splash10-004i-1514037019-77be269ba2dd85c94f6b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crocin 20V, Negative-QTOF	splash10-0c29-3914005115-42287fc2024b10a75c14	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crocin 40V, Negative-QTOF	splash10-0uml-8933015221-e452e968e696d68b4e6f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crocin 10V, Positive-QTOF	splash10-0a70-0101229114-188a76b2b8dade56be41	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crocin 20V, Positive-QTOF	splash10-0ce9-0384029001-234bd0906e1d9e993e0b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crocin 40V, Positive-QTOF	splash10-001i-0491033013-b4cd69b33ee6311f8a36	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crocin 10V, Negative-QTOF	splash10-0pk9-0018019003-dec192fc122debfcf133	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crocin 20V, Negative-QTOF	splash10-0bt9-4200019082-19b8afa05b75bf20b85b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crocin 40V, Negative-QTOF	splash10-0a4i-2000009001-de243920ac2be1b58304	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB11874

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Crocin

METLIN ID

Not Available

PubChem Compound

5281233

PDB ID

Not Available

ChEBI ID

79068

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1281461

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Ochiai T, Shimeno H, Mishima K, Iwasaki K, Fujiwara M, Tanaka H, Shoyama Y, Toda A, Eyanagi R, Soeda S: Protective effects of carotenoids from saffron on neuronal injury in vitro and in vivo. Biochim Biophys Acta. 2007 Apr;1770(4):578-84. Epub 2006 Dec 5. [PubMed:17215084 ]
Carmona M, Zalacain A, Sanchez AM, Novella JL, Alonso GL: Crocetin esters, picrocrocin and its related compounds present in Crocus sativus stigmas and Gardenia jasminoides fruits. Tentative identification of seven new compounds by LC-ESI-MS. J Agric Food Chem. 2006 Feb 8;54(3):973-9. [PubMed:16448211 ]

Showing metabocard for Crocin (HMDB0002398)

MOL for HMDB0002398 (Crocin)

3D MOL for HMDB0002398 (Crocin)

3D SDF for HMDB0002398 (Crocin)

3D-SDF for HMDB0002398 (Crocin)

PDB for HMDB0002398 (Crocin)

3D PDB for HMDB0002398 (Crocin)

SMILES for HMDB0002398 (Crocin)

INCHI for HMDB0002398 (Crocin)

Structure for HMDB0002398 (Crocin)

3D Structure for HMDB0002398 (Crocin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra