NP-MRD: Showing NP-Card for 1beta,8beta-epoxy-2alpha-methoxy-12alpha-hydroxy-6-oxogermacra-9(10),7(11+ (NP0041254)

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Record Information

Version

2.0

Created at

2021-06-20 23:12:50 UTC

Updated at

2021-06-30 00:15:39 UTC

NP-MRD ID

NP0041254

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1beta,8beta-epoxy-2alpha-methoxy-12alpha-hydroxy-6-oxogermacra-9(10),7(11+

Provided By

JEOL Database JEOL Logo

Description

(2S,6S,8S,9R,10Z,11aS)-2-Hydroxy-3,6,10-trimethyl-8-methoxy-9,11a-epoxy-2,6,7,8,9,11a-hexahydrocyclodeca[b]furan-4(5H)-one belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals. 1beta,8beta-epoxy-2alpha-methoxy-12alpha-hydroxy-6-oxogermacra-9(10),7(11+ is found in Commiphora opobalsamum. 1beta,8beta-epoxy-2alpha-methoxy-12alpha-hydroxy-6-oxogermacra-9(10),7(11+ was first documented in 2012 (Yang, J.-L., et al.). Based on a literature review very few articles have been published on (2S,6S,8S,9R,10Z,11aS)-2-Hydroxy-3,6,10-trimethyl-8-methoxy-9,11a-epoxy-2,6,7,8,9,11a-hexahydrocyclodeca[b]furan-4(5H)-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101123D          

 43 45  0  0  0  0            999 V2000
    1.5900   -2.4030    1.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1043   -1.2673    0.8635 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1184   -1.5981   -0.1236 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3059   -1.6039    0.5313 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9558   -0.2017    0.8515 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9068   -0.3805    2.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7696    0.4291   -0.3274 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0820    1.5621   -1.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7893    2.6349   -0.5947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7997    1.3365   -2.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5247    1.8170   -3.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6026    2.8356   -3.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1651    1.0469   -4.7937 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3903    1.8574   -5.6458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3966   -0.0748   -4.3433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8931    0.2707   -3.0521 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5846    0.5040   -3.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2102   -0.1055   -2.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6531   -0.1896   -1.8185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1326   -0.5299   -1.2030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9562   -0.8036   -2.1212 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0885   -3.0916    0.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9615   -1.2351   -1.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2590    0.2690   -2.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8747    0.3267   -0.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0326    0.4005   -0.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
  3  4  1  0  0  0  0
 20 18  1  0  0  0  0
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 20 43  1  1  0  0  0
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 17 39  1  0  0  0  0
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 14 38  1  0  0  0  0
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  6 29  1  0  0  0  0
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  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
M  END

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
    1.5900   -2.4030    1.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1043   -1.2673    0.8635 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1184   -1.5981   -0.1236 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3059   -1.6039    0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9558   -0.2017    0.8515 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9068   -0.3805    2.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7696    0.4291   -0.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0820    1.5621   -1.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7893    2.6349   -0.5947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7997    1.3365   -2.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5247    1.8170   -3.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6026    2.8356   -3.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1651    1.0469   -4.7937 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3903    1.8574   -5.6458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3966   -0.0748   -4.3433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8931    0.2707   -3.0521 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.2102   -0.1055   -2.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6531   -0.1896   -1.8185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1326   -0.5299   -1.2030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9562   -0.8036   -2.1212 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0885   -3.0916    0.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3222   -2.0612    2.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7830   -2.9180    2.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3254   -2.5826   -0.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9915   -2.1649   -0.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1728    0.4918    1.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3706   -0.7738    2.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3477    0.5778    2.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6859    0.8970    0.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1273   -0.3468   -1.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7687    3.2643   -2.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5454    2.3918   -3.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0326    0.4005   -0.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  6
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 20 18  1  0
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M  END


  Mrv1652306212101123D          

 43 45  0  0  0  0            999 V2000
    1.5900   -2.4030    1.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1043   -1.2673    0.8635 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1184   -1.5981   -0.1236 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3059   -1.6039    0.5313 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9558   -0.2017    0.8515 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9068   -0.3805    2.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7696    0.4291   -0.3274 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0820    1.5621   -1.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7893    2.6349   -0.5947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7997    1.3365   -2.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5247    1.8170   -3.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6026    2.8356   -3.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1651    1.0469   -4.7937 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3903    1.8574   -5.6458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3966   -0.0748   -4.3433 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2102   -0.1055   -2.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6531   -0.1896   -1.8185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1326   -0.5299   -1.2030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9562   -0.8036   -2.1212 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0885   -3.0916    0.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3222   -2.0612    2.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0326    0.4005   -0.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
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  3  4  1  0  0  0  0
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  2  1  1  0  0  0  0
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 14 38  1  0  0  0  0
 12 34  1  0  0  0  0
 12 35  1  0  0  0  0
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  6 29  1  0  0  0  0
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  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0041254

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])O[C@@]23O[C@]([H])(C(=C2[H])C([H])([H])[H])[C@@]([H])(OC([H])([H])[H])C([H])([H])[C@]([H])(C([H])([H])[H])C([H])([H])C(=O)C3=C1C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H22O5/c1-8-5-11(17)13-10(3)15(18)21-16(13)7-9(2)14(20-16)12(6-8)19-4/h7-8,12,14-15,18H,5-6H2,1-4H3/t8-,12+,14-,15+,16+/m1/s1

> <INCHI_KEY>
FAKVNSNOGLNXQL-OTPVYWDLSA-N

> <FORMULA>
C16H22O5

> <MOLECULAR_WEIGHT>
294.347

> <EXACT_MASS>
294.146723808

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.74713753049595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3S,8S,10S,11R)-3-hydroxy-10-methoxy-4,8,12-trimethyl-2,14-dioxatricyclo[9.2.1.0^{1,5}]tetradeca-4,12-dien-6-one

> <ALOGPS_LOGP>
0.91

> <JCHEM_LOGP>
2.267467779

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.688314640531141

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8818147357527857

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
77.17340000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.94e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,8S,10S,11R)-3-hydroxy-10-methoxy-4,8,12-trimethyl-2,14-dioxatricyclo[9.2.1.0^{1,5}]tetradeca-4,12-dien-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
    1.5900   -2.4030    1.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1043   -1.2673    0.8635 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1184   -1.5981   -0.1236 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3059   -1.6039    0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9558   -0.2017    0.8515 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9068   -0.3805    2.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7696    0.4291   -0.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0820    1.5621   -1.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7893    2.6349   -0.5947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7997    1.3365   -2.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5247    1.8170   -3.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6026    2.8356   -3.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1651    1.0469   -4.7937 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3903    1.8574   -5.6458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3966   -0.0748   -4.3433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8931    0.2707   -3.0521 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5846    0.5040   -3.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2102   -0.1055   -2.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6531   -0.1896   -1.8185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1326   -0.5299   -1.2030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9562   -0.8036   -2.1212 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0885   -3.0916    0.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3222   -2.0612    2.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7830   -2.9180    2.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3254   -2.5826   -0.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9915   -2.1649   -0.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2376   -2.1755    1.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1728    0.4918    1.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7203   -1.0729    1.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3706   -0.7738    2.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3477    0.5778    2.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6859    0.8970    0.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1273   -0.3468   -1.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7687    3.2643   -2.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3466    3.6556   -4.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5454    2.3918   -3.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0497    0.6787   -5.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3144    1.3533   -6.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0549    1.0264   -3.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9615   -1.2351   -1.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2590    0.2690   -2.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8747    0.3267   -0.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0326    0.4005   -0.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  6
 16 17  1  0
  3  4  1  0
 20 18  1  0
 18 17  2  0
  7  8  1  0
 18 19  1  0
  8 10  1  0
 16 10  1  0
  3 20  1  0
 16 21  1  0
  4  5  1  0
  8  9  2  0
  5  7  1  0
 13 14  1  0
 20 21  1  0
 11 12  1  0
 10 11  2  0
  5  6  1  0
 11 13  1  0
  3  2  1  0
 13 15  1  0
  2  1  1  0
  3 25  1  6
  4 26  1  0
  4 27  1  0
  5 28  1  1
 20 43  1  1
  7 32  1  0
  7 33  1  0
 13 37  1  6
 17 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 14 38  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
  6 29  1  0
  6 30  1  0
  6 31  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       1.590  -2.403   1.567  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.104  -1.267   0.864  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.118  -1.598  -0.124  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.306  -1.604   0.531  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.956  -0.202   0.852  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.907  -0.381   2.047  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.770   0.429  -0.327  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.082   1.562  -1.118  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.789   2.635  -0.595  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.800   1.337  -2.558  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.525   1.817  -3.572  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.603   2.836  -3.577  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.165   1.047  -4.794  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.390   1.857  -5.646  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.397  -0.075  -4.343  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.893   0.271  -3.052  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.585   0.504  -3.153  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.210  -0.106  -2.131  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.653  -0.190  -1.819  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.133  -0.530  -1.203  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.956  -0.804  -2.121  0.00  0.00           O+0
HETATM   22  H   UNK     0       2.088  -3.092   0.878  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.322  -2.061   2.303  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.783  -2.918   2.094  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.325  -2.583  -0.562  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.992  -2.165  -0.117  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.238  -2.176   1.464  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.173   0.492   1.181  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.720  -1.073   1.805  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.371  -0.774   2.918  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.348   0.578   2.342  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.686   0.897   0.059  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.127  -0.347  -1.013  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.769   3.264  -2.584  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.347   3.656  -4.255  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.545   2.392  -3.912  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.050   0.679  -5.324  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.314   1.353  -6.472  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.055   1.026  -3.972  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.962  -1.235  -1.722  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.259   0.269  -2.607  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.875   0.327  -0.879  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.033   0.401  -0.645  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    3    1                                                       
CONECT    3    4   20    2   25                                             
CONECT    4    3    5   26   27                                             
CONECT    5    4    7    6   28                                             
CONECT    6    5   29   30   31                                             
CONECT    7    8    5   32   33                                             
CONECT    8    7   10    9                                                  
CONECT    9    8                                                            
CONECT   10    8   16   11                                                  
CONECT   11   12   10   13                                                  
CONECT   12   11   34   35   36                                             
CONECT   13   14   11   15   37                                             
CONECT   14   13   38                                                       
CONECT   15   16   13                                                       
CONECT   16   15   17   10   21                                             
CONECT   17   16   18   39                                                  
CONECT   18   20   17   19                                                  
CONECT   19   18   40   41   42                                             
CONECT   20   18    3   21   43                                             
CONECT   21   16   20                                                       
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    3                                                            
CONECT   26    4                                                            
CONECT   27    4                                                            
CONECT   28    5                                                            
CONECT   29    6                                                            
CONECT   30    6                                                            
CONECT   31    6                                                            
CONECT   32    7                                                            
CONECT   33    7                                                            
CONECT   34   12                                                            
CONECT   35   12                                                            
CONECT   36   12                                                            
CONECT   37   13                                                            
CONECT   38   14                                                            
CONECT   39   17                                                            
CONECT   40   19                                                            
CONECT   41   19                                                            
CONECT   42   19                                                            
CONECT   43   20                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

RDKit          3D

43 45  0  0  0  0  0  0  0  0999 V2000
    1.5900   -2.4030    1.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1043   -1.2673    0.8635 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1184   -1.5981   -0.1236 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3059   -1.6039    0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9558   -0.2017    0.8515 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9068   -0.3805    2.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7696    0.4291   -0.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0820    1.5621   -1.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7893    2.6349   -0.5947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7997    1.3365   -2.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5247    1.8170   -3.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6026    2.8356   -3.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1651    1.0469   -4.7937 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3903    1.8574   -5.6458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3966   -0.0748   -4.3433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8931    0.2707   -3.0521 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5846    0.5040   -3.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2102   -0.1055   -2.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6531   -0.1896   -1.8185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1326   -0.5299   -1.2030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9562   -0.8036   -2.1212 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0885   -3.0916    0.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3222   -2.0612    2.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7830   -2.9180    2.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3254   -2.5826   -0.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9915   -2.1649   -0.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2376   -2.1755    1.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1728    0.4918    1.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7203   -1.0729    1.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3706   -0.7738    2.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3477    0.5778    2.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6859    0.8970    0.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1273   -0.3468   -1.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7687    3.2643   -2.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3466    3.6556   -4.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5454    2.3918   -3.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0497    0.6787   -5.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3144    1.3533   -6.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0549    1.0264   -3.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9615   -1.2351   -1.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2590    0.2690   -2.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8747    0.3267   -0.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0326    0.4005   -0.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  6
 16 17  1  0
  3  4  1  0
 20 18  1  0
 18 17  2  0
  7  8  1  0
 18 19  1  0
  8 10  1  0
 16 10  1  0
  3 20  1  0
 16 21  1  0
  4  5  1  0
  8  9  2  0
  5  7  1  0
 13 14  1  0
 20 21  1  0
 11 12  1  0
 10 11  2  0
  5  6  1  0
 11 13  1  0
  3  2  1  0
 13 15  1  0
  2  1  1  0
  3 25  1  6
  4 26  1  0
  4 27  1  0
  5 28  1  1
 20 43  1  1
  7 32  1  0
  7 33  1  0
 13 37  1  6
 17 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 14 38  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
  6 29  1  0
  6 30  1  0
  6 31  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₁₆H₂₂O₅

Average Mass

294.3470 Da

Monoisotopic Mass

294.14672 Da

IUPAC Name

(1S,3S,8S,10S,11R)-3-hydroxy-10-methoxy-4,8,12-trimethyl-2,14-dioxatricyclo[9.2.1.0^{1,5}]tetradeca-4,12-dien-6-one

Traditional Name

(1S,3S,8S,10S,11R)-3-hydroxy-10-methoxy-4,8,12-trimethyl-2,14-dioxatricyclo[9.2.1.0^{1,5}]tetradeca-4,12-dien-6-one

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])O[C@@]23O[C@]([H])(C(=C2[H])C([H])([H])[H])[C@@]([H])(OC([H])([H])[H])C([H])([H])[C@]([H])(C([H])([H])[H])C([H])([H])C(=O)C3=C1C([H])([H])[H]

InChI Identifier

InChI=1S/C16H22O5/c1-8-5-11(17)13-10(3)15(18)21-16(13)7-9(2)14(20-16)12(6-8)19-4/h7-8,12,14-15,18H,5-6H2,1-4H3/t8-,12+,14-,15+,16+/m1/s1

InChI Key

FAKVNSNOGLNXQL-OTPVYWDLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Commiphora opobalsamum	JEOL database	Yang, J.-L., et al, Phytochem. 76, 124 (2012)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

Alternative Parents

Substituents

Ketal
Dihydrofuran
Ketone
Hemiacetal
Oxacycle
Organoheterocyclic compound
Dialkyl ether
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aldehyde
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	0.91	ALOGPS
logP	2.27	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	11.69	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.17 m³·mol⁻¹	ChemAxon
Polarizability	31.75 Å³	ChemAxon
Number of Rings	3	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

101574640

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang, J.-L., et al. (2012). Yang, J.-L., et al, Phytochem. 76, 124 (2012). Phytochem..

Showing NP-Card for 1beta,8beta-epoxy-2alpha-methoxy-12alpha-hydroxy-6-oxogermacra-9(10),7(11+ (NP0041254)

MOL for NP0041254 (1beta,8beta-epoxy-2alpha-methoxy-12alpha-hydroxy-6-oxogermacra-9(10),7(11+)

3D MOL for NP0041254 (1beta,8beta-epoxy-2alpha-methoxy-12alpha-hydroxy-6-oxogermacra-9(10),7(11+)

3D SDF for NP0041254 (1beta,8beta-epoxy-2alpha-methoxy-12alpha-hydroxy-6-oxogermacra-9(10),7(11+)

3D-SDF for NP0041254 (1beta,8beta-epoxy-2alpha-methoxy-12alpha-hydroxy-6-oxogermacra-9(10),7(11+)

PDB for NP0041254 (1beta,8beta-epoxy-2alpha-methoxy-12alpha-hydroxy-6-oxogermacra-9(10),7(11+)

3D PDB for NP0041254 (1beta,8beta-epoxy-2alpha-methoxy-12alpha-hydroxy-6-oxogermacra-9(10),7(11+)

SMILES for NP0041254 (1beta,8beta-epoxy-2alpha-methoxy-12alpha-hydroxy-6-oxogermacra-9(10),7(11+)

INCHI for NP0041254 (1beta,8beta-epoxy-2alpha-methoxy-12alpha-hydroxy-6-oxogermacra-9(10),7(11+)

Structure for NP0041254 (1beta,8beta-epoxy-2alpha-methoxy-12alpha-hydroxy-6-oxogermacra-9(10),7(11+)

3D Structure for NP0041254 (1beta,8beta-epoxy-2alpha-methoxy-12alpha-hydroxy-6-oxogermacra-9(10),7(11+)