NP-MRD: Showing NP-Card for gusanlungionoside A (NP0035860)

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Record Information

Version

2.0

Created at

2021-06-20 19:11:19 UTC

Updated at

2021-06-30 00:07:08 UTC

NP-MRD ID

NP0035860

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gusanlungionoside A

Provided By

JEOL Database JEOL Logo

Description

gusanlungionoside A is found in Arcangelisia gusanlung. gusanlungionoside A was first documented in 2011 (Yu, L. -L., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121113D          

 76 78  0  0  0  0            999 V2000
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M  END

     RDKit          3D

 76 78  0  0  0  0  0  0  0  0999 V2000
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 23 25  1  0
 25 16  1  0
  6  7  1  0
  4  3  1  0
 33 31  1  0
 31 29  1  0
 29 28  1  0
 28 27  1  0
 31 32  1  0
 33 34  1  0
  3  2  2  0
 27 35  1  0
 35 33  1  0
  2 10  1  0
 35 36  1  0
 10  7  1  0
 29 30  1  0
 23 24  1  0
 25 26  1  0
 16 15  1  0
 27 26  1  0
 16 56  1  1
 21 61  1  6
 22 62  1  0
 25 65  1  6
 18 57  1  1
 19 58  1  0
 19 59  1  0
 24 64  1  0
 23 63  1  1
 20 60  1  0
  6 41  1  0
  6 42  1  0
  3 40  1  0
 11 50  1  0
 12 51  1  0
 13 52  1  6
  1 37  1  0
  1 38  1  0
  1 39  1  0
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
  9 48  1  0
 14 53  1  0
 14 54  1  0
 14 55  1  0
 27 66  1  6
 31 71  1  6
 32 72  1  0
 33 73  1  1
 34 74  1  0
 29 67  1  1
 35 75  1  6
 36 76  1  0
 30 68  1  0
 30 69  1  0
 30 70  1  0
M  END


  Mrv1652306202121113D          

 76 78  0  0  0  0            999 V2000
   -4.9482   -3.9709    1.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6187   -3.0421    2.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4230   -3.0072    3.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0751   -2.2134    4.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8526   -2.1865    5.3878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7287   -1.5311    4.4768 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2910   -1.0274    3.0860 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2056    0.1478    2.6623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8518   -0.4794    3.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3292   -2.2267    2.0730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0444   -1.7742    0.6526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125   -2.0663   -0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5946   -1.5996   -1.4027 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3034   -2.7928   -2.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4046   -0.8133   -1.3297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761    0.5728   -1.0930 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0742    1.1684   -2.3280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3437    2.5756   -2.1931 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8767    3.0731   -3.5403 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0280    2.3074   -3.9067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0690    3.3159   -1.7859 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3130    4.7121   -1.6130 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4691    2.7363   -0.4760 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7403    3.3587   -0.2104 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6183    1.2147   -0.5509 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8723    0.7569    0.7913 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8287   -0.2992    0.8665 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6201   -0.9954    2.0955 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4239   -2.1825    2.2192 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6285   -3.3917    1.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7857   -2.0708    1.5042 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7474   -2.9304    2.1169 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2586   -0.6193    1.5684 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5488   -0.5147    0.9474 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2536    0.3100    0.8734 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2641    1.5790    1.5695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0942   -4.6197    0.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7978   -4.6223    1.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2089   -3.4068    0.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3374   -3.5856    3.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7900   -0.6942    5.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0069   -2.2528    4.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8404    0.6368    1.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2347   -0.1744    2.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2391    0.9169    3.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1491   -1.2722    3.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5024   -0.0373    2.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7936    0.3003    3.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5327   -2.9279    2.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8110   -1.1757    0.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1413   -2.6548    0.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4192   -1.0236   -1.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0353   -2.4490   -3.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4496   -3.3741   -1.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1704   -3.4566   -2.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4779    0.6746   -0.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1372    2.7076   -1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660    4.1269   -3.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1338    2.9406   -4.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7531    1.3742   -3.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6961    3.2142   -2.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4999    5.0665   -1.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1808    3.0210    0.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1610    2.8648    0.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4683    0.9723   -1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6987   -1.0046    0.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5944   -2.3185    3.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1811   -4.3216    1.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6725   -3.4539    2.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3914   -3.3119    0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7109   -2.3849    0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6160   -2.6270    1.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4102   -0.3286    2.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8119    0.4233    1.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5643    0.5402   -0.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6522    1.4660    2.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 22  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 18 19  1  0  0  0  0
 12 13  1  0  0  0  0
 13 15  1  0  0  0  0
  4  5  2  0  0  0  0
  2  1  1  0  0  0  0
 19 20  1  0  0  0  0
  7  8  1  6  0  0  0
 16 17  1  0  0  0  0
  7  9  1  0  0  0  0
  6  4  1  0  0  0  0
 10 49  1  1  0  0  0
 17 18  1  0  0  0  0
 13 14  1  0  0  0  0
 18 21  1  0  0  0  0
 21 23  1  0  0  0  0
 23 25  1  0  0  0  0
 25 16  1  0  0  0  0
  6  7  1  0  0  0  0
  4  3  1  0  0  0  0
 33 31  1  0  0  0  0
 31 29  1  0  0  0  0
 29 28  1  0  0  0  0
 28 27  1  0  0  0  0
 31 32  1  0  0  0  0
 33 34  1  0  0  0  0
  3  2  2  0  0  0  0
 27 35  1  0  0  0  0
 35 33  1  0  0  0  0
  2 10  1  0  0  0  0
 35 36  1  0  0  0  0
 10  7  1  0  0  0  0
 29 30  1  0  0  0  0
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 16 15  1  0  0  0  0
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 22 62  1  0  0  0  0
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 18 57  1  1  0  0  0
 19 58  1  0  0  0  0
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 24 64  1  0  0  0  0
 23 63  1  1  0  0  0
 20 60  1  0  0  0  0
  6 41  1  0  0  0  0
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  3 40  1  0  0  0  0
 11 50  1  0  0  0  0
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 13 52  1  6  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
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  8 43  1  0  0  0  0
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  9 48  1  0  0  0  0
 14 53  1  0  0  0  0
 14 54  1  0  0  0  0
 14 55  1  0  0  0  0
 27 66  1  6  0  0  0
 31 71  1  6  0  0  0
 32 72  1  0  0  0  0
 33 73  1  1  0  0  0
 34 74  1  0  0  0  0
 29 67  1  1  0  0  0
 35 75  1  6  0  0  0
 36 76  1  0  0  0  0
 30 68  1  0  0  0  0
 30 69  1  0  0  0  0
 30 70  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035860

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]([H])(C(\[H])=C(/[H])[C@]2([H])C(=C([H])C(=O)C([H])([H])C2(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])[C@]([H])(O[C@]2([H])O[C@@]([H])(C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]2([H])O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H40O11/c1-11-8-14(27)9-25(4,5)15(11)7-6-12(2)33-24-22(20(31)18(29)16(10-26)35-24)36-23-21(32)19(30)17(28)13(3)34-23/h6-8,12-13,15-24,26,28-32H,9-10H2,1-5H3/b7-6+/t12-,13-,15+,16+,17-,18+,19+,20-,21-,22+,23-,24+/m0/s1

> <INCHI_KEY>
HNFRYUMXAKNBBJ-STRBEBIRSA-N

> <FORMULA>
C25H40O11

> <MOLECULAR_WEIGHT>
516.584

> <EXACT_MASS>
516.257062108

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
53.52236336159863

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S)-4-[(1E,3S)-3-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}but-1-en-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one

> <ALOGPS_LOGP>
-0.26

> <JCHEM_LOGP>
-0.2282774446666677

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.72014446746197

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.100262191905518

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810839073103974

> <JCHEM_POLAR_SURFACE_AREA>
175.37

> <JCHEM_REFRACTIVITY>
126.99000000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-4-[(1E,3S)-3-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}but-1-en-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 76 78  0  0  0  0  0  0  0  0999 V2000
   -4.9482   -3.9709    1.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6187   -3.0421    2.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4230   -3.0072    3.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0751   -2.2134    4.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8526   -2.1865    5.3878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7287   -1.5311    4.4768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2910   -1.0274    3.0860 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2056    0.1478    2.6623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8518   -0.4794    3.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3292   -2.2267    2.0730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0444   -1.7742    0.6526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125   -2.0663   -0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5946   -1.5996   -1.4027 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3034   -2.7928   -2.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4046   -0.8133   -1.3297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761    0.5728   -1.0930 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0742    1.1684   -2.3280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3437    2.5756   -2.1931 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8767    3.0731   -3.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0280    2.3074   -3.9067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0690    3.3159   -1.7859 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3130    4.7121   -1.6130 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4691    2.7363   -0.4760 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7403    3.3587   -0.2104 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6183    1.2147   -0.5509 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8723    0.7569    0.7913 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8287   -0.2992    0.8665 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6201   -0.9954    2.0955 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4239   -2.1825    2.2192 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6285   -3.3917    1.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7857   -2.0708    1.5042 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7474   -2.9304    2.1169 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2586   -0.6193    1.5684 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5488   -0.5147    0.9474 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2536    0.3100    0.8734 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2641    1.5790    1.5695 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7978   -4.6223    1.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2089   -3.4068    0.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3374   -3.5856    3.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7900   -0.6942    5.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0069   -2.2528    4.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.2347   -0.1744    2.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2391    0.9169    3.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1491   -1.2722    3.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5024   -0.0373    2.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7936    0.3003    3.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5327   -2.9279    2.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8110   -1.1757    0.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1413   -2.6548    0.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4192   -1.0236   -1.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0353   -2.4490   -3.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4496   -3.3741   -1.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1704   -3.4566   -2.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4779    0.6746   -0.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1372    2.7076   -1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660    4.1269   -3.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1338    2.9406   -4.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7531    1.3742   -3.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6961    3.2142   -2.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4999    5.0665   -1.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1808    3.0210    0.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1610    2.8648    0.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4683    0.9723   -1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6987   -1.0046    0.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5944   -2.3185    3.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1811   -4.3216    1.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6725   -3.4539    2.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3914   -3.3119    0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7109   -2.3849    0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6160   -2.6270    1.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4102   -0.3286    2.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8119    0.4233    1.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5643    0.5402   -0.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6522    1.4660    2.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 22  1  0
 10 11  1  0
 11 12  2  0
 18 19  1  0
 12 13  1  0
 13 15  1  0
  4  5  2  0
  2  1  1  0
 19 20  1  0
  7  8  1  6
 16 17  1  0
  7  9  1  0
  6  4  1  0
 10 49  1  1
 17 18  1  0
 13 14  1  0
 18 21  1  0
 21 23  1  0
 23 25  1  0
 25 16  1  0
  6  7  1  0
  4  3  1  0
 33 31  1  0
 31 29  1  0
 29 28  1  0
 28 27  1  0
 31 32  1  0
 33 34  1  0
  3  2  2  0
 27 35  1  0
 35 33  1  0
  2 10  1  0
 35 36  1  0
 10  7  1  0
 29 30  1  0
 23 24  1  0
 25 26  1  0
 16 15  1  0
 27 26  1  0
 16 56  1  1
 21 61  1  6
 22 62  1  0
 25 65  1  6
 18 57  1  1
 19 58  1  0
 19 59  1  0
 24 64  1  0
 23 63  1  1
 20 60  1  0
  6 41  1  0
  6 42  1  0
  3 40  1  0
 11 50  1  0
 12 51  1  0
 13 52  1  6
  1 37  1  0
  1 38  1  0
  1 39  1  0
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
  9 48  1  0
 14 53  1  0
 14 54  1  0
 14 55  1  0
 27 66  1  6
 31 71  1  6
 32 72  1  0
 33 73  1  1
 34 74  1  0
 29 67  1  1
 35 75  1  6
 36 76  1  0
 30 68  1  0
 30 69  1  0
 30 70  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.948  -3.971   1.018  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.619  -3.042   2.159  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.423  -3.007   3.236  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.075  -2.213   4.437  0.00  0.00           C+0
HETATM    5  O   UNK     0      -5.853  -2.187   5.388  0.00  0.00           O+0
HETATM    6  C   UNK     0      -3.729  -1.531   4.477  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.291  -1.027   3.086  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.206   0.148   2.662  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.852  -0.479   3.212  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.329  -2.227   2.073  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.044  -1.774   0.653  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.913  -2.066  -0.010  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.595  -1.600  -1.403  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.303  -2.793  -2.305  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.405  -0.813  -1.330  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.676   0.573  -1.093  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.074   1.168  -2.328  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.344   2.576  -2.193  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.877   3.073  -3.540  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.028   2.307  -3.907  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.069   3.316  -1.786  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.313   4.712  -1.613  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.469   2.736  -0.476  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.740   3.359  -0.210  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.618   1.215  -0.551  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.872   0.757   0.791  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.829  -0.299   0.867  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.620  -0.995   2.095  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.424  -2.183   2.219  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.629  -3.392   1.738  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.786  -2.071   1.504  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.747  -2.930   2.117  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.259  -0.619   1.568  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.549  -0.515   0.947  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.254   0.310   0.873  0.00  0.00           C+0
HETATM   36  O   UNK     0       3.264   1.579   1.569  0.00  0.00           O+0
HETATM   37  H   UNK     0      -4.094  -4.620   0.797  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.798  -4.622   1.252  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.209  -3.407   0.118  0.00  0.00           H+0
HETATM   40  H   UNK     0      -6.337  -3.586   3.311  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.790  -0.694   5.183  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.007  -2.253   4.879  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.840   0.637   1.753  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.235  -0.174   2.475  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.239   0.917   3.443  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.149  -1.272   3.492  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.502  -0.037   2.273  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.794   0.300   3.980  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.533  -2.928   2.368  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.811  -1.176   0.163  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.141  -2.655   0.482  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.419  -1.024  -1.841  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.035  -2.449  -3.310  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.450  -3.374  -1.937  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.170  -3.457  -2.385  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.478   0.675  -0.350  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.137   2.708  -1.445  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.166   4.127  -3.498  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.134   2.941  -4.334  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.753   1.374  -3.827  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.696   3.214  -2.566  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.500   5.066  -1.197  0.00  0.00           H+0
HETATM   63  H   UNK     0      -0.181   3.021   0.361  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.161   2.865   0.527  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.468   0.972  -1.202  0.00  0.00           H+0
HETATM   66  H   UNK     0       1.699  -1.005   0.038  0.00  0.00           H+0
HETATM   67  H   UNK     0       2.594  -2.318   3.294  0.00  0.00           H+0
HETATM   68  H   UNK     0       2.181  -4.322   1.902  0.00  0.00           H+0
HETATM   69  H   UNK     0       0.673  -3.454   2.269  0.00  0.00           H+0
HETATM   70  H   UNK     0       1.391  -3.312   0.671  0.00  0.00           H+0
HETATM   71  H   UNK     0       3.711  -2.385   0.456  0.00  0.00           H+0
HETATM   72  H   UNK     0       5.616  -2.627   1.782  0.00  0.00           H+0
HETATM   73  H   UNK     0       4.410  -0.329   2.616  0.00  0.00           H+0
HETATM   74  H   UNK     0       5.812   0.423   1.024  0.00  0.00           H+0
HETATM   75  H   UNK     0       3.564   0.540  -0.151  0.00  0.00           H+0
HETATM   76  H   UNK     0       2.652   1.466   2.327  0.00  0.00           H+0
CONECT    1    2   37   38   39                                             
CONECT    2    1    3   10                                                  
CONECT    3    4    2   40                                                  
CONECT    4    5    6    3                                                  
CONECT    5    4                                                            
CONECT    6    4    7   41   42                                             
CONECT    7    8    9    6   10                                             
CONECT    8    7   43   44   45                                             
CONECT    9    7   46   47   48                                             
CONECT   10   11   49    2    7                                             
CONECT   11   10   12   50                                                  
CONECT   12   11   13   51                                                  
CONECT   13   12   15   14   52                                             
CONECT   14   13   53   54   55                                             
CONECT   15   13   16                                                       
CONECT   16   17   25   15   56                                             
CONECT   17   16   18                                                       
CONECT   18   19   17   21   57                                             
CONECT   19   18   20   58   59                                             
CONECT   20   19   60                                                       
CONECT   21   22   18   23   61                                             
CONECT   22   21   62                                                       
CONECT   23   21   25   24   63                                             
CONECT   24   23   64                                                       
CONECT   25   23   16   26   65                                             
CONECT   26   25   27                                                       
CONECT   27   28   35   26   66                                             
CONECT   28   29   27                                                       
CONECT   29   31   28   30   67                                             
CONECT   30   29   68   69   70                                             
CONECT   31   33   29   32   71                                             
CONECT   32   31   72                                                       
CONECT   33   31   34   35   73                                             
CONECT   34   33   74                                                       
CONECT   35   27   33   36   75                                             
CONECT   36   35   76                                                       
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    3                                                            
CONECT   41    6                                                            
CONECT   42    6                                                            
CONECT   43    8                                                            
CONECT   44    8                                                            
CONECT   45    8                                                            
CONECT   46    9                                                            
CONECT   47    9                                                            
CONECT   48    9                                                            
CONECT   49   10                                                            
CONECT   50   11                                                            
CONECT   51   12                                                            
CONECT   52   13                                                            
CONECT   53   14                                                            
CONECT   54   14                                                            
CONECT   55   14                                                            
CONECT   56   16                                                            
CONECT   57   18                                                            
CONECT   58   19                                                            
CONECT   59   19                                                            
CONECT   60   20                                                            
CONECT   61   21                                                            
CONECT   62   22                                                            
CONECT   63   23                                                            
CONECT   64   24                                                            
CONECT   65   25                                                            
CONECT   66   27                                                            
CONECT   67   29                                                            
CONECT   68   30                                                            
CONECT   69   30                                                            
CONECT   70   30                                                            
CONECT   71   31                                                            
CONECT   72   32                                                            
CONECT   73   33                                                            
CONECT   74   34                                                            
CONECT   75   35                                                            
CONECT   76   36                                                            
MASTER        0    0    0    0    0    0    0    0   76    0  156    0
END

RDKit          3D

76 78  0  0  0  0  0  0  0  0999 V2000
   -4.9482   -3.9709    1.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6187   -3.0421    2.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4230   -3.0072    3.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0751   -2.2134    4.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8526   -2.1865    5.3878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7287   -1.5311    4.4768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2910   -1.0274    3.0860 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2056    0.1478    2.6623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8518   -0.4794    3.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3292   -2.2267    2.0730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0444   -1.7742    0.6526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125   -2.0663   -0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5946   -1.5996   -1.4027 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3034   -2.7928   -2.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4046   -0.8133   -1.3297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761    0.5728   -1.0930 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0742    1.1684   -2.3280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3437    2.5756   -2.1931 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8767    3.0731   -3.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0280    2.3074   -3.9067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0690    3.3159   -1.7859 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3130    4.7121   -1.6130 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4691    2.7363   -0.4760 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7403    3.3587   -0.2104 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6183    1.2147   -0.5509 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8723    0.7569    0.7913 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8287   -0.2992    0.8665 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6201   -0.9954    2.0955 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4239   -2.1825    2.2192 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6285   -3.3917    1.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7857   -2.0708    1.5042 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7474   -2.9304    2.1169 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2586   -0.6193    1.5684 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5488   -0.5147    0.9474 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2536    0.3100    0.8734 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2641    1.5790    1.5695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0942   -4.6197    0.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7978   -4.6223    1.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2089   -3.4068    0.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3374   -3.5856    3.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7900   -0.6942    5.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₄₀O₁₁

Average Mass

516.5840 Da

Monoisotopic Mass

516.25706 Da

IUPAC Name

(4S)-4-[(1E,3S)-3-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}but-1-en-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one

Traditional Name

(4S)-4-[(1E,3S)-3-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}but-1-en-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]([H])(C(\[H])=C(/[H])[C@]2([H])C(=C([H])C(=O)C([H])([H])C2(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])[C@]([H])(O[C@]2([H])O[C@@]([H])(C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]2([H])O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C25H40O11/c1-11-8-14(27)9-25(4,5)15(11)7-6-12(2)33-24-22(20(31)18(29)16(10-26)35-24)36-23-21(32)19(30)17(28)13(3)34-23/h6-8,12-13,15-24,26,28-32H,9-10H2,1-5H3/b7-6+/t12-,13-,15+,16+,17-,18+,19+,20-,21-,22+,23-,24+/m0/s1

InChI Key

HNFRYUMXAKNBBJ-STRBEBIRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arcangelisia gusanlung	JEOL database	Yu, L. -L., et al, J. Nat. Prod. 74, 1009 (2011)

Chemical Taxonomy

Classification

Not classified

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	-0.26	ALOGPS
logP	-0.23	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.1	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	175.37 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	126.99 m³·mol⁻¹	ChemAxon
Polarizability	53.52 Å³	ChemAxon
Number of Rings	3	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

Not Available

References

General References

Yu, L. -L., et al. (2011). Yu, L. -L., et al, J. Nat. Prod. 74, 1009 (2011). J. Nat. Prod..

Showing NP-Card for gusanlungionoside A (NP0035860)

MOL for NP0035860 (gusanlungionoside A)

3D MOL for NP0035860 (gusanlungionoside A)

3D SDF for NP0035860 (gusanlungionoside A)

3D-SDF for NP0035860 (gusanlungionoside A)

PDB for NP0035860 (gusanlungionoside A)

3D PDB for NP0035860 (gusanlungionoside A)

SMILES for NP0035860 (gusanlungionoside A)

INCHI for NP0035860 (gusanlungionoside A)

Structure for NP0035860 (gusanlungionoside A)

3D Structure for NP0035860 (gusanlungionoside A)