NP-MRD: Showing NP-Card for (1''s,3r,4''s,5r,5's,6''r,8''s,12''r)-5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0⁴,¹²]dodecan]-6''-yl acetate (NP0147383)

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Record Information

Version

2.0

Created at

2022-09-02 02:58:41 UTC

Updated at

2022-09-02 02:58:41 UTC

NP-MRD ID

NP0147383

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1''s,3r,4''s,5r,5's,6''r,8''s,12''r)-5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0⁴,¹²]dodecan]-6''-yl acetate

Description

(1''S,3R,4''S,5R,5'S,6''R,8''S,12''R)-5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]Oxatricyclo[6.3.1.0⁴,¹²]Dodecane]-6''-yl acetate belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom). (1''s,3r,4''s,5r,5's,6''r,8''s,12''r)-5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0⁴,¹²]dodecan]-6''-yl acetate is found in Leonurus cardiaca. Based on a literature review very few articles have been published on (1''S,3R,4''S,5R,5'S,6''R,8''S,12''R)-5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]Oxatricyclo[6.3.1.0⁴,¹²]Dodecane]-6''-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022204582D          

 30 34  0  0  1  0            999 V2000
    3.5810   -2.1831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4202   -1.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0406   -0.8301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6391   -1.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4783   -0.2994    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3031   -0.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7093   -0.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5836   -1.4136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0660   -0.0817    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2517   -0.2141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1258    0.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9412    0.6451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4551    1.1052    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3163    1.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4085    1.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0986    2.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8352    2.0095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9607    1.0325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5204    1.6386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1917    0.7337    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6040    0.5160    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8142    1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6379    1.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9367    0.5913    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5757    1.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2695    0.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0593   -0.1311    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5811   -0.7701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2356   -0.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2977    0.0695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20  9  1  1  0  0  0
 13 20  1  0  0  0  0
 18 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 24 29  1  0  0  0  0
 24 30  1  1  0  0  0
 21 30  1  6  0  0  0
M  END

     RDKit          3D

 60 64  0  0  0  0  0  0  0  0999 V2000
    2.1483    3.9021   -2.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2501    3.1693   -1.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3054    3.4021   -0.0266 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3789    2.2529   -1.7264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5227    1.4810   -0.9209 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3338    2.4304   -0.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3404    0.7381   -1.9796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0959    0.7374   -3.1435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4978   -0.0086   -1.4531 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5948   -1.3289   -1.9669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0436   -2.2148   -0.9685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2239   -3.4386   -1.2330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2017   -1.4249    0.2279 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5852   -0.7547    0.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0372   -2.0215    1.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7854   -1.7877    2.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8323   -0.7754    1.7792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7770   -0.7052    0.2467 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4677   -2.0884   -0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2133   -0.2818   -0.0223 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2031    0.3434   -0.2361 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0824   -0.1905   -1.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4184   -0.5333   -0.8105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3552    0.1797    0.5061 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5234    1.1816    0.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6286    0.4953    0.9219 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3558   -0.8271    1.1181 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1493   -1.3196    2.1569 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8829   -0.7772    1.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1409    0.7119    0.6907 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7820    4.9274   -2.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2784    3.3981   -3.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1736    4.0331   -1.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0623    3.5216   -0.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3808    2.4284   -0.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2811    2.4082    0.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4157    0.5633   -1.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9051   -0.6918   -0.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2839   -1.4647    0.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5935    0.2228    0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2176   -3.1369    1.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8996   -1.6982    2.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2137   -2.7589    2.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9896   -1.5157    3.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1843    0.2275    2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1251   -0.9482    2.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6206   -2.3463   -1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718   -2.8393    0.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5634   -2.3243    0.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5919    0.4625    0.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6196   -0.9595   -1.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3139    0.6260   -2.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6424   -1.6159   -0.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2817   -0.1638   -1.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2177    1.9500    1.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6011    1.6690   -0.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4767   -1.4130    0.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0625   -0.9430    2.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8255   -0.3787    2.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4777   -1.7867    1.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  5  4  1  6
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 24 30  1  1
 21  5  1  0
 21 30  1  1
 20  9  1  0
 29 24  1  0
 20 13  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  6 34  1  0
  6 35  1  0
  6 36  1  0
  9 37  1  1
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 19 47  1  0
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 20 50  1  1
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 23 53  1  0
 23 54  1  0
 25 55  1  0
 25 56  1  0
 27 57  1  6
 28 58  1  0
 29 59  1  0
 29 60  1  0
M  END


  Mrv1652309022204582D          

 30 34  0  0  1  0            999 V2000
    3.5810   -2.1831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4202   -1.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0406   -0.8301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6391   -1.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4783   -0.2994    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3031   -0.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7093   -0.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5836   -1.4136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0660   -0.0817    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2517   -0.2141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1258    0.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9412    0.6451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4551    1.1052    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3163    1.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4085    1.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0986    2.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8352    2.0095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9607    1.0325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5204    1.6386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1917    0.7337    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6040    0.5160    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8142    1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6379    1.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9367    0.5913    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5757    1.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2695    0.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0593   -0.1311    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5811   -0.7701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2356   -0.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2977    0.0695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20  9  1  1  0  0  0
 13 20  1  0  0  0  0
 18 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 24 29  1  0  0  0  0
 24 30  1  1  0  0  0
 21 30  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0147383

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@]1(C)C(=O)[C@H]2OC(=O)[C@@]3(C)CCC[C@@](C)([C@@H]23)[C@@]11CC[C@@]2(CO[C@@H](O)C2)O1

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O8/c1-12(23)29-20(4)16(25)14-15-18(2,17(26)28-14)6-5-7-19(15,3)22(20)9-8-21(30-22)10-13(24)27-11-21/h13-15,24H,5-11H2,1-4H3/t13-,14+,15+,18+,19+,20+,21-,22+/m1/s1

> <INCHI_KEY>
YPFSOWQXNOLVDV-UFLPTDMQSA-N

> <FORMULA>
C22H30O8

> <MOLECULAR_WEIGHT>
422.474

> <EXACT_MASS>
422.194067926

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
42.58848782669647

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1''S,3R,4''S,5R,5'S,6''R,8''S,12''R)-5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0^{4,12}]dodecane]-6''-yl acetate

> <ALOGPS_LOGP>
1.27

> <JCHEM_LOGP>
2.1654451780000006

> <ALOGPS_LOGS>
-3.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.12516627781772

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.367811772498861

> <JCHEM_PKA_STRONGEST_BASIC>
-3.946707168041356

> <JCHEM_POLAR_SURFACE_AREA>
108.36000000000003

> <JCHEM_REFRACTIVITY>
100.7457

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1''S,3R,4''S,5R,5'S,6''R,8''S,12''R)-5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0^{4,12}]dodecane]-6''-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       6.684  -4.075   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.384  -2.565   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       7.542  -1.550   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.926  -2.069   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.626  -0.559   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.166  -0.526   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.191  -1.117   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.956  -2.639   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.990  -0.152   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.470  -0.400   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.235   0.970   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.757   1.204   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.850   2.063   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.590   2.609   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.763   3.601   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.051   4.445   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.426   3.751   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.660   1.927   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.705   3.059   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.225   1.370   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.861   0.963   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.253   2.452   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.791   2.539   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.349   1.104   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.541   2.078   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.836   1.245   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.444  -0.245   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.418  -1.437   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.906  -0.332   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.156   0.130   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   21                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   20                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18    9   13                                                  
CONECT   21   18    5   22   30                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   29   30                                             
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   24                                                       
CONECT   30   24   21                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Value	Source
(1''S,3R,4''s,5R,5's,6''r,8''s,12''r)-5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0,]dodecane]-6''-yl acetic acid	Generator

Chemical Formula

C₂₂H₃₀O₈

Average Mass

422.4740 Da

Monoisotopic Mass

422.19407 Da

IUPAC Name

(1''S,3R,4''S,5R,5'S,6''R,8''S,12''R)-5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0^{4,12}]dodecane]-6''-yl acetate

Traditional Name

(1''S,3R,4''S,5R,5'S,6''R,8''S,12''R)-5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0^{4,12}]dodecane]-6''-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@]1(C)C(=O)[C@H]2OC(=O)[C@@]3(C)CCC[C@@](C)([C@@H]23)[C@@]11CC[C@@]2(CO[C@@H](O)C2)O1

InChI Identifier

InChI=1S/C22H30O8/c1-12(23)29-20(4)16(25)14-15-18(2,17(26)28-14)6-5-7-19(15,3)22(20)9-8-21(30-22)10-13(24)27-11-21/h13-15,24H,5-11H2,1-4H3/t13-,14+,15+,18+,19+,20+,21-,22+/m1/s1

InChI Key

YPFSOWQXNOLVDV-UFLPTDMQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Leonurus cardiaca	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-acyloxy ketones

Alternative Parents

Substituents

Alpha-acyloxy ketone
Dicarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Hemiacetal
Ketone
Lactone
Carboxylic acid derivative
Ether
Dialkyl ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
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	1.27	ALOGPS
logP	2.17	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	12.37	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	100.75 m³·mol⁻¹	ChemAxon
Polarizability	42.59 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

162968353

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1''s,3r,4''s,5r,5's,6''r,8''s,12''r)-5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0⁴,¹²]dodecan]-6''-yl acetate (NP0147383)

MOL for NP0147383 ((1''s,3r,4''s,5r,5's,6''r,8''s,12''r)-5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0⁴,¹²]dodecan]-6''-yl acetate)

3D MOL for NP0147383 ((1''s,3r,4''s,5r,5's,6''r,8''s,12''r)-5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0⁴,¹²]dodecan]-6''-yl acetate)

3D SDF for NP0147383 ((1''s,3r,4''s,5r,5's,6''r,8''s,12''r)-5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0⁴,¹²]dodecan]-6''-yl acetate)

3D-SDF for NP0147383 ((1''s,3r,4''s,5r,5's,6''r,8''s,12''r)-5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0⁴,¹²]dodecan]-6''-yl acetate)

PDB for NP0147383 ((1''s,3r,4''s,5r,5's,6''r,8''s,12''r)-5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0⁴,¹²]dodecan]-6''-yl acetate)

3D PDB for NP0147383 ((1''s,3r,4''s,5r,5's,6''r,8''s,12''r)-5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0⁴,¹²]dodecan]-6''-yl acetate)

SMILES for NP0147383 ((1''s,3r,4''s,5r,5's,6''r,8''s,12''r)-5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0⁴,¹²]dodecan]-6''-yl acetate)

INCHI for NP0147383 ((1''s,3r,4''s,5r,5's,6''r,8''s,12''r)-5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0⁴,¹²]dodecan]-6''-yl acetate)

Structure for NP0147383 ((1''s,3r,4''s,5r,5's,6''r,8''s,12''r)-5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0⁴,¹²]dodecan]-6''-yl acetate)

3D Structure for NP0147383 ((1''s,3r,4''s,5r,5's,6''r,8''s,12''r)-5-hydroxy-1'',6'',8''-trimethyl-2'',5''-dioxodispiro[bis(oxolane)-3,2':5',7''-[3]oxatricyclo[6.3.1.0⁴,¹²]dodecan]-6''-yl acetate)