NP-MRD: Showing NP-Card for chloctanspirone A (NP0040992)

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Record Information

Version

2.0

Created at

2021-06-20 23:01:24 UTC

Updated at

2021-06-30 00:15:15 UTC

NP-MRD ID

NP0040992

Secondary Accession Numbers

None

Natural Product Identification

Common Name

chloctanspirone A

Provided By

JEOL Database JEOL Logo

Description

(1S,2R,4R,5'S,6S,6'R,7Z)-3'-chloro-5',6,6'-trihydroxy-7-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,6-dimethylspiro[bicyclo[2.2.2]Octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione 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. chloctanspirone A is found in Penicillium solitum and Penicillium terrestre. chloctanspirone A was first documented in 2011 (Li, D., et al.). Based on a literature review very few articles have been published on (1S,2R,4R,5'S,6S,6'R,7Z)-3'-chloro-5',6,6'-trihydroxy-7-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,6-dimethylspiro[bicyclo[2.2.2]Octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101013D          

 52 54  0  0  0  0            999 V2000
    5.0196   -5.5608    2.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6997   -4.5779    1.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8456   -3.5547    1.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5517   -2.6203    0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6983   -1.5916    0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3725   -0.6342   -0.5076 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0589   -0.8581   -1.6872 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5025    0.3845   -0.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2319    1.3435   -1.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8130    1.2454   -2.5695 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2303    2.4388   -1.1388 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0105    3.4036   -2.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0899    1.7527   -0.7111 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8506    0.7446    0.4730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1716   -0.7051    0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0765   -1.0463   -1.1472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4895   -1.7108    1.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5298   -3.3739    0.6573 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6954   -1.3337    2.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6976    0.0899    2.8171 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8264    0.2635    3.6713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8338    1.0608    1.6281 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.6822    0.7879    0.8619 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1304    2.2220    1.2717 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6319    2.3465    1.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4563    2.6030    2.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7304    3.1594    0.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7414    4.3804    0.2588 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7560   -6.5713    2.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0916   -5.5381    2.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4777   -5.3496    3.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2055   -4.7332    0.3611 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3427   -3.4098    2.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0551   -2.7818   -0.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2153   -1.4712    1.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3497    2.8784   -3.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7231    4.1763   -2.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7574    0.7928    1.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8584    0.1135    1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8699    3.3370    1.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9487    1.6169    2.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2415    2.2128    0.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6325    3.5610    2.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 28  1  0  0  0  0
 15 16  2  0  0  0  0
 25 28  1  0  0  0  0
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 11  9  1  0  0  0  0
 11 12  1  6  0  0  0
 25 26  1  0  0  0  0
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 13 41  1  0  0  0  0
 13 42  1  0  0  0  0
  5 36  1  0  0  0  0
  4 35  1  0  0  0  0
  3 34  1  0  0  0  0
  2 33  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  7 37  1  0  0  0  0
 23 47  1  0  0  0  0
 21 45  1  0  0  0  0
 12 38  1  0  0  0  0
 12 39  1  0  0  0  0
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 26 49  1  0  0  0  0
 26 50  1  0  0  0  0
 26 51  1  0  0  0  0
 27 52  1  0  0  0  0
M  END

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
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    3.8456   -3.5547    1.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2319    1.3435   -1.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2303    2.4388   -1.1388 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0105    3.4036   -2.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4895   -1.7108    1.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6976    0.0899    2.8171 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8264    0.2635    3.6713 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1820    0.9996    1.1202 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6822    0.7879    0.8619 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1304    2.2220    1.2717 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.4563    2.6030    2.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0551   -2.7818   -0.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5500    1.2580   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7972    2.5348   -0.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7360    2.0887    1.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6325    3.5610    2.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
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 15 16  2  0
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M  END


  Mrv1652306212101013D          

 52 54  0  0  0  0            999 V2000
    5.0196   -5.5608    2.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6997   -4.5779    1.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8456   -3.5547    1.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5517   -2.6203    0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6983   -1.5916    0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3725   -0.6342   -0.5076 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0589   -0.8581   -1.6872 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5025    0.3845   -0.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2319    1.3435   -1.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8130    1.2454   -2.5695 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2303    2.4388   -1.1388 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0105    3.4036   -2.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0899    1.7527   -0.7111 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.0765   -1.0463   -1.1472 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0916   -5.5381    2.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2055   -4.7332    0.3611 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3427   -3.4098    2.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2153   -1.4712    1.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3497    2.8784   -3.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7231    4.1763   -2.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5500    1.2580   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7972    2.5348   -0.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8940   -2.0846    3.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7904    0.2837    3.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6747    1.0772    4.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7360    2.0887    1.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7574    0.7928    1.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8584    0.1135    1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8699    3.3370    1.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9487    1.6169    2.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2415    2.2128    0.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6325    3.5610    2.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 28  1  0  0  0  0
 15 16  2  0  0  0  0
 25 28  1  0  0  0  0
 22 20  1  0  0  0  0
 28 29  2  0  0  0  0
  9  8  1  0  0  0  0
 17 18  1  0  0  0  0
  9 10  2  0  0  0  0
 14 22  1  0  0  0  0
  8  6  2  0  0  0  0
 14 24  1  0  0  0  0
  6  5  1  0  0  0  0
 20 19  1  0  0  0  0
  5  4  2  0  0  0  0
 24  8  1  0  0  0  0
  4  3  1  0  0  0  0
 19 17  2  0  0  0  0
  3  2  2  0  0  0  0
 14 13  1  0  0  0  0
  2  1  1  0  0  0  0
 17 15  1  0  0  0  0
  6  7  1  0  0  0  0
 13 11  1  0  0  0  0
 22 23  1  0  0  0  0
 20 21  1  0  0  0  0
 11  9  1  0  0  0  0
 11 12  1  6  0  0  0
 25 26  1  0  0  0  0
 24 25  1  0  0  0  0
 25 27  1  1  0  0  0
 14 15  1  6  0  0  0
 22 46  1  1  0  0  0
 20 44  1  1  0  0  0
 19 43  1  0  0  0  0
 24 48  1  1  0  0  0
 13 41  1  0  0  0  0
 13 42  1  0  0  0  0
  5 36  1  0  0  0  0
  4 35  1  0  0  0  0
  3 34  1  0  0  0  0
  2 33  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  7 37  1  0  0  0  0
 23 47  1  0  0  0  0
 21 45  1  0  0  0  0
 12 38  1  0  0  0  0
 12 39  1  0  0  0  0
 12 40  1  0  0  0  0
 26 49  1  0  0  0  0
 26 50  1  0  0  0  0
 26 51  1  0  0  0  0
 27 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040992

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O\C(\C(\[H])=C(/[H])\C(\[H])=C(/[H])C([H])([H])[H])=C1/C(=O)[C@@]2(C(=O)[C@](O[H])(C([H])([H])[H])[C@@]1([H])[C@]1(C(=O)C(Cl)=C([H])[C@]([H])(O[H])[C@]1([H])O[H])C2([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H23ClO7/c1-4-5-6-7-11(23)13-14-20(3,29)18(28)19(2,17(13)27)9-21(14)15(25)10(22)8-12(24)16(21)26/h4-8,12,14,16,23-24,26,29H,9H2,1-3H3/b5-4+,7-6+,13-11-/t12-,14-,16-,19+,20-,21-/m0/s1

> <INCHI_KEY>
PHXAMGFMNFACCT-ZTZVJVCXSA-N

> <FORMULA>
C21H23ClO7

> <MOLECULAR_WEIGHT>
422.86

> <EXACT_MASS>
422.1132308

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
41.74611661035094

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,4R,5'S,6Z,6'R,7S)-3'-chloro-5',6',7-trihydroxy-6-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,7-dimethylspiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione

> <ALOGPS_LOGP>
1.38

> <JCHEM_LOGP>
1.631117004

> <ALOGPS_LOGS>
-3.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.820901086631153

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.028633109642174

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3748520015416856

> <JCHEM_POLAR_SURFACE_AREA>
132.13

> <JCHEM_REFRACTIVITY>
109.79719999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4R,5'S,6Z,6'R,7S)-3'-chloro-5',6',7-trihydroxy-6-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,7-dimethylspiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
    5.0196   -5.5608    2.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6997   -4.5779    1.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8456   -3.5547    1.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5517   -2.6203    0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6983   -1.5916    0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3725   -0.6342   -0.5076 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0589   -0.8581   -1.6872 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5025    0.3845   -0.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2319    1.3435   -1.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8130    1.2454   -2.5695 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2303    2.4388   -1.1388 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0105    3.4036   -2.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0899    1.7527   -0.7111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8506    0.7446    0.4730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1716   -0.7051    0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0765   -1.0463   -1.1472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4895   -1.7108    1.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5298   -3.3739    0.6573 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6954   -1.3337    2.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6976    0.0899    2.8171 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8264    0.2635    3.6713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8338    1.0608    1.6281 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1820    0.9996    1.1202 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6822    0.7879    0.8619 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1304    2.2220    1.2717 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6319    2.3465    1.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4563    2.6030    2.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7304    3.1594    0.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7414    4.3804    0.2588 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7560   -6.5713    2.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0916   -5.5381    2.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4777   -5.3496    3.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2055   -4.7332    0.3611 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3427   -3.4098    2.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0551   -2.7818   -0.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2153   -1.4712    1.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7539   -0.2155   -2.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9426    3.9129   -2.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3497    2.8784   -3.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7231    4.1763   -2.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5500    1.2580   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7972    2.5348   -0.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8940   -2.0846    3.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7904    0.2837    3.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6747    1.0772    4.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7360    2.0887    1.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7574    0.7928    1.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8584    0.1135    1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8699    3.3370    1.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9487    1.6169    2.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2415    2.2128    0.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6325    3.5610    2.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 28  1  0
 15 16  2  0
 25 28  1  0
 22 20  1  0
 28 29  2  0
  9  8  1  0
 17 18  1  0
  9 10  2  0
 14 22  1  0
  8  6  2  0
 14 24  1  0
  6  5  1  0
 20 19  1  0
  5  4  2  0
 24  8  1  0
  4  3  1  0
 19 17  2  0
  3  2  2  0
 14 13  1  0
  2  1  1  0
 17 15  1  0
  6  7  1  0
 13 11  1  0
 22 23  1  0
 20 21  1  0
 11  9  1  0
 11 12  1  6
 25 26  1  0
 24 25  1  0
 25 27  1  1
 14 15  1  6
 22 46  1  1
 20 44  1  1
 19 43  1  0
 24 48  1  1
 13 41  1  0
 13 42  1  0
  5 36  1  0
  4 35  1  0
  3 34  1  0
  2 33  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  7 37  1  0
 23 47  1  0
 21 45  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 26 49  1  0
 26 50  1  0
 26 51  1  0
 27 52  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       5.020  -5.561   2.391  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.700  -4.578   1.312  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.846  -3.555   1.462  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.552  -2.620   0.398  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.698  -1.592   0.538  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.373  -0.634  -0.508  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.059  -0.858  -1.687  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.502   0.385  -0.362  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.232   1.343  -1.495  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.813   1.245  -2.570  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.230   2.439  -1.139  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.011   3.404  -2.298  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.090   1.753  -0.711  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.851   0.745   0.473  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.172  -0.705   0.031  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.077  -1.046  -1.147  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.490  -1.711   1.099  0.00  0.00           C+0
HETATM   18 Cl   UNK     0      -1.530  -3.374   0.657  0.00  0.00          Cl+0
HETATM   19  C   UNK     0      -1.695  -1.334   2.369  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.698   0.090   2.817  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.826   0.264   3.671  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.834   1.061   1.628  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.182   1.000   1.120  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.682   0.788   0.862  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.130   2.222   1.272  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.632   2.346   1.547  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.456   2.603   2.468  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.730   3.159   0.116  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.741   4.380   0.259  0.00  0.00           O+0
HETATM   30  H   UNK     0       4.756  -6.571   2.064  0.00  0.00           H+0
HETATM   31  H   UNK     0       6.092  -5.538   2.609  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.478  -5.350   3.318  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.205  -4.733   0.361  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.343  -3.410   2.415  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.055  -2.782  -0.555  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.215  -1.471   1.501  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.754  -0.216  -2.365  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.943   3.913  -2.569  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.350   2.878  -3.189  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.723   4.176  -2.042  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.550   1.258  -1.575  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.797   2.535  -0.403  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.894  -2.085   3.130  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.790   0.284   3.399  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.675   1.077   4.186  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.736   2.089   1.985  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.757   0.793   1.887  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.858   0.114   1.704  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.870   3.337   1.953  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.949   1.617   2.300  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.241   2.213   0.648  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.633   3.561   2.588  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    3    1   33                                                  
CONECT    3    4    2   34                                                  
CONECT    4    5    3   35                                                  
CONECT    5    6    4   36                                                  
CONECT    6    8    5    7                                                  
CONECT    7    6   37                                                       
CONECT    8    9    6   24                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11   28   13    9   12                                             
CONECT   12   11   38   39   40                                             
CONECT   13   14   11   41   42                                             
CONECT   14   22   24   13   15                                             
CONECT   15   16   17   14                                                  
CONECT   16   15                                                            
CONECT   17   18   19   15                                                  
CONECT   18   17                                                            
CONECT   19   20   17   43                                                  
CONECT   20   22   19   21   44                                             
CONECT   21   20   45                                                       
CONECT   22   20   14   23   46                                             
CONECT   23   22   47                                                       
CONECT   24   14    8   25   48                                             
CONECT   25   28   26   24   27                                             
CONECT   26   25   49   50   51                                             
CONECT   27   25   52                                                       
CONECT   28   11   25   29                                                  
CONECT   29   28                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    2                                                            
CONECT   34    3                                                            
CONECT   35    4                                                            
CONECT   36    5                                                            
CONECT   37    7                                                            
CONECT   38   12                                                            
CONECT   39   12                                                            
CONECT   40   12                                                            
CONECT   41   13                                                            
CONECT   42   13                                                            
CONECT   43   19                                                            
CONECT   44   20                                                            
CONECT   45   21                                                            
CONECT   46   22                                                            
CONECT   47   23                                                            
CONECT   48   24                                                            
CONECT   49   26                                                            
CONECT   50   26                                                            
CONECT   51   26                                                            
CONECT   52   27                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  108    0
END

RDKit          3D

52 54  0  0  0  0  0  0  0  0999 V2000
    5.0196   -5.5608    2.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6997   -4.5779    1.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8456   -3.5547    1.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5517   -2.6203    0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6983   -1.5916    0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3725   -0.6342   -0.5076 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0589   -0.8581   -1.6872 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5025    0.3845   -0.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2319    1.3435   -1.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8130    1.2454   -2.5695 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2303    2.4388   -1.1388 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0105    3.4036   -2.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0899    1.7527   -0.7111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8506    0.7446    0.4730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1716   -0.7051    0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0765   -1.0463   -1.1472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4895   -1.7108    1.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5298   -3.3739    0.6573 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6954   -1.3337    2.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6976    0.0899    2.8171 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8264    0.2635    3.6713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8338    1.0608    1.6281 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1820    0.9996    1.1202 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6822    0.7879    0.8619 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1304    2.2220    1.2717 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6319    2.3465    1.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4563    2.6030    2.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7304    3.1594    0.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7414    4.3804    0.2588 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7560   -6.5713    2.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0916   -5.5381    2.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4777   -5.3496    3.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2055   -4.7332    0.3611 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3427   -3.4098    2.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0551   -2.7818   -0.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2153   -1.4712    1.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7539   -0.2155   -2.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9426    3.9129   -2.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3497    2.8784   -3.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7231    4.1763   -2.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5500    1.2580   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7972    2.5348   -0.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8940   -2.0846    3.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7904    0.2837    3.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6747    1.0772    4.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7360    2.0887    1.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7574    0.7928    1.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8584    0.1135    1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8699    3.3370    1.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9487    1.6169    2.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2415    2.2128    0.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6325    3.5610    2.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 28  1  0
 15 16  2  0
 25 28  1  0
 22 20  1  0
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  9  8  1  0
 17 18  1  0
  9 10  2  0
 14 22  1  0
  8  6  2  0
 14 24  1  0
  6  5  1  0
 20 19  1  0
  5  4  2  0
 24  8  1  0
  4  3  1  0
 19 17  2  0
  3  2  2  0
 14 13  1  0
  2  1  1  0
 17 15  1  0
  6  7  1  0
 13 11  1  0
 22 23  1  0
 20 21  1  0
 11  9  1  0
 11 12  1  6
 25 26  1  0
 24 25  1  0
 25 27  1  1
 14 15  1  6
 22 46  1  1
 20 44  1  1
 19 43  1  0
 24 48  1  1
 13 41  1  0
 13 42  1  0
  5 36  1  0
  4 35  1  0
  3 34  1  0
  2 33  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  7 37  1  0
 23 47  1  0
 21 45  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 26 49  1  0
 26 50  1  0
 26 51  1  0
 27 52  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₃ClO₇

Average Mass

422.8600 Da

Monoisotopic Mass

422.11323 Da

IUPAC Name

(1S,2R,4R,5'S,6Z,6'R,7S)-3'-chloro-5',6',7-trihydroxy-6-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,7-dimethylspiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione

Traditional Name

(1S,2R,4R,5'S,6Z,6'R,7S)-3'-chloro-5',6',7-trihydroxy-6-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-4,7-dimethylspiro[bicyclo[2.2.2]octane-2,1'-cyclohexan]-3'-ene-2',5,8-trione

CAS Registry Number

Not Available

SMILES

[H]O\C(\C(\[H])=C(/[H])\C(\[H])=C(/[H])C([H])([H])[H])=C1/C(=O)[C@@]2(C(=O)[C@](O[H])(C([H])([H])[H])[C@@]1([H])[C@]1(C(=O)C(Cl)=C([H])[C@]([H])(O[H])[C@]1([H])O[H])C2([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C21H23ClO7/c1-4-5-6-7-11(23)13-14-20(3,29)18(28)19(2,17(13)27)9-21(14)15(25)10(22)8-12(24)16(21)26/h4-8,12,14,16,23-24,26,29H,9H2,1-3H3/b5-4+,7-6+,13-11-/t12-,14-,16-,19+,20-,21-/m0/s1

InChI Key

PHXAMGFMNFACCT-ZTZVJVCXSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, 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
Penicillium solitum	LOTUS Database	35616633
Penicillium terrestre	JEOL database	Li, D., et al, Tetrahedron 67, 7913 (2011)

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
Acyloin
Alpha-haloketone
Alpha-chloroketone
Cyclic alcohol
Vinylogous acid
Tertiary alcohol
Secondary alcohol
Chloroalkene
Haloalkene
Vinyl halide
Vinyl chloride
Polyol
Enol
Organic oxide
Organohalogen compound
Organochloride
Hydrocarbon derivative
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.38	ALOGPS
logP	1.63	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.03	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	109.8 m³·mol⁻¹	ChemAxon
Polarizability	41.75 Å³	ChemAxon
Number of Rings	3	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

29214494

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54772158

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li, D., et al. (2011). Li, D., et al, Tetrahedron 67, 7913 (2011). Tetrahedron.

Showing NP-Card for chloctanspirone A (NP0040992)

MOL for NP0040992 (chloctanspirone A)

3D MOL for NP0040992 (chloctanspirone A)

3D SDF for NP0040992 (chloctanspirone A)

3D-SDF for NP0040992 (chloctanspirone A)

PDB for NP0040992 (chloctanspirone A)

3D PDB for NP0040992 (chloctanspirone A)

SMILES for NP0040992 (chloctanspirone A)

INCHI for NP0040992 (chloctanspirone A)

Structure for NP0040992 (chloctanspirone A)

3D Structure for NP0040992 (chloctanspirone A)