NP-MRD: Showing NP-Card for ent-13,16beta-dihydroxykauran-17-acetoxy-19-oic acid (NP0030227)

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Record Information

Version

2.0

Created at

2021-06-19 21:38:13 UTC

Updated at

2021-06-29 23:58:04 UTC

NP-MRD ID

NP0030227

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ent-13,16beta-dihydroxykauran-17-acetoxy-19-oic acid

Provided By

JEOL Database JEOL Logo

Description

ent-13,16beta-dihydroxykauran-17-acetoxy-19-oic acid is found in Mucor recurvatus. ent-13,16beta-dihydroxykauran-17-acetoxy-19-oic acid was first documented in 2007 (Yang, L.M. et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123383D          

 62 65  0  0  0  0            999 V2000
    2.0417    6.4852    0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6839    5.4656   -0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9244    5.6606   -1.5141 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3073    4.2883   -0.3153 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0420    3.1929   -1.2148 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6379    2.5727   -1.0455 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3276    3.3430   -1.8088 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5485    1.1315   -1.6068 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2319    0.2902   -0.5345 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1605   -0.7081   -1.2324 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.8190    2.4526   -1.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5356    0.6971   -1.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5966   -1.2494   -2.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4496   -1.2189    0.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4103   -2.3904   -0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
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 25 24  1  0  0  0  0
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  6  5  1  0  0  0  0
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M  END

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306192123383D          

 62 65  0  0  0  0            999 V2000
    2.0417    6.4852    0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6839    5.4656   -0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2088   -2.8922    2.1132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0708   -4.3477    3.3279 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7979   -0.4322    0.4045 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7150    0.5911    1.1264 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0670    1.9381    1.4563 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0818    2.4454    0.3966 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4926    3.6709    0.8421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0064    1.3871    0.2089 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6947    6.1526    1.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1230    6.6435    0.4679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5533    7.4335    0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8190    2.4526   -1.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2036    3.5300   -2.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0140    4.2730   -1.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115    1.1296   -2.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356    0.6971   -1.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5966   -1.2494   -2.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9623   -0.1779   -1.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4496   -1.2189    0.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4103   -2.3904   -0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0189   -2.8800   -0.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7605   -1.7857    3.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0537   -0.2690    3.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4981   -0.5750    2.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0706   -2.7065    1.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0121   -1.8729    2.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8871   -4.3188    2.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4967   -3.5327    3.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2016   -5.5020    2.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6824   -4.9516    0.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0283   -5.7838    0.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2133   -4.9469   -0.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8151   -4.4229   -0.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8434   -4.1018    3.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4712   -0.9727   -0.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5730    0.7837    0.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1598    0.1795    2.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8486    2.6826    1.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5359    1.8581    2.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0939    3.9499    0.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8382    1.7778   -0.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4516    1.0880    1.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0  0  0  0
 17 18  1  0  0  0  0
  9  8  1  6  0  0  0
 13 23  1  0  0  0  0
 26  6  1  0  0  0  0
  6  8  1  0  0  0  0
 12 11  1  0  0  0  0
 26 27  1  1  0  0  0
 11 10  1  0  0  0  0
 13 14  1  1  0  0  0
 10  9  1  0  0  0  0
 18 19  1  0  0  0  0
 23  9  1  0  0  0  0
 18 20  1  1  0  0  0
 12 18  1  0  0  0  0
  6  5  1  0  0  0  0
 13 15  1  0  0  0  0
 20 21  2  0  0  0  0
 13 12  1  0  0  0  0
 20 22  1  0  0  0  0
 12 41  1  6  0  0  0
 16 17  1  0  0  0  0
 23 55  1  6  0  0  0
 16 15  1  0  0  0  0
  6  7  1  6  0  0  0
 23 24  1  0  0  0  0
  5  4  1  0  0  0  0
  9 28  1  0  0  0  0
  4  2  1  0  0  0  0
  2  1  1  0  0  0  0
 26 25  1  0  0  0  0
  2  3  2  0  0  0  0
 26 28  1  0  0  0  0
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  8 35  1  0  0  0  0
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  5 32  1  0  0  0  0
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  7 34  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030227

> <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@]4(O[H])C([H])([H])OC(=O)C([H])([H])[H])C([H])([H])C([H])([H])[C@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O6/c1-14(23)28-13-22(27)12-20-9-5-15-18(2,7-4-8-19(15,3)17(24)25)16(20)6-10-21(22,26)11-20/h15-16,26-27H,4-13H2,1-3H3,(H,24,25)/t15-,16-,18+,19+,20-,21-,22-/m0/s1

> <INCHI_KEY>
PCBAVLDOHNSHSL-TUUFXUNSSA-N

> <FORMULA>
C22H34O6

> <MOLECULAR_WEIGHT>
394.508

> <EXACT_MASS>
394.235538815

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
42.58282797148067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,5R,9S,10R,13S,14S)-14-[(acetyloxy)methyl]-13,14-dihydroxy-5,9-dimethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

> <ALOGPS_LOGP>
1.50

> <JCHEM_LOGP>
2.1531387589999986

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.811143883209514

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.458080506341532

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4158422104745476

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
101.41449999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,5R,9S,10R,13S,14S)-14-[(acetyloxy)methyl]-13,14-dihydroxy-5,9-dimethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
    2.0417    6.4852    0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6839    5.4656   -0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9244    5.6606   -1.5141 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3073    4.2883   -0.3153 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0420    3.1929   -1.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6379    2.5727   -1.0455 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3276    3.3430   -1.8088 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5485    1.1315   -1.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2319    0.2902   -0.5345 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1605   -0.7081   -1.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7821   -1.7279   -0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849   -2.5271    0.4437 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2145   -1.5885    1.3319 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5391   -1.0216    2.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4049   -2.4465    1.8658 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9863   -3.7440    2.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0837   -4.5984    1.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1655   -3.8518    1.1366 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8418   -4.7986    0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2312   -3.6173    2.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2088   -2.8922    2.1132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0708   -4.3477    3.3279 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7979   -0.4322    0.4045 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7150    0.5911    1.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0670    1.9381    1.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0818    2.4454    0.3966 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4926    3.6709    0.8421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0064    1.3871    0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6947    6.1526    1.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1230    6.6435    0.4679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5533    7.4335    0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8190    2.4526   -1.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2036    3.5300   -2.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0140    4.2730   -1.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115    1.1296   -2.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356    0.6971   -1.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5966   -1.2494   -2.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9623   -0.1779   -1.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4496   -1.2189    0.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4103   -2.3904   -0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0189   -2.8800   -0.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7605   -1.7857    3.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0537   -0.2690    3.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4981   -0.5750    2.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0706   -2.7065    1.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0121   -1.8729    2.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8871   -4.3188    2.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4967   -3.5327    3.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2016   -5.5020    2.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6824   -4.9516    0.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0283   -5.7838    0.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2133   -4.9469   -0.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8151   -4.4229   -0.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8434   -4.1018    3.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4712   -0.9727   -0.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5730    0.7837    0.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1598    0.1795    2.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8486    2.6826    1.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5359    1.8581    2.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0939    3.9499    0.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8382    1.7778   -0.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4516    1.0880    1.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 17 18  1  0
  9  8  1  6
 13 23  1  0
 26  6  1  0
  6  8  1  0
 12 11  1  0
 26 27  1  1
 11 10  1  0
 13 14  1  1
 10  9  1  0
 18 19  1  0
 23  9  1  0
 18 20  1  1
 12 18  1  0
  6  5  1  0
 13 15  1  0
 20 21  2  0
 13 12  1  0
 20 22  1  0
 12 41  1  6
 16 17  1  0
 23 55  1  6
 16 15  1  0
  6  7  1  6
 23 24  1  0
  5  4  1  0
  9 28  1  0
  4  2  1  0
  2  1  1  0
 26 25  1  0
  2  3  2  0
 26 28  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 15 45  1  0
 15 46  1  0
 11 39  1  0
 11 40  1  0
 10 37  1  0
 10 38  1  0
 28 61  1  0
 28 62  1  0
 25 58  1  0
 25 59  1  0
 24 56  1  0
 24 57  1  0
  8 35  1  0
  8 36  1  0
 27 60  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
 19 51  1  0
 19 52  1  0
 19 53  1  0
  5 32  1  0
  5 33  1  0
 22 54  1  0
  7 34  1  0
  1 29  1  0
  1 30  1  0
  1 31  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       2.042   6.485   0.461  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.684   5.466  -0.574  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.924   5.661  -1.514  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.307   4.288  -0.315  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.042   3.193  -1.215  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.638   2.573  -1.046  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.328   3.343  -1.809  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.549   1.131  -1.607  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.232   0.290  -0.535  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.161  -0.708  -1.232  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.782  -1.728  -0.284  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.685  -2.527   0.444  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.215  -1.589   1.332  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.539  -1.022   2.555  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.405  -2.446   1.866  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.986  -3.744   2.554  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.084  -4.598   1.673  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.165  -3.852   1.137  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.842  -4.799   0.116  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.231  -3.617   2.209  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.209  -2.892   2.113  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.071  -4.348   3.328  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.798  -0.432   0.405  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.715   0.591   1.126  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.067   1.938   1.456  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.082   2.445   0.397  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.493   3.671   0.842  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.006   1.387   0.209  0.00  0.00           C+0
HETATM   29  H   UNK     0       1.695   6.153   1.443  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.123   6.644   0.468  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.553   7.434   0.220  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.819   2.453  -1.004  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.204   3.530  -2.247  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.014   4.273  -1.856  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.012   1.130  -2.564  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.536   0.697  -1.800  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.597  -1.249  -2.004  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.962  -0.178  -1.762  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.450  -1.219   0.416  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.410  -2.390  -0.887  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.019  -2.880  -0.363  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.761  -1.786   3.303  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.054  -0.269   3.082  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.498  -0.575   2.295  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.071  -2.707   1.032  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.012  -1.873   2.575  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.887  -4.319   2.802  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.497  -3.533   3.510  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.202  -5.502   2.226  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.682  -4.952   0.822  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.028  -5.784   0.561  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.213  -4.947  -0.769  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.815  -4.423  -0.217  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.843  -4.102   3.879  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.471  -0.973  -0.281  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.573   0.784   0.471  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.160   0.180   2.037  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.849   2.683   1.648  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.536   1.858   2.414  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.094   3.950   0.123  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.838   1.778  -0.393  0.00  0.00           H+0
HETATM   62  H   UNK     0      -1.452   1.088   1.156  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5    6    4   32   33                                             
CONECT    6   26    8    5    7                                             
CONECT    7    6   34                                                       
CONECT    8    9    6   35   36                                             
CONECT    9    8   10   23   28                                             
CONECT   10   11    9   37   38                                             
CONECT   11   12   10   39   40                                             
CONECT   12   11   18   13   41                                             
CONECT   13   23   14   15   12                                             
CONECT   14   13   42   43   44                                             
CONECT   15   13   16   45   46                                             
CONECT   16   17   15   47   48                                             
CONECT   17   18   16   49   50                                             
CONECT   18   17   19   20   12                                             
CONECT   19   18   51   52   53                                             
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   54                                                       
CONECT   23   13    9   55   24                                             
CONECT   24   25   23   56   57                                             
CONECT   25   24   26   58   59                                             
CONECT   26    6   27   25   28                                             
CONECT   27   26   60                                                       
CONECT   28    9   26   61   62                                             
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    5                                                            
CONECT   33    5                                                            
CONECT   34    7                                                            
CONECT   35    8                                                            
CONECT   36    8                                                            
CONECT   37   10                                                            
CONECT   38   10                                                            
CONECT   39   11                                                            
CONECT   40   11                                                            
CONECT   41   12                                                            
CONECT   42   14                                                            
CONECT   43   14                                                            
CONECT   44   14                                                            
CONECT   45   15                                                            
CONECT   46   15                                                            
CONECT   47   16                                                            
CONECT   48   16                                                            
CONECT   49   17                                                            
CONECT   50   17                                                            
CONECT   51   19                                                            
CONECT   52   19                                                            
CONECT   53   19                                                            
CONECT   54   22                                                            
CONECT   55   23                                                            
CONECT   56   24                                                            
CONECT   57   24                                                            
CONECT   58   25                                                            
CONECT   59   25                                                            
CONECT   60   27                                                            
CONECT   61   28                                                            
CONECT   62   28                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  130    0
END

RDKit          3D

62 65  0  0  0  0  0  0  0  0999 V2000
    2.0417    6.4852    0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6839    5.4656   -0.5742 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0420    3.1929   -1.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6379    2.5727   -1.0455 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3276    3.3430   -1.8088 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2319    0.2902   -0.5345 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1605   -0.7081   -1.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7821   -1.7279   -0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2145   -1.5885    1.3319 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.0708   -4.3477    3.3279 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7979   -0.4322    0.4045 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7150    0.5911    1.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0670    1.9381    1.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0818    2.4454    0.3966 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4926    3.6709    0.8421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0064    1.3871    0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6947    6.1526    1.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1230    6.6435    0.4679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5533    7.4335    0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8190    2.4526   -1.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2036    3.5300   -2.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0140    4.2730   -1.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115    1.1296   -2.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356    0.6971   -1.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5966   -1.2494   -2.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9623   -0.1779   -1.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4496   -1.2189    0.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4103   -2.3904   -0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0189   -2.8800   -0.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7605   -1.7857    3.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0537   -0.2690    3.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4981   -0.5750    2.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0706   -2.7065    1.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0121   -1.8729    2.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8871   -4.3188    2.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4967   -3.5327    3.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2016   -5.5020    2.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6824   -4.9516    0.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0283   -5.7838    0.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2133   -4.9469   -0.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8151   -4.4229   -0.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8434   -4.1018    3.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4712   -0.9727   -0.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5730    0.7837    0.4706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1598    0.1795    2.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8486    2.6826    1.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5359    1.8581    2.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0939    3.9499    0.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8382    1.7778   -0.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4516    1.0880    1.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 17 18  1  0
  9  8  1  6
 13 23  1  0
 26  6  1  0
  6  8  1  0
 12 11  1  0
 26 27  1  1
 11 10  1  0
 13 14  1  1
 10  9  1  0
 18 19  1  0
 23  9  1  0
 18 20  1  1
 12 18  1  0
  6  5  1  0
 13 15  1  0
 20 21  2  0
 13 12  1  0
 20 22  1  0
 12 41  1  6
 16 17  1  0
 23 55  1  6
 16 15  1  0
  6  7  1  6
 23 24  1  0
  5  4  1  0
  9 28  1  0
  4  2  1  0
  2  1  1  0
 26 25  1  0
  2  3  2  0
 26 28  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 15 45  1  0
 15 46  1  0
 11 39  1  0
 11 40  1  0
 10 37  1  0
 10 38  1  0
 28 61  1  0
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 25 58  1  0
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 24 56  1  0
 24 57  1  0
  8 35  1  0
  8 36  1  0
 27 60  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
 19 51  1  0
 19 52  1  0
 19 53  1  0
  5 32  1  0
  5 33  1  0
 22 54  1  0
  7 34  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₄O₆

Average Mass

394.5080 Da

Monoisotopic Mass

394.23554 Da

IUPAC Name

(1S,4S,5R,9S,10R,13S,14S)-14-[(acetyloxy)methyl]-13,14-dihydroxy-5,9-dimethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

Traditional Name

(1S,4S,5R,9S,10R,13S,14S)-14-[(acetyloxy)methyl]-13,14-dihydroxy-5,9-dimethyltetracyclo[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@]4(O[H])C([H])([H])OC(=O)C([H])([H])[H])C([H])([H])C([H])([H])[C@]12[H]

InChI Identifier

InChI=1S/C22H34O6/c1-14(23)28-13-22(27)12-20-9-5-15-18(2,7-4-8-19(15,3)17(24)25)16(20)6-10-21(22,26)11-20/h15-16,26-27H,4-13H2,1-3H3,(H,24,25)/t15-,16-,18+,19+,20-,21-,22-/m0/s1

InChI Key

PCBAVLDOHNSHSL-TUUFXUNSSA-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
Mucor recurvatus	JEOL database	Yang, L.M. et al, Phytochemistry 68, 562(2007)

Chemical Taxonomy

Classification

Not classified

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	1.5	ALOGPS
logP	2.15	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.46	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	101.41 m³·mol⁻¹	ChemAxon
Polarizability	42.58 Å³	ChemAxon
Number of Rings	4	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

Not Available

References

General References

Yang, L.M. et al. (2007). Yang, L.M. et al, Phytochemistry 68, 562(2007). Phytochem..

Showing NP-Card for ent-13,16beta-dihydroxykauran-17-acetoxy-19-oic acid (NP0030227)

MOL for NP0030227 (ent-13,16beta-dihydroxykauran-17-acetoxy-19-oic acid)

3D MOL for NP0030227 (ent-13,16beta-dihydroxykauran-17-acetoxy-19-oic acid)

3D SDF for NP0030227 (ent-13,16beta-dihydroxykauran-17-acetoxy-19-oic acid)

3D-SDF for NP0030227 (ent-13,16beta-dihydroxykauran-17-acetoxy-19-oic acid)

PDB for NP0030227 (ent-13,16beta-dihydroxykauran-17-acetoxy-19-oic acid)

3D PDB for NP0030227 (ent-13,16beta-dihydroxykauran-17-acetoxy-19-oic acid)

SMILES for NP0030227 (ent-13,16beta-dihydroxykauran-17-acetoxy-19-oic acid)

INCHI for NP0030227 (ent-13,16beta-dihydroxykauran-17-acetoxy-19-oic acid)

Structure for NP0030227 (ent-13,16beta-dihydroxykauran-17-acetoxy-19-oic acid)

3D Structure for NP0030227 (ent-13,16beta-dihydroxykauran-17-acetoxy-19-oic acid)