NP-MRD: Showing NP-Card for Hebelophyllene F (NP0001590)

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Record Information

Version

1.0

Created at

2020-09-23 01:57:42 UTC

Updated at

2021-08-10 02:55:29 UTC

NP-MRD ID

NP0001590

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hebelophyllene F

Provided By

NPAtlas

Description

Methyl 2-[(1S)-2-[(2S)-2-hydroxy-3-(oxiran-2-yl)but-3-en-1-yl]-3,3-dimethylcyclobutyl]prop-2-enoate belongs to the class of organic compounds known as enoate esters. These are an alpha,beta-unsaturated carboxylic ester of general formula R1C(R2)=C(R3)C(=O)OR4 (R4= organyl compound) in which the ester C=O function is conjugated to a C=C double bond at the alpha,beta position. Hebelophyllene F is found in Hebeloma longicaudum. It was first documented in 1999 (PMID: 10096864). Based on a literature review very few articles have been published on methyl 2-[(1S)-2-[(2S)-2-hydroxy-3-(oxiran-2-yl)but-3-en-1-yl]-3,3-dimethylcyclobutyl]prop-2-enoate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117433D          

 44 45  0  0  0  0            999 V2000
   -2.9805    1.7523   -1.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2446    0.4886   -0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6637    0.0349   -0.6411 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0175   -0.5028    0.7271 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5142    0.6931    0.2215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1999   -0.5361   -0.5034 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3033   -1.5018   -1.5018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8355    0.1471   -0.6425 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2761   -0.7970   -0.4166 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6605   -0.4038   -0.4804 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2266    0.8995   -0.6926 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6661    1.9586   -1.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633    1.0475   -0.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2838    0.0669    0.1481 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3447    2.2330   -0.4570 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7060    2.4039   -0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8066   -0.7491    1.0217 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4472   -1.3797    0.9453 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4148   -0.8745    2.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5266   -2.8821    0.9847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8258    2.4434   -1.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0180    2.1915   -1.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0379   -0.4491   -1.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3196   -0.3809    1.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6358   -1.4222    0.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3625   -1.0086    0.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5219   -1.1252   -2.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8344    0.4381   -1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8107    1.0617   -0.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0975   -1.6874   -1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3455   -1.1666   -1.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2776    2.8900   -1.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6752    2.0693   -1.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7906    3.4538    0.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2864    2.3486   -1.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0446    1.6773    0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8453    0.1640    1.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6285   -1.4329    1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8368    0.1173    1.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2720   -0.7641    2.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1416   -1.6517    2.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1907   -3.3223    1.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5614   -3.2294    0.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1039   -3.3130    0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  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
 11 12  2  3  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
  5  3  1  0  0  0  0
 18  9  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  3 23  1  6  0  0  0
  4 24  1  0  0  0  0
  4 25  1  0  0  0  0
  6 26  1  1  0  0  0
  7 27  1  0  0  0  0
  8 28  1  0  0  0  0
  8 29  1  0  0  0  0
  9 30  1  6  0  0  0
 10 31  1  6  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
 16 34  1  0  0  0  0
 16 35  1  0  0  0  0
 16 36  1  0  0  0  0
 17 37  1  0  0  0  0
 17 38  1  0  0  0  0
 19 39  1  0  0  0  0
 19 40  1  0  0  0  0
 19 41  1  0  0  0  0
 20 42  1  0  0  0  0
 20 43  1  0  0  0  0
 20 44  1  0  0  0  0
M  END

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
   -2.9805    1.7523   -1.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2446    0.4886   -0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6637    0.0349   -0.6411 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0175   -0.5028    0.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5142    0.6931    0.2215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1999   -0.5361   -0.5034 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3033   -1.5018   -1.5018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8355    0.1471   -0.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2761   -0.7970   -0.4166 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6605   -0.4038   -0.4804 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2266    0.8995   -0.6926 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6661    1.9586   -1.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633    1.0475   -0.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2838    0.0669    0.1481 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3447    2.2330   -0.4570 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7060    2.4039   -0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8066   -0.7491    1.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4472   -1.3797    0.9453 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4148   -0.8745    2.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5266   -2.8821    0.9847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8258    2.4434   -1.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0180    2.1915   -1.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0379   -0.4491   -1.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3196   -0.3809    1.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6358   -1.4222    0.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3625   -1.0086    0.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5219   -1.1252   -2.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8344    0.4381   -1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8107    1.0617   -0.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0975   -1.6874   -1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3455   -1.1666   -1.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2776    2.8900   -1.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6752    2.0693   -1.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7906    3.4538    0.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2864    2.3486   -1.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0446    1.6773    0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8453    0.1640    1.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6285   -1.4329    1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8368    0.1173    1.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2720   -0.7641    2.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1416   -1.6517    2.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1907   -3.3223    1.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5614   -3.2294    0.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1039   -3.3130    0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  2  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 10 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
  5  3  1  0
 18  9  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  6
  4 24  1  0
  4 25  1  0
  6 26  1  1
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  6
 10 31  1  6
 12 32  1  0
 12 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
M  END


  Mrv1652306242117433D          

 44 45  0  0  0  0            999 V2000
   -2.9805    1.7523   -1.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2446    0.4886   -0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6637    0.0349   -0.6411 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0175   -0.5028    0.7271 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5142    0.6931    0.2215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1999   -0.5361   -0.5034 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3033   -1.5018   -1.5018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8355    0.1471   -0.6425 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2761   -0.7970   -0.4166 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6605   -0.4038   -0.4804 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2266    0.8995   -0.6926 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6661    1.9586   -1.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633    1.0475   -0.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2838    0.0669    0.1481 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3447    2.2330   -0.4570 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7060    2.4039   -0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8066   -0.7491    1.0217 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4472   -1.3797    0.9453 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4148   -0.8745    2.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5266   -2.8821    0.9847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8258    2.4434   -1.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0180    2.1915   -1.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0379   -0.4491   -1.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3196   -0.3809    1.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6358   -1.4222    0.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3625   -1.0086    0.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5219   -1.1252   -2.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8344    0.4381   -1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8107    1.0617   -0.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0975   -1.6874   -1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3455   -1.1666   -1.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2776    2.8900   -1.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6752    2.0693   -1.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7906    3.4538    0.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2864    2.3486   -1.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0446    1.6773    0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8453    0.1640    1.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6285   -1.4329    1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8368    0.1173    1.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2720   -0.7641    2.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1416   -1.6517    2.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1907   -3.3223    1.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5614   -3.2294    0.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1039   -3.3130    0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  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
 11 12  2  3  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
  5  3  1  0  0  0  0
 18  9  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  3 23  1  6  0  0  0
  4 24  1  0  0  0  0
  4 25  1  0  0  0  0
  6 26  1  1  0  0  0
  7 27  1  0  0  0  0
  8 28  1  0  0  0  0
  8 29  1  0  0  0  0
  9 30  1  6  0  0  0
 10 31  1  6  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
 16 34  1  0  0  0  0
 16 35  1  0  0  0  0
 16 36  1  0  0  0  0
 17 37  1  0  0  0  0
 17 38  1  0  0  0  0
 19 39  1  0  0  0  0
 19 40  1  0  0  0  0
 19 41  1  0  0  0  0
 20 42  1  0  0  0  0
 20 43  1  0  0  0  0
 20 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001590

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]([H])(C(=C([H])[H])[C@]1([H])OC1([H])[H])C([H])([H])[C@@]1([H])[C@@]([H])(C(=C([H])[H])C(=O)OC([H])([H])[H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H24O4/c1-9(15(18)19-5)11-7-16(3,4)12(11)6-13(17)10(2)14-8-20-14/h11-14,17H,1-2,6-8H2,3-5H3/t11-,12+,13+,14-/m1/s1

> <INCHI_KEY>
KZIUKKDHFYKXJA-ZIHBUVQPSA-N

> <FORMULA>
C16H24O4

> <MOLECULAR_WEIGHT>
280.364

> <EXACT_MASS>
280.167459253

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.29355699380058

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-[(1S,2S)-2-[(2S)-2-hydroxy-3-[(2S)-oxiran-2-yl]but-3-en-1-yl]-3,3-dimethylcyclobutyl]prop-2-enoate

> <ALOGPS_LOGP>
2.00

> <JCHEM_LOGP>
2.187106694666666

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.547122398344019

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9968886629643254

> <JCHEM_POLAR_SURFACE_AREA>
59.06

> <JCHEM_REFRACTIVITY>
75.81

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.59e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-[(1S,2S)-2-[(2S)-2-hydroxy-3-[(2S)-oxiran-2-yl]but-3-en-1-yl]-3,3-dimethylcyclobutyl]prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
   -2.9805    1.7523   -1.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2446    0.4886   -0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6637    0.0349   -0.6411 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0175   -0.5028    0.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5142    0.6931    0.2215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1999   -0.5361   -0.5034 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3033   -1.5018   -1.5018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8355    0.1471   -0.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2761   -0.7970   -0.4166 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6605   -0.4038   -0.4804 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2266    0.8995   -0.6926 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6661    1.9586   -1.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633    1.0475   -0.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2838    0.0669    0.1481 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3447    2.2330   -0.4570 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7060    2.4039   -0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8066   -0.7491    1.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4472   -1.3797    0.9453 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4148   -0.8745    2.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5266   -2.8821    0.9847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8258    2.4434   -1.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0180    2.1915   -1.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0379   -0.4491   -1.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3196   -0.3809    1.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6358   -1.4222    0.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3625   -1.0086    0.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5219   -1.1252   -2.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8344    0.4381   -1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8107    1.0617   -0.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0975   -1.6874   -1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3455   -1.1666   -1.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2776    2.8900   -1.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6752    2.0693   -1.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7906    3.4538    0.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2864    2.3486   -1.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0446    1.6773    0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8453    0.1640    1.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6285   -1.4329    1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8368    0.1173    1.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2720   -0.7641    2.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1416   -1.6517    2.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1907   -3.3223    1.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5614   -3.2294    0.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1039   -3.3130    0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  2  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 10 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
  5  3  1  0
 18  9  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  6
  4 24  1  0
  4 25  1  0
  6 26  1  1
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  6
 10 31  1  6
 12 32  1  0
 12 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  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      -2.981   1.752  -1.066  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.245   0.489  -0.753  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.664   0.035  -0.641  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.018  -0.503   0.727  0.00  0.00           C+0
HETATM    5  O   UNK     0      -5.514   0.693   0.222  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.200  -0.536  -0.503  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.303  -1.502  -1.502  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.836   0.147  -0.643  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.276  -0.797  -0.417  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.661  -0.404  -0.480  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.227   0.900  -0.693  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.666   1.959  -1.162  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.663   1.048  -0.315  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.284   0.067   0.148  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.345   2.233  -0.457  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.706   2.404  -0.108  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.807  -0.749   1.022  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.447  -1.380   0.945  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.415  -0.875   2.064  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.527  -2.882   0.985  0.00  0.00           C+0
HETATM   21  H   UNK     0      -3.826   2.443  -1.237  0.00  0.00           H+0
HETATM   22  H   UNK     0      -2.018   2.192  -1.177  0.00  0.00           H+0
HETATM   23  H   UNK     0      -5.038  -0.449  -1.545  0.00  0.00           H+0
HETATM   24  H   UNK     0      -4.320  -0.381   1.556  0.00  0.00           H+0
HETATM   25  H   UNK     0      -5.636  -1.422   0.682  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.362  -1.009   0.458  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.522  -1.125  -2.386  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.834   0.438  -1.714  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.811   1.062  -0.032  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.098  -1.687  -1.136  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.345  -1.167  -1.038  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.278   2.890  -1.252  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.675   2.069  -1.490  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.791   3.454   0.277  0.00  0.00           H+0
HETATM   35  H   UNK     0       6.286   2.349  -1.055  0.00  0.00           H+0
HETATM   36  H   UNK     0       6.045   1.677   0.645  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.845   0.164   1.665  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.628  -1.433   1.254  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.837   0.117   1.912  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.272  -0.764   2.958  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.142  -1.652   2.407  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.191  -3.322   1.932  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.561  -3.229   0.781  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.104  -3.313   0.162  0.00  0.00           H+0
CONECT    1    2   21   22                                                  
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5   23                                             
CONECT    4    3    5   24   25                                             
CONECT    5    4    3                                                       
CONECT    6    2    7    8   26                                             
CONECT    7    6   27                                                       
CONECT    8    6    9   28   29                                             
CONECT    9    8   10   18   30                                             
CONECT   10    9   11   17   31                                             
CONECT   11   10   12   13                                                  
CONECT   12   11   32   33                                                  
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   34   35   36                                             
CONECT   17   10   18   37   38                                             
CONECT   18   17   19   20    9                                             
CONECT   19   18   39   40   41                                             
CONECT   20   18   42   43   44                                             
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    3                                                            
CONECT   24    4                                                            
CONECT   25    4                                                            
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28    8                                                            
CONECT   29    8                                                            
CONECT   30    9                                                            
CONECT   31   10                                                            
CONECT   32   12                                                            
CONECT   33   12                                                            
CONECT   34   16                                                            
CONECT   35   16                                                            
CONECT   36   16                                                            
CONECT   37   17                                                            
CONECT   38   17                                                            
CONECT   39   19                                                            
CONECT   40   19                                                            
CONECT   41   19                                                            
CONECT   42   20                                                            
CONECT   43   20                                                            
CONECT   44   20                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   90    0
END

RDKit          3D

44 45  0  0  0  0  0  0  0  0999 V2000
   -2.9805    1.7523   -1.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2446    0.4886   -0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6637    0.0349   -0.6411 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0175   -0.5028    0.7271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5142    0.6931    0.2215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1999   -0.5361   -0.5034 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3033   -1.5018   -1.5018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8355    0.1471   -0.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2761   -0.7970   -0.4166 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6605   -0.4038   -0.4804 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2266    0.8995   -0.6926 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6661    1.9586   -1.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633    1.0475   -0.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2838    0.0669    0.1481 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3447    2.2330   -0.4570 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7060    2.4039   -0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8066   -0.7491    1.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4472   -1.3797    0.9453 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4148   -0.8745    2.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5266   -2.8821    0.9847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8258    2.4434   -1.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0180    2.1915   -1.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0379   -0.4491   -1.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3196   -0.3809    1.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6358   -1.4222    0.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3625   -1.0086    0.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5219   -1.1252   -2.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8344    0.4381   -1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8107    1.0617   -0.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0975   -1.6874   -1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3455   -1.1666   -1.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2776    2.8900   -1.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6752    2.0693   -1.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7906    3.4538    0.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2864    2.3486   -1.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0446    1.6773    0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8453    0.1640    1.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6285   -1.4329    1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8368    0.1173    1.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2720   -0.7641    2.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1416   -1.6517    2.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1907   -3.3223    1.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5614   -3.2294    0.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1039   -3.3130    0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  2  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 10 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
  5  3  1  0
 18  9  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  6
  4 24  1  0
  4 25  1  0
  6 26  1  1
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  6
 10 31  1  6
 12 32  1  0
 12 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 19 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Methyl 2-[(1S)-2-[(2S)-2-hydroxy-3-(oxiran-2-yl)but-3-en-1-yl]-3,3-dimethylcyclobutyl]prop-2-enoic acid	Generator

Chemical Formula

C₁₆H₂₄O₄

Average Mass

280.3640 Da

Monoisotopic Mass

280.16746 Da

IUPAC Name

methyl 2-[(1S,2S)-2-[(2S)-2-hydroxy-3-[(2S)-oxiran-2-yl]but-3-en-1-yl]-3,3-dimethylcyclobutyl]prop-2-enoate

Traditional Name

methyl 2-[(1S,2S)-2-[(2S)-2-hydroxy-3-[(2S)-oxiran-2-yl]but-3-en-1-yl]-3,3-dimethylcyclobutyl]prop-2-enoate

CAS Registry Number

Not Available

SMILES

[H]O[C@]([H])(C(=C([H])[H])[C@]1([H])OC1([H])[H])C([H])([H])[C@@]1([H])[C@@]([H])(C(=C([H])[H])C(=O)OC([H])([H])[H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C16H24O4/c1-9(15(18)19-5)11-7-16(3,4)12(11)6-13(17)10(2)14-8-20-14/h11-14,17H,1-2,6-8H2,3-5H3/t11-,12+,13+,14-/m1/s1

InChI Key

KZIUKKDHFYKXJA-ZIHBUVQPSA-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
Hebeloma longicaudum	NPAtlas	10096864

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as enoate esters. These are an alpha,beta-unsaturated carboxylic ester of general formula R1C(R2)=C(R3)C(=O)OR4 (R4= organyl compound) in which the ester C=O function is conjugated to a C=C double bond at the alpha,beta position.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Enoate esters

Alternative Parents

Substituents

Enoate ester
Methyl ester
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2	ALOGPS
logP	2.19	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	14.55	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.06 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	75.81 m³·mol⁻¹	ChemAxon
Polarizability	31.29 Å³	ChemAxon
Number of Rings	2	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

NPA018778

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78438525

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139588334

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wichlacz M, Ayer WA, Trifonov LS, Chakravarty P, Khasa D: A caryophyllene-related sesquiterpene and two 6, 7-seco-caryophyllenes from liquid cultures of hebeloma longicaudum J Nat Prod. 1999 Mar;62(3):484-6. doi: 10.1021/np9803171. [PubMed:10096864 ]

Showing NP-Card for Hebelophyllene F (NP0001590)

MOL for NP0001590 (Hebelophyllene F)

3D MOL for NP0001590 (Hebelophyllene F)

3D SDF for NP0001590 (Hebelophyllene F)

3D-SDF for NP0001590 (Hebelophyllene F)

PDB for NP0001590 (Hebelophyllene F)

3D PDB for NP0001590 (Hebelophyllene F)

SMILES for NP0001590 (Hebelophyllene F)

INCHI for NP0001590 (Hebelophyllene F)

Structure for NP0001590 (Hebelophyllene F)

3D Structure for NP0001590 (Hebelophyllene F)