NP-MRD: Showing NP-Card for Tagetenolone (NP0003657)

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Record Information

Version

2.0

Created at

2020-12-09 00:50:57 UTC

Updated at

2021-07-15 16:47:01 UTC

NP-MRD ID

NP0003657

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tagetenolone

Provided By

NPAtlas

Description

Tagetenolone is found in Alternaria tagetica. Tagetenolone was first documented in 2001 (PMID: 11312841). Based on a literature review very few articles have been published on 4-hydroxy-6-[4-hydroxy-6-(hydroxymethyl)-2-methoxy-3-methylphenyl]-5-methylhex-3-en-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117493D          

 43 43  0  0  0  0            999 V2000
   -2.4763   -2.6622    0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5253   -1.6862    1.0677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6532   -0.3804    0.5217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5421    0.4879    1.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3374    0.0537    2.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7121    1.7323    0.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5756    2.6330    1.2923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0283    2.1037   -0.4661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1744    1.2506   -1.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4656    1.7068   -2.3407 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5108    1.9731   -3.3017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9432   -0.0180   -0.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0476   -0.9635   -1.2251 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2350   -1.2798   -0.5879 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8597   -2.4043   -1.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3224   -0.3572   -0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9728    0.2437   -1.4669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7988   -0.0037    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9166    0.9465    0.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4432    1.2587    2.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4150    1.4705   -0.0449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7240   -2.5510   -0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4618   -2.4348    1.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1737   -3.6234    0.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3538   -0.3551    2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8212   -0.6950    2.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6335    0.9045    2.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7624    3.5689    1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1564    3.1057   -0.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178    1.2492   -2.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1974    2.8176   -2.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9898    1.0477   -3.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1766   -0.6834   -2.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5830   -1.9540   -1.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0962   -1.8642    0.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3808   -3.1350   -0.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1114   -2.8081   -2.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6056   -1.8559   -2.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9232   -0.2083   -1.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3854   -0.3764    1.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6357    1.6478    2.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3476    1.8699    2.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8052    0.2280    2.6914 H   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  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 12  3  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  5 25  1  0  0  0  0
  5 26  1  0  0  0  0
  5 27  1  0  0  0  0
  7 28  1  0  0  0  0
  8 29  1  0  0  0  0
 10 30  1  0  0  0  0
 10 31  1  0  0  0  0
 11 32  1  0  0  0  0
 13 33  1  0  0  0  0
 13 34  1  0  0  0  0
 14 35  1  1  0  0  0
 15 36  1  0  0  0  0
 15 37  1  0  0  0  0
 15 38  1  0  0  0  0
 17 39  1  0  0  0  0
 18 40  1  0  0  0  0
 20 41  1  0  0  0  0
 20 42  1  0  0  0  0
 20 43  1  0  0  0  0
M  END

     RDKit          3D

 43 43  0  0  0  0  0  0  0  0999 V2000
   -2.4763   -2.6622    0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5253   -1.6862    1.0677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6532   -0.3804    0.5217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5421    0.4879    1.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3374    0.0537    2.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7121    1.7323    0.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5756    2.6330    1.2923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0283    2.1037   -0.4661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1744    1.2506   -1.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4656    1.7068   -2.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5108    1.9731   -3.3017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9432   -0.0180   -0.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0476   -0.9635   -1.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2350   -1.2798   -0.5879 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8597   -2.4043   -1.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3224   -0.3572   -0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9728    0.2437   -1.4669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7988   -0.0037    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9166    0.9465    0.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4432    1.2587    2.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4150    1.4705   -0.0449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7240   -2.5510   -0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4618   -2.4348    1.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1737   -3.6234    0.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3538   -0.3551    2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8212   -0.6950    2.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6335    0.9045    2.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7624    3.5689    1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1564    3.1057   -0.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178    1.2492   -2.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1974    2.8176   -2.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9898    1.0477   -3.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1766   -0.6834   -2.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5830   -1.9540   -1.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0962   -1.8642    0.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3808   -3.1350   -0.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1114   -2.8081   -2.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6056   -1.8559   -2.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9232   -0.2083   -1.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3854   -0.3764    1.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6357    1.6478    2.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3476    1.8699    2.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8052    0.2280    2.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 12  3  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  5 26  1  0
  5 27  1  0
  7 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  1
 15 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 20 41  1  0
 20 42  1  0
 20 43  1  0
M  END


  Mrv1652306242117493D          

 43 43  0  0  0  0            999 V2000
   -2.4763   -2.6622    0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5253   -1.6862    1.0677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6532   -0.3804    0.5217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5421    0.4879    1.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3374    0.0537    2.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7121    1.7323    0.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5756    2.6330    1.2923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0283    2.1037   -0.4661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1744    1.2506   -1.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4656    1.7068   -2.3407 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5108    1.9731   -3.3017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9432   -0.0180   -0.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0476   -0.9635   -1.2251 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2350   -1.2798   -0.5879 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8597   -2.4043   -1.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3224   -0.3572   -0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9728    0.2437   -1.4669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7988   -0.0037    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9166    0.9465    0.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4432    1.2587    2.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4150    1.4705   -0.0449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7240   -2.5510   -0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4618   -2.4348    1.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1737   -3.6234    0.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3538   -0.3551    2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8212   -0.6950    2.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6335    0.9045    2.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7624    3.5689    1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1564    3.1057   -0.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178    1.2492   -2.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1974    2.8176   -2.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9898    1.0477   -3.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1766   -0.6834   -2.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5830   -1.9540   -1.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0962   -1.8642    0.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3808   -3.1350   -0.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1114   -2.8081   -2.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6056   -1.8559   -2.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9232   -0.2083   -1.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3854   -0.3764    1.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6357    1.6478    2.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3476    1.8699    2.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8052    0.2280    2.6914 H   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  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 12  3  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  5 25  1  0  0  0  0
  5 26  1  0  0  0  0
  5 27  1  0  0  0  0
  7 28  1  0  0  0  0
  8 29  1  0  0  0  0
 10 30  1  0  0  0  0
 10 31  1  0  0  0  0
 11 32  1  0  0  0  0
 13 33  1  0  0  0  0
 13 34  1  0  0  0  0
 14 35  1  1  0  0  0
 15 36  1  0  0  0  0
 15 37  1  0  0  0  0
 15 38  1  0  0  0  0
 17 39  1  0  0  0  0
 18 40  1  0  0  0  0
 20 41  1  0  0  0  0
 20 42  1  0  0  0  0
 20 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003657

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O\C(=C(\[H])C(=O)C([H])([H])[H])[C@]([H])(C([H])([H])[H])C([H])([H])C1=C(C([H])=C(O[H])C(=C1OC([H])([H])[H])C([H])([H])[H])C([H])([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H22O5/c1-9(14(19)6-10(2)18)5-13-12(8-17)7-15(20)11(3)16(13)21-4/h6-7,9,17,19-20H,5,8H2,1-4H3/b14-6-/t9-/m1/s1

> <INCHI_KEY>
VMNFFGLULPDOOU-UHFFFAOYSA-N

> <FORMULA>
C16H22O5

> <MOLECULAR_WEIGHT>
294.347

> <EXACT_MASS>
294.146723808

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.63193577752877

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3Z,5R)-4-hydroxy-6-[4-hydroxy-6-(hydroxymethyl)-2-methoxy-3-methylphenyl]-5-methylhex-3-en-2-one

> <ALOGPS_LOGP>
1.72

> <JCHEM_LOGP>
2.0952026146666665

> <ALOGPS_LOGS>
-3.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.176782244916327

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.171362743634935

> <JCHEM_PKA_STRONGEST_BASIC>
-2.829305037389318

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
82.63209999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3Z,5R)-4-hydroxy-6-[4-hydroxy-6-(hydroxymethyl)-2-methoxy-3-methylphenyl]-5-methylhex-3-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 43 43  0  0  0  0  0  0  0  0999 V2000
   -2.4763   -2.6622    0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5253   -1.6862    1.0677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6532   -0.3804    0.5217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5421    0.4879    1.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3374    0.0537    2.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7121    1.7323    0.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5756    2.6330    1.2923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0283    2.1037   -0.4661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1744    1.2506   -1.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4656    1.7068   -2.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5108    1.9731   -3.3017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9432   -0.0180   -0.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0476   -0.9635   -1.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2350   -1.2798   -0.5879 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8597   -2.4043   -1.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3224   -0.3572   -0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9728    0.2437   -1.4669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7988   -0.0037    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9166    0.9465    0.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4432    1.2587    2.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4150    1.4705   -0.0449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7240   -2.5510   -0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4618   -2.4348    1.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1737   -3.6234    0.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3538   -0.3551    2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8212   -0.6950    2.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6335    0.9045    2.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7624    3.5689    1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1564    3.1057   -0.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178    1.2492   -2.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1974    2.8176   -2.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9898    1.0477   -3.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1766   -0.6834   -2.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5830   -1.9540   -1.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0962   -1.8642    0.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3808   -3.1350   -0.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1114   -2.8081   -2.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6056   -1.8559   -2.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9232   -0.2083   -1.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3854   -0.3764    1.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6357    1.6478    2.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3476    1.8699    2.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8052    0.2280    2.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 12  3  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  5 26  1  0
  5 27  1  0
  7 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  1
 15 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 20 41  1  0
 20 42  1  0
 20 43  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.476  -2.662   0.609  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.525  -1.686   1.068  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.653  -0.380   0.522  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.542   0.488   1.182  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.337   0.054   2.342  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.712   1.732   0.668  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.576   2.633   1.292  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.028   2.104  -0.466  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.174   1.251  -1.086  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.466   1.707  -2.341  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.511   1.973  -3.302  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.943  -0.018  -0.616  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.048  -0.964  -1.225  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.235  -1.280  -0.588  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.860  -2.404  -1.518  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.322  -0.357  -0.349  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.973   0.244  -1.467  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.799  -0.004   0.806  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.917   0.947   0.969  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.443   1.259   2.325  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.415   1.470  -0.045  0.00  0.00           O+0
HETATM   22  H   UNK     0      -2.724  -2.551  -0.465  0.00  0.00           H+0
HETATM   23  H   UNK     0      -3.462  -2.435   1.121  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.174  -3.623   0.963  0.00  0.00           H+0
HETATM   25  H   UNK     0      -4.354  -0.355   2.001  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.821  -0.695   2.945  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.634   0.905   2.977  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.762   3.569   1.055  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.156   3.106  -0.846  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.418   1.249  -2.637  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.197   2.818  -2.104  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.990   1.048  -3.368  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.177  -0.683  -2.321  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.583  -1.954  -1.378  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.096  -1.864   0.380  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.381  -3.135  -0.905  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.111  -2.808  -2.195  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.606  -1.856  -2.131  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.923  -0.208  -1.572  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.385  -0.376   1.742  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.636   1.648   2.997  0.00  0.00           H+0
HETATM   42  H   UNK     0       5.348   1.870   2.270  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.805   0.228   2.691  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4   25   26   27                                             
CONECT    6    4    7    8                                                  
CONECT    7    6   28                                                       
CONECT    8    6    9   29                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11   30   31                                             
CONECT   11   10   32                                                       
CONECT   12    9   13    3                                                  
CONECT   13   12   14   33   34                                             
CONECT   14   13   15   16   35                                             
CONECT   15   14   36   37   38                                             
CONECT   16   14   17   18                                                  
CONECT   17   16   39                                                       
CONECT   18   16   19   40                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   41   42   43                                             
CONECT   21   19                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    5                                                            
CONECT   26    5                                                            
CONECT   27    5                                                            
CONECT   28    7                                                            
CONECT   29    8                                                            
CONECT   30   10                                                            
CONECT   31   10                                                            
CONECT   32   11                                                            
CONECT   33   13                                                            
CONECT   34   13                                                            
CONECT   35   14                                                            
CONECT   36   15                                                            
CONECT   37   15                                                            
CONECT   38   15                                                            
CONECT   39   17                                                            
CONECT   40   18                                                            
CONECT   41   20                                                            
CONECT   42   20                                                            
CONECT   43   20                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   86    0
END

RDKit          3D

43 43  0  0  0  0  0  0  0  0999 V2000
   -2.4763   -2.6622    0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5253   -1.6862    1.0677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6532   -0.3804    0.5217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5421    0.4879    1.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3374    0.0537    2.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7121    1.7323    0.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5756    2.6330    1.2923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0283    2.1037   -0.4661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1744    1.2506   -1.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4656    1.7068   -2.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5108    1.9731   -3.3017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9432   -0.0180   -0.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0476   -0.9635   -1.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2350   -1.2798   -0.5879 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8597   -2.4043   -1.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3224   -0.3572   -0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9728    0.2437   -1.4669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7988   -0.0037    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9166    0.9465    0.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4432    1.2587    2.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4150    1.4705   -0.0449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7240   -2.5510   -0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4618   -2.4348    1.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1737   -3.6234    0.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3538   -0.3551    2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8212   -0.6950    2.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6335    0.9045    2.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7624    3.5689    1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1564    3.1057   -0.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178    1.2492   -2.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1974    2.8176   -2.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9898    1.0477   -3.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1766   -0.6834   -2.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5830   -1.9540   -1.3780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0962   -1.8642    0.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3808   -3.1350   -0.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1114   -2.8081   -2.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6056   -1.8559   -2.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9232   -0.2083   -1.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3854   -0.3764    1.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6357    1.6478    2.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3476    1.8699    2.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8052    0.2280    2.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 12  3  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  5 26  1  0
  5 27  1  0
  7 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  1
 15 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 20 41  1  0
 20 42  1  0
 20 43  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₆H₂₂O₅

Average Mass

294.3470 Da

Monoisotopic Mass

294.14672 Da

IUPAC Name

(3Z,5R)-4-hydroxy-6-[4-hydroxy-6-(hydroxymethyl)-2-methoxy-3-methylphenyl]-5-methylhex-3-en-2-one

Traditional Name

(3Z,5R)-4-hydroxy-6-[4-hydroxy-6-(hydroxymethyl)-2-methoxy-3-methylphenyl]-5-methylhex-3-en-2-one

CAS Registry Number

Not Available

SMILES

COC1=C(CC(C)C(O)=CC(C)=O)C(CO)=CC(O)=C1C

InChI Identifier

InChI=1S/C16H22O5/c1-9(14(19)6-10(2)18)5-13-12(8-17)7-15(20)11(3)16(13)21-4/h6-7,9,17,19-20H,5,8H2,1-4H3

InChI Key

VMNFFGLULPDOOU-UHFFFAOYSA-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
Alternaria tagetica	NPAtlas	11312841

Chemical Taxonomy

Classification

Not classified

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	1.72	ALOGPS
logP	2.1	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.17	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	82.63 m³·mol⁻¹	ChemAxon
Polarizability	31.63 Å³	ChemAxon
Number of Rings	1	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

NPAtlas ID

NPA012522

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78435982

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85196914

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gamboa-Angulo MM, Garcia-Sosa K, Alejos-Gonzalez F, Escalante-Erosa F, Delgado-Lamas G, Pena-Rodriguez LM: Tagetolone and tagetenolone: two phytotoxic polyketides from Alternaria tagetica. J Agric Food Chem. 2001 Mar;49(3):1228-32. doi: 10.1021/jf000872k. [PubMed:11312841 ]

Showing NP-Card for Tagetenolone (NP0003657)

MOL for NP0003657 (Tagetenolone)

3D MOL for NP0003657 (Tagetenolone)

3D SDF for NP0003657 (Tagetenolone)

3D-SDF for NP0003657 (Tagetenolone)

PDB for NP0003657 (Tagetenolone)

3D PDB for NP0003657 (Tagetenolone)

SMILES for NP0003657 (Tagetenolone)

INCHI for NP0003657 (Tagetenolone)

Structure for NP0003657 (Tagetenolone)

3D Structure for NP0003657 (Tagetenolone)