NP-MRD: Showing NP-Card for (-)-Mycaloside K (NP0082050)

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Record Information

Version

1.0

Created at

2022-04-29 03:06:15 UTC

Updated at

2022-04-29 03:06:15 UTC

NP-MRD ID

NP0082050

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Mycaloside K

Description

[(2R,3R,4R,5R,6R)-6-{[(1S,2R,5S,6R,10R,11S,12S,14R,15R)-6,12-dihydroxy-14-[(2S,3E,5R)-1-hydroxy-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-5-yl]oxy}-4-{[(2S,3S,4R,5R)-4,5-dihydroxy-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. (-)-Mycaloside K is found in Agelas sp. and Mycale laxissima. Based on a literature review very few articles have been published on [(2R,3R,4R,5R,6R)-6-{[(1S,2R,5S,6R,10R,11S,12S,14R,15R)-6,12-dihydroxy-14-[(2S,3E,5R)-1-hydroxy-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-5-yl]oxy}-4-{[(2S,3S,4R,5R)-4,5-dihydroxy-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292205062D          

 77 84  0  0  1  0            999 V2000
    1.6692   -0.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3889    0.7252    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.7328    1.2106    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0131    0.4347    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4813   -0.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8377    0.4615    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0670    1.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3842    1.7170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3574    2.5416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1613   -0.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4849   -0.6154    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -6.1717    0.6255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9838    0.7707    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -8.0762    1.6918    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.6081    1.0611    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.3278    0.2852    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.5156    0.1400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8596   -0.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7659   -1.3503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5832   -1.4631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8941   -2.2273    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7113   -2.3402    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2177   -1.6888    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9068   -0.9247    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0895   -0.8118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4131   -0.2733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2304   -0.3862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0349   -1.8017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0222   -3.1044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3877   -2.8787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3626   -1.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6141   -2.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1460   -3.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8571    0.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  1  0  0  0
  7 11  1  6  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 14 18  1  6  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
  5 21  1  6  0  0  0
  3 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  6  0  0  0
 28 31  1  6  0  0  0
 32 31  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 32 37  1  0  0  0  0
 37 38  1  1  0  0  0
 36 39  1  6  0  0  0
 40 39  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 40 45  1  0  0  0  0
 45 46  1  1  0  0  0
 47 46  1  1  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 47 52  1  0  0  0  0
 51 53  1  6  0  0  0
 53 54  1  0  0  0  0
 50 55  1  6  0  0  0
 49 56  1  6  0  0  0
 48 57  1  1  0  0  0
 44 58  1  6  0  0  0
 43 59  1  6  0  0  0
 35 60  1  1  0  0  0
 61 60  1  1  0  0  0
 61 62  1  0  0  0  0
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 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
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 65 67  1  1  0  0  0
 67 68  1  0  0  0  0
 64 69  1  1  0  0  0
 63 70  1  1  0  0  0
 62 71  1  6  0  0  0
 34 72  1  6  0  0  0
 72 73  1  0  0  0  0
 73 74  1  0  0  0  0
 74 75  2  0  0  0  0
 74 76  1  0  0  0  0
 25 77  1  6  0  0  0
M  END

     RDKit          3D

163170  0  0  0  0  0  0  0  0999 V2000
   -2.1134   -2.8754   -5.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6201   -2.6424   -3.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7971   -1.5282   -0.8818 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2047   -1.4320    0.3856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -0.1742    1.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5282    0.6985    0.2895 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8401    0.3895    0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3453    1.3646   -0.9273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1567    2.4429   -0.2483 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3281    3.6836   -1.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3707    2.7334    1.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0405    3.1957    2.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4880    3.5024    2.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3104    2.8463    1.0329 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4662    1.9155    0.1610 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3502    1.4778   -0.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1638    1.1263    0.6612 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1801    2.0302    0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.8998   -2.6966    2.1242 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304292205062D          

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   -3.7659   -1.3503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5832   -1.4631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8941   -2.2273    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7113   -2.3402    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2177   -1.6888    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9068   -0.9247    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0895   -0.8118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4131   -0.2733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2304   -0.3862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0349   -1.8017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0222   -3.1044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3877   -2.8787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3626   -1.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8944   -2.1380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6141   -2.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8020   -3.0591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1460   -3.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8571    0.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  1  0  0  0
  7 11  1  6  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 14 18  1  6  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
  5 21  1  6  0  0  0
  3 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  6  0  0  0
 28 31  1  6  0  0  0
 32 31  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 32 37  1  0  0  0  0
 37 38  1  1  0  0  0
 36 39  1  6  0  0  0
 40 39  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 40 45  1  0  0  0  0
 45 46  1  1  0  0  0
 47 46  1  1  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 47 52  1  0  0  0  0
 51 53  1  6  0  0  0
 53 54  1  0  0  0  0
 50 55  1  6  0  0  0
 49 56  1  6  0  0  0
 48 57  1  1  0  0  0
 44 58  1  6  0  0  0
 43 59  1  6  0  0  0
 35 60  1  1  0  0  0
 61 60  1  1  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 63 64  1  0  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 61 66  1  0  0  0  0
 65 67  1  1  0  0  0
 67 68  1  0  0  0  0
 64 69  1  1  0  0  0
 63 70  1  1  0  0  0
 62 71  1  6  0  0  0
 34 72  1  6  0  0  0
 72 73  1  0  0  0  0
 73 74  1  0  0  0  0
 74 75  2  0  0  0  0
 74 76  1  0  0  0  0
 25 77  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0082050

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H](C)\C=C\[C@H](CO)[C@H]1C[C@H](O)[C@H]2[C@@H]3CC=C4[C@@H](O)[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O[C@@H]1O[C@H](COC(C)=O)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O[C@@H]2OC[C@@H](O)[C@@H](O)[C@@H]2O[C@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C53H86O24/c1-21(2)22(3)7-8-24(16-54)28-15-29(58)35-25-9-10-27-36(60)31(12-14-52(27,5)26(25)11-13-53(28,35)6)71-50-44(68)46(45(34(74-50)20-69-23(4)57)75-48-42(66)40(64)38(62)32(17-55)72-48)76-51-47(37(61)30(59)19-70-51)77-49-43(67)41(65)39(63)33(18-56)73-49/h7-8,10,21-22,24-26,28-51,54-56,58-68H,9,11-20H2,1-6H3/b8-7+/t22-,24+,25+,26-,28+,29-,30+,31-,32+,33+,34+,35+,36+,37+,38-,39-,40-,41-,42+,43+,44+,45+,46+,47-,48-,49+,50+,51-,52+,53+/m0/s1

> <INCHI_KEY>
XVNMNJMQUFORCD-DQRCMMSRSA-N

> <FORMULA>
C53H86O24

> <MOLECULAR_WEIGHT>
1107.247

> <EXACT_MASS>
1106.550903649

> <JCHEM_ACCEPTOR_COUNT>
23

> <JCHEM_ATOM_COUNT>
163

> <JCHEM_AVERAGE_POLARIZABILITY>
117.32024193833081

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3R,4R,5R,6R)-6-{[(1S,2R,5S,6R,10R,11S,12S,14R,15R)-6,12-dihydroxy-14-[(2S,3E,5R)-1-hydroxy-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxy}-4-{[(2S,3S,4R,5R)-4,5-dihydroxy-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
-0.81

> <JCHEM_LOGP>
-2.5603815906666636

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.182575176210664

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.75206770173926

> <JCHEM_PKA_STRONGEST_BASIC>
-3.648377575208073

> <JCHEM_POLAR_SURFACE_AREA>
383.36000000000007

> <JCHEM_REFRACTIVITY>
263.77560000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.80e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4R,5R,6R)-6-{[(1S,2R,5S,6R,10R,11S,12S,14R,15R)-6,12-dihydroxy-14-[(2S,3E,5R)-1-hydroxy-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxy}-4-{[(2S,3S,4R,5R)-4,5-dihydroxy-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       3.116  -0.095   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.593   1.354   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.585   2.531   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.101   2.260   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.625   0.811   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.632  -0.366   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.164   0.862   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.592   2.341   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.317   3.205   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.267   4.744   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.109  -0.354   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.634  -0.144   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.580  -1.359   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.105  -1.149   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.050  -2.365   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.576  -2.154   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.470  -3.791   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.685   0.278   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.529  -1.781   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.474  -2.997   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.296  -0.574   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.062   3.979   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.546   4.250   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.553   3.073   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.077   1.625   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.084   0.447   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.432   0.718   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.955   2.167   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.963   3.344   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.486   4.793   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -3.471   2.438   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -4.464   1.261   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -3.941  -0.188   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -4.933  -1.365   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -6.449  -1.094   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -6.973   0.354   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -5.980   1.532   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -6.503   2.980   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -8.489   0.625   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -9.012   2.074   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -8.019   3.251   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -8.542   4.699   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -10.058   4.971   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -11.051   3.793   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -10.528   2.345   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0     -11.521   1.168   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0     -13.036   1.439   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -13.560   2.887   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -15.076   3.158   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -16.068   1.981   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0     -15.545   0.532   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0     -14.029   0.261   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0     -16.538  -0.645   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0     -18.054  -0.374   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0     -17.584   2.252   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0     -15.599   4.606   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0     -12.567   4.064   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0     -12.118   4.904   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0     -10.582   6.419   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      -7.030  -2.521   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      -8.555  -2.731   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      -9.136  -4.158   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0     -10.661  -4.368   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0     -11.606  -3.153   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0     -11.026  -1.726   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0      -9.500  -1.515   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0     -11.971  -0.510   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0     -13.497  -0.721   0.000  0.00  0.00           O+0
HETATM   69  O   UNK     0     -13.132  -3.363   0.000  0.00  0.00           O+0
HETATM   70  O   UNK     0     -11.241  -5.795   0.000  0.00  0.00           O+0
HETATM   71  O   UNK     0      -8.190  -5.373   0.000  0.00  0.00           O+0
HETATM   72  C   UNK     0      -4.410  -2.814   0.000  0.00  0.00           C+0
HETATM   73  O   UNK     0      -5.403  -3.991   0.000  0.00  0.00           O+0
HETATM   74  C   UNK     0      -4.880  -5.439   0.000  0.00  0.00           C+0
HETATM   75  O   UNK     0      -3.364  -5.710   0.000  0.00  0.00           O+0
HETATM   76  C   UNK     0      -5.872  -6.617   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0       1.600   0.176   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   25                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7   21                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9                                                            
CONECT   11    7   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   14                                                            
CONECT   19   11   20                                                       
CONECT   20   19                                                            
CONECT   21    5                                                            
CONECT   22    3   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24    2   26   77                                             
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   24   30                                                  
CONECT   30   29                                                            
CONECT   31   28   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   72                                                  
CONECT   35   34   36   60                                                  
CONECT   36   35   37   39                                                  
CONECT   37   36   32   38                                                  
CONECT   38   37                                                            
CONECT   39   36   40                                                       
CONECT   40   39   41   45                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   59                                                  
CONECT   44   43   45   58                                                  
CONECT   45   44   40   46                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   52                                                  
CONECT   48   47   49   57                                                  
CONECT   49   48   50   56                                                  
CONECT   50   49   51   55                                                  
CONECT   51   50   52   53                                                  
CONECT   52   51   47                                                       
CONECT   53   51   54                                                       
CONECT   54   53                                                            
CONECT   55   50                                                            
CONECT   56   49                                                            
CONECT   57   48                                                            
CONECT   58   44                                                            
CONECT   59   43                                                            
CONECT   60   35   61                                                       
CONECT   61   60   62   66                                                  
CONECT   62   61   63   71                                                  
CONECT   63   62   64   70                                                  
CONECT   64   63   65   69                                                  
CONECT   65   64   66   67                                                  
CONECT   66   65   61                                                       
CONECT   67   65   68                                                       
CONECT   68   67                                                            
CONECT   69   64                                                            
CONECT   70   63                                                            
CONECT   71   62                                                            
CONECT   72   34   73                                                       
CONECT   73   72   74                                                       
CONECT   74   73   75   76                                                  
CONECT   75   74                                                            
CONECT   76   74                                                            
CONECT   77   25                                                            
MASTER        0    0    0    0    0    0    0    0   77    0  168    0
END

View in JSmol

Synonyms

Value

Source

Generator

Chemical Formula

C₅₃H₈₆O₂₄

Average Mass

1107.2470 Da

Monoisotopic Mass

1106.55090 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H](C)\C=C\[C@H](CO)[C@H]1C[C@H](O)[C@H]2[C@@H]3CC=C4[C@@H](O)[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O[C@@H]1O[C@H](COC(C)=O)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O[C@@H]2OC[C@@H](O)[C@@H](O)[C@@H]2O[C@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H]1O

InChI Identifier

InChI=1S/C53H86O24/c1-21(2)22(3)7-8-24(16-54)28-15-29(58)35-25-9-10-27-36(60)31(12-14-52(27,5)26(25)11-13-53(28,35)6)71-50-44(68)46(45(34(74-50)20-69-23(4)57)75-48-42(66)40(64)38(62)32(17-55)72-48)76-51-47(37(61)30(59)19-70-51)77-49-43(67)41(65)39(63)33(18-56)73-49/h7-8,10,21-22,24-26,28-51,54-56,58-68H,9,11-20H2,1-6H3/b8-7+/t22-,24+,25+,26-,28+,29-,30+,31-,32+,33+,34+,35+,36+,37+,38-,39-,40-,41-,42+,43+,44+,45+,46+,47-,48-,49+,50+,51-,52+,53+/m0/s1

InChI Key

XVNMNJMQUFORCD-DQRCMMSRSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agelas sp.	Animalia	KNApSAcK
Mycale laxissima	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal glycosides

Alternative Parents

Substituents

Diterpene glycoside
Ergostane-skeleton
Steroidal glycoside
Trihydroxy bile acid, alcohol, or derivatives
Oligosaccharide
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
21-hydroxysteroid
Diterpenoid
Hydroxysteroid
15-hydroxysteroid
4-hydroxysteroid
Terpene glycoside
Delta-5-steroid
Fatty acyl glycoside
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Fatty alcohol
Fatty acyl
Oxane
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

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	-0.81	ALOGPS
logP	-2.6	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.75	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	23	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	383.36 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	263.78 m³·mol⁻¹	ChemAxon
Polarizability	117.32 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162923687

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Mycaloside K (NP0082050)

MOL for NP0082050 ((-)-Mycaloside K)

3D MOL for NP0082050 ((-)-Mycaloside K)

3D SDF for NP0082050 ((-)-Mycaloside K)

3D-SDF for NP0082050 ((-)-Mycaloside K)

PDB for NP0082050 ((-)-Mycaloside K)

3D PDB for NP0082050 ((-)-Mycaloside K)

SMILES for NP0082050 ((-)-Mycaloside K)

INCHI for NP0082050 ((-)-Mycaloside K)

Structure for NP0082050 ((-)-Mycaloside K)

3D Structure for NP0082050 ((-)-Mycaloside K)