NP-MRD: Showing NP-Card for (1R,3S,4S,7S,11S,12S,14S)-14-acetoxy-3,4-epoxy-7-hydroxy-8(17),18-dolabel+ (NP0041889)

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Record Information

Version

2.0

Created at

2021-06-20 23:41:40 UTC

Updated at

2021-06-30 00:16:40 UTC

NP-MRD ID

NP0041889

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1R,3S,4S,7S,11S,12S,14S)-14-acetoxy-3,4-epoxy-7-hydroxy-8(17),18-dolabel+

Provided By

JEOL Database JEOL Logo

Description

(1R,3S,5S,8S,12S,13S,15S)-8-hydroxy-1,5-dimethyl-9-methylidene-13-(prop-1-en-2-yl)-4-oxatricyclo[10.3.0.0³,⁵]Pentadecan-15-yl acetate belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). (1R,3S,4S,7S,11S,12S,14S)-14-acetoxy-3,4-epoxy-7-hydroxy-8(17),18-dolabel+ is found in Dilophus spiralis. (1R,3S,4S,7S,11S,12S,14S)-14-acetoxy-3,4-epoxy-7-hydroxy-8(17),18-dolabel+ was first documented in 2012 (Ioannou, E., et al.). Based on a literature review very few articles have been published on (1R,3S,5S,8S,12S,13S,15S)-8-hydroxy-1,5-dimethyl-9-methylidene-13-(prop-1-en-2-yl)-4-oxatricyclo[10.3.0.0³,⁵]Pentadecan-15-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101413D          

 60 62  0  0  0  0            999 V2000
   -1.5856   -1.7090    1.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5296   -2.0384    2.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2392    2.3670    3.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306212101413D          

 60 62  0  0  0  0            999 V2000
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    1.6357   -2.7721   -0.5850 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5614   -2.3192   -1.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4328   -4.1011    0.1028 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1416   -4.2538    0.9126 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1011   -3.4185    2.2037 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6374   -4.1553    3.1846 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6821   -0.2273    3.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8481    0.0755    3.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0531   -1.2797    2.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6086    0.0589    0.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0157    2.1024    0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5435    2.8790    5.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0634    2.4242    4.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5106    3.4503    2.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7930    1.7239    2.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6037    2.8373    4.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6527    3.1231    2.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5100    3.8471    0.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5873    2.4915   -0.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1647    2.1871   -3.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0805    3.1008   -2.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0931    3.9579   -3.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0783   -0.4133    2.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8274    0.8551    1.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8328    1.2712    2.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8133   -0.2142   -0.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0950   -0.1673   -1.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2973   -2.0734    0.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1295   -1.6366   -1.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0118   -3.1697   -1.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9750   -1.7981   -2.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4363   -4.8794   -0.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2891   -4.3261    0.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7313   -4.0726    0.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0678   -5.3146    1.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1214   -3.3486    2.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5803   -4.0296    2.9834 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0  0  0  0
 10  6  1  0  0  0  0
  6  5  1  0  0  0  0
  4  3  1  0  0  0  0
 21 22  1  6  0  0  0
 19 21  1  0  0  0  0
  2  1  2  3  0  0  0
  2 25  1  0  0  0  0
 16 17  1  1  0  0  0
 25 24  1  0  0  0  0
  6  7  1  0  0  0  0
 24 23  1  0  0  0  0
  7  9  1  0  0  0  0
 23 21  1  0  0  0  0
  7  8  2  3  0  0  0
  5 16  1  0  0  0  0
  5 33  1  6  0  0  0
 18 19  1  0  0  0  0
 11 12  1  0  0  0  0
 25 26  1  0  0  0  0
 21 20  1  0  0  0  0
 19 20  1  0  0  0  0
  5  4  1  0  0  0  0
 19 51  1  1  0  0  0
 16 18  1  0  0  0  0
 12 13  1  0  0  0  0
  2  3  1  0  0  0  0
 13 15  2  0  0  0  0
 16 11  1  0  0  0  0
 13 14  1  0  0  0  0
 26 60  1  0  0  0  0
 18 49  1  0  0  0  0
 18 50  1  0  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
 25 59  1  1  0  0  0
 24 57  1  0  0  0  0
 24 58  1  0  0  0  0
 23 55  1  0  0  0  0
 23 56  1  0  0  0  0
 11 42  1  6  0  0  0
 10 40  1  0  0  0  0
 10 41  1  0  0  0  0
  6 34  1  6  0  0  0
 22 52  1  0  0  0  0
 22 53  1  0  0  0  0
 22 54  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
 17 46  1  0  0  0  0
 17 47  1  0  0  0  0
 17 48  1  0  0  0  0
  9 37  1  0  0  0  0
  9 38  1  0  0  0  0
  9 39  1  0  0  0  0
  8 35  1  0  0  0  0
  8 36  1  0  0  0  0
 14 43  1  0  0  0  0
 14 44  1  0  0  0  0
 14 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0041889

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C(=C([H])[H])C([H])([H])C([H])([H])[C@@]2([H])[C@@]([H])(C(=C([H])[H])C([H])([H])[H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]2(C([H])([H])[H])C([H])([H])[C@]2([H])O[C@@]2(C([H])([H])[H])C([H])([H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O4/c1-13(2)16-11-19(25-15(4)23)21(5)12-20-22(6,26-20)10-9-18(24)14(3)7-8-17(16)21/h16-20,24H,1,3,7-12H2,2,4-6H3/t16-,17+,18+,19+,20+,21-,22+/m1/s1

> <INCHI_KEY>
XPUKBYCPQHTOBB-BHMKJSQQSA-N

> <FORMULA>
C22H34O4

> <MOLECULAR_WEIGHT>
362.51

> <EXACT_MASS>
362.245709575

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
40.74083808067857

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3S,5S,8S,12S,13S,15S)-8-hydroxy-1,5-dimethyl-9-methylidene-13-(prop-1-en-2-yl)-4-oxatricyclo[10.3.0.0^{3,5}]pentadecan-15-yl acetate

> <ALOGPS_LOGP>
3.64

> <JCHEM_LOGP>
3.315679105

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.628307876945307

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9613781346241232

> <JCHEM_POLAR_SURFACE_AREA>
59.06

> <JCHEM_REFRACTIVITY>
101.1255

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,5S,8S,12S,13S,15S)-8-hydroxy-1,5-dimethyl-9-methylidene-13-(prop-1-en-2-yl)-4-oxatricyclo[10.3.0.0^{3,5}]pentadecan-15-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
   -1.5856   -1.7090    1.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5296   -2.0384    2.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0405   -1.0256    3.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3873   -0.4393    2.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3192    0.4995    1.4616 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8045    1.9636    1.7120 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2392    2.3670    3.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875    2.5665    4.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2486    2.6066    3.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9277    2.8965    1.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5932    2.1035    0.1066 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7396    2.1363   -1.0548 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8911    3.2116   -1.8759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9522    3.1001   -3.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6689    4.1380   -1.7010 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6804    0.6566    0.6865 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9164    0.5868    1.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359   -0.3708   -0.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7322   -1.8204   -0.0836 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9375   -2.7002   -1.1968 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6357   -2.7721   -0.5850 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5614   -2.3192   -1.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4328   -4.1011    0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1416   -4.2538    0.9126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1011   -3.4185    2.2037 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6374   -4.1553    3.1846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0152   -0.7112    1.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0646   -2.4109    0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1754   -1.5216    4.1018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6821   -0.2273    3.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8481    0.0755    3.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0531   -1.2797    2.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6086    0.0589    0.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0157    2.1024    0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5435    2.8790    5.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0634    2.4242    4.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5106    3.4503    2.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6527    3.1231    2.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5100    3.8471    0.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5873    2.4915   -0.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1647    2.1871   -3.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0805    3.1008   -2.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0931    3.9579   -3.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0783   -0.4133    2.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8274    0.8551    1.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8328    1.2712    2.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8133   -0.2142   -0.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0950   -0.1673   -1.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2973   -2.0734    0.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1295   -1.6366   -1.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0118   -3.1697   -1.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9750   -1.7981   -2.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4363   -4.8794   -0.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2891   -4.3261    0.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7313   -4.0726    0.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0678   -5.3146    1.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1214   -3.3486    2.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5803   -4.0296    2.9834 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  6  1  0
  6  5  1  0
  4  3  1  0
 21 22  1  6
 19 21  1  0
  2  1  2  3
  2 25  1  0
 16 17  1  1
 25 24  1  0
  6  7  1  0
 24 23  1  0
  7  9  1  0
 23 21  1  0
  7  8  2  3
  5 16  1  0
  5 33  1  6
 18 19  1  0
 11 12  1  0
 25 26  1  0
 21 20  1  0
 19 20  1  0
  5  4  1  0
 19 51  1  1
 16 18  1  0
 12 13  1  0
  2  3  1  0
 13 15  2  0
 16 11  1  0
 13 14  1  0
 26 60  1  0
 18 49  1  0
 18 50  1  0
  4 31  1  0
  4 32  1  0
  3 29  1  0
  3 30  1  0
 25 59  1  1
 24 57  1  0
 24 58  1  0
 23 55  1  0
 23 56  1  0
 11 42  1  6
 10 40  1  0
 10 41  1  0
  6 34  1  6
 22 52  1  0
 22 53  1  0
 22 54  1  0
  1 27  1  0
  1 28  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
  8 35  1  0
  8 36  1  0
 14 43  1  0
 14 44  1  0
 14 45  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      -1.586  -1.709   1.388  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.530  -2.038   2.154  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.041  -1.026   3.132  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.387  -0.439   2.687  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.319   0.500   1.462  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.805   1.964   1.712  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.239   2.367   3.062  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.988   2.567   4.161  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.249   2.607   3.102  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.928   2.897   1.225  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.593   2.103   0.107  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.740   2.136  -1.055  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.891   3.212  -1.876  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.952   3.100  -3.038  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.669   4.138  -1.701  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.680   0.657   0.687  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.916   0.587   1.617  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.836  -0.371  -0.472  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.732  -1.820  -0.084  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.938  -2.700  -1.197  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.636  -2.772  -0.585  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.561  -2.319  -1.533  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.433  -4.101   0.103  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.142  -4.254   0.913  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.101  -3.418   2.204  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.637  -4.155   3.185  0.00  0.00           O+0
HETATM   27  H   UNK     0      -2.015  -0.711   1.422  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.065  -2.411   0.714  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.175  -1.522   4.102  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.682  -0.227   3.319  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.848   0.076   3.536  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.053  -1.280   2.476  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.609   0.059   0.750  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.016   2.102   0.989  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.544   2.879   5.102  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.063   2.424   4.160  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.511   3.450   2.455  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.793   1.724   2.753  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.604   2.837   4.112  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.653   3.123   2.013  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.510   3.847   0.875  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.587   2.491  -0.146  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.165   2.187  -3.599  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.081   3.101  -2.680  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.093   3.958  -3.701  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.078  -0.413   2.027  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.827   0.855   1.069  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.833   1.271   2.466  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.813  -0.214  -0.948  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.095  -0.167  -1.251  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.297  -2.073   0.802  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.130  -1.637  -1.033  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.012  -3.170  -1.916  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.975  -1.798  -2.403  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.436  -4.879  -0.672  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.289  -4.326   0.752  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.731  -4.073   0.279  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.068  -5.315   1.191  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.121  -3.349   2.595  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.580  -4.030   2.983  0.00  0.00           H+0
CONECT    1    2   27   28                                                  
CONECT    2    1   25    3                                                  
CONECT    3    4    2   29   30                                             
CONECT    4    3    5   31   32                                             
CONECT    5    6   16   33    4                                             
CONECT    6   10    5    7   34                                             
CONECT    7    6    9    8                                                  
CONECT    8    7   35   36                                                  
CONECT    9    7   37   38   39                                             
CONECT   10   11    6   40   41                                             
CONECT   11   10   12   16   42                                             
CONECT   12   11   13                                                       
CONECT   13   12   15   14                                                  
CONECT   14   13   43   44   45                                             
CONECT   15   13                                                            
CONECT   16   17    5   18   11                                             
CONECT   17   16   46   47   48                                             
CONECT   18   19   16   49   50                                             
CONECT   19   21   18   20   51                                             
CONECT   20   21   19                                                       
CONECT   21   22   19   23   20                                             
CONECT   22   21   52   53   54                                             
CONECT   23   24   21   55   56                                             
CONECT   24   25   23   57   58                                             
CONECT   25    2   24   26   59                                             
CONECT   26   25   60                                                       
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    4                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    6                                                            
CONECT   35    8                                                            
CONECT   36    8                                                            
CONECT   37    9                                                            
CONECT   38    9                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   10                                                            
CONECT   42   11                                                            
CONECT   43   14                                                            
CONECT   44   14                                                            
CONECT   45   14                                                            
CONECT   46   17                                                            
CONECT   47   17                                                            
CONECT   48   17                                                            
CONECT   49   18                                                            
CONECT   50   18                                                            
CONECT   51   19                                                            
CONECT   52   22                                                            
CONECT   53   22                                                            
CONECT   54   22                                                            
CONECT   55   23                                                            
CONECT   56   23                                                            
CONECT   57   24                                                            
CONECT   58   24                                                            
CONECT   59   25                                                            
CONECT   60   26                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  124    0
END

RDKit          3D

60 62  0  0  0  0  0  0  0  0999 V2000
   -1.5856   -1.7090    1.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5296   -2.0384    2.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0405   -1.0256    3.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3873   -0.4393    2.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3192    0.4995    1.4616 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8045    1.9636    1.7120 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2392    2.3670    3.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875    2.5665    4.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2486    2.6066    3.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9277    2.8965    1.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5932    2.1035    0.1066 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7396    2.1363   -1.0548 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8911    3.2116   -1.8759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9522    3.1001   -3.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6689    4.1380   -1.7010 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6804    0.6566    0.6865 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9164    0.5868    1.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359   -0.3708   -0.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7322   -1.8204   -0.0836 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9375   -2.7002   -1.1968 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6357   -2.7721   -0.5850 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5614   -2.3192   -1.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4328   -4.1011    0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1416   -4.2538    0.9126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1011   -3.4185    2.2037 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6374   -4.1553    3.1846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0152   -0.7112    1.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0646   -2.4109    0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1754   -1.5216    4.1018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6821   -0.2273    3.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8481    0.0755    3.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0531   -1.2797    2.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6086    0.0589    0.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0157    2.1024    0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5435    2.8790    5.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0634    2.4242    4.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5106    3.4503    2.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7930    1.7239    2.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6037    2.8373    4.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6527    3.1231    2.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5100    3.8471    0.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5873    2.4915   -0.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1647    2.1871   -3.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0805    3.1008   -2.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0931    3.9579   -3.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0783   -0.4133    2.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8274    0.8551    1.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8328    1.2712    2.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8133   -0.2142   -0.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0950   -0.1673   -1.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2973   -2.0734    0.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1295   -1.6366   -1.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0118   -3.1697   -1.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9750   -1.7981   -2.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4363   -4.8794   -0.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2891   -4.3261    0.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7313   -4.0726    0.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0678   -5.3146    1.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1214   -3.3486    2.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5803   -4.0296    2.9834 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  6  1  0
  6  5  1  0
  4  3  1  0
 21 22  1  6
 19 21  1  0
  2  1  2  3
  2 25  1  0
 16 17  1  1
 25 24  1  0
  6  7  1  0
 24 23  1  0
  7  9  1  0
 23 21  1  0
  7  8  2  3
  5 16  1  0
  5 33  1  6
 18 19  1  0
 11 12  1  0
 25 26  1  0
 21 20  1  0
 19 20  1  0
  5  4  1  0
 19 51  1  1
 16 18  1  0
 12 13  1  0
  2  3  1  0
 13 15  2  0
 16 11  1  0
 13 14  1  0
 26 60  1  0
 18 49  1  0
 18 50  1  0
  4 31  1  0
  4 32  1  0
  3 29  1  0
  3 30  1  0
 25 59  1  1
 24 57  1  0
 24 58  1  0
 23 55  1  0
 23 56  1  0
 11 42  1  6
 10 40  1  0
 10 41  1  0
  6 34  1  6
 22 52  1  0
 22 53  1  0
 22 54  1  0
  1 27  1  0
  1 28  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
  8 35  1  0
  8 36  1  0
 14 43  1  0
 14 44  1  0
 14 45  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(1R,3S,5S,8S,12S,13S,15S)-8-Hydroxy-1,5-dimethyl-9-methylidene-13-(prop-1-en-2-yl)-4-oxatricyclo[10.3.0.0,]pentadecan-15-yl acetic acid	Generator

Chemical Formula

C₂₂H₃₄O₄

Average Mass

362.5100 Da

Monoisotopic Mass

362.24571 Da

IUPAC Name

(1R,3S,5S,8S,12S,13S,15S)-8-hydroxy-1,5-dimethyl-9-methylidene-13-(prop-1-en-2-yl)-4-oxatricyclo[10.3.0.0^{3,5}]pentadecan-15-yl acetate

Traditional Name

(1R,3S,5S,8S,12S,13S,15S)-8-hydroxy-1,5-dimethyl-9-methylidene-13-(prop-1-en-2-yl)-4-oxatricyclo[10.3.0.0^{3,5}]pentadecan-15-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C(=C([H])[H])C([H])([H])C([H])([H])[C@@]2([H])[C@@]([H])(C(=C([H])[H])C([H])([H])[H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]2(C([H])([H])[H])C([H])([H])[C@]2([H])O[C@@]2(C([H])([H])[H])C([H])([H])C1([H])[H]

InChI Identifier

InChI=1S/C22H34O4/c1-13(2)16-11-19(25-15(4)23)21(5)12-20-22(6,26-20)10-9-18(24)14(3)7-8-17(16)21/h16-20,24H,1,3,7-12H2,2,4-6H3/t16-,17+,18+,19+,20+,21-,22+/m1/s1

InChI Key

XPUKBYCPQHTOBB-BHMKJSQQSA-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
Dictyota spiralis	JEOL database	Ioannou, E., et al, Eur. J. Org. Chem. 2012, 5177

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Carboxylic acid esters

Alternative Parents

Substituents

Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	3.64	ALOGPS
logP	3.32	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	14.63	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	101.13 m³·mol⁻¹	ChemAxon
Polarizability	40.74 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

29215027

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70676030

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ioannou, E., et al. (2012). Ioannou, E., et al, Eur. J. Org. Chem. 2012, 5177. Eur. J. Org. Chem..

Showing NP-Card for (1R,3S,4S,7S,11S,12S,14S)-14-acetoxy-3,4-epoxy-7-hydroxy-8(17),18-dolabel+ (NP0041889)

MOL for NP0041889 ((1R,3S,4S,7S,11S,12S,14S)-14-acetoxy-3,4-epoxy-7-hydroxy-8(17),18-dolabel+)

3D MOL for NP0041889 ((1R,3S,4S,7S,11S,12S,14S)-14-acetoxy-3,4-epoxy-7-hydroxy-8(17),18-dolabel+)

3D SDF for NP0041889 ((1R,3S,4S,7S,11S,12S,14S)-14-acetoxy-3,4-epoxy-7-hydroxy-8(17),18-dolabel+)

3D-SDF for NP0041889 ((1R,3S,4S,7S,11S,12S,14S)-14-acetoxy-3,4-epoxy-7-hydroxy-8(17),18-dolabel+)

PDB for NP0041889 ((1R,3S,4S,7S,11S,12S,14S)-14-acetoxy-3,4-epoxy-7-hydroxy-8(17),18-dolabel+)

3D PDB for NP0041889 ((1R,3S,4S,7S,11S,12S,14S)-14-acetoxy-3,4-epoxy-7-hydroxy-8(17),18-dolabel+)

SMILES for NP0041889 ((1R,3S,4S,7S,11S,12S,14S)-14-acetoxy-3,4-epoxy-7-hydroxy-8(17),18-dolabel+)

INCHI for NP0041889 ((1R,3S,4S,7S,11S,12S,14S)-14-acetoxy-3,4-epoxy-7-hydroxy-8(17),18-dolabel+)

Structure for NP0041889 ((1R,3S,4S,7S,11S,12S,14S)-14-acetoxy-3,4-epoxy-7-hydroxy-8(17),18-dolabel+)

3D Structure for NP0041889 ((1R,3S,4S,7S,11S,12S,14S)-14-acetoxy-3,4-epoxy-7-hydroxy-8(17),18-dolabel+)