NP-MRD: Showing NP-Card for cyclohexyl 11-(acetyloxy)-2-hydroxy-10,15-dimethyl-4,9,13-trioxatetracyclo[10.3.0.0³,⁵.0⁸,¹⁰]pentadeca-1(12),14-diene-5-carboxylate (NP0239355)

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Record Information

Version

2.0

Created at

2022-09-06 22:56:02 UTC

Updated at

2022-09-06 22:56:02 UTC

NP-MRD ID

NP0239355

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cyclohexyl 11-(acetyloxy)-2-hydroxy-10,15-dimethyl-4,9,13-trioxatetracyclo[10.3.0.0³,⁵.0⁸,¹⁰]pentadeca-1(12),14-diene-5-carboxylate

Description

Neolitrane belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups. cyclohexyl 11-(acetyloxy)-2-hydroxy-10,15-dimethyl-4,9,13-trioxatetracyclo[10.3.0.0³,⁵.0⁸,¹⁰]pentadeca-1(12),14-diene-5-carboxylate is found in Neolitsea parvigemma. cyclohexyl 11-(acetyloxy)-2-hydroxy-10,15-dimethyl-4,9,13-trioxatetracyclo[10.3.0.0³,⁵.0⁸,¹⁰]pentadeca-1(12),14-diene-5-carboxylate was first documented in 2005 (PMID: 15702642). Based on a literature review very few articles have been published on Neolitrane.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072200562D          

 31 35  0  0  0  0            999 V2000
    0.0009    0.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6683    0.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5821   -0.4420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4220    0.7140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0894    0.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7569    0.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5019    1.4987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1694    1.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8368    1.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6214    1.7536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5819    0.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2493    0.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9167    0.7140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -0.5555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0563   -1.1686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2493   -1.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5849   -2.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0999   -2.7612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4053   -2.1800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7409   -2.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5614   -3.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8969   -3.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4120   -4.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5915   -4.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2560   -3.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5819   -1.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7569   -1.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0894   -1.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2824   -1.1686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8345   -0.5555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1200   -0.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  6 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 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
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 16 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 61 65  0  0  0  0  0  0  0  0999 V2000
    5.6056    2.3510   -2.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1090    0.9611   -1.7912 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7430   -0.0541   -2.1813 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9334    0.7372   -1.0886 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4152   -0.5446   -0.7905 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3845   -0.8094    0.6864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827   -1.7500    1.3974 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7191   -1.6567    2.6501 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8931   -0.5935    2.8171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3652   -0.1561    4.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6651   -0.0361    1.5727 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8584    1.1162    1.2157 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3014    2.2251    1.9948 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4044    1.0726    1.3087 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0318    0.4917    2.6063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4531    0.0290    1.3436 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9314    0.3207    1.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6370    0.8834    1.9897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5087   -0.0750   -0.0541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8582    0.1425   -0.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6129   -1.1591   -0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0897   -0.8241   -0.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3968    0.4144   -1.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2928    0.5781   -2.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0510    1.0526   -1.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1661   -1.3784    0.9876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0047   -1.5962   -0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292   -1.9066   -0.7610 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9647   -2.2242   -1.9720 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1059   -0.8421   -1.4205 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5546    0.0849   -2.4453 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7253    2.2658   -2.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3257    3.0077   -1.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3032    2.7012   -3.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1551   -1.2604   -1.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1229   -2.3474    3.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906   -0.3186    4.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5216   -0.7388    4.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1618    0.9291    4.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1215    1.4548    0.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9297    3.0532    1.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0265    2.1243    1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3130    0.6549    0.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3855   -1.7733    0.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3283   -1.7161   -1.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7318   -1.6579   -0.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3107   -0.5807    0.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4065    0.3480   -1.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3779    1.3200   -0.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5520    1.3365   -3.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0714   -0.3538   -2.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1725    0.9128   -2.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1645    2.1125   -1.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6686   -1.8640    1.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0446   -2.0420    1.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3625   -0.6563   -0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6180   -2.4075   -0.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9484   -2.4178    0.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5886    1.1480   -2.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1724    0.0487   -3.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5302   -0.1374   -2.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  6
 16 17  1  1
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 11  9  1  0
  9 10  1  0
  9  8  2  0
  8  7  1  0
 30  5  1  0
 25 20  1  0
  7  6  1  0
 16 14  1  0
 30 28  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  5 35  1  6
 12 40  1  6
 13 41  1  0
 14 42  1  1
 26 54  1  0
 26 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  1
 31 59  1  0
 31 60  1  0
 31 61  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
 25 53  1  0
 10 37  1  0
 10 38  1  0
 10 39  1  0
  8 36  1  0
M  END


  Mrv1652309072200562D          

 31 35  0  0  0  0            999 V2000
    0.0009    0.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6683    0.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5821   -0.4420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4220    0.7140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0894    0.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7569    0.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5019    1.4987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1694    1.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8368    1.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6214    1.7536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5819    0.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2493    0.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9167    0.7140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -0.5555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0563   -1.1686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2493   -1.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5849   -2.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0999   -2.7612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4053   -2.1800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7409   -2.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5614   -3.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8969   -3.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4120   -4.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5915   -4.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2560   -3.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5819   -1.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7569   -1.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0894   -1.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2824   -1.1686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8345   -0.5555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1200   -0.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  6 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 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
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 16 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0239355

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1C2=C(C(O)C3OC3(CCC3OC13C)C(=O)OC1CCCCC1)C(C)=CO2

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O8/c1-12-11-27-18-16(12)17(25)19-23(31-19,21(26)29-14-7-5-4-6-8-14)10-9-15-22(3,30-15)20(18)28-13(2)24/h11,14-15,17,19-20,25H,4-10H2,1-3H3

> <INCHI_KEY>
IFHVFPIPGFCERI-UHFFFAOYSA-N

> <FORMULA>
C23H30O8

> <MOLECULAR_WEIGHT>
434.485

> <EXACT_MASS>
434.194067926

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
45.33838826411586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
cyclohexyl 11-(acetyloxy)-2-hydroxy-10,15-dimethyl-4,9,13-trioxatetracyclo[10.3.0.0^{3,5}.0^{8,10}]pentadeca-1(12),14-diene-5-carboxylate

> <JCHEM_LOGP>
2.7126104216666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.829342078812594

> <JCHEM_PKA_STRONGEST_BASIC>
-2.82331061625443

> <JCHEM_POLAR_SURFACE_AREA>
111.03000000000002

> <JCHEM_REFRACTIVITY>
106.53049999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
cyclohexyl 11-(acetyloxy)-2-hydroxy-10,15-dimethyl-4,9,13-trioxatetracyclo[10.3.0.0^{3,5}.0^{8,10}]pentadeca-1(12),14-diene-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       0.002   1.612   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.248   0.707   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.087  -0.825   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.654   1.333   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.900   0.428   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.146   1.333   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.670   2.798   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.916   3.703   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.162   2.798   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.627   3.273   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.686   1.333   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.932   0.428   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.178   1.333   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.408  -1.037   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.438  -2.181   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.932  -2.502   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.558  -3.908   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.653  -5.154   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      10.090  -4.069   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.716  -5.476   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.248  -5.637   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.874  -7.044   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.969  -8.290   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.438  -8.129   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.811  -6.722   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.686  -3.407   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.146  -3.407   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.900  -2.502   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.394  -2.181   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.424  -1.037   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.091  -0.267   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    6   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14   16                                                       
CONECT   16   15   14   17   26                                             
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26   16   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28   30                                                       
CONECT   30   29   28    5   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₀O₈

Average Mass

434.4850 Da

Monoisotopic Mass

434.19407 Da

IUPAC Name

cyclohexyl 11-(acetyloxy)-2-hydroxy-10,15-dimethyl-4,9,13-trioxatetracyclo[10.3.0.0^{3,5}.0^{8,10}]pentadeca-1(12),14-diene-5-carboxylate

Traditional Name

cyclohexyl 11-(acetyloxy)-2-hydroxy-10,15-dimethyl-4,9,13-trioxatetracyclo[10.3.0.0^{3,5}.0^{8,10}]pentadeca-1(12),14-diene-5-carboxylate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1C2=C(C(O)C3OC3(CCC3OC13C)C(=O)OC1CCCCC1)C(C)=CO2

InChI Identifier

InChI=1S/C23H30O8/c1-12-11-27-18-16(12)17(25)19-23(31-19,21(26)29-14-7-5-4-6-8-14)10-9-15-22(3,30-15)20(18)28-13(2)24/h11,14-15,17,19-20,25H,4-10H2,1-3H3

InChI Key

IFHVFPIPGFCERI-UHFFFAOYSA-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
Neolitsea parvigemma	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Germacrane sesquiterpenoids

Alternative Parents

Substituents

Germacrane sesquiterpenoid
Dicarboxylic acid or derivatives
Oxirane carboxylic acid
Oxirane carboxylic acid or derivatives
Furan
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
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	2.71	ChemAxon
pKa (Strongest Acidic)	12.83	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	111.03 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	106.53 m³·mol⁻¹	ChemAxon
Polarizability	45.34 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

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

101713483

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen KS, Hsieh PW, Hwang TL, Chang FR, Wu YC: Anti-inflammatory furanogermacrane sesquiterpenes from Neolitsea parvigemma. Nat Prod Res. 2005 Apr;19(3):283-6. doi: 10.1080/14786410410001714669. [PubMed:15702642 ]
LOTUS database [Link]

Showing NP-Card for cyclohexyl 11-(acetyloxy)-2-hydroxy-10,15-dimethyl-4,9,13-trioxatetracyclo[10.3.0.0³,⁵.0⁸,¹⁰]pentadeca-1(12),14-diene-5-carboxylate (NP0239355)

MOL for NP0239355 (cyclohexyl 11-(acetyloxy)-2-hydroxy-10,15-dimethyl-4,9,13-trioxatetracyclo[10.3.0.0³,⁵.0⁸,¹⁰]pentadeca-1(12),14-diene-5-carboxylate)

3D MOL for NP0239355 (cyclohexyl 11-(acetyloxy)-2-hydroxy-10,15-dimethyl-4,9,13-trioxatetracyclo[10.3.0.0³,⁵.0⁸,¹⁰]pentadeca-1(12),14-diene-5-carboxylate)

3D SDF for NP0239355 (cyclohexyl 11-(acetyloxy)-2-hydroxy-10,15-dimethyl-4,9,13-trioxatetracyclo[10.3.0.0³,⁵.0⁸,¹⁰]pentadeca-1(12),14-diene-5-carboxylate)

3D-SDF for NP0239355 (cyclohexyl 11-(acetyloxy)-2-hydroxy-10,15-dimethyl-4,9,13-trioxatetracyclo[10.3.0.0³,⁵.0⁸,¹⁰]pentadeca-1(12),14-diene-5-carboxylate)

PDB for NP0239355 (cyclohexyl 11-(acetyloxy)-2-hydroxy-10,15-dimethyl-4,9,13-trioxatetracyclo[10.3.0.0³,⁵.0⁸,¹⁰]pentadeca-1(12),14-diene-5-carboxylate)

3D PDB for NP0239355 (cyclohexyl 11-(acetyloxy)-2-hydroxy-10,15-dimethyl-4,9,13-trioxatetracyclo[10.3.0.0³,⁵.0⁸,¹⁰]pentadeca-1(12),14-diene-5-carboxylate)

SMILES for NP0239355 (cyclohexyl 11-(acetyloxy)-2-hydroxy-10,15-dimethyl-4,9,13-trioxatetracyclo[10.3.0.0³,⁵.0⁸,¹⁰]pentadeca-1(12),14-diene-5-carboxylate)

INCHI for NP0239355 (cyclohexyl 11-(acetyloxy)-2-hydroxy-10,15-dimethyl-4,9,13-trioxatetracyclo[10.3.0.0³,⁵.0⁸,¹⁰]pentadeca-1(12),14-diene-5-carboxylate)

Structure for NP0239355 (cyclohexyl 11-(acetyloxy)-2-hydroxy-10,15-dimethyl-4,9,13-trioxatetracyclo[10.3.0.0³,⁵.0⁸,¹⁰]pentadeca-1(12),14-diene-5-carboxylate)

3D Structure for NP0239355 (cyclohexyl 11-(acetyloxy)-2-hydroxy-10,15-dimethyl-4,9,13-trioxatetracyclo[10.3.0.0³,⁵.0⁸,¹⁰]pentadeca-1(12),14-diene-5-carboxylate)