NP-MRD: Showing NP-Card for Leopersin N (NP0078571)

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Record Information

Version

2.0

Created at

2022-04-28 23:37:42 UTC

Updated at

2022-04-28 23:37:42 UTC

NP-MRD ID

NP0078571

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Leopersin N

Description

Leopersin N 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). Leopersin N is found in Leonurus persicus. Based on a literature review very few articles have been published on Leopersin N.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201372D          

 31 35  0  0  1  0            999 V2000
    0.8999    2.4241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2583    1.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3867    1.0905    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1567    0.7942    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7982    1.3129    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6699    2.1278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5836    0.7182    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5397   -0.1056    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8043   -0.4795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7604   -1.3034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1128   -0.0296    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3157   -0.2425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1330    0.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9569    0.4937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3615   -0.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9390   -0.8275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5135   -1.5343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9129   -2.2562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7244   -1.7749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8732    1.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6973    1.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9171    0.6588    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2288    0.2041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6055    1.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2507    0.5995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9611   -0.1730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1369   -0.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4158   -0.8614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2394   -0.8117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5061    1.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100    1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 15  1  6  0  0  0
  8 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
  7 23  1  6  0  0  0
 22 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
 22 27  1  0  0  0  0
 26 28  1  1  0  0  0
 28 29  1  0  0  0  0
  5 30  1  1  0  0  0
  3 31  1  6  0  0  0
M  END

     RDKit          3D

 63 67  0  0  0  0  0  0  0  0999 V2000
    6.2513   -1.8234   -0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0573   -2.1985    0.4041 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2159   -1.1001    0.4891 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8311   -1.4088   -0.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0742   -0.1932    0.4972 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1808    0.8480   -0.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8354    0.6143   -1.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0318    0.2908   -0.0998 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7624   -0.4450    0.7458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2665   -0.5184   -0.5165 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9223    0.1042   -1.7206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8469   -1.9109   -0.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8816   -2.9543   -0.6370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2833   -2.4356   -0.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4045   -1.4138    0.4463 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7488   -2.1427    1.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5383   -0.4737    0.1843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6597   -0.8251   -0.2253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0712    0.7789    0.4848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7876    0.7564    1.0283 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9539    1.7816    0.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4906    2.7045   -0.1977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4717    1.6128    0.5048 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1480    1.6588    1.9835 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0888    2.7126   -0.1873 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1271    4.0150    0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5475    5.0601   -0.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8613    4.3127    1.0950 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1881   -0.5982    0.6777 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8900    0.1389    1.7123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8867   -0.8157    1.8339 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9383   -2.6935   -0.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7898   -1.0897    0.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0889   -1.3996   -1.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6404   -0.1764    0.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7877   -1.4275   -1.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4900   -2.3454    0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2731    1.8668   -0.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0183    0.6622   -1.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9436   -0.2202   -1.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5790    1.5742   -1.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9675    0.3748   -1.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3835    1.0201   -2.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8977   -0.5850   -2.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6072   -1.9413   -1.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0439   -2.1646   -0.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7075   -3.4118    0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7341   -3.7902   -1.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6104   -2.0575   -1.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9607   -3.2834   -0.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4768   -1.5584    2.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2493   -3.1107    1.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8479   -2.2600    2.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8199    0.8925    2.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8351    2.1313    2.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0812    0.6136    2.3494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9683    2.1335    2.5560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0835    4.9930   -1.7299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3103    6.0625   -0.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6243    4.8920   -0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6109   -1.0334    1.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2339    0.0341    2.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3043    1.1653    1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
 15 29  1  0
 29 20  1  0
 20 19  1  0
 19 17  1  0
 17 18  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 23 25  1  6
 25 26  1  0
 26 27  1  0
 26 28  2  0
  5 30  1  0
 30 31  1  0
 31  3  1  0
  5  9  1  1
 29 10  1  0
 23  8  1  0
 17 15  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  6
  4 36  1  0
  4 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
 11 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 16 51  1  0
 16 52  1  0
 16 53  1  0
 29 61  1  1
 20 54  1  1
 24 55  1  0
 24 56  1  0
 24 57  1  0
 27 58  1  0
 27 59  1  0
 27 60  1  0
 30 62  1  0
 30 63  1  0
M  END


  Mrv1652304292201372D          

 31 35  0  0  1  0            999 V2000
    0.8999    2.4241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2583    1.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3867    1.0905    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1567    0.7942    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7982    1.3129    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6699    2.1278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5836    0.7182    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5397   -0.1056    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8043   -0.4795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7604   -1.3034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1128   -0.0296    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3157   -0.2425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1330    0.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9569    0.4937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3615   -0.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9390   -0.8275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5135   -1.5343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9129   -2.2562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7244   -1.7749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8732    1.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6973    1.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9171    0.6588    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2288    0.2041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6055    1.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2507    0.5995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9611   -0.1730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1369   -0.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4158   -0.8614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2394   -0.8117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5061    1.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100    1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 15  1  6  0  0  0
  8 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
  7 23  1  6  0  0  0
 22 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
 22 27  1  0  0  0  0
 26 28  1  1  0  0  0
 28 29  1  0  0  0  0
  5 30  1  1  0  0  0
  3 31  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0078571

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1C[C@]2(CC[C@]3(O2)[C@@]2(C)CCC[C@@]4(C)[C@@H]2[C@H](OC4=O)C(=O)[C@]3(C)OC(C)=O)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O8/c1-13(24)30-21(4)17(25)15-16-19(2,18(26)29-15)7-6-8-20(16,3)23(21)10-9-22(31-23)11-14(27-5)28-12-22/h14-16H,6-12H2,1-5H3/t14-,15+,16+,19+,20+,21+,22-,23+/m1/s1

> <INCHI_KEY>
CHGSKJMRTUWQRQ-JTAQILMUSA-N

> <FORMULA>
C23H32O8

> <MOLECULAR_WEIGHT>
436.501

> <EXACT_MASS>
436.20971799

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
45.09346711919097

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <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-methoxy-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>
2.16

> <JCHEM_LOGP>
2.808571681666665

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.117365048550834

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8172729652933746

> <JCHEM_POLAR_SURFACE_AREA>
97.36000000000003

> <JCHEM_REFRACTIVITY>
105.49690000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1''S,3R,4''S,5R,5'S,6''R,8''S,12''R)-5-methoxy-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                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       1.680   4.525   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.482   3.557   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.722   2.036   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.159   1.483   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.357   2.451   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.117   3.972   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.823   1.341   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.741  -0.197   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.368  -0.895   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.286  -2.433   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.077  -0.055   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.589  -0.453   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.248   0.840   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.786   0.922   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.275  -0.333   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.486  -1.545   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.692  -2.864   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.437  -4.212   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.219  -3.313   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.363   2.783   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.902   2.714   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.312   1.230   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.027   0.381   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.597   2.079   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.801   1.119   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.261  -0.323   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.722  -0.255   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.110  -1.608   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      11.647  -1.515   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.678   3.242   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.765   2.436   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   13   31                                             
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7   30                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   20   23                                             
CONECT    8    7    9   15   16                                             
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12    3   14                                                  
CONECT   14   13                                                            
CONECT   15    8                                                            
CONECT   16    8   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    7   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   27                                             
CONECT   23   22    7                                                       
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26   22                                                       
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30    5                                                            
CONECT   31    3                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₂O₈

Average Mass

436.5010 Da

Monoisotopic Mass

436.20972 Da

IUPAC Name

(1''S,3R,4''S,5R,5'S,6''R,8''S,12''R)-5-methoxy-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-methoxy-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

CO[C@H]1C[C@]2(CC[C@]3(O2)[C@@]2(C)CCC[C@@]4(C)[C@@H]2[C@H](OC4=O)C(=O)[C@]3(C)OC(C)=O)CO1

InChI Identifier

InChI=1S/C23H32O8/c1-13(24)30-21(4)17(25)15-16-19(2,18(26)29-15)7-6-8-20(16,3)23(21)10-9-22(31-23)11-14(27-5)28-12-22/h14-16H,6-12H2,1-5H3/t14-,15+,16+,19+,20+,21+,22-,23+/m1/s1

InChI Key

CHGSKJMRTUWQRQ-JTAQILMUSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 persicus	Plant	KNApSAcK

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
Ketone
Lactone
Acetal
Carboxylic acid derivative
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Ether
Organic oxide
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.16	ALOGPS
logP	2.81	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	14.12	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	97.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	105.5 m³·mol⁻¹	ChemAxon
Polarizability	45.09 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

C00042689

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

15834303

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Leopersin N (NP0078571)

MOL for NP0078571 (Leopersin N)

3D MOL for NP0078571 (Leopersin N)

3D SDF for NP0078571 (Leopersin N)

3D-SDF for NP0078571 (Leopersin N)

PDB for NP0078571 (Leopersin N)

3D PDB for NP0078571 (Leopersin N)

SMILES for NP0078571 (Leopersin N)

INCHI for NP0078571 (Leopersin N)

Structure for NP0078571 (Leopersin N)

3D Structure for NP0078571 (Leopersin N)