NP-MRD: Showing NP-Card for (1r,2s,3s,4r,5s,6r,7r,8r,9r,12s)-4-(acetyloxy)-3,12-dihydroxy-6-isopropyl-5-({3-[(r)-methanesulfinyl]propanoyl}oxy)-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl butanoate (NP0199521)

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Record Information

Version

2.0

Created at

2022-09-04 18:10:49 UTC

Updated at

2022-09-04 18:10:49 UTC

NP-MRD ID

NP0199521

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3s,4r,5s,6r,7r,8r,9r,12s)-4-(acetyloxy)-3,12-dihydroxy-6-isopropyl-5-({3-[(r)-methanesulfinyl]propanoyl}oxy)-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl butanoate

Description

(1R,2S,3S,4R,5S,6R,7R,8R,9R,12S)-4-(acetyloxy)-3,12-dihydroxy-5-({3-[(R)-methanesulfinyl]propanoyl}oxy)-3,9-dimethyl-13-methylidene-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0²,⁷]Pentadecan-9-yl butanoate belongs to the class of organic compounds known as eunicellane and asbestinane diterpenoids. These are diterpenoids with a structure based on either the eunicellane (5,14-cyclocembrane) or the asbestinane skeleton. (1r,2s,3s,4r,5s,6r,7r,8r,9r,12s)-4-(acetyloxy)-3,12-dihydroxy-6-isopropyl-5-({3-[(r)-methanesulfinyl]propanoyl}oxy)-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl butanoate is found in Klyxum simplex. Based on a literature review very few articles have been published on (1R,2S,3S,4R,5S,6R,7R,8R,9R,12S)-4-(acetyloxy)-3,12-dihydroxy-5-({3-[(R)-methanesulfinyl]propanoyl}oxy)-3,9-dimethyl-13-methylidene-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0²,⁷]Pentadecan-9-yl butanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042220102D          

 41 43  0  0  1  0            999 V2000
   -0.1669   -3.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3180   -2.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027   -3.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8873   -2.8311    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6173   -1.7511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8873   -0.6712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3722   -1.3386    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3722   -2.1636    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0867   -2.5761    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6170   -3.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5564   -3.2081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8011   -2.1636    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5156   -2.5761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5156   -3.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2301   -3.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8011   -3.8136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5156   -0.9261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0880   -1.3386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3735   -0.1011    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
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    2.3722    0.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7738    1.0911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1669   -1.3386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1669   -2.1636    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9515   -2.4186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  6  5  1  6  0  0  0
  7  6  1  6  0  0  0
  8  7  1  6  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  1  0  0  0
  9 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  6  0  0  0
 17 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 30 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
  2 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  CHG  2  23   1  25  -1
M  END

     RDKit          3D

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   -4.1615    0.1246    3.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4803    1.9934   -0.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2418    0.7157   -0.8427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6729    0.7026   -2.2883 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8319   -0.0342   -2.4719 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8682    0.1827   -5.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4118   -1.5125   -3.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2058   -0.3072    2.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3277    0.7818    2.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1136   -1.0289    2.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1456   -2.5374    3.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4022   -2.5502    1.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1498    1.3954    0.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2819    0.3547    2.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8731   -1.6814    2.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1877    0.6750    3.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0401    2.3440   -1.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6896   -0.1732   -0.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1661    0.7515   -0.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8404    1.7742   -2.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6157   -0.9992   -2.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
 37 36  1  0
 36 35  1  0
 35 33  1  0
 33 34  2  0
 33 32  1  0
 30 32  1  1
 30 31  1  0
 30 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 40  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  1
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  6 30  1  0
 26  7  1  0
  8  4  1  0
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 35 78  1  0
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 31 76  1  0
 38 84  1  0
 38 85  1  0
 39 86  1  0
 39 87  1  0
 40 88  1  6
 41 89  1  0
  1 42  1  0
  1 43  1  0
  3 44  1  0
  3 45  1  0
  4 46  1  6
  6 47  1  6
  7 48  1  1
  8 49  1  1
 10 50  1  0
 10 51  1  0
 10 52  1  0
 11 53  1  0
 12 54  1  6
 15 55  1  0
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 15 57  1  0
 17 58  1  1
 21 59  1  0
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 22 61  1  0
 22 62  1  0
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 24 64  1  0
 24 65  1  0
 26 66  1  1
 27 67  1  0
 28 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  0
 29 72  1  0
 29 73  1  0
M  CHG  2  23   1  25  -1
M  END


  Mrv1652309042220102D          

 41 43  0  0  1  0            999 V2000
   -0.1669   -3.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3180   -2.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027   -3.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8873   -2.8311    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6173   -1.7511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8873   -0.6712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3722   -1.3386    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3722   -2.1636    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0867   -2.5761    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6170   -3.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5564   -3.2081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8011   -2.1636    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5156   -2.5761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5156   -3.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2301   -3.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8011   -3.8136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8011   -1.3386    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5156   -0.9261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2301   -1.3386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2301   -2.1636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9445   -0.9261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6590   -1.3386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3735   -0.9261    0.0000 S   0  3  1  0  0  0  0  0  0  0  0  0
    8.0880   -1.3386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3735   -0.1011    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.0867   -0.9261    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0867   -0.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3722    0.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8011    0.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027   -0.4163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5876    0.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6177    0.2512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9533    1.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7738    1.0911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4684    1.6723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8039    2.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3190    3.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3180   -0.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1669   -1.3386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1669   -2.1636    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9515   -2.4186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  6  5  1  6  0  0  0
  7  6  1  6  0  0  0
  8  7  1  6  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  1  0  0  0
  9 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  6  0  0  0
 17 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 30 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
  2 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  CHG  2  23   1  25  -1
M  END
> <DATABASE_ID>
NP0199521

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)O[C@]1(C)CC[C@H](O)C(=C)C[C@H]2O[C@@H]1[C@H]1[C@@H]2[C@](C)(O)[C@H](OC(C)=O)[C@@H](OC(=O)CC[S@@+](C)[O-])[C@@H]1C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O10S/c1-9-10-22(34)40-29(6)13-11-19(32)17(4)15-20-25-24(27(29)38-20)23(16(2)3)26(39-21(33)12-14-41(8)36)28(30(25,7)35)37-18(5)31/h16,19-20,23-28,32,35H,4,9-15H2,1-3,5-8H3/t19-,20+,23+,24+,25+,26-,27+,28+,29+,30-,41+/m0/s1

> <INCHI_KEY>
HTSABVDYBJWUCZ-HGHCFPOXSA-N

> <FORMULA>
C30H48O10S

> <MOLECULAR_WEIGHT>
600.76

> <EXACT_MASS>
600.29681892

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
63.8104096683392

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3S,4R,5S,6R,7R,8R,9R,12S)-4-(acetyloxy)-3,12-dihydroxy-5-({3-[(R)-methanesulfinyl]propanoyl}oxy)-3,9-dimethyl-13-methylidene-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0^{2,7}]pentadecan-9-yl butanoate

> <JCHEM_LOGP>
0.9368598423333325

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.666446588461802

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.587701454558886

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9630000013423983

> <JCHEM_POLAR_SURFACE_AREA>
145.66

> <JCHEM_REFRACTIVITY>
152.0966

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S,4R,5S,6R,7R,8R,9R,12S)-4-(acetyloxy)-3,12-dihydroxy-6-isopropyl-5-({3-[(R)-methanesulfinyl]propanoyl}oxy)-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0^{2,7}]pentadecan-9-yl butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.312  -6.531   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.594  -5.285   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.058  -5.761   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.523  -5.285   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.019  -3.269   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.523  -1.253   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.428  -2.499   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.428  -4.039   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.762  -4.809   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.752  -5.989   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.772  -5.989   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.095  -4.039   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.429  -4.809   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.429  -6.349   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.763  -7.119   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.095  -7.119   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.095  -2.499   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.429  -1.729   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.763  -2.499   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.763  -4.039   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      11.096  -1.729   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.430  -2.499   0.000  0.00  0.00           C+0
HETATM   23  S   UNK     0      13.764  -1.729   0.000  0.00  0.00           S+1
HETATM   24  C   UNK     0      15.098  -2.499   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.764  -0.189   0.000  0.00  0.00           O-1
HETATM   26  C   UNK     0       5.762  -1.729   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.762  -0.189   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.428   0.581   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.095   0.581   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.058  -0.777   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.963   0.469   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.153   0.469   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.779   1.876   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.311   2.037   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.874   3.122   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.501   4.528   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.595   5.774   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.594  -1.253   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.312  -2.499   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.312  -4.039   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -1.776  -4.515   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   40                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   30                                                  
CONECT    7    6    8   26                                                  
CONECT    8    7    4    9                                                  
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   17    7   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    6   31   32   38                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   30   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39    2   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,3S,4R,5S,6R,7R,8R,9R,12S)-4-(Acetyloxy)-3,12-dihydroxy-5-({3-[(R)-methanesulfinyl]propanoyl}oxy)-3,9-dimethyl-13-methylidene-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0,]pentadecan-9-yl butanoic acid	Generator
(1R,2S,3S,4R,5S,6R,7R,8R,9R,12S)-4-(Acetyloxy)-3,12-dihydroxy-5-({3-[(R)-methanesulphinyl]propanoyl}oxy)-3,9-dimethyl-13-methylidene-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0,]pentadecan-9-yl butanoate	Generator
(1R,2S,3S,4R,5S,6R,7R,8R,9R,12S)-4-(Acetyloxy)-3,12-dihydroxy-5-({3-[(R)-methanesulphinyl]propanoyl}oxy)-3,9-dimethyl-13-methylidene-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0,]pentadecan-9-yl butanoic acid	Generator

Chemical Formula

C₃₀H₄₈O₁₀S

Average Mass

600.7600 Da

Monoisotopic Mass

600.29682 Da

IUPAC Name

Traditional Name

(1R,2S,3S,4R,5S,6R,7R,8R,9R,12S)-4-(acetyloxy)-3,12-dihydroxy-6-isopropyl-5-({3-[(R)-methanesulfinyl]propanoyl}oxy)-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0^{2,7}]pentadecan-9-yl butanoate

CAS Registry Number

Not Available

SMILES

CCCC(=O)O[C@]1(C)CC[C@H](O)C(=C)C[C@H]2O[C@@H]1[C@H]1[C@@H]2[C@](C)(O)[C@H](OC(C)=O)[C@@H](OC(=O)CC[S@@+](C)[O-])[C@@H]1C(C)C

InChI Identifier

InChI=1S/C30H48O10S/c1-9-10-22(34)40-29(6)13-11-19(32)17(4)15-20-25-24(27(29)38-20)23(16(2)3)26(39-21(33)12-14-41(8)36)28(30(25,7)35)37-18(5)31/h16,19-20,23-28,32,35H,4,9-15H2,1-3,5-8H3/t19-,20+,23+,24+,25+,26-,27+,28+,29+,30-,41+/m0/s1

InChI Key

HTSABVDYBJWUCZ-HGHCFPOXSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Klyxum simplex	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eunicellane and asbestinane diterpenoids. These are diterpenoids with a structure based on either the eunicellane (5,14-cyclocembrane) or the asbestinane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Eunicellane and asbestinane diterpenoids

Alternative Parents

Substituents

Cladiellane diterpenoid
Eunicellane-type diterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Cyclitol or derivatives
Fatty acyl
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Sulfoxide
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Sulfinyl compound
Organosulfur compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
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	0.94	ChemAxon
pKa (Strongest Acidic)	13.59	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	145.66 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	152.1 m³·mol⁻¹	ChemAxon
Polarizability	63.81 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

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

162885770

PDB ID

Not Available

ChEBI ID

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Good Scents ID

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References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,3s,4r,5s,6r,7r,8r,9r,12s)-4-(acetyloxy)-3,12-dihydroxy-6-isopropyl-5-({3-[(r)-methanesulfinyl]propanoyl}oxy)-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl butanoate (NP0199521)

MOL for NP0199521 ((1r,2s,3s,4r,5s,6r,7r,8r,9r,12s)-4-(acetyloxy)-3,12-dihydroxy-6-isopropyl-5-({3-[(r)-methanesulfinyl]propanoyl}oxy)-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl butanoate)

3D MOL for NP0199521 ((1r,2s,3s,4r,5s,6r,7r,8r,9r,12s)-4-(acetyloxy)-3,12-dihydroxy-6-isopropyl-5-({3-[(r)-methanesulfinyl]propanoyl}oxy)-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl butanoate)

3D SDF for NP0199521 ((1r,2s,3s,4r,5s,6r,7r,8r,9r,12s)-4-(acetyloxy)-3,12-dihydroxy-6-isopropyl-5-({3-[(r)-methanesulfinyl]propanoyl}oxy)-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl butanoate)

3D-SDF for NP0199521 ((1r,2s,3s,4r,5s,6r,7r,8r,9r,12s)-4-(acetyloxy)-3,12-dihydroxy-6-isopropyl-5-({3-[(r)-methanesulfinyl]propanoyl}oxy)-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl butanoate)

PDB for NP0199521 ((1r,2s,3s,4r,5s,6r,7r,8r,9r,12s)-4-(acetyloxy)-3,12-dihydroxy-6-isopropyl-5-({3-[(r)-methanesulfinyl]propanoyl}oxy)-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl butanoate)

3D PDB for NP0199521 ((1r,2s,3s,4r,5s,6r,7r,8r,9r,12s)-4-(acetyloxy)-3,12-dihydroxy-6-isopropyl-5-({3-[(r)-methanesulfinyl]propanoyl}oxy)-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl butanoate)

SMILES for NP0199521 ((1r,2s,3s,4r,5s,6r,7r,8r,9r,12s)-4-(acetyloxy)-3,12-dihydroxy-6-isopropyl-5-({3-[(r)-methanesulfinyl]propanoyl}oxy)-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl butanoate)

INCHI for NP0199521 ((1r,2s,3s,4r,5s,6r,7r,8r,9r,12s)-4-(acetyloxy)-3,12-dihydroxy-6-isopropyl-5-({3-[(r)-methanesulfinyl]propanoyl}oxy)-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl butanoate)

Structure for NP0199521 ((1r,2s,3s,4r,5s,6r,7r,8r,9r,12s)-4-(acetyloxy)-3,12-dihydroxy-6-isopropyl-5-({3-[(r)-methanesulfinyl]propanoyl}oxy)-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl butanoate)

3D Structure for NP0199521 ((1r,2s,3s,4r,5s,6r,7r,8r,9r,12s)-4-(acetyloxy)-3,12-dihydroxy-6-isopropyl-5-({3-[(r)-methanesulfinyl]propanoyl}oxy)-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl butanoate)