NP-MRD: Showing NP-Card for GlcCer(d18:1/24:1(15Z)) (NP0136764)

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Record Information

Version

2.0

Created at

2022-05-12 15:23:00 UTC

Updated at

2022-05-12 15:23:00 UTC

NP-MRD ID

NP0136764

Secondary Accession Numbers

None

Natural Product Identification

Common Name

GlcCer(d18:1/24:1(15Z))

Description

Glucosylceramide (d18:1/24:1(15Z)), also known as N-nervonoyl-beta-D-glucosylsphingosine or β-D-glucosyl-N-(nervonoyl)sphingosine, belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety. A D-glucosyl-N-acylsphingosine in which the ceramide N-acyl group is nervonoyl. GlcCer(d18:1/24:1(15Z)) was first documented in 1984 (PMID: 6423755). Glucosylceramide (d18:1/24:1(15Z)) is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 3289655) (PMID: 3752966) (PMID: 3364161).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304202019562D          

 57 57  0  0  1  0            999 V2000
   11.0929   -6.4510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8024   -6.8719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5217   -6.4678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2313   -6.8887    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9506   -6.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6601   -6.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3794   -6.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0890   -6.9222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8082   -6.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5178   -6.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2371   -6.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9467   -6.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6659   -6.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3755   -6.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0947   -6.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8044   -6.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5236   -6.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2332   -7.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2216   -7.7136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5314   -5.6429    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2507   -5.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2605   -4.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9603   -5.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6796   -5.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3892   -5.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1084   -5.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8180   -5.6934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5373   -5.2893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2469   -5.7102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9662   -5.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6757   -5.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3950   -5.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1046   -5.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3784   -6.8635    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.3784   -7.6885    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.6639   -6.4510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6639   -8.1010    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9495   -6.8635    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9495   -7.6885    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.6639   -8.9260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2349   -6.4510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5205   -6.8635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2349   -8.1010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0929   -8.1010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8239   -5.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5334   -5.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2393   -7.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2527   -5.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9623   -5.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9575   -6.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6716   -7.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6708   -7.9308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3848   -8.3440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3840   -9.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0981   -9.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0972  -10.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8113  -10.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
  4 19  1  1  0  0  0
  3 20  1  6  0  0  0
 22 21  2  0  0  0  0
 20 21  1  0  0  0  0
 23 21  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 28 27  1  0  0  0  0
 29 28  1  0  0  0  0
 30 29  1  0  0  0  0
 31 30  1  0  0  0  0
 32 31  1  0  0  0  0
 33 32  1  0  0  0  0
 35 34  1  0  0  0  0
 36 34  1  0  0  0  0
 37 35  1  0  0  0  0
 38 36  1  0  0  0  0
 39 37  1  0  0  0  0
 39 38  1  0  0  0  0
 34  1  1  1  0  0  0
 37 40  1  1  0  0  0
 38 41  1  1  0  0  0
 42 41  1  0  0  0  0
 39 43  1  6  0  0  0
 35 44  1  6  0  0  0
 45 33  1  0  0  0  0
 46 45  1  0  0  0  0
 47 18  1  0  0  0  0
 48 46  1  0  0  0  0
 49 48  2  0  0  0  0
 50 49  1  0  0  0  0
 51 50  1  0  0  0  0
 52 51  1  0  0  0  0
 53 52  1  0  0  0  0
 54 53  1  0  0  0  0
 55 54  1  0  0  0  0
 56 55  1  0  0  0  0
 57 56  1  0  0  0  0
M  END

     RDKit          3D

148148  0  0  0  0  0  0  0  0999 V2000
   17.7572    4.0577    0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4514    2.8094    1.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8212    1.6052    0.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5057    0.3711    1.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0321    0.3001    1.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2190    0.1908    0.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7482    0.2444    0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0676   -0.7245    1.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1026   -2.1529    0.8858 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9387   -2.7955    0.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7078   -2.0436    0.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5934   -2.4034    1.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5466   -1.3412    1.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2915   -1.3508    1.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4393   -0.1230    1.4832 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0408   -0.1694    0.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4350    1.0587   -0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2276    1.6746    0.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9212    0.9925   -0.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5557    0.5351   -1.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1322    0.0801   -1.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6300   -0.5341   -2.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8294   -0.7285   -2.5741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0741   -1.6868   -1.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0752   -2.3499   -1.2499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2361   -1.2459   -0.7423 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4090   -0.8124   -0.2484 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5689   -0.7560   -1.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0359   -1.8509   -1.7841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3608   -2.7372   -2.5504 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7735   -2.6461   -3.9007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1196   -2.8516   -4.0397 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9731   -1.6430   -3.9834 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6028   -3.9576   -3.0753 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.7464   -4.5797   -3.4831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4356   -4.9276   -2.8746 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8809   -6.0903   -2.2789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4482   -4.1493   -2.0233 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2130   -4.7630   -2.0834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9686   -1.2454    1.1081 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2104   -2.5881    1.1918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2279   -0.4206    1.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1995    0.8755    1.3314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4225    1.7201    1.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5718    2.5404    0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7651    3.4500    0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9753    2.5601    0.5181 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2128    3.3984    0.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.8229   -0.5296    0.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
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   15.9424   -0.6855    1.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.5212    1.0228   -0.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.5607   -0.7395   -0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3141    0.2939   -0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5605    1.2862    0.8139 H   0  0  0  0  0  0  0  0  0  0  0  0
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   12.0742   -0.3635    1.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
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   10.2057   -2.3484   -0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8071   -0.9567    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6817   -2.2557    1.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5268   -1.1109    2.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3777    0.9211   -1.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2648    1.8601   -0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4135    1.9482    1.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1097    2.6996   -0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1267    1.7524    0.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8585    0.1117    0.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2669   -0.1908   -1.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5927    1.4505   -2.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9927   -0.6164   -0.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4824    0.9768   -1.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1233   -1.5385   -2.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8448    0.1183   -3.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2769   -1.3856   -3.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4203    0.1461   -2.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304202019562D          

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M  END
> <DATABASE_ID>
NP0136764

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C48H91NO8/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-44(52)49-41(40-56-48-47(55)46(54)45(53)43(39-50)57-48)42(51)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h17-18,35,37,41-43,45-48,50-51,53-55H,3-16,19-34,36,38-40H2,1-2H3,(H,49,52)/b18-17-,37-35+/t41-,42+,43+,45+,46-,47+,48+/m0/s1

> <INCHI_KEY>
WBOZIXHPUPAOIA-JZZPSRGZSA-N

> <FORMULA>
C48H91NO8

> <MOLECULAR_WEIGHT>
810.238

> <EXACT_MASS>
809.674468893

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
148

> <JCHEM_AVERAGE_POLARIZABILITY>
103.8863047392247

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(15Z)-N-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]tetracos-15-enamide

> <ALOGPS_LOGP>
9.12

> <JCHEM_LOGP>
12.289147161333336

> <ALOGPS_LOGS>
-6.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.015713374329472

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.181223595454354

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0489165328949444

> <JCHEM_POLAR_SURFACE_AREA>
148.71

> <JCHEM_REFRACTIVITY>
236.11360000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
40

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.40e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(15Z)-N-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]tetracos-15-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  O   UNK     0      20.707 -12.042   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      22.031 -12.828   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.374 -12.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.698 -12.859   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.041 -12.105   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.366 -12.890   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.708 -12.136   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.033 -12.921   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.375 -12.167   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      32.700 -12.953   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      34.043 -12.198   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.367 -12.984   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      36.710 -12.230   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      38.034 -13.016   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      39.377 -12.261   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      40.702 -13.047   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      42.044 -12.293   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      43.369 -13.078   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      24.680 -14.399   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0      23.392 -10.533   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      24.735  -9.779   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      24.753  -8.239   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      26.059 -10.565   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      27.402  -9.810   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      28.727 -10.596   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      30.069  -9.842   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      31.394 -10.628   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      32.736  -9.873   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      34.061 -10.659   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      35.404  -9.905   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      36.728 -10.690   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      38.071  -9.936   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      39.395 -10.722   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      19.373 -12.812   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      19.373 -14.352   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      18.039 -12.042   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      18.039 -15.122   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      16.706 -12.812   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      16.706 -14.352   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      18.039 -16.662   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      15.372 -12.042   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      14.038 -12.812   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      15.372 -15.122   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      20.707 -15.122   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      40.738  -9.968   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      42.062 -10.753   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      43.380 -14.788   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      43.405  -9.999   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      44.730 -10.785   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      44.721 -12.493   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      46.054 -13.264   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      46.052 -14.804   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      47.385 -15.575   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      47.383 -17.115   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      48.716 -17.887   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      48.715 -19.427   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      50.048 -20.198   0.000  0.00  0.00           C+0
CONECT    1    2   34                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   47                                                       
CONECT   19    4                                                            
CONECT   20    3   21                                                       
CONECT   21   22   20   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   45                                                       
CONECT   34   35   36    1                                                  
CONECT   35   34   37   44                                                  
CONECT   36   34   38                                                       
CONECT   37   35   39   40                                                  
CONECT   38   36   39   41                                                  
CONECT   39   37   38   43                                                  
CONECT   40   37                                                            
CONECT   41   38   42                                                       
CONECT   42   41                                                            
CONECT   43   39                                                            
CONECT   44   35                                                            
CONECT   45   33   46                                                       
CONECT   46   45   48                                                       
CONECT   47   18                                                            
CONECT   48   46   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  114    0
END

View in JSmol

Synonyms

Value	Source
1-O-beta-D-Glucopyranosyl-N-(nervonoyl)sphingosine	ChEBI
beta-D-Glucosyl-N-(15Z-tetracosenoyl)-sphing-4E-enine	ChEBI
beta-GlcCer (C24:1)	ChEBI
C24:1 beta-D-Glucosyl ceramide	ChEBI
C24:1 beta-GlcCer	ChEBI
C24:1 GlcCer	ChEBI
C24:1-beta-Glucosyl ceramide	ChEBI
D-Glucosyl-beta-1,1' N-(15Z-tetracosenoyl)-D-erythro-sphingosine	ChEBI
GlcCer(D18:1/24:1(15Z))	ChEBI
Glucosyl(beta) ceramide (D18:1/24:1(15Z))	ChEBI
N-(15Z-Tetracosenoyl)-1-beta-glucosyl-sphing-4-ene	ChEBI
N-(15Z-Tetracosenoyl)-1-beta-glucosyl-sphing-4-enine	ChEBI
N-Nervonoyl-beta-D-glucosylsphingosine	ChEBI
N-Nervonoyl-beta-glucosylsphingosine	ChEBI
N-Nervonoylglucosylsphingosine	ChEBI
N-Nervonyl-beta-D-glucosylsphingosine	ChEBI
N-Nervonyl-beta-glucosylsphingosine	ChEBI
N-Nervonylglucosylsphingosine	ChEBI
1-O-b-D-Glucopyranosyl-N-(nervonoyl)sphingosine	Generator
1-O-Β-D-glucopyranosyl-N-(nervonoyl)sphingosine	Generator
b-D-Glucosyl-N-(15Z-tetracosenoyl)-sphing-4E-enine	Generator
Β-D-glucosyl-N-(15Z-tetracosenoyl)-sphing-4E-enine	Generator
b-GlcCer (C24:1)	Generator
Β-glccer (C24:1)	Generator
C24:1 b-D-Glucosyl ceramide	Generator
C24:1 Β-D-glucosyl ceramide	Generator
C24:1 b-GlcCer	Generator
C24:1 Β-glccer	Generator
C24:1-b-Glucosyl ceramide	Generator
C24:1-Β-glucosyl ceramide	Generator
D-Glucosyl-b-1,1' N-(15Z-tetracosenoyl)-D-erythro-sphingosine	Generator
D-Glucosyl-β-1,1' N-(15Z-tetracosenoyl)-D-erythro-sphingosine	Generator
Glucosyl(b) ceramide (D18:1/24:1(15Z))	Generator
Glucosyl(β) ceramide (D18:1/24:1(15Z))	Generator
N-(15Z-Tetracosenoyl)-1-b-glucosyl-sphing-4-ene	Generator
N-(15Z-Tetracosenoyl)-1-β-glucosyl-sphing-4-ene	Generator
N-(15Z-Tetracosenoyl)-1-b-glucosyl-sphing-4-enine	Generator
N-(15Z-Tetracosenoyl)-1-β-glucosyl-sphing-4-enine	Generator
N-Nervonoyl-b-D-glucosylsphingosine	Generator
N-Nervonoyl-β-D-glucosylsphingosine	Generator
N-Nervonoyl-b-glucosylsphingosine	Generator
N-Nervonoyl-β-glucosylsphingosine	Generator
N-Nervonyl-b-D-glucosylsphingosine	Generator
N-Nervonyl-β-D-glucosylsphingosine	Generator
N-Nervonyl-b-glucosylsphingosine	Generator
N-Nervonyl-β-glucosylsphingosine	Generator
b-D-Glucosyl-N-(nervonoyl)sphingosine	HMDB
Β-D-glucosyl-N-(nervonoyl)sphingosine	HMDB
1-O-b-D-Glucopyranosyl-ceramide	HMDB
1-O-beta-delta-Glucopyranosyl-ceramide	HMDB
Ganglioside GL1a	HMDB
Gaucher cerebroside	HMDB
GLC-beta1->1'cer	HMDB
GLC-beta1->1'cer(D18:1/24:1	HMDB
GlcCeramide	HMDB
Glucocerebroside	HMDB
Glucosylceramide	HMDB

Chemical Formula

C₄₈H₉₁NO₈

Average Mass

810.2380 Da

Monoisotopic Mass

809.67447 Da

IUPAC Name

(15Z)-N-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]tetracos-15-enamide

Traditional Name

(15Z)-N-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]tetracos-15-enamide

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCCCC\C=C/CCCCCCCC

InChI Identifier

InChI=1S/C48H91NO8/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-44(52)49-41(40-56-48-47(55)46(54)45(53)43(39-50)57-48)42(51)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h17-18,35,37,41-43,45-48,50-51,53-55H,3-16,19-34,36,38-40H2,1-2H3,(H,49,52)/b18-17-,37-35+/t41-,42+,43+,45+,46-,47+,48+/m0/s1

InChI Key

WBOZIXHPUPAOIA-JZZPSRGZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Glycosphingolipids

Direct Parent

Glycosyl-N-acylsphingosines

Alternative Parents

Substituents

Glycosyl-n-acylsphingosine
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Fatty amide
Fatty acyl
Monosaccharide
N-acyl-amine
Oxane
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organic oxygen compound
Organic nitrogen compound
Primary alcohol
Carbonyl group
Organooxygen compound
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

beta-D-glucosyl-N-acylsphingosine (CHEBI:84746 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	9.12	ALOGPS
logP	12.29	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Acidic)	12.18	ChemAxon
pKa (Strongest Basic)	-1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	148.71 Å²	ChemAxon
Rotatable Bond Count	40	ChemAxon
Refractivity	236.11 m³·mol⁻¹	ChemAxon
Polarizability	103.89 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0004975

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023562

KNApSAcK ID

Not Available

Chemspider ID

16744960

KEGG Compound ID

C01190

BioCyc ID

GLUCOSYL_CERAMIDE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

7228

PubChem Compound

20057357

PDB ID

Not Available

ChEBI ID

76302

Good Scents ID

Not Available

References

General References

Hara A, Kitazawa N, Taketomi T: Abnormalities of glycosphingolipids in mucopolysaccharidosis type III B. J Lipid Res. 1984 Feb;25(2):175-84. [PubMed:6423755 ]
Beutler E: Gaucher disease. Blood Rev. 1988 Mar;2(1):59-70. doi: 10.1016/0268-960x(88)90009-4. [PubMed:3289655 ]
Kaye EM, Ullman MD, Wilson ER, Barranger JA: Type 2 and type 3 Gaucher disease: a morphological and biochemical study. Ann Neurol. 1986 Aug;20(2):223-30. doi: 10.1002/ana.410200208. [PubMed:3752966 ]
Conradi NG, Kalimo H, Sourander P: Reactions of vessel walls and brain parenchyma to the accumulation of Gaucher cells in the Norrbottnian type (type III) of Gaucher disease. Acta Neuropathol. 1988;75(4):385-90. doi: 10.1007/BF00687792. [PubMed:3364161 ]

Showing NP-Card for GlcCer(d18:1/24:1(15Z)) (NP0136764)

MOL for NP0136764 (GlcCer(d18:1/24:1(15Z)))

3D MOL for NP0136764 (GlcCer(d18:1/24:1(15Z)))

3D SDF for NP0136764 (GlcCer(d18:1/24:1(15Z)))

3D-SDF for NP0136764 (GlcCer(d18:1/24:1(15Z)))

PDB for NP0136764 (GlcCer(d18:1/24:1(15Z)))

3D PDB for NP0136764 (GlcCer(d18:1/24:1(15Z)))

SMILES for NP0136764 (GlcCer(d18:1/24:1(15Z)))

INCHI for NP0136764 (GlcCer(d18:1/24:1(15Z)))

Structure for NP0136764 (GlcCer(d18:1/24:1(15Z)))

3D Structure for NP0136764 (GlcCer(d18:1/24:1(15Z)))