NP-MRD: Showing NP-Card for steviol-16alpha,17-epoxide (NP0030226)

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Record Information

Version

2.0

Created at

2021-06-19 21:38:11 UTC

Updated at

2021-06-29 23:58:04 UTC

NP-MRD ID

NP0030226

Secondary Accession Numbers

None

Natural Product Identification

Common Name

steviol-16alpha,17-epoxide

Provided By

JEOL Database JEOL Logo

Description

Steviol 16alpha,17-epoxide belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. steviol-16alpha,17-epoxide is found in M. recurvatus MR 36. steviol-16alpha,17-epoxide was first documented in 2006 (PMID: 17067160). Based on a literature review very few articles have been published on Steviol 16alpha,17-epoxide (PMID: 17207824).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123383D          

 54 58  0  0  0  0            999 V2000
   -2.0314    0.8617   -1.6266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7988    1.7029   -1.2279 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5105    2.7013   -2.3932 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5547    3.8044   -2.5489 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7762    4.5734   -1.2530 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1300    3.6747   -0.0395 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1185    4.5915    1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5558    3.1224   -0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0201    2.2392    0.6056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3603    3.7404   -0.9819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0370    2.5524    0.0763 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1501    1.6510    1.3198 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.5564    0.0123    0.3562 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2353   -1.3091    0.2969 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6227   -2.1307   -0.6671 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.4528   -1.5903   -2.0858 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8612   -0.1173   -2.2142 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4906    0.7931   -1.0072 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0090   -1.8610   -0.1425 C   0  0  2  0  0  0  0  0  0  0  0  0
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 10 37  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652306192123383D          

 54 58  0  0  0  0            999 V2000
   -2.0314    0.8617   -1.6266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7988    1.7029   -1.2279 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -5.2241    3.2917   -0.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0989    3.1145    0.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9820    0.9462    1.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3344    2.2480    2.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9481    1.6087    1.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0498    0.2755    2.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2686   -1.2261   -0.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2733   -1.7951    1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7669   -3.8764    0.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0426   -2.1894   -2.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5892   -1.7232   -2.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9553   -0.0910   -2.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4880    0.2752   -3.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3142    1.5235   -0.9488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1803   -3.2440   -1.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2051   -2.0481   -0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2015   -0.7029    1.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7758    0.1383    0.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0  0  0  0
 14 15  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
  5  6  1  0  0  0  0
 14 24  1  1  0  0  0
  2 20  1  0  0  0  0
 16 21  1  0  0  0  0
 21 24  1  0  0  0  0
 11 12  1  0  0  0  0
 16 17  1  6  0  0  0
 12 13  1  0  0  0  0
  2  1  1  6  0  0  0
 13 14  1  0  0  0  0
  6  7  1  0  0  0  0
 20 14  1  0  0  0  0
  6  8  1  6  0  0  0
 11  6  1  0  0  0  0
 21 22  1  0  0  0  0
  2  3  1  0  0  0  0
  8  9  2  0  0  0  0
  2 11  1  0  0  0  0
  8 10  1  0  0  0  0
 11 38  1  1  0  0  0
  4  5  1  0  0  0  0
 20 50  1  1  0  0  0
  4  3  1  0  0  0  0
 21 23  1  1  0  0  0
 22 23  1  0  0  0  0
 16 15  1  0  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
  3 28  1  0  0  0  0
  3 29  1  0  0  0  0
 12 39  1  0  0  0  0
 12 40  1  0  0  0  0
 13 41  1  0  0  0  0
 13 42  1  0  0  0  0
 15 43  1  0  0  0  0
 15 44  1  0  0  0  0
 18 46  1  0  0  0  0
 18 47  1  0  0  0  0
 19 48  1  0  0  0  0
 19 49  1  0  0  0  0
 24 53  1  0  0  0  0
 24 54  1  0  0  0  0
 17 45  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  7 34  1  0  0  0  0
  7 35  1  0  0  0  0
  7 36  1  0  0  0  0
 22 51  1  0  0  0  0
 22 52  1  0  0  0  0
 10 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030226

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@]3([H])C([H])([H])C([H])([H])[C@]4(O[H])C([H])([H])[C@]3(C([H])([H])[C@@]43OC3([H])[H])C([H])([H])C([H])([H])[C@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O4/c1-16-6-3-7-17(2,15(21)22)13(16)4-8-18-10-19(23,9-5-14(16)18)20(11-18)12-24-20/h13-14,23H,3-12H2,1-2H3,(H,21,22)/t13-,14-,16+,17+,18-,19-,20-/m0/s1

> <INCHI_KEY>
BRTPCGPOJBLZMP-ZFSQYJSHSA-N

> <FORMULA>
C20H30O4

> <MOLECULAR_WEIGHT>
334.456

> <EXACT_MASS>
334.214409446

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
36.71620894623995

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,2S,4'S,5'R,9'S,10'R,13'S)-13'-hydroxy-5',9'-dimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane]-5'-carboxylic acid

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
2.873716920999999

> <ALOGPS_LOGS>
-4.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.580821108551142

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.518149488538696

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4195488528501965

> <JCHEM_POLAR_SURFACE_AREA>
70.06

> <JCHEM_REFRACTIVITY>
88.75289999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2S,4'S,5'R,9'S,10'R,13'S)-13'-hydroxy-5',9'-dimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane]-5'-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 58  0  0  0  0  0  0  0  0999 V2000
   -2.0314    0.8617   -1.6266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7988    1.7029   -1.2279 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5105    2.7013   -2.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5547    3.8044   -2.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7762    4.5734   -1.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1300    3.6747   -0.0395 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1185    4.5915    1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5558    3.1224   -0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0201    2.2392    0.6056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3603    3.7404   -0.9819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0370    2.5524    0.0763 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1501    1.6510    1.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1483    0.8853    1.5451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5564    0.0123    0.3562 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2353   -1.3091    0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6227   -2.1307   -0.6671 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2794   -3.5037   -0.6182 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4528   -1.5903   -2.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8612   -0.1173   -2.2142 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4906    0.7931   -1.0072 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0090   -1.8610   -0.1425 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2566   -2.5638   -0.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6004   -2.9404    0.6034 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0099   -0.5424    0.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8695    1.4768   -1.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8116    0.1975   -2.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4144    0.2544   -0.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4647    3.1796   -2.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375    2.1738   -3.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2174    4.5039   -3.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003    3.3910   -2.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5464    5.3370   -1.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543    5.1289   -1.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7626    5.4663    1.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1087    4.9560    1.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4977    4.0830    2.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2241    3.2917   -0.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0989    3.1145    0.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9820    0.9462    1.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3344    2.2480    2.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9481    1.6087    1.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0498    0.2755    2.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2686   -1.2261   -0.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2733   -1.7951    1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7669   -3.8764    0.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0426   -2.1894   -2.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5892   -1.7232   -2.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9553   -0.0910   -2.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4880    0.2752   -3.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3142    1.5235   -0.9488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1803   -3.2440   -1.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2051   -2.0481   -0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2015   -0.7029    1.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7758    0.1383    0.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 14 15  1  0
 16 18  1  0
 18 19  1  0
  5  6  1  0
 14 24  1  1
  2 20  1  0
 16 21  1  0
 21 24  1  0
 11 12  1  0
 16 17  1  6
 12 13  1  0
  2  1  1  6
 13 14  1  0
  6  7  1  0
 20 14  1  0
  6  8  1  6
 11  6  1  0
 21 22  1  0
  2  3  1  0
  8  9  2  0
  2 11  1  0
  8 10  1  0
 11 38  1  1
  4  5  1  0
 20 50  1  1
  4  3  1  0
 21 23  1  1
 22 23  1  0
 16 15  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  3 28  1  0
  3 29  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 15 43  1  0
 15 44  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 24 53  1  0
 24 54  1  0
 17 45  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
 22 51  1  0
 22 52  1  0
 10 37  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.031   0.862  -1.627  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.799   1.703  -1.228  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.510   2.701  -2.393  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.555   3.804  -2.549  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.776   4.573  -1.253  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.130   3.675  -0.040  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.119   4.591   1.208  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.556   3.122  -0.098  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.020   2.239   0.606  0.00  0.00           O+0
HETATM   10  O   UNK     0      -4.360   3.740  -0.982  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.037   2.552   0.076  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.150   1.651   1.320  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.148   0.885   1.545  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.556   0.012   0.356  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.235  -1.309   0.297  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.623  -2.131  -0.667  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.279  -3.504  -0.618  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.453  -1.590  -2.086  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.861  -0.117  -2.214  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.491   0.793  -1.007  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.009  -1.861  -0.143  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.257  -2.564  -0.616  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.600  -2.940   0.603  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.010  -0.542   0.586  0.00  0.00           C+0
HETATM   25  H   UNK     0      -2.869   1.477  -1.961  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.812   0.198  -2.466  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.414   0.254  -0.807  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.465   3.180  -2.231  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.438   2.174  -3.350  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.217   4.504  -3.324  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.500   3.391  -2.913  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.546   5.337  -1.419  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.854   5.129  -1.030  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.763   5.466   1.055  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.109   4.956   1.426  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.498   4.083   2.100  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.224   3.292  -0.865  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.099   3.115   0.225  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.982   0.946   1.239  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.334   2.248   2.218  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.948   1.609   1.754  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.050   0.276   2.452  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.269  -1.226  -0.037  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.273  -1.795   1.282  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.767  -3.876   0.141  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.043  -2.189  -2.792  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.589  -1.723  -2.401  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.955  -0.091  -2.317  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.488   0.275  -3.164  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.314   1.524  -0.949  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.180  -3.244  -1.455  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.205  -2.048  -0.536  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.201  -0.703   1.654  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.776   0.138   0.200  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2   20    1    3   11                                             
CONECT    3    2    4   28   29                                             
CONECT    4    5    3   30   31                                             
CONECT    5    6    4   32   33                                             
CONECT    6    5    7    8   11                                             
CONECT    7    6   34   35   36                                             
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   37                                                       
CONECT   11   12    6    2   38                                             
CONECT   12   11   13   39   40                                             
CONECT   13   12   14   41   42                                             
CONECT   14   15   24   13   20                                             
CONECT   15   14   16   43   44                                             
CONECT   16   18   21   17   15                                             
CONECT   17   16   45                                                       
CONECT   18   16   19   46   47                                             
CONECT   19   20   18   48   49                                             
CONECT   20   19    2   14   50                                             
CONECT   21   16   24   22   23                                             
CONECT   22   21   23   51   52                                             
CONECT   23   21   22                                                       
CONECT   24   14   21   53   54                                             
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    3                                                            
CONECT   29    3                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    5                                                            
CONECT   34    7                                                            
CONECT   35    7                                                            
CONECT   36    7                                                            
CONECT   37   10                                                            
CONECT   38   11                                                            
CONECT   39   12                                                            
CONECT   40   12                                                            
CONECT   41   13                                                            
CONECT   42   13                                                            
CONECT   43   15                                                            
CONECT   44   15                                                            
CONECT   45   17                                                            
CONECT   46   18                                                            
CONECT   47   18                                                            
CONECT   48   19                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   22                                                            
CONECT   52   22                                                            
CONECT   53   24                                                            
CONECT   54   24                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  116    0
END

RDKit          3D

54 58  0  0  0  0  0  0  0  0999 V2000
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   -5.2241    3.2917   -0.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9820    0.9462    1.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2686   -1.2261   -0.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2733   -1.7951    1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0426   -2.1894   -2.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5892   -1.7232   -2.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9553   -0.0910   -2.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4880    0.2752   -3.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3142    1.5235   -0.9488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1803   -3.2440   -1.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2051   -2.0481   -0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2015   -0.7029    1.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7758    0.1383    0.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
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  5  6  1  0
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  1 25  1  0
  1 26  1  0
  1 27  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
 22 51  1  0
 22 52  1  0
 10 37  1  0
M  END

View in JSmol

Synonyms

Value	Source
Steviol 16a,17-epoxide	Generator
Steviol 16α,17-epoxide	Generator

Chemical Formula

C₂₀H₃₀O₄

Average Mass

334.4560 Da

Monoisotopic Mass

334.21441 Da

IUPAC Name

(1'S,2S,4'S,5'R,9'S,10'R,13'S)-13'-hydroxy-5',9'-dimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane]-5'-carboxylic acid

Traditional Name

(1'S,2S,4'S,5'R,9'S,10'R,13'S)-13'-hydroxy-5',9'-dimethylspiro[oxirane-2,14'-tetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane]-5'-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@]3([H])C([H])([H])C([H])([H])[C@]4(O[H])C([H])([H])[C@]3(C([H])([H])[C@@]43OC3([H])[H])C([H])([H])C([H])([H])[C@]12[H]

InChI Identifier

InChI=1S/C20H30O4/c1-16-6-3-7-17(2,15(21)22)13(16)4-8-18-10-19(23,9-5-14(16)18)20(11-18)12-24-20/h13-14,23H,3-12H2,1-2H3,(H,21,22)/t13-,14-,16+,17+,18-,19-,20-/m0/s1

InChI Key

BRTPCGPOJBLZMP-ZFSQYJSHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
M. recurvatus MR 36	JEOL database	Yang, L.M. et al, Phytochemistry 68, 562(2007)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Cyclic alcohol
Tertiary alcohol
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
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	2.49	ALOGPS
logP	2.87	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.52	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.75 m³·mol⁻¹	ChemAxon
Polarizability	36.72 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

17219513

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16059814

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang LM, Hsu FL, Chang SF, Cheng JT, Hsu JY, Hsu CY, Liu PC, Lin SJ: Microbial metabolism of steviol and steviol-16alpha,17-epoxide. Phytochemistry. 2007 Feb;68(4):562-70. doi: 10.1016/j.phytochem.2006.11.021. Epub 2007 Jan 17. [PubMed:17207824 ]
Chang SF, Yang LM, Hsu FL, Hsu JY, Liaw JH, Lin SJ: Transformation of steviol-16alpha,17-epoxide by Streptomyces griseus and Cunninghamella bainieri. J Nat Prod. 2006 Oct;69(10):1450-5. doi: 10.1021/np0602564. [PubMed:17067160 ]
Yang, L.M. et al. (2007). Yang, L.M. et al, Phytochemistry 68, 562(2007). Phytochem..

Showing NP-Card for steviol-16alpha,17-epoxide (NP0030226)

MOL for NP0030226 (steviol-16alpha,17-epoxide)

3D MOL for NP0030226 (steviol-16alpha,17-epoxide)

3D SDF for NP0030226 (steviol-16alpha,17-epoxide)

3D-SDF for NP0030226 (steviol-16alpha,17-epoxide)

PDB for NP0030226 (steviol-16alpha,17-epoxide)

3D PDB for NP0030226 (steviol-16alpha,17-epoxide)

SMILES for NP0030226 (steviol-16alpha,17-epoxide)

INCHI for NP0030226 (steviol-16alpha,17-epoxide)

Structure for NP0030226 (steviol-16alpha,17-epoxide)

3D Structure for NP0030226 (steviol-16alpha,17-epoxide)