NP-MRD: Showing NP-Card for 3alpha-acetoxy-maoesin A (NP0035637)

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Record Information

Version

2.0

Created at

2021-06-20 19:01:40 UTC

Updated at

2021-06-30 00:06:46 UTC

NP-MRD ID

NP0035637

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3alpha-acetoxy-maoesin A

Provided By

JEOL Database JEOL Logo

Description

3Alpha-Acetoxymaoesin A, also known as 3α-acetoxymaoesin a, belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 3alpha-acetoxy-maoesin A is found in Isodon eriocalyx. 3alpha-acetoxy-maoesin A was first documented in 2010 (Li, X. -N., et al.). Based on a literature review very few articles have been published on 3alpha-Acetoxymaoesin A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121013D          

 64 68  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202121013D          

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    0.2689   -1.1131   -1.8086 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0605    1.2784   -2.4840 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4157    2.7029   -2.0499 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4597    3.1871   -0.8818 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0088    4.5241   -0.5750 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9491    5.5052   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2926    6.8183   -0.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1544    5.3552   -0.6403 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4087    2.2492    0.3790 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6122    2.6349    1.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8829    2.4869    1.2148 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8436    3.7537    1.9024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9639    4.0391    2.6214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8260    5.3765    3.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9514    3.3233    2.7081 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3094    1.3468   -2.9261 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0468    0.2546   -3.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1215    0.3735   -3.7792 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3422   -4.3954   -5.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0029   -1.4509   -1.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0271   -3.9964   -1.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4515   -3.9118   -0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3066   -4.1211   -1.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6049   -2.3514   -0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -0.0372    1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4076   -1.0573    2.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6591    0.7505   -0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2144    1.0590   -0.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9791   -0.6399   -0.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4193   -0.3074   -1.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5177   -1.5387   -2.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6617    1.0102   -3.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4784    2.7984   -1.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2546    3.3878   -2.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4944    3.2160   -1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250    7.6228   -0.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5211    6.9979   -0.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0827    6.8186    0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6209    3.7013    1.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5859    2.0924    2.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5678    2.4121    0.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7671    2.4958    0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9944    1.7192    1.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8772    5.4308    3.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6366    5.5090    4.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854    6.1663    2.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 45  1  6  0  0  0
 19 20  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 29 31  2  0  0  0  0
 14 15  1  1  0  0  0
 14 17  1  0  0  0  0
 11 12  1  0  0  0  0
 13 11  1  0  0  0  0
  7  2  1  0  0  0  0
 17  9  1  0  0  0  0
  2  1  2  3  0  0  0
 28 29  1  0  0  0  0
 17 49  1  6  0  0  0
 18 32  1  0  0  0  0
 29 30  1  0  0  0  0
  5 33  1  6  0  0  0
 19 18  1  0  0  0  0
 33 32  1  0  0  0  0
 20 25  1  0  0  0  0
 33 34  2  0  0  0  0
 25 13  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  0  0  0  0
 14 18  1  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
 17  5  1  0  0  0  0
  3  4  2  0  0  0  0
  9  8  1  0  0  0  0
 15 16  1  0  0  0  0
 28 27  1  0  0  0  0
  8  7  1  0  0  0  0
 20 21  1  0  0  0  0
  7  6  1  0  0  0  0
 21 22  1  0  0  0  0
  6  5  1  0  0  0  0
 22 24  2  0  0  0  0
 14 13  1  0  0  0  0
 22 23  1  0  0  0  0
 30 62  1  0  0  0  0
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 19 51  1  0  0  0  0
 19 52  1  0  0  0  0
 20 53  1  6  0  0  0
 18 50  1  6  0  0  0
 11 43  1  1  0  0  0
  9 42  1  1  0  0  0
  8 40  1  0  0  0  0
  8 41  1  0  0  0  0
  7 39  1  1  0  0  0
  6 37  1  0  0  0  0
  6 38  1  0  0  0  0
 26 57  1  0  0  0  0
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 26 59  1  0  0  0  0
 27 60  1  0  0  0  0
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  1 35  1  0  0  0  0
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 16 48  1  0  0  0  0
 23 54  1  0  0  0  0
 23 55  1  0  0  0  0
 23 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035637

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]12[C@]3([H])OC(=O)[C@@]45C(=O)C(=C([H])[H])[C@@]([H])(C4([H])[H])C([H])([H])[C@@]([H])(O[C@]([H])(O[H])[C@]1([H])[C@](C([H])([H])[H])(C([H])([H])OC(=O)C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])C3([H])[H])[C@@]25[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O10/c1-10-13-5-14-17-23(7-13,19(10)28)21(30)34-16-6-15(32-12(3)27)22(4,9-31-11(2)26)18(20(29)33-14)24(16,17)8-25/h13-18,20,25,29H,1,5-9H2,2-4H3/t13-,14-,15-,16-,17-,18-,20+,22-,23+,24+/m1/s1

> <INCHI_KEY>
WSLLKHLHBNYZFR-OAIRYGIMSA-N

> <FORMULA>
C24H30O10

> <MOLECULAR_WEIGHT>
478.494

> <EXACT_MASS>
478.183897166

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
47.592161975269605

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,4S,6R,8S,9R,10R,11R,13R,16S,17S)-11-(acetyloxy)-8-hydroxy-17-(hydroxymethyl)-10-methyl-3-methylidene-2,15-dioxo-7,14-dioxapentacyclo[7.6.2.1^{1,4}.0^{6,16}.0^{13,17}]octadecan-10-yl]methyl acetate

> <ALOGPS_LOGP>
0.06

> <JCHEM_LOGP>
-0.41738962433333304

> <ALOGPS_LOGS>
-2.46

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.002682537936302

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.128698123093391

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8006819765031556

> <JCHEM_POLAR_SURFACE_AREA>
145.66

> <JCHEM_REFRACTIVITY>
112.27759999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.65e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,4S,6R,8S,9R,10R,11R,13R,16S,17S)-11-(acetyloxy)-8-hydroxy-17-(hydroxymethyl)-10-methyl-3-methylidene-2,15-dioxo-7,14-dioxapentacyclo[7.6.2.1^{1,4}.0^{6,16}.0^{13,17}]octadecan-10-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 68  0  0  0  0  0  0  0  0999 V2000
    1.7080   -4.4736   -4.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7332   -3.4066   -3.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3082   -2.0327   -3.8367 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5571   -1.0739   -2.6875 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7322   -1.8399   -2.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2255   -3.2815   -2.0026 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0616   -3.4371   -1.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3868   -2.1029   -0.6191 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1516   -1.5505    0.4574 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6638   -0.3284    0.9931 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5911   -0.5402    1.5940 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6254    0.7509   -0.1052 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2426    0.2812   -1.3284 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7660    0.1381   -1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4807   -0.2132   -2.1958 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0605    1.2784   -2.4840 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4157    2.7029   -2.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4597    3.1871   -0.8818 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0088    4.5241   -0.5750 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2926    6.8183   -0.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1544    5.3552   -0.6403 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4087    2.2492    0.3790 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6122    2.6349    1.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8829    2.4869    1.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8436    3.7537    1.9024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9639    4.0391    2.6214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8260    5.3765    3.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9514    3.3233    2.7081 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3094    1.3468   -2.9261 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0468    0.2546   -3.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1215    0.3735   -3.7792 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0530   -5.4445   -3.8852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3422   -4.3954   -5.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0029   -1.4509   -1.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6502   -1.7807   -2.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0271   -3.9964   -1.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4515   -3.9118   -0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3066   -4.1211   -1.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6049   -2.3514   -0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4076   -1.0573    2.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9791   -0.6399   -0.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4193   -0.3074   -1.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5177   -1.5387   -2.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6617    1.0102   -3.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4944    3.2160   -1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0827    6.8186    0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6209    3.7013    1.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5859    2.0924    2.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5678    2.4121    0.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7671    2.4958    0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9944    1.7192    1.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8772    5.4308    3.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6366    5.5090    4.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854    6.1663    2.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 45  1  6
 19 20  1  0
 25 26  1  1
 25 27  1  0
 29 31  2  0
 14 15  1  1
 14 17  1  0
 11 12  1  0
 13 11  1  0
  7  2  1  0
 17  9  1  0
  2  1  2  3
 28 29  1  0
 17 49  1  6
 18 32  1  0
 29 30  1  0
  5 33  1  6
 19 18  1  0
 33 32  1  0
 20 25  1  0
 33 34  2  0
 25 13  1  0
  9 10  1  0
 11 10  1  0
 14 18  1  0
  5  3  1  0
  3  2  1  0
 17  5  1  0
  3  4  2  0
  9  8  1  0
 15 16  1  0
 28 27  1  0
  8  7  1  0
 20 21  1  0
  7  6  1  0
 21 22  1  0
  6  5  1  0
 22 24  2  0
 14 13  1  0
 22 23  1  0
 30 62  1  0
 30 63  1  0
 30 64  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  6
 18 50  1  6
 11 43  1  1
  9 42  1  1
  8 40  1  0
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  7 39  1  1
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 26 57  1  0
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 27 60  1  0
 27 61  1  0
 15 46  1  0
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 12 44  1  0
  1 35  1  0
  1 36  1  0
 16 48  1  0
 23 54  1  0
 23 55  1  0
 23 56  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       1.708  -4.474  -4.224  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.733  -3.407  -3.422  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.308  -2.033  -3.837  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.768  -1.770  -4.898  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.557  -1.074  -2.688  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.732  -1.840  -2.023  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.225  -3.281  -2.003  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.062  -3.437  -1.006  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.387  -2.103  -0.619  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.152  -1.551   0.457  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.664  -0.328   0.993  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.591  -0.540   1.594  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.625   0.751  -0.105  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.243   0.281  -1.328  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.766   0.138  -1.013  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.481  -0.213  -2.196  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.269  -1.113  -1.809  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.061   1.278  -2.484  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.416   2.703  -2.050  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.460   3.187  -0.882  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.009   4.524  -0.575  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.949   5.505  -0.507  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.293   6.818  -0.209  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.154   5.355  -0.640  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.409   2.249   0.379  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.612   2.635   1.291  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.883   2.487   1.215  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.844   3.754   1.902  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.964   4.039   2.621  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.826   5.377   3.281  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.951   3.323   2.708  0.00  0.00           O+0
HETATM   32  O   UNK     0       1.309   1.347  -2.926  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.047   0.255  -3.196  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.122   0.374  -3.779  0.00  0.00           O+0
HETATM   35  H   UNK     0       2.053  -5.444  -3.885  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.342  -4.395  -5.245  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.003  -1.451  -1.038  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.650  -1.781  -2.627  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.027  -3.996  -1.791  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.452  -3.912  -0.096  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.307  -4.121  -1.415  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.605  -2.351  -0.224  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.367  -0.037   1.778  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.408  -1.057   2.398  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.659   0.751  -0.487  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.214   1.059  -0.656  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.979  -0.640  -0.280  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.419  -0.307  -1.950  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.518  -1.539  -2.449  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.662   1.010  -3.361  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.478   2.798  -1.803  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.255   3.388  -2.894  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.494   3.216  -1.248  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.025   7.623  -0.321  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.521   6.998  -0.917  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.083   6.819   0.816  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.621   3.701   1.537  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.586   2.092   2.241  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.568   2.412   0.803  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.767   2.496   0.578  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.994   1.719   1.983  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.877   5.431   3.821  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.637   5.509   4.003  0.00  0.00           H+0
HETATM   64  H   UNK     0      -1.885   6.166   2.529  0.00  0.00           H+0
CONECT    1    2   35   36                                                  
CONECT    2    7    1    3                                                  
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5   33    3   17    6                                             
CONECT    6    7    5   37   38                                             
CONECT    7    2    8    6   39                                             
CONECT    8    9    7   40   41                                             
CONECT    9   17   10    8   42                                             
CONECT   10    9   11                                                       
CONECT   11   12   13   10   43                                             
CONECT   12   11   44                                                       
CONECT   13   45   11   25   14                                             
CONECT   14   15   17   18   13                                             
CONECT   15   14   16   46   47                                             
CONECT   16   15   48                                                       
CONECT   17   14    9   49    5                                             
CONECT   18   32   19   14   50                                             
CONECT   19   20   18   51   52                                             
CONECT   20   19   25   21   53                                             
CONECT   21   20   22                                                       
CONECT   22   21   24   23                                                  
CONECT   23   22   54   55   56                                             
CONECT   24   22                                                            
CONECT   25   26   27   20   13                                             
CONECT   26   25   57   58   59                                             
CONECT   27   25   28   60   61                                             
CONECT   28   29   27                                                       
CONECT   29   31   28   30                                                  
CONECT   30   29   62   63   64                                             
CONECT   31   29                                                            
CONECT   32   18   33                                                       
CONECT   33    5   32   34                                                  
CONECT   34   33                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    6                                                            
CONECT   38    6                                                            
CONECT   39    7                                                            
CONECT   40    8                                                            
CONECT   41    8                                                            
CONECT   42    9                                                            
CONECT   43   11                                                            
CONECT   44   12                                                            
CONECT   45   13                                                            
CONECT   46   15                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   17                                                            
CONECT   50   18                                                            
CONECT   51   19                                                            
CONECT   52   19                                                            
CONECT   53   20                                                            
CONECT   54   23                                                            
CONECT   55   23                                                            
CONECT   56   23                                                            
CONECT   57   26                                                            
CONECT   58   26                                                            
CONECT   59   26                                                            
CONECT   60   27                                                            
CONECT   61   27                                                            
CONECT   62   30                                                            
CONECT   63   30                                                            
CONECT   64   30                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  136    0
END

RDKit          3D

64 68  0  0  0  0  0  0  0  0999 V2000
    1.7080   -4.4736   -4.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7332   -3.4066   -3.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3082   -2.0327   -3.8367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7676   -1.7702   -4.8978 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5571   -1.0739   -2.6875 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7322   -1.8399   -2.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2255   -3.2815   -2.0026 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0616   -3.4371   -1.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3868   -2.1029   -0.6191 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1516   -1.5505    0.4574 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6638   -0.3284    0.9931 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5911   -0.5402    1.5940 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6254    0.7509   -0.1052 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2426    0.2812   -1.3284 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7660    0.1381   -1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4807   -0.2132   -2.1958 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2689   -1.1131   -1.8086 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0605    1.2784   -2.4840 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4157    2.7029   -2.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4597    3.1871   -0.8818 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0088    4.5241   -0.5750 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9491    5.5052   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2926    6.8183   -0.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1544    5.3552   -0.6403 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4087    2.2492    0.3790 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6122    2.6349    1.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8829    2.4869    1.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8436    3.7537    1.9024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9639    4.0391    2.6214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8260    5.3765    3.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9514    3.3233    2.7081 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3094    1.3468   -2.9261 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0468    0.2546   -3.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1215    0.3735   -3.7792 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0530   -5.4445   -3.8852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3422   -4.3954   -5.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0029   -1.4509   -1.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6502   -1.7807   -2.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0271   -3.9964   -1.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4515   -3.9118   -0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3066   -4.1211   -1.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6049   -2.3514   -0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -0.0372    1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4076   -1.0573    2.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6591    0.7505   -0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2144    1.0590   -0.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9791   -0.6399   -0.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4193   -0.3074   -1.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5177   -1.5387   -2.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6617    1.0102   -3.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4784    2.7984   -1.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2546    3.3878   -2.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4944    3.2160   -1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250    7.6228   -0.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5211    6.9979   -0.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0827    6.8186    0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6209    3.7013    1.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5859    2.0924    2.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5678    2.4121    0.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7671    2.4958    0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9944    1.7192    1.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8772    5.4308    3.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6366    5.5090    4.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854    6.1663    2.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 45  1  6
 19 20  1  0
 25 26  1  1
 25 27  1  0
 29 31  2  0
 14 15  1  1
 14 17  1  0
 11 12  1  0
 13 11  1  0
  7  2  1  0
 17  9  1  0
  2  1  2  3
 28 29  1  0
 17 49  1  6
 18 32  1  0
 29 30  1  0
  5 33  1  6
 19 18  1  0
 33 32  1  0
 20 25  1  0
 33 34  2  0
 25 13  1  0
  9 10  1  0
 11 10  1  0
 14 18  1  0
  5  3  1  0
  3  2  1  0
 17  5  1  0
  3  4  2  0
  9  8  1  0
 15 16  1  0
 28 27  1  0
  8  7  1  0
 20 21  1  0
  7  6  1  0
 21 22  1  0
  6  5  1  0
 22 24  2  0
 14 13  1  0
 22 23  1  0
 30 62  1  0
 30 63  1  0
 30 64  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  6
 18 50  1  6
 11 43  1  1
  9 42  1  1
  8 40  1  0
  8 41  1  0
  7 39  1  1
  6 37  1  0
  6 38  1  0
 26 57  1  0
 26 58  1  0
 26 59  1  0
 27 60  1  0
 27 61  1  0
 15 46  1  0
 15 47  1  0
 12 44  1  0
  1 35  1  0
  1 36  1  0
 16 48  1  0
 23 54  1  0
 23 55  1  0
 23 56  1  0
M  END

View in JSmol

Synonyms

Value	Source
3a-Acetoxymaoesin a	Generator
3Α-acetoxymaoesin a	Generator

Chemical Formula

C₂₄H₃₀O₁₀

Average Mass

478.4940 Da

Monoisotopic Mass

478.18390 Da

IUPAC Name

[(1S,4S,6R,8S,9R,10R,11R,13R,16S,17S)-11-(acetyloxy)-8-hydroxy-17-(hydroxymethyl)-10-methyl-3-methylidene-2,15-dioxo-7,14-dioxapentacyclo[7.6.2.1^{1,4}.0^{6,16}.0^{13,17}]octadecan-10-yl]methyl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]12[C@]3([H])OC(=O)[C@@]45C(=O)C(=C([H])[H])[C@@]([H])(C4([H])[H])C([H])([H])[C@@]([H])(O[C@]([H])(O[H])[C@]1([H])[C@](C([H])([H])[H])(C([H])([H])OC(=O)C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])C3([H])[H])[C@@]25[H]

InChI Identifier

InChI=1S/C24H30O10/c1-10-13-5-14-17-23(7-13,19(10)28)21(30)34-16-6-15(32-12(3)27)22(4,9-31-11(2)26)18(20(29)33-14)24(16,17)8-25/h13-18,20,25,29H,1,5-9H2,2-4H3/t13-,14-,15-,16-,17-,18-,20+,22-,23+,24+/m1/s1

InChI Key

WSLLKHLHBNYZFR-OAIRYGIMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Isodon eriocalyx	JEOL database	Li, X. -N., et al, J. Nat. Prod. 73, 1803 (2010)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Kaurane diterpenoid
Tricarboxylic acid or derivatives
Delta valerolactone
Delta_valerolactone
Oxane
Lactone
Ketone
Hemiacetal
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.06	ALOGPS
logP	-0.42	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	12.13	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	145.66 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	112.28 m³·mol⁻¹	ChemAxon
Polarizability	47.59 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

50901148

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li, X. -N., et al. (2010). Li, X. -N., et al, J. Nat. Prod. 73, 1803 (2010). J. Nat. Prod..

Showing NP-Card for 3alpha-acetoxy-maoesin A (NP0035637)

MOL for NP0035637 (3alpha-acetoxy-maoesin A)

3D MOL for NP0035637 (3alpha-acetoxy-maoesin A)

3D SDF for NP0035637 (3alpha-acetoxy-maoesin A)

3D-SDF for NP0035637 (3alpha-acetoxy-maoesin A)

PDB for NP0035637 (3alpha-acetoxy-maoesin A)

3D PDB for NP0035637 (3alpha-acetoxy-maoesin A)

SMILES for NP0035637 (3alpha-acetoxy-maoesin A)

INCHI for NP0035637 (3alpha-acetoxy-maoesin A)

Structure for NP0035637 (3alpha-acetoxy-maoesin A)

3D Structure for NP0035637 (3alpha-acetoxy-maoesin A)