NP-MRD: Showing NP-Card for (2e,4e)-n-[(1s,2s,4's,5'r,6s)-4-chloro-5'-hydroxy-5-oxo-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-oxolan]-3-en-4'-yl]-4,6-dimethyldodeca-2,4-dienimidic acid (NP0242783)

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Record Information

Version

2.0

Created at

2022-09-07 03:10:30 UTC

Updated at

2022-09-07 03:10:31 UTC

NP-MRD ID

NP0242783

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,4e)-n-[(1s,2s,4's,5'r,6s)-4-chloro-5'-hydroxy-5-oxo-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-oxolan]-3-en-4'-yl]-4,6-dimethyldodeca-2,4-dienimidic acid

Description

Aranochlor B belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. (2e,4e)-n-[(1s,2s,4's,5'r,6s)-4-chloro-5'-hydroxy-5-oxo-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-oxolan]-3-en-4'-yl]-4,6-dimethyldodeca-2,4-dienimidic acid was first documented in 1998 (PMID: 9630868). Based on a literature review very few articles have been published on Aranochlor B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072205102D          

 30 32  0  0  1  0            999 V2000
   -3.6834   -8.1728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3979   -7.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3979   -6.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6834   -6.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9690   -6.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2545   -6.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5400   -6.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5400   -7.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8255   -6.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1111   -6.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1111   -7.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6034   -6.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6034   -5.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3179   -5.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0323   -5.6978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3179   -4.4603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0323   -4.0478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1186   -3.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9256   -3.0558    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4406   -2.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7762   -1.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2913   -0.9673    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5967   -1.5485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9322   -0.7948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0816   -2.2159    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5665   -2.8833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7460   -2.9696    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3381   -3.7703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7860   -4.3834    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9575   -5.1904    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  4  0  0  0
 14 16  2  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 27 26  1  6  0  0  0
 25 27  1  0  0  0  0
 19 27  1  0  0  0  0
 19 28  1  1  0  0  0
 28 29  1  0  0  0  0
 17 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END

     RDKit          3D

 62 64  0  0  0  0  0  0  0  0999 V2000
    1.5721   -3.9947   -3.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8553   -3.4184   -1.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7182   -3.4813   -0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0200   -2.7761   -0.7297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8242   -2.7630    0.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3305   -2.0725    1.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1438   -0.5100    1.5600 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6445   -0.1099    2.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0052   -0.3365    0.7532 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4392    0.2317   -0.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0466    1.0931   -0.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8573    0.8212   -1.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5099    0.8598   -1.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3647    1.4083   -2.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9256    1.8723   -3.5792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6197    1.5462   -2.1052 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4068    1.2571   -0.9875 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8961    2.2164    0.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3835    3.5715   -0.5057 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1857    4.0057   -1.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1022    4.4597   -0.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3540    4.9705   -1.3378 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4036    4.5021    0.8672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7254    4.0098    1.7364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6485    5.2231    1.1176 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7349    4.7418    1.7632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7862    4.5612    0.4357 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4150    3.1992   -1.3945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7962    1.9080   -1.0682 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6373    1.3032   -1.9421 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9616   -3.6785   -3.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5832   -3.5803   -3.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5649   -5.0914   -3.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0291   -4.0808   -1.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4550   -2.4082   -2.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1009   -3.1639    0.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9825   -4.5506   -0.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9946   -1.8357   -1.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6250   -3.4725   -1.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8439   -2.3226    0.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0447   -3.8410    0.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2809   -2.4421    2.0063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9354   -2.2729    2.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0864   -0.0852    1.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4424    0.0832    3.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0480   -1.0119    3.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8537    0.6562    2.8220 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0979   -1.0364    1.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7031    1.6647   -1.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500    0.2443   -0.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0013    1.6387    0.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2786    1.2329   -2.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9474    0.3285   -0.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5544    1.8906   -4.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4601    0.2288   -0.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4968    1.9706    1.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8123    2.2046    0.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1545    3.9941   -2.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5673    6.3143    1.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6336    5.2297    0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2409    1.9941   -0.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0665    0.5339   -1.4778 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
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 23 24  2  0
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 29 17  1  0
 27 25  1  0
 27 19  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
  6 43  1  0
  7 44  1  6
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  8 46  1  0
  8 47  1  0
  9 48  1  0
 11 49  1  0
 11 50  1  0
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 12 52  1  0
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 15 54  1  0
 17 55  1  1
 18 56  1  0
 18 57  1  0
 29 61  1  1
 30 62  1  0
 20 58  1  0
 25 59  1  6
 27 60  1  6
M  END


  Mrv1652309072205102D          

 30 32  0  0  1  0            999 V2000
   -3.6834   -8.1728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3979   -7.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3979   -6.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6834   -6.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9690   -6.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2545   -6.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5400   -6.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5400   -7.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8255   -6.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1111   -6.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1111   -7.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6034   -6.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6034   -5.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3179   -5.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0323   -5.6978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3179   -4.4603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0323   -4.0478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1186   -3.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9256   -3.0558    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4406   -2.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7762   -1.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2913   -0.9673    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5967   -1.5485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9322   -0.7948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0816   -2.2159    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5665   -2.8833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7460   -2.9696    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3381   -3.7703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7860   -4.3834    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9575   -5.1904    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  4  0  0  0
 14 16  2  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 27 26  1  6  0  0  0
 25 27  1  0  0  0  0
 19 27  1  0  0  0  0
 19 28  1  1  0  0  0
 28 29  1  0  0  0  0
 17 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0242783

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC(C)\C=C(/C)\C=C\C(O)=N[C@H]1C[C@]2(O[C@H]1O)C=C(Cl)C(=O)[C@H]1O[C@H]21

> <INCHI_IDENTIFIER>
InChI=1S/C23H32ClNO5/c1-4-5-6-7-8-14(2)11-15(3)9-10-18(26)25-17-13-23(30-22(17)28)12-16(24)19(27)20-21(23)29-20/h9-12,14,17,20-22,28H,4-8,13H2,1-3H3,(H,25,26)/b10-9+,15-11+/t14?,17-,20+,21-,22+,23+/m0/s1

> <INCHI_KEY>
JXZMSDXQKQMWKD-IPANMSLJSA-N

> <FORMULA>
C23H32ClNO5

> <MOLECULAR_WEIGHT>
437.96

> <EXACT_MASS>
437.1969008

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
47.82816042897605

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E)-N-[(1S,2S,4'S,5'R,6S)-4-chloro-5'-hydroxy-5-oxo-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-oxolan]-3-en-4'-yl]-4,6-dimethyldodeca-2,4-dienimidic acid

> <JCHEM_LOGP>
5.031984064333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.807747385591005

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.906655533196851

> <JCHEM_PKA_STRONGEST_BASIC>
2.6926672290818687

> <JCHEM_POLAR_SURFACE_AREA>
91.65

> <JCHEM_REFRACTIVITY>
117.91209999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E)-N-[(1S,2S,4'S,5'R,6S)-4-chloro-5'-hydroxy-5-oxo-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-oxolan]-3-en-4'-yl]-4,6-dimethyldodeca-2,4-dienimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.876 -15.256   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.209 -14.486   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.209 -12.946   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.876 -12.176   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.542 -12.946   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.208 -12.176   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.875 -12.946   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.875 -14.486   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.541 -12.176   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.207 -12.946   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.207 -14.486   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.126 -12.176   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.126 -10.636   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.460  -9.866   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.794 -10.636   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       2.460  -8.326   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       3.794  -7.556   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.955  -6.024   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.461  -5.704   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.556  -4.458   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.182  -3.051   0.000  0.00  0.00           C+0
HETATM   22 Cl   UNK     0       4.277  -1.806   0.000  0.00  0.00          Cl+0
HETATM   23  C   UNK     0       6.714  -2.890   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.340  -1.484   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.619  -4.136   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.524  -5.382   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.993  -5.543   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.231  -7.038   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.201  -8.182   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.521  -9.689   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   29                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   27   28                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25   27                                                       
CONECT   27   26   25   19                                                  
CONECT   28   19   29                                                       
CONECT   29   28   17   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₂ClNO₅

Average Mass

437.9600 Da

Monoisotopic Mass

437.19690 Da

IUPAC Name

(2E,4E)-N-[(1S,2S,4'S,5'R,6S)-4-chloro-5'-hydroxy-5-oxo-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-oxolan]-3-en-4'-yl]-4,6-dimethyldodeca-2,4-dienimidic acid

Traditional Name

(2E,4E)-N-[(1S,2S,4'S,5'R,6S)-4-chloro-5'-hydroxy-5-oxo-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-oxolan]-3-en-4'-yl]-4,6-dimethyldodeca-2,4-dienimidic acid

CAS Registry Number

Not Available

SMILES

CCCCCCC(C)\C=C(/C)\C=C\C(O)=N[C@H]1C[C@]2(O[C@H]1O)C=C(Cl)C(=O)[C@H]1O[C@H]21

InChI Identifier

InChI=1S/C23H32ClNO5/c1-4-5-6-7-8-14(2)11-15(3)9-10-18(26)25-17-13-23(30-22(17)28)12-16(24)19(27)20-21(23)29-20/h9-12,14,17,20-22,28H,4-8,13H2,1-3H3,(H,25,26)/b10-9+,15-11+/t14?,17-,20+,21-,22+,23+/m0/s1

InChI Key

JXZMSDXQKQMWKD-IPANMSLJSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
N-acyl-amine
Alpha-haloketone
Alpha-chloroketone
Oxolane
Carboxamide group
Hemiacetal
Secondary carboxylic acid amide
Oxacycle
Chloroalkene
Dialkyl ether
Oxirane
Ether
Carboxylic acid derivative
Vinyl chloride
Haloalkene
Organoheterocyclic compound
Vinyl halide
Organonitrogen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Organohalogen compound
Organochloride
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	5.03	ChemAxon
pKa (Strongest Acidic)	5.91	ChemAxon
pKa (Strongest Basic)	2.69	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.65 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	117.91 m³·mol⁻¹	ChemAxon
Polarizability	47.83 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

C00016046

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

101942169

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mukhopadhyay T, Bhat RG, Roy K, Vijayakumar EK, Ganguli BN: Aranochlor A and aranochlor B, two new metabolites from Pseudoarachniotus roseus: production, isolation, structure elucidation and biological properties. J Antibiot (Tokyo). 1998 Apr;51(4):439-41. doi: 10.7164/antibiotics.51.439. [PubMed:9630868 ]
LOTUS database [Link]

Showing NP-Card for (2e,4e)-n-[(1s,2s,4's,5'r,6s)-4-chloro-5'-hydroxy-5-oxo-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-oxolan]-3-en-4'-yl]-4,6-dimethyldodeca-2,4-dienimidic acid (NP0242783)

MOL for NP0242783 ((2e,4e)-n-[(1s,2s,4's,5'r,6s)-4-chloro-5'-hydroxy-5-oxo-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-oxolan]-3-en-4'-yl]-4,6-dimethyldodeca-2,4-dienimidic acid)

3D MOL for NP0242783 ((2e,4e)-n-[(1s,2s,4's,5'r,6s)-4-chloro-5'-hydroxy-5-oxo-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-oxolan]-3-en-4'-yl]-4,6-dimethyldodeca-2,4-dienimidic acid)

3D SDF for NP0242783 ((2e,4e)-n-[(1s,2s,4's,5'r,6s)-4-chloro-5'-hydroxy-5-oxo-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-oxolan]-3-en-4'-yl]-4,6-dimethyldodeca-2,4-dienimidic acid)

3D-SDF for NP0242783 ((2e,4e)-n-[(1s,2s,4's,5'r,6s)-4-chloro-5'-hydroxy-5-oxo-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-oxolan]-3-en-4'-yl]-4,6-dimethyldodeca-2,4-dienimidic acid)

PDB for NP0242783 ((2e,4e)-n-[(1s,2s,4's,5'r,6s)-4-chloro-5'-hydroxy-5-oxo-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-oxolan]-3-en-4'-yl]-4,6-dimethyldodeca-2,4-dienimidic acid)

3D PDB for NP0242783 ((2e,4e)-n-[(1s,2s,4's,5'r,6s)-4-chloro-5'-hydroxy-5-oxo-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-oxolan]-3-en-4'-yl]-4,6-dimethyldodeca-2,4-dienimidic acid)

SMILES for NP0242783 ((2e,4e)-n-[(1s,2s,4's,5'r,6s)-4-chloro-5'-hydroxy-5-oxo-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-oxolan]-3-en-4'-yl]-4,6-dimethyldodeca-2,4-dienimidic acid)

INCHI for NP0242783 ((2e,4e)-n-[(1s,2s,4's,5'r,6s)-4-chloro-5'-hydroxy-5-oxo-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-oxolan]-3-en-4'-yl]-4,6-dimethyldodeca-2,4-dienimidic acid)

Structure for NP0242783 ((2e,4e)-n-[(1s,2s,4's,5'r,6s)-4-chloro-5'-hydroxy-5-oxo-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-oxolan]-3-en-4'-yl]-4,6-dimethyldodeca-2,4-dienimidic acid)

3D Structure for NP0242783 ((2e,4e)-n-[(1s,2s,4's,5'r,6s)-4-chloro-5'-hydroxy-5-oxo-7-oxaspiro[bicyclo[4.1.0]heptane-2,2'-oxolan]-3-en-4'-yl]-4,6-dimethyldodeca-2,4-dienimidic acid)