NP-MRD: Showing NP-Card for (1s,2r,5s,6s,9r,10s,13r)-5,13-dihydroxy-2,6,10-trimethyl-11-oxo-8-oxatetracyclo[7.3.1.0¹,⁵.0⁶,¹⁰]tridecan-9-yl 2-methylcyclopent-1-ene-1-carboxylate (NP0306154)

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Record Information

Version

2.0

Created at

2022-09-10 22:27:28 UTC

Updated at

2022-09-10 22:27:29 UTC

NP-MRD ID

NP0306154

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,5s,6s,9r,10s,13r)-5,13-dihydroxy-2,6,10-trimethyl-11-oxo-8-oxatetracyclo[7.3.1.0¹,⁵.0⁶,¹⁰]tridecan-9-yl 2-methylcyclopent-1-ene-1-carboxylate

Description

(1S,2R,5S,6S,9R,10S,13R)-5,13-dihydroxy-2,6,10-trimethyl-11-oxo-8-oxatetracyclo[7.3.1.0¹,⁵.0⁶,¹⁰]Tridecan-9-yl 2-methylcyclopent-1-ene-1-carboxylate belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. (1s,2r,5s,6s,9r,10s,13r)-5,13-dihydroxy-2,6,10-trimethyl-11-oxo-8-oxatetracyclo[7.3.1.0¹,⁵.0⁶,¹⁰]tridecan-9-yl 2-methylcyclopent-1-ene-1-carboxylate is found in Illicium verum. Based on a literature review very few articles have been published on (1S,2R,5S,6S,9R,10S,13R)-5,13-dihydroxy-2,6,10-trimethyl-11-oxo-8-oxatetracyclo[7.3.1.0¹,⁵.0⁶,¹⁰]Tridecan-9-yl 2-methylcyclopent-1-ene-1-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112200272D          

 28 32  0  0  1  0            999 V2000
   -1.5569   -2.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7767   -3.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1011   -2.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0870   -1.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7943   -1.3345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6345   -1.3590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6486   -0.5341    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1819   -0.5866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1902    0.2407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7628   -0.0075    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9390    0.7985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7954   -0.1908    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6351   -1.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418   -0.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8614    0.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3326   -0.4751    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2721   -1.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9408    0.3950    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6834    1.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8472    1.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4258    2.0355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4983    0.5465    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3185    0.6627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5483   -0.6220    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2347   -1.3851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5579   -3.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896   -3.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5353   -3.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 10 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  1  0  0  0
 18 24  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  1  0  0  0
  3 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  2 28  1  0  0  0  0
M  END

     RDKit          3D

 58 62  0  0  0  0  0  0  0  0999 V2000
    5.0595   -1.8100   -0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8613   -0.5480    0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6847    0.0060    0.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3586   -0.4712    0.1109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3487   -1.5377   -0.5459 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2098    0.2022    0.3996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0615   -0.1713   -0.0068 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3327   -1.5107    0.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9757   -2.0682   -0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6726   -0.9039   -1.4427 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1261   -1.1929   -2.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7942   -0.3887   -0.5792 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8717   -0.0309   -1.3847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2766   -1.3170    0.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9959   -0.3761    1.4561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5283    1.0068    1.1382 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2471    1.8433    2.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3663    0.8091    0.2415 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2055    1.9271   -0.7897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0312    1.5013   -1.5674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4817    2.2209   -2.3410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5104    0.1106   -1.3761 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5292   -0.1907   -2.4021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0586    0.6664    0.9139 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0850    0.0851    2.1573 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424    1.2670    1.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2416    1.1464    1.9137 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9533    0.2440    0.9404 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1300   -2.0900   -0.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6070   -1.7358   -1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5357   -2.6709    0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2714   -2.5116   -1.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7015   -2.8601   -0.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8176   -0.4406   -3.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7407   -2.1942   -3.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2447   -1.2689   -2.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4988   -0.7984   -1.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5207   -1.8246    1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0316   -2.0119    0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7890   -0.6301    2.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1071   -0.4859    1.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3307    1.5271    0.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2334    2.2895    2.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8029    1.2884    3.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6217    2.7049    2.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0803    2.8890   -0.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1386    1.9857   -1.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7373   -1.2493   -2.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2353    0.2338   -3.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4663    0.3329   -2.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5689    1.6602    0.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4719    0.5674    2.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7543    2.1179    0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0678    1.3388    2.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1765    0.6939    2.9079 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6692    2.1692    1.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4169    0.8487    0.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7071   -0.3941    1.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 12  1  0
 12 13  1  6
 12 10  1  0
 10 11  1  6
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  6
  6  4  1  0
  4  5  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 28  1  0
 28 27  1  0
 27 26  1  0
  7 24  1  0
 24 25  1  0
 24 18  1  0
 18 19  1  6
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  6
 18 16  1  0
 18 12  1  0
 22 10  1  0
 22  7  1  0
 26  3  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 16 42  1  6
 15 40  1  0
 15 41  1  0
 14 38  1  0
 14 39  1  0
 13 37  1  0
 11 34  1  0
 11 35  1  0
 11 36  1  0
  9 32  1  0
  9 33  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 28 57  1  0
 28 58  1  0
 27 55  1  0
 27 56  1  0
 26 53  1  0
 26 54  1  0
 24 51  1  1
 25 52  1  0
 19 46  1  0
 19 47  1  0
 23 48  1  0
 23 49  1  0
 23 50  1  0
M  END


  Mrv1652309112200272D          

 28 32  0  0  1  0            999 V2000
   -1.5569   -2.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7767   -3.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1011   -2.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0870   -1.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7943   -1.3345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6345   -1.3590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6486   -0.5341    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1819   -0.5866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1902    0.2407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7628   -0.0075    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9390    0.7985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7954   -0.1908    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6351   -1.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418   -0.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8614    0.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3326   -0.4751    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2721   -1.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9408    0.3950    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6834    1.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8472    1.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4258    2.0355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4983    0.5465    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3185    0.6627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5483   -0.6220    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2347   -1.3851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5579   -3.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896   -3.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5353   -3.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 10 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  1  0  0  0
 18 24  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  1  0  0  0
  3 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  2 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0306154

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@]2(O)[C@]3(C)CO[C@]4(OC(=O)C5=C(C)CCC5)[C@H](O)[C@]12CC(=O)[C@]34C

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O6/c1-12-6-5-7-14(12)16(24)28-22-17(25)20-10-15(23)19(22,4)18(3,11-27-22)21(20,26)9-8-13(20)2/h13,17,25-26H,5-11H2,1-4H3/t13-,17-,18-,19-,20+,21+,22+/m1/s1

> <INCHI_KEY>
SGFRFWVBCRSHNZ-GKRFIZMWSA-N

> <FORMULA>
C22H30O6

> <MOLECULAR_WEIGHT>
390.476

> <EXACT_MASS>
390.204238686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
41.46716641289235

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,5S,6S,9R,10S,13R)-5,13-dihydroxy-2,6,10-trimethyl-11-oxo-8-oxatetracyclo[7.3.1.0^{1,5}.0^{6,10}]tridecan-9-yl 2-methylcyclopent-1-ene-1-carboxylate

> <JCHEM_LOGP>
2.827672453666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.902405210985368

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.659705163436318

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3159848129327187

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
100.20369999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,6S,9R,10S,13R)-5,13-dihydroxy-2,6,10-trimethyl-11-oxo-8-oxatetracyclo[7.3.1.0^{1,5}.0^{6,10}]tridecan-9-yl 2-methylcyclopent-1-ene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.906  -5.206   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.450  -5.707   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.189  -4.824   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.162  -3.284   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.483  -2.491   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       1.184  -2.537   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.211  -0.997   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.340  -1.095   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.355   0.449   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.424  -0.014   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.753   1.490   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.351  -0.356   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.052  -1.867   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.305  -0.784   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.341   0.653   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.354  -0.887   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.241  -2.423   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.623   0.737   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.142   2.354   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.581   2.476   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.795   3.800   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.930   1.020   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.595   1.237   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.890  -1.161   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.305  -2.585   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.041  -5.750   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.541  -7.206   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.999  -7.180   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4   26                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   22   24                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   22                                             
CONECT   11   10                                                            
CONECT   12   10   13   14   18                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12   19   24                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   10    7   23                                             
CONECT   23   22                                                            
CONECT   24   18    7   25                                                  
CONECT   25   24                                                            
CONECT   26    3   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    2                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,5S,6S,9R,10S,13R)-5,13-Dihydroxy-2,6,10-trimethyl-11-oxo-8-oxatetracyclo[7.3.1.0,.0,]tridecan-9-yl 2-methylcyclopent-1-ene-1-carboxylic acid	Generator

Chemical Formula

C₂₂H₃₀O₆

Average Mass

390.4760 Da

Monoisotopic Mass

390.20424 Da

IUPAC Name

(1S,2R,5S,6S,9R,10S,13R)-5,13-dihydroxy-2,6,10-trimethyl-11-oxo-8-oxatetracyclo[7.3.1.0^{1,5}.0^{6,10}]tridecan-9-yl 2-methylcyclopent-1-ene-1-carboxylate

Traditional Name

(1S,2R,5S,6S,9R,10S,13R)-5,13-dihydroxy-2,6,10-trimethyl-11-oxo-8-oxatetracyclo[7.3.1.0^{1,5}.0^{6,10}]tridecan-9-yl 2-methylcyclopent-1-ene-1-carboxylate

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@]2(O)[C@]3(C)CO[C@]4(OC(=O)C5=C(C)CCC5)[C@H](O)[C@]12CC(=O)[C@]34C

InChI Identifier

InChI=1S/C22H30O6/c1-12-6-5-7-14(12)16(24)28-22-17(25)20-10-15(23)19(22,4)18(3,11-27-22)21(20,26)9-8-13(20)2/h13,17,25-26H,5-11H2,1-4H3/t13-,17-,18-,19-,20+,21+,22+/m1/s1

InChI Key

SGFRFWVBCRSHNZ-GKRFIZMWSA-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
Illicium verum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Oxepane
Ketal
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Oxacycle
Alcohol
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	2.83	ChemAxon
pKa (Strongest Acidic)	12.66	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	100.2 m³·mol⁻¹	ChemAxon
Polarizability	41.47 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00057731

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

163059583

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,5s,6s,9r,10s,13r)-5,13-dihydroxy-2,6,10-trimethyl-11-oxo-8-oxatetracyclo[7.3.1.0¹,⁵.0⁶,¹⁰]tridecan-9-yl 2-methylcyclopent-1-ene-1-carboxylate (NP0306154)

MOL for NP0306154 ((1s,2r,5s,6s,9r,10s,13r)-5,13-dihydroxy-2,6,10-trimethyl-11-oxo-8-oxatetracyclo[7.3.1.0¹,⁵.0⁶,¹⁰]tridecan-9-yl 2-methylcyclopent-1-ene-1-carboxylate)

3D MOL for NP0306154 ((1s,2r,5s,6s,9r,10s,13r)-5,13-dihydroxy-2,6,10-trimethyl-11-oxo-8-oxatetracyclo[7.3.1.0¹,⁵.0⁶,¹⁰]tridecan-9-yl 2-methylcyclopent-1-ene-1-carboxylate)

3D SDF for NP0306154 ((1s,2r,5s,6s,9r,10s,13r)-5,13-dihydroxy-2,6,10-trimethyl-11-oxo-8-oxatetracyclo[7.3.1.0¹,⁵.0⁶,¹⁰]tridecan-9-yl 2-methylcyclopent-1-ene-1-carboxylate)

3D-SDF for NP0306154 ((1s,2r,5s,6s,9r,10s,13r)-5,13-dihydroxy-2,6,10-trimethyl-11-oxo-8-oxatetracyclo[7.3.1.0¹,⁵.0⁶,¹⁰]tridecan-9-yl 2-methylcyclopent-1-ene-1-carboxylate)

PDB for NP0306154 ((1s,2r,5s,6s,9r,10s,13r)-5,13-dihydroxy-2,6,10-trimethyl-11-oxo-8-oxatetracyclo[7.3.1.0¹,⁵.0⁶,¹⁰]tridecan-9-yl 2-methylcyclopent-1-ene-1-carboxylate)

3D PDB for NP0306154 ((1s,2r,5s,6s,9r,10s,13r)-5,13-dihydroxy-2,6,10-trimethyl-11-oxo-8-oxatetracyclo[7.3.1.0¹,⁵.0⁶,¹⁰]tridecan-9-yl 2-methylcyclopent-1-ene-1-carboxylate)

SMILES for NP0306154 ((1s,2r,5s,6s,9r,10s,13r)-5,13-dihydroxy-2,6,10-trimethyl-11-oxo-8-oxatetracyclo[7.3.1.0¹,⁵.0⁶,¹⁰]tridecan-9-yl 2-methylcyclopent-1-ene-1-carboxylate)

INCHI for NP0306154 ((1s,2r,5s,6s,9r,10s,13r)-5,13-dihydroxy-2,6,10-trimethyl-11-oxo-8-oxatetracyclo[7.3.1.0¹,⁵.0⁶,¹⁰]tridecan-9-yl 2-methylcyclopent-1-ene-1-carboxylate)

Structure for NP0306154 ((1s,2r,5s,6s,9r,10s,13r)-5,13-dihydroxy-2,6,10-trimethyl-11-oxo-8-oxatetracyclo[7.3.1.0¹,⁵.0⁶,¹⁰]tridecan-9-yl 2-methylcyclopent-1-ene-1-carboxylate)

3D Structure for NP0306154 ((1s,2r,5s,6s,9r,10s,13r)-5,13-dihydroxy-2,6,10-trimethyl-11-oxo-8-oxatetracyclo[7.3.1.0¹,⁵.0⁶,¹⁰]tridecan-9-yl 2-methylcyclopent-1-ene-1-carboxylate)