NP-MRD: Showing NP-Card for (-)-Sipholenoside A (NP0080888)

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Record Information

Version

2.0

Created at

2022-04-29 01:52:14 UTC

Updated at

2022-04-29 01:52:14 UTC

NP-MRD ID

NP0080888

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Sipholenoside A

Description

(5AR,6R,7S,9aR)-6-{2-[(1R,3aR,5Z,6R,8aR)-1,4,4,6-tetramethyl-1-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-decahydroazulen-5-ylidene]ethyl}-7-hydroxy-2,2,5a,7-tetramethyl-decahydro-1-benzoxepin-3-one belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (-)-Sipholenoside A is found in Siphonochalina siphonella. Based on a literature review very few articles have been published on (5aR,6R,7S,9aR)-6-{2-[(1R,3aR,5Z,6R,8aR)-1,4,4,6-tetramethyl-1-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-decahydroazulen-5-ylidene]ethyl}-7-hydroxy-2,2,5a,7-tetramethyl-decahydro-1-benzoxepin-3-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203522D          

 44 48  0  0  1  0            999 V2000
    9.1694   -4.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9127   -4.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5577   -4.3505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0962   -5.6692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5819   -6.3142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7569   -6.3142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2425   -5.6692    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4261   -4.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4267   -5.7922    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1253   -6.5602    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6397   -7.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4554   -7.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3473   -6.2857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4627   -7.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9123   -5.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2137   -4.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6993   -3.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8950   -3.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2500   -3.4034    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2500   -2.5784    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8950   -2.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6993   -2.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0573   -2.9909    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8823   -2.9909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4654   -2.3235    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9805   -2.9909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6285   -1.5147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2277   -1.2323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7719    0.1220    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5538    0.3851    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.3663   -4.5511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0966   -4.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6813   -5.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8962   -5.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7295   -6.1980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  1  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  6  0  0  0
 10 13  1  6  0  0  0
 10 14  1  1  0  0  0
  9 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  1  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 27  1  6  0  0  0
 25 28  1  1  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  1  0  0  0
 33 36  1  1  0  0  0
 32 37  1  6  0  0  0
 31 38  1  1  0  0  0
 25 39  1  6  0  0  0
 18 40  1  0  0  0  0
 18 41  1  0  0  0  0
  7 42  1  6  0  0  0
  4 43  1  0  0  0  0
  4 44  1  0  0  0  0
M  END

     RDKit          3D

104108  0  0  0  0  0  0  0  0999 V2000
    8.6579   -0.8754   -1.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5217   -0.4929   -0.5308 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3431   -0.6455   -1.2521 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2438   -0.1155   -0.5665 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.9383   -1.3046    0.9804 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0918   -1.7956    2.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
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 14 63  1  1
 15 64  1  0
 15 65  1  0
 15 66  1  0
 17 67  1  0
 18 68  1  0
 18 69  1  0
 19 70  1  6
 21 71  1  0
 21 72  1  0
 21 73  1  0
 22 74  1  0
 23 75  1  0
 23 76  1  0
 24 77  1  0
 24 78  1  0
 25 79  1  1
 28 80  1  0
 28 81  1  0
 28 82  1  0
 29 83  1  0
 29 84  1  0
 29 85  1  0
 32 86  1  0
 32 87  1  0
 33 88  1  0
 33 89  1  0
 35 90  1  0
 35 91  1  0
 35 92  1  0
 37 93  1  0
 37 94  1  0
 37 95  1  0
 38 96  1  0
 38 97  1  0
 38 98  1  0
 39 99  1  1
 40100  1  0
 41101  1  1
 42102  1  0
 43103  1  1
 44104  1  0
M  END


  Mrv1652304292203522D          

 44 48  0  0  1  0            999 V2000
    9.1694   -4.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9127   -4.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5577   -4.3505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0962   -5.6692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5819   -6.3142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7569   -6.3142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2425   -5.6692    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4261   -4.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4267   -5.7922    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1253   -6.5602    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6397   -7.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4554   -7.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3473   -6.2857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4627   -7.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9123   -5.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2137   -4.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6993   -3.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8950   -3.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2500   -3.4034    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2500   -2.5784    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8950   -2.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6993   -2.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0573   -2.9909    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8823   -2.9909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4654   -2.3235    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9805   -2.9909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4654   -3.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6285   -1.5147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0096   -0.9692    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2277   -1.2323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6089   -0.6867    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7719    0.1220    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5538    0.3851    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1727   -0.1604    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9546    0.1027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7169    1.1939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1531    0.6676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8270   -0.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8581   -1.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3663   -4.5511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0966   -4.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6813   -5.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8962   -5.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7295   -6.1980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  1  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  6  0  0  0
 10 13  1  6  0  0  0
 10 14  1  1  0  0  0
  9 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  1  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 27  1  6  0  0  0
 25 28  1  1  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  1  0  0  0
 33 36  1  1  0  0  0
 32 37  1  6  0  0  0
 31 38  1  1  0  0  0
 25 39  1  6  0  0  0
 18 40  1  0  0  0  0
 18 41  1  0  0  0  0
  7 42  1  6  0  0  0
  4 43  1  0  0  0  0
  4 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0080888

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@]2(C)CC[C@@H]3[C@H]2CC[C@@H](C)\C(=C\C[C@H]2[C@@](C)(O)CC[C@H]4OC(C)(C)C(=O)CC[C@]24C)C3(C)C)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C36H60O8/c1-20-10-11-24-23(14-19-36(24,9)44-31-30(40)29(39)28(38)21(2)42-31)32(3,4)22(20)12-13-25-34(7)17-15-26(37)33(5,6)43-27(34)16-18-35(25,8)41/h12,20-21,23-25,27-31,38-41H,10-11,13-19H2,1-9H3/b22-12-/t20-,21+,23-,24-,25-,27-,28+,29-,30-,31+,34-,35+,36-/m1/s1

> <INCHI_KEY>
HNSOBKBOFOVHBX-QFGLVIAYSA-N

> <FORMULA>
C36H60O8

> <MOLECULAR_WEIGHT>
620.868

> <EXACT_MASS>
620.428818892

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
104

> <JCHEM_AVERAGE_POLARIZABILITY>
71.99718911033119

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5aR,6R,7S,9aR)-6-{2-[(1R,3aR,5Z,6R,8aR)-1,4,4,6-tetramethyl-1-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-decahydroazulen-5-ylidene]ethyl}-7-hydroxy-2,2,5a,7-tetramethyl-decahydro-1-benzoxepin-3-one

> <ALOGPS_LOGP>
5.10

> <JCHEM_LOGP>
4.733551676666666

> <ALOGPS_LOGS>
-5.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.259573769665888

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.222673990643747

> <JCHEM_PKA_STRONGEST_BASIC>
-2.906203151246487

> <JCHEM_POLAR_SURFACE_AREA>
125.68000000000002

> <JCHEM_REFRACTIVITY>
169.11430000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.76e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5aR,6R,7S,9aR)-6-{2-[(1R,3aR,5Z,6R,8aR)-1,4,4,6-tetramethyl-1-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-hexahydro-2H-azulen-5-ylidene]ethyl}-7-hydroxy-2,2,5a,7-tetramethyl-hexahydro-1-benzoxepin-3-one

> <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      17.116  -8.413   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.504  -9.081   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      19.708  -8.121   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      18.846 -10.583   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      17.886 -11.787   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      16.346 -11.787   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.386 -10.583   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.729  -9.081   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.863 -10.812   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.301 -12.246   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.261 -13.450   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.784 -13.220   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.848 -11.733   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.064 -13.163   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.903  -9.608   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.466  -8.175   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.505  -6.971   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.004  -7.313   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.800  -6.353   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.800  -4.813   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.004  -3.853   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.505  -4.196   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.174  -5.583   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.714  -5.583   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.335  -4.337   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.430  -5.583   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.335  -6.829   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.640  -2.828   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.485  -1.809   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.025  -2.300   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.870  -1.282   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.174   0.228   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.634   0.719   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.789  -0.299   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.249   0.192   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       6.938   2.229   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       4.019   1.246   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.410  -1.773   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.202  -3.295   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      10.017  -8.495   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      11.380  -8.807   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      14.338  -9.454   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      20.340 -10.206   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      20.028 -11.570   0.000  0.00  0.00           C+0
CONECT    1    2    8                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   43   44                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9   42                                             
CONECT    8    7    1                                                       
CONECT    9    7   10   15                                                  
CONECT   10    9   11   13   14                                             
CONECT   11   10   12                                                       
CONECT   12   11    6                                                       
CONECT   13   10                                                            
CONECT   14   10                                                            
CONECT   15    9   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19   40   41                                             
CONECT   19   18   20   27                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   17   24                                                  
CONECT   24   23                                                            
CONECT   25   20   26   28   39                                             
CONECT   26   25   27                                                       
CONECT   27   26   19                                                       
CONECT   28   25   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   38                                                  
CONECT   32   31   33   37                                                  
CONECT   33   32   34   36                                                  
CONECT   34   33   29   35                                                  
CONECT   35   34                                                            
CONECT   36   33                                                            
CONECT   37   32                                                            
CONECT   38   31                                                            
CONECT   39   25                                                            
CONECT   40   18                                                            
CONECT   41   18                                                            
CONECT   42    7                                                            
CONECT   43    4                                                            
CONECT   44    4                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₆₀O₈

Average Mass

620.8680 Da

Monoisotopic Mass

620.42882 Da

IUPAC Name

(5aR,6R,7S,9aR)-6-{2-[(1R,3aR,5Z,6R,8aR)-1,4,4,6-tetramethyl-1-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-decahydroazulen-5-ylidene]ethyl}-7-hydroxy-2,2,5a,7-tetramethyl-decahydro-1-benzoxepin-3-one

Traditional Name

(5aR,6R,7S,9aR)-6-{2-[(1R,3aR,5Z,6R,8aR)-1,4,4,6-tetramethyl-1-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-hexahydro-2H-azulen-5-ylidene]ethyl}-7-hydroxy-2,2,5a,7-tetramethyl-hexahydro-1-benzoxepin-3-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@]2(C)CC[C@@H]3[C@H]2CC[C@@H](C)\C(=C\C[C@H]2[C@@](C)(O)CC[C@H]4OC(C)(C)C(=O)CC[C@]24C)C3(C)C)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C36H60O8/c1-20-10-11-24-23(14-19-36(24,9)44-31-30(40)29(39)28(38)21(2)42-31)32(3,4)22(20)12-13-25-34(7)17-15-26(37)33(5,6)43-27(34)16-18-35(25,8)41/h12,20-21,23-25,27-31,38-41H,10-11,13-19H2,1-9H3/b22-12-/t20-,21+,23-,24-,25-,27-,28+,29-,30-,31+,34-,35+,36-/m1/s1

InChI Key

HNSOBKBOFOVHBX-QFGLVIAYSA-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
Callyspongia siphonella	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Oxepane
Oxane
Monosaccharide
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	5.1	ALOGPS
logP	4.73	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	12.22	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	169.11 m³·mol⁻¹	ChemAxon
Polarizability	72 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

163185122

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Sipholenoside A (NP0080888)

MOL for NP0080888 ((-)-Sipholenoside A)

3D MOL for NP0080888 ((-)-Sipholenoside A)

3D SDF for NP0080888 ((-)-Sipholenoside A)

3D-SDF for NP0080888 ((-)-Sipholenoside A)

PDB for NP0080888 ((-)-Sipholenoside A)

3D PDB for NP0080888 ((-)-Sipholenoside A)

SMILES for NP0080888 ((-)-Sipholenoside A)

INCHI for NP0080888 ((-)-Sipholenoside A)

Structure for NP0080888 ((-)-Sipholenoside A)

3D Structure for NP0080888 ((-)-Sipholenoside A)