NP-MRD: Showing NP-Card for 12beta-hydroxy-1alpha,6alpha-diacetoxy-ent-kaura-9(11),16-dien-15-one (NP0034029)

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Record Information

Version

2.0

Created at

2021-06-20 17:52:41 UTC

Updated at

2021-06-30 00:04:09 UTC

NP-MRD ID

NP0034029

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12beta-hydroxy-1alpha,6alpha-diacetoxy-ent-kaura-9(11),16-dien-15-one

Provided By

JEOL Database JEOL Logo

Description

CHEMBL496475 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. 12beta-hydroxy-1alpha,6alpha-diacetoxy-ent-kaura-9(11),16-dien-15-one is found in Jungermannia atrobrunnea. 12beta-hydroxy-1alpha,6alpha-diacetoxy-ent-kaura-9(11),16-dien-15-one was first documented in 2008 (Qu, J. -B., et al.). Based on a literature review very few articles have been published on CHEMBL496475.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202119523D          

 62 65  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202119523D          

 62 65  0  0  0  0            999 V2000
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    1.6598    2.5460    0.9651 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9950    2.5757    1.2323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5747    3.8803    0.7792 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385    1.6778    1.7548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3303    1.1396    0.4416 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0076    2.5074    0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0814    0.5858   -0.9680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2538    0.8557   -1.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6365    0.3025   -2.9472 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9420   -0.2499   -2.8730 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6233   -0.7245   -3.5051 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7823   -0.1734   -3.2356 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0124   -4.0344   -2.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8374   -3.3133   -3.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.8758    1.3757    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8950    0.9680    0.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6966   -0.8548    1.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2103   -1.2483    2.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2713   -1.0915    4.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6043   -1.9854    2.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2185    2.3089    2.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4167    1.4978    4.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5267    1.1521    2.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3968   -0.5716    3.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3369    0.4737    4.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0941    2.4670    3.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5405    1.5945    3.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5924    0.4706    1.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4524    3.9840   -0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0855    4.7052    1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6426    3.9036    1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1191    3.0904    1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100    3.1270   -0.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9960    2.4198   -0.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9934    1.5201   -1.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6897    1.1485   -3.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9553   -0.8769   -2.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8011   -0.9163   -4.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8956    0.8683   -3.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5385   -0.7698   -3.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 13  1  0  0  0  0
 27 28  1  0  0  0  0
 23 25  1  0  0  0  0
 29  2  1  0  0  0  0
 12  7  1  0  0  0  0
  5  3  1  6  0  0  0
  7  6  1  0  0  0  0
 12 39  1  1  0  0  0
  6  5  1  0  0  0  0
 13 14  1  1  0  0  0
 25  5  1  0  0  0  0
 13 15  1  0  0  0  0
 13 12  1  0  0  0  0
 18 19  1  0  0  0  0
 23 18  1  0  0  0  0
 23 24  1  6  0  0  0
 23 12  1  0  0  0  0
  7  8  1  0  0  0  0
  2  3  1  0  0  0  0
  2  1  2  3  0  0  0
 17 16  1  0  0  0  0
  3  4  2  0  0  0  0
 17 18  1  0  0  0  0
  8  9  1  0  0  0  0
 25 26  2  0  0  0  0
  9 10  1  0  0  0  0
  5 30  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 29 27  1  0  0  0  0
 20 22  2  0  0  0  0
 27 26  1  0  0  0  0
  9 11  2  0  0  0  0
 29 30  1  0  0  0  0
 17 48  1  0  0  0  0
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 16 46  1  0  0  0  0
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 18 50  1  1  0  0  0
  7 35  1  6  0  0  0
  6 33  1  0  0  0  0
  6 34  1  0  0  0  0
 30 61  1  0  0  0  0
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 27 58  1  6  0  0  0
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  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
 10 36  1  0  0  0  0
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 10 38  1  0  0  0  0
 21 51  1  0  0  0  0
 21 52  1  0  0  0  0
 21 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034029

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C([H])=C2[C@@]3(C(=O)C(=C([H])[H])[C@@]1([H])C3([H])[H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]1([H])[C@@]2(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O6/c1-12-15-10-24(21(12)28)11-17(29-13(2)25)20-22(4,5)8-7-19(30-14(3)26)23(20,6)18(24)9-16(15)27/h9,15-17,19-20,27H,1,7-8,10-11H2,2-6H3/t15-,16-,17+,19+,20-,23-,24+/m1/s1

> <INCHI_KEY>
XFKVVBCVBXGLMH-JNEANYDJSA-N

> <FORMULA>
C24H32O6

> <MOLECULAR_WEIGHT>
416.514

> <EXACT_MASS>
416.21988875

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
44.755256563813106

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3S,4R,8S,9R,12R,13R)-8-(acetyloxy)-12-hydroxy-5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-10-en-3-yl acetate

> <ALOGPS_LOGP>
1.95

> <JCHEM_LOGP>
2.2450273063333315

> <ALOGPS_LOGS>
-4.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.480749259063362

> <JCHEM_PKA_STRONGEST_BASIC>
-3.025920274085686

> <JCHEM_POLAR_SURFACE_AREA>
89.90000000000002

> <JCHEM_REFRACTIVITY>
110.09090000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,4R,8S,9R,12R,13R)-8-(acetyloxy)-12-hydroxy-5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-10-en-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
    1.1729   -3.1814   -2.9485 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5728   -2.0119   -2.7129 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6367    0.6576    0.5935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9018    0.2342    0.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8917    1.2738    0.7456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2014   -0.8308   -0.2011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2910    0.0710    1.1096 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5528    0.1994    2.6640 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1969   -1.1064    3.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6108    1.5166    2.8465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9414    1.3489    1.3608 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6598    2.5460    0.9651 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9950    2.5757    1.2323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5747    3.8803    0.7792 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385    1.6778    1.7548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3303    1.1396    0.4416 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0076    2.5074    0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0814    0.5858   -0.9680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2538    0.8557   -1.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6365    0.3025   -2.9472 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9420   -0.2499   -2.8730 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6233   -0.7245   -3.5051 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7823   -0.1734   -3.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0124   -4.0344   -2.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8728   -1.2675    0.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6592    2.2280    0.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8758    1.3757    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6966   -0.8548    1.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4167    1.4978    4.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5267    1.1521    2.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3968   -0.5716    3.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3369    0.4737    4.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0941    2.4670    3.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5405    1.5945    3.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5924    0.4706    1.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4524    3.9840   -0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0855    4.7052    1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6426    3.9036    1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1191    3.0904    1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100    3.1270   -0.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9960    2.4198   -0.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9934    1.5201   -1.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6897    1.1485   -3.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9553   -0.8769   -2.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8011   -0.9163   -4.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8956    0.8683   -3.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5385   -0.7698   -3.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 13  1  0
 27 28  1  0
 23 25  1  0
 29  2  1  0
 12  7  1  0
  5  3  1  6
  7  6  1  0
 12 39  1  1
  6  5  1  0
 13 14  1  1
 25  5  1  0
 13 15  1  0
 13 12  1  0
 18 19  1  0
 23 18  1  0
 23 24  1  6
 23 12  1  0
  7  8  1  0
  2  3  1  0
  2  1  2  3
 17 16  1  0
  3  4  2  0
 17 18  1  0
  8  9  1  0
 25 26  2  0
  9 10  1  0
  5 30  1  0
 19 20  1  0
 20 21  1  0
 29 27  1  0
 20 22  2  0
 27 26  1  0
  9 11  2  0
 29 30  1  0
 17 48  1  0
 17 49  1  0
 16 46  1  0
 16 47  1  0
 18 50  1  1
  7 35  1  6
  6 33  1  0
  6 34  1  0
 30 61  1  0
 30 62  1  0
 29 60  1  6
 27 58  1  6
 26 57  1  0
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 14 42  1  0
 15 43  1  0
 15 44  1  0
 15 45  1  0
 24 54  1  0
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  1 31  1  0
  1 32  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 21 51  1  0
 21 52  1  0
 21 53  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       1.173  -3.181  -2.949  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.573  -2.012  -2.713  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.384  -1.768  -1.585  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.647  -2.584  -0.718  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.911  -0.336  -1.695  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.351  -0.171  -1.260  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.563  -0.246   0.259  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.637   0.658   0.594  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.902   0.234   0.318  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.892   1.274   0.746  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.201  -0.831  -0.201  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.291   0.071   1.110  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.553   0.199   2.664  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.197  -1.106   3.196  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.474   1.354   3.108  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.192   0.348   3.378  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.611   1.517   2.846  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.941   1.349   1.361  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.660   2.546   0.965  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.995   2.576   1.232  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.575   3.880   0.779  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.639   1.678   1.755  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.330   1.140   0.442  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.008   2.507   0.188  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.081   0.586  -0.968  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.254   0.856  -1.593  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.637   0.303  -2.947  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.942  -0.250  -2.873  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.623  -0.725  -3.505  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.782  -0.173  -3.236  0.00  0.00           C+0
HETATM   31  H   UNK     0       1.012  -4.034  -2.294  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.837  -3.313  -3.796  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.974  -0.943  -1.730  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.742   0.780  -1.648  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.873  -1.268   0.515  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.659   2.228   0.266  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.876   1.376   1.833  0.00  0.00           H+0
HETATM   38  H   UNK     0      -6.895   0.968   0.435  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.697  -0.855   1.050  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.210  -1.248   2.806  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.271  -1.091   4.290  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.604  -1.985   2.919  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.219   2.309   2.652  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.417   1.498   4.194  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.527   1.152   2.896  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.397  -0.572   3.258  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.337   0.474   4.459  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.094   2.467   3.022  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.541   1.595   3.424  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.592   0.471   1.244  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.452   3.984  -0.302  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.086   4.705   1.303  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.643   3.904   1.014  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.119   3.090   1.104  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.410   3.127  -0.493  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.996   2.420  -0.267  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.993   1.520  -1.164  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.690   1.149  -3.643  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.955  -0.877  -2.128  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.801  -0.916  -4.568  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.896   0.868  -3.560  0.00  0.00           H+0
HETATM   62  H   UNK     0      -1.539  -0.770  -3.765  0.00  0.00           H+0
CONECT    1    2   31   32                                                  
CONECT    2   29    3    1                                                  
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    3    6   25   30                                             
CONECT    6    7    5   33   34                                             
CONECT    7   12    6    8   35                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9   36   37   38                                             
CONECT   11    9                                                            
CONECT   12    7   39   13   23                                             
CONECT   13   16   14   15   12                                             
CONECT   14   13   40   41   42                                             
CONECT   15   13   43   44   45                                             
CONECT   16   13   17   46   47                                             
CONECT   17   16   18   48   49                                             
CONECT   18   19   23   17   50                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   51   52   53                                             
CONECT   22   20                                                            
CONECT   23   25   18   24   12                                             
CONECT   24   23   54   55   56                                             
CONECT   25   23    5   26                                                  
CONECT   26   25   27   57                                                  
CONECT   27   28   29   26   58                                             
CONECT   28   27   59                                                       
CONECT   29    2   27   30   60                                             
CONECT   30    5   29   61   62                                             
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    6                                                            
CONECT   34    6                                                            
CONECT   35    7                                                            
CONECT   36   10                                                            
CONECT   37   10                                                            
CONECT   38   10                                                            
CONECT   39   12                                                            
CONECT   40   14                                                            
CONECT   41   14                                                            
CONECT   42   14                                                            
CONECT   43   15                                                            
CONECT   44   15                                                            
CONECT   45   15                                                            
CONECT   46   16                                                            
CONECT   47   16                                                            
CONECT   48   17                                                            
CONECT   49   17                                                            
CONECT   50   18                                                            
CONECT   51   21                                                            
CONECT   52   21                                                            
CONECT   53   21                                                            
CONECT   54   24                                                            
CONECT   55   24                                                            
CONECT   56   24                                                            
CONECT   57   26                                                            
CONECT   58   27                                                            
CONECT   59   28                                                            
CONECT   60   29                                                            
CONECT   61   30                                                            
CONECT   62   30                                                            
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
    1.1729   -3.1814   -2.9485 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5728   -2.0119   -2.7129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3838   -1.7678   -1.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6471   -2.5843   -0.7182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9110   -0.3361   -1.6950 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3512   -0.1705   -1.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5630   -0.2455    0.2589 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6367    0.6576    0.5935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9018    0.2342    0.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8917    1.2738    0.7456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2014   -0.8308   -0.2011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2910    0.0710    1.1096 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5528    0.1994    2.6640 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1969   -1.1064    3.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4738    1.3544    3.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1924    0.3477    3.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6108    1.5166    2.8465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9414    1.3489    1.3608 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6598    2.5460    0.9651 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9950    2.5757    1.2323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5747    3.8803    0.7792 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385    1.6778    1.7548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3303    1.1396    0.4416 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0076    2.5074    0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0814    0.5858   -0.9680 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2538    0.8557   -1.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6365    0.3025   -2.9472 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9420   -0.2499   -2.8730 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6233   -0.7245   -3.5051 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7823   -0.1734   -3.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0124   -4.0344   -2.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8374   -3.3133   -3.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9745   -0.9432   -1.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7423    0.7795   -1.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8728   -1.2675    0.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6592    2.2280    0.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8758    1.3757    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8950    0.9680    0.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6966   -0.8548    1.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2103   -1.2483    2.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2713   -1.0915    4.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6043   -1.9854    2.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2185    2.3089    2.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4167    1.4978    4.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5267    1.1521    2.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3968   -0.5716    3.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3369    0.4737    4.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0941    2.4670    3.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5405    1.5945    3.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5924    0.4706    1.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4524    3.9840   -0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0855    4.7052    1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6426    3.9036    1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1191    3.0904    1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100    3.1270   -0.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9960    2.4198   -0.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9934    1.5201   -1.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6897    1.1485   -3.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9553   -0.8769   -2.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8011   -0.9163   -4.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8956    0.8683   -3.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5385   -0.7698   -3.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 13  1  0
 27 28  1  0
 23 25  1  0
 29  2  1  0
 12  7  1  0
  5  3  1  6
  7  6  1  0
 12 39  1  1
  6  5  1  0
 13 14  1  1
 25  5  1  0
 13 15  1  0
 13 12  1  0
 18 19  1  0
 23 18  1  0
 23 24  1  6
 23 12  1  0
  7  8  1  0
  2  3  1  0
  2  1  2  3
 17 16  1  0
  3  4  2  0
 17 18  1  0
  8  9  1  0
 25 26  2  0
  9 10  1  0
  5 30  1  0
 19 20  1  0
 20 21  1  0
 29 27  1  0
 20 22  2  0
 27 26  1  0
  9 11  2  0
 29 30  1  0
 17 48  1  0
 17 49  1  0
 16 46  1  0
 16 47  1  0
 18 50  1  1
  7 35  1  6
  6 33  1  0
  6 34  1  0
 30 61  1  0
 30 62  1  0
 29 60  1  6
 27 58  1  6
 26 57  1  0
 28 59  1  0
 14 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 15 45  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
  1 31  1  0
  1 32  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 21 51  1  0
 21 52  1  0
 21 53  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₄H₃₂O₆

Average Mass

416.5140 Da

Monoisotopic Mass

416.21989 Da

IUPAC Name

(1S,3S,4R,8S,9R,12R,13R)-8-(acetyloxy)-12-hydroxy-5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-10-en-3-yl acetate

Traditional Name

(1S,3S,4R,8S,9R,12R,13R)-8-(acetyloxy)-12-hydroxy-5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-10-en-3-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C([H])=C2[C@@]3(C(=O)C(=C([H])[H])[C@@]1([H])C3([H])[H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]1([H])[C@@]2(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C24H32O6/c1-12-15-10-24(21(12)28)11-17(29-13(2)25)20-22(4,5)8-7-19(30-14(3)26)23(20,6)18(24)9-16(15)27/h9,15-17,19-20,27H,1,7-8,10-11H2,2-6H3/t15-,16-,17+,19+,20-,23-,24+/m1/s1

InChI Key

XFKVVBCVBXGLMH-JNEANYDJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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
Jungermannia atrobrunnea	JEOL database	Qu, J. -B., et al, J. Nat. Prod. 71, 1418 (2008)

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
Dicarboxylic acid or derivatives
Secondary alcohol
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	1.95	ALOGPS
logP	2.25	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	14.48	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.09 m³·mol⁻¹	ChemAxon
Polarizability	44.76 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24706369

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25019750

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Qu, J. -B., et al. (2008). Qu, J. -B., et al, J. Nat. Prod. 71, 1418 (2008). J. Nat. Prod..

Showing NP-Card for 12beta-hydroxy-1alpha,6alpha-diacetoxy-ent-kaura-9(11),16-dien-15-one (NP0034029)

MOL for NP0034029 (12beta-hydroxy-1alpha,6alpha-diacetoxy-ent-kaura-9(11),16-dien-15-one)

3D MOL for NP0034029 (12beta-hydroxy-1alpha,6alpha-diacetoxy-ent-kaura-9(11),16-dien-15-one)

3D SDF for NP0034029 (12beta-hydroxy-1alpha,6alpha-diacetoxy-ent-kaura-9(11),16-dien-15-one)

3D-SDF for NP0034029 (12beta-hydroxy-1alpha,6alpha-diacetoxy-ent-kaura-9(11),16-dien-15-one)

PDB for NP0034029 (12beta-hydroxy-1alpha,6alpha-diacetoxy-ent-kaura-9(11),16-dien-15-one)

3D PDB for NP0034029 (12beta-hydroxy-1alpha,6alpha-diacetoxy-ent-kaura-9(11),16-dien-15-one)

SMILES for NP0034029 (12beta-hydroxy-1alpha,6alpha-diacetoxy-ent-kaura-9(11),16-dien-15-one)

INCHI for NP0034029 (12beta-hydroxy-1alpha,6alpha-diacetoxy-ent-kaura-9(11),16-dien-15-one)

Structure for NP0034029 (12beta-hydroxy-1alpha,6alpha-diacetoxy-ent-kaura-9(11),16-dien-15-one)

3D Structure for NP0034029 (12beta-hydroxy-1alpha,6alpha-diacetoxy-ent-kaura-9(11),16-dien-15-one)