NP-MRD: Showing NP-Card for (-)-Ircinianin sulfate (NP0083323)

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Record Information

Version

2.0

Created at

2022-04-29 04:22:09 UTC

Updated at

2022-04-29 04:22:09 UTC

NP-MRD ID

NP0083323

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Ircinianin sulfate

Description

[(2S,3'S,3'aR,5'S,7'aR)-5'-[(1E)-5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3',4-dimethyl-5-oxo-1',2',3',3'a,5',7'a-hexahydro-5H-spiro[furan-2,4'-indene]-3-yl]oxidanesulfonic acid belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (-)-Ircinianin sulfate is found in Ircinia wistarii. Based on a literature review very few articles have been published on [(2S,3'S,3'aR,5'S,7'aR)-5'-[(1E)-5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3',4-dimethyl-5-oxo-1',2',3',3'a,5',7'a-hexahydro-5H-spiro[furan-2,4'-indene]-3-yl]oxidanesulfonic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206222D          

 32 35  0  0  1  0            999 V2000
    3.0460    3.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7969    2.6988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8763    1.8777    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2048    1.3983    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4539    1.7402    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3746    2.5614    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6237    2.9032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5444    3.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7935    4.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7141    4.8874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0367    5.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1161    6.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8271    6.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6488    7.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1724    7.3538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5016    6.5973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2158    4.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7023    0.9535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0308    0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0239   -0.3508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3675    0.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6290    1.7471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1496    2.4186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3285    2.3392    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4927    2.2598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2491    3.1604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4078    1.5180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5808    0.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4532    0.6116    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2781    0.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5396    1.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9627   -0.0518    0.0000 C   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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  2  0  0  0  0
  8  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  2  0  0  0  0
  8 17  1  0  0  0  0
  5 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  2  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  2  0  0  0  0
 24 27  1  0  0  0  0
 21 28  1  0  0  0  0
  4 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  3 31  1  1  0  0  0
 29 32  1  6  0  0  0
M  END

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
   -3.8085    1.9096    3.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512    1.6299    2.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3729    0.4511    1.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0002   -0.7081    2.0210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6369   -1.0478    2.0209 S   0  0  1  0  0  6  0  0  0  0  0  0
   -4.7691   -2.5527    1.7824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3274   -0.7696    3.3280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4102   -0.3231    0.7379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2952    0.6616    0.6282 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0801    2.0302    0.6024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9340    2.6528    1.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0249    3.9083    1.7039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0771   -0.0717    1.2267 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0725   -0.1070    0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2167    0.4469    0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2591    1.0838    2.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4485    0.4690   -0.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1722   -0.2315   -1.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4307   -0.2073   -2.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5522   -0.8964   -1.6340 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4740   -0.3035   -0.7849 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3161   -1.3128   -0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9142   -2.4357   -0.9734 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8697   -2.2213   -1.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5593   -1.4511    1.4694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2489   -2.0416    0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5397   -1.3821   -0.7903 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8889   -1.7501   -1.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1345   -0.5825   -2.3074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7042    0.6014   -1.4690 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3735    1.7813   -2.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5041    0.0934   -0.7477 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6472    1.2601    4.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6265    2.9395    3.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8319    1.8510    2.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3583    0.6603    0.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1439    0.4657    2.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583   -0.5608   -0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0655    0.3658    2.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    1.9309    2.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2624    1.5180    2.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6306    1.5371   -0.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2634    0.0186    0.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3749    0.2659   -2.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8493   -1.2820   -1.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2520   -0.6977   -3.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7392    0.8464   -2.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5217    0.7353   -0.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1724   -1.2502    0.2780 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3407   -2.9520   -2.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3597   -1.9695    2.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6014   -3.0404    0.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8011   -1.7502   -1.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7927   -2.7136   -1.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6742   -1.9305   -0.6585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4464   -0.6531   -3.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1990   -0.5058   -2.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5278    0.8787   -0.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9146    1.4703   -3.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7578    2.5118   -1.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3604    2.2464   -2.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6143    0.4806   -1.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 29  1  0
 29 28  1  0
 28 27  1  0
 27 26  1  0
 26 25  2  0
 25 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 24  2  0
 24 23  1  0
 23 22  1  0
 22 21  2  0
 13  9  1  0
  9 10  1  6
 10 11  1  0
 11 12  2  0
 11  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  5  4  1  1
  5  8  1  0
  5  6  2  0
  5  7  2  0
  9 32  1  0
 32 30  1  0
 32 27  1  0
 21 20  1  0
  3  9  1  0
 31 59  1  0
 31 60  1  0
 31 61  1  0
 30 58  1  1
 29 56  1  0
 29 57  1  0
 28 54  1  0
 28 55  1  0
 27 53  1  6
 26 52  1  0
 25 51  1  0
 13 37  1  1
 14 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 24 50  1  0
 22 49  1  0
 21 48  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  8 36  1  0
 32 62  1  6
M  END


  Mrv1652304292206222D          

 32 35  0  0  1  0            999 V2000
    3.0460    3.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7969    2.6988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8763    1.8777    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2048    1.3983    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4539    1.7402    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3746    2.5614    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6237    2.9032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5444    3.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7935    4.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7141    4.8874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0367    5.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1161    6.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8271    6.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6488    7.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1724    7.3538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5016    6.5973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2158    4.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7023    0.9535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0308    0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0239   -0.3508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3675    0.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6290    1.7471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1496    2.4186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3285    2.3392    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4927    2.2598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2491    3.1604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4078    1.5180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5808    0.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4532    0.6116    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2781    0.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5396    1.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9627   -0.0518    0.0000 C   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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  2  0  0  0  0
  8  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  2  0  0  0  0
  8 17  1  0  0  0  0
  5 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  2  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  2  0  0  0  0
 24 27  1  0  0  0  0
 21 28  1  0  0  0  0
  4 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  3 31  1  1  0  0  0
 29 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0083323

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@@H]2C=C[C@@H](\C=C(/C)CCCC3=COC=C3)[C@@]3(OC(=O)C(C)=C3OS(O)(=O)=O)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O7S/c1-15(5-4-6-18-11-12-29-14-18)13-20-10-9-19-8-7-16(2)21(19)24(20)22(31-32(26,27)28)17(3)23(25)30-24/h9-14,16,19-21H,4-8H2,1-3H3,(H,26,27,28)/b15-13+/t16-,19+,20-,21+,24+/m0/s1

> <INCHI_KEY>
UMNWICRUKDNAMG-MEUNUUFJSA-N

> <FORMULA>
C24H30O7S

> <MOLECULAR_WEIGHT>
462.56

> <EXACT_MASS>
462.17122448

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
47.83302543045111

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2S,3'S,3'aR,5'S,7'aR)-5'-[(1E)-5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3',4-dimethyl-5-oxo-1',2',3',3'a,5',7'a-hexahydro-5H-spiro[furan-2,4'-indene]-3-yl]oxidanesulfonic acid

> <ALOGPS_LOGP>
1.23

> <JCHEM_LOGP>
3.4390995480364355

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.3792158481628016

> <JCHEM_PKA_STRONGEST_BASIC>
-2.801372221240585

> <JCHEM_POLAR_SURFACE_AREA>
103.04

> <JCHEM_REFRACTIVITY>
121.36019999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.58e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3'S,3'aR,5'S,7'aR)-5'-[(1E)-5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3',4-dimethyl-5-oxo-1',2',3',3'a,5',7'a-hexahydrospiro[furan-2,4'-indene]-3-yloxidanesulfonic acid

> <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       5.686   5.676   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.088   5.038   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.236   3.505   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.982   2.610   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.581   3.248   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.433   4.781   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.031   5.419   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.883   6.952   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.481   7.590   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.333   9.123   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.069   9.761   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.217  11.294   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.544  12.075   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.211  13.579   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.322  13.727   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.936  12.315   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.136   7.847   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.044   1.780   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.791   0.885   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.778  -0.655   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.553   1.801   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.041   3.261   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.146   4.515   0.000  0.00  0.00           O+0
HETATM   24  S   UNK     0       0.613   4.366   0.000  0.00  0.00           S+0
HETATM   25  O   UNK     0      -0.920   4.218   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.465   5.899   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.761   2.834   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.084   1.337   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.446   1.142   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.986   1.129   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.474   2.589   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.530  -0.097   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5   29                                                  
CONECT    5    4    6   18   22                                             
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17    8                                                            
CONECT   18    5   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   28                                                  
CONECT   22   21    5   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24                                                            
CONECT   28   21                                                            
CONECT   29    4   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30    3                                                       
CONECT   32   29                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
[(2S,3's,3'AR,5's,7'ar)-5'-[(1E)-5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3',4-dimethyl-5-oxo-1',2',3',3'a,5',7'a-hexahydro-5H-spiro[furan-2,4'-indene]-3-yl]oxidanesulfonate	Generator
[(2S,3's,3'AR,5's,7'ar)-5'-[(1E)-5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3',4-dimethyl-5-oxo-1',2',3',3'a,5',7'a-hexahydro-5H-spiro[furan-2,4'-indene]-3-yl]oxidanesulphonate	Generator
[(2S,3's,3'AR,5's,7'ar)-5'-[(1E)-5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3',4-dimethyl-5-oxo-1',2',3',3'a,5',7'a-hexahydro-5H-spiro[furan-2,4'-indene]-3-yl]oxidanesulphonic acid	Generator

Chemical Formula

C₂₄H₃₀O₇S

Average Mass

462.5600 Da

Monoisotopic Mass

462.17122 Da

IUPAC Name

[(2S,3'S,3'aR,5'S,7'aR)-5'-[(1E)-5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3',4-dimethyl-5-oxo-1',2',3',3'a,5',7'a-hexahydro-5H-spiro[furan-2,4'-indene]-3-yl]oxidanesulfonic acid

Traditional Name

(2S,3'S,3'aR,5'S,7'aR)-5'-[(1E)-5-(furan-3-yl)-2-methylpent-1-en-1-yl]-3',4-dimethyl-5-oxo-1',2',3',3'a,5',7'a-hexahydrospiro[furan-2,4'-indene]-3-yloxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@@H]2C=C[C@@H](\C=C(/C)CCCC3=COC=C3)[C@@]3(OC(=O)C(C)=C3OS(O)(=O)=O)[C@H]12

InChI Identifier

InChI=1S/C24H30O7S/c1-15(5-4-6-18-11-12-29-14-18)13-20-10-9-19-8-7-16(2)21(19)24(20)22(31-32(26,27)28)17(3)23(25)30-24/h9-14,16,19-21H,4-8H2,1-3H3,(H,26,27,28)/b15-13+/t16-,19+,20-,21+,24+/m0/s1

InChI Key

UMNWICRUKDNAMG-MEUNUUFJSA-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
Ircinia wistarii	Animalia	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Monoterpenoid
11-noriridane monoterpenoid
Bicyclic monoterpenoid
Aromatic monoterpenoid
Sulfuric acid ester
Sulfate-ester
Sulfuric acid monoester
2-furanone
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Organic sulfuric acid or derivatives
Furan
Dihydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	1.23	ALOGPS
logP	3.44	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	-1.4	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.04 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	121.36 m³·mol⁻¹	ChemAxon
Polarizability	47.83 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

163106185

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Ircinianin sulfate (NP0083323)

MOL for NP0083323 ((-)-Ircinianin sulfate)

3D MOL for NP0083323 ((-)-Ircinianin sulfate)

3D SDF for NP0083323 ((-)-Ircinianin sulfate)

3D-SDF for NP0083323 ((-)-Ircinianin sulfate)

PDB for NP0083323 ((-)-Ircinianin sulfate)

3D PDB for NP0083323 ((-)-Ircinianin sulfate)

SMILES for NP0083323 ((-)-Ircinianin sulfate)

INCHI for NP0083323 ((-)-Ircinianin sulfate)

Structure for NP0083323 ((-)-Ircinianin sulfate)

3D Structure for NP0083323 ((-)-Ircinianin sulfate)