NP-MRD: Showing NP-Card for (2z,4e)-3-methyl-5-[(1s)-2,6,6-trimethyl-4-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-yl]penta-2,4-dienoic acid (NP0310452)

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Record Information

Version

2.0

Created at

2022-09-11 05:46:15 UTC

Updated at

2022-09-11 05:46:16 UTC

NP-MRD ID

NP0310452

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z,4e)-3-methyl-5-[(1s)-2,6,6-trimethyl-4-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-yl]penta-2,4-dienoic acid

Description

(2Z,4E)-3-methyl-5-[(1S)-2,6,6-trimethyl-4-oxo-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-yl]penta-2,4-dienoic acid belongs to the class of organic compounds known as abscisic acids and derivatives. These are terpene compounds containing the abscisic acid moiety, which is characterized by a 3-methylpenta-2,4-dienoic acid attached to the C1 carbon of a 4-oxocyclohex-2-ene moiety. (2z,4e)-3-methyl-5-[(1s)-2,6,6-trimethyl-4-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-yl]penta-2,4-dienoic acid is found in Nicotiana tabacum. Based on a literature review very few articles have been published on (2Z,4E)-3-methyl-5-[(1S)-2,6,6-trimethyl-4-oxo-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-yl]penta-2,4-dienoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112207462D          

 30 31  0  0  1  0            999 V2000
    1.1419   -1.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773   -1.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773   -2.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372   -3.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3562   -4.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1517   -2.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1517   -1.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9377   -2.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9078   -1.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372   -1.5246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0593   -0.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2079   -1.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8611   -0.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2426    0.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7428   -0.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2537   -0.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0701   -0.7972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9482   -1.6821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0628   -0.7699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4871   -0.0966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3116   -0.1254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7487    0.5743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5518    1.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0641    1.7629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3614    1.3027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5376    2.1485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5369    1.3315    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0360    2.0566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6319    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7468    0.9102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 10 19  1  6  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END

     RDKit          3D

 60 61  0  0  0  0  0  0  0  0999 V2000
    1.3354   -2.1523   -2.4147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0483   -2.2876   -0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1646   -3.4820   -0.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9046   -3.7097    0.9714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2362   -4.7777    1.5539 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2197   -2.5965    1.6789 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0407   -1.3491    1.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7496   -0.3691    2.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5016   -1.8330    1.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6423   -1.0505   -0.1340 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3133    0.0285   -0.8496 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429    0.7623   -0.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9234    1.8079   -1.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4127    2.1231   -2.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9222    2.5320   -0.7756 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5574    2.3909    0.5076 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2518    1.5706    1.3881 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6347    3.2332    0.8600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7314   -1.0544   -0.2869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4228    0.0704    0.0614 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2930   -0.2449    1.0762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2827    0.6560    1.3285 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0035    0.2570    2.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0089    1.2318    2.7925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2411    0.5686    0.1306 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4058    1.2554    0.3609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4684    1.1431   -1.0080 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2114    0.9098   -2.1872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0777    0.6702   -1.1496 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3205    1.7614   -1.6386 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3619   -1.8358   -2.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0582   -3.1200   -2.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6627   -1.4064   -2.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4576   -4.3516   -1.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8269   -2.5122    1.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3087   -2.7538    2.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2464   -0.5239    2.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8918    0.6793    2.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4734   -0.6211    3.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0603   -1.2404    2.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9995   -1.8490    0.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5740   -2.8708    1.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9894    0.3035   -1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6535    0.4973    0.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    1.4187   -3.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3050    2.1578   -2.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7427    3.1403   -2.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3427    3.3320   -1.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4028    3.2463    0.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7083    0.8303    0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9529    1.7051    1.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3151    0.3670    3.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5092   -0.7058    2.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6148    2.1386    2.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4103   -0.5176   -0.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0593    0.6412    0.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5025    2.2661   -0.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8187    1.4120   -2.9457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0482   -0.0797   -1.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8636    2.1873   -2.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10 19  1  1
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 10  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
 13 15  2  0
 15 16  1  0
 16 18  1  0
 16 17  2  0
  7 10  1  0
 29 20  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
 12 44  1  0
 11 43  1  0
 20 50  1  1
 22 51  1  1
 23 52  1  0
 23 53  1  0
 24 54  1  0
 25 55  1  6
 26 56  1  0
 27 57  1  1
 28 58  1  0
 29 59  1  6
 30 60  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
  9 42  1  0
 15 48  1  0
 18 49  1  0
M  END


  Mrv1652309112207462D          

 30 31  0  0  1  0            999 V2000
    1.1419   -1.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773   -1.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773   -2.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372   -3.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3562   -4.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1517   -2.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1517   -1.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9377   -2.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9078   -1.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372   -1.5246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0593   -0.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2079   -1.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8611   -0.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2426    0.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7428   -0.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2537   -0.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0701   -0.7972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9482   -1.6821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0628   -0.7699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4871   -0.0966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3116   -0.1254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7487    0.5743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5518    1.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0641    1.7629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3614    1.3027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5376    2.1485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5369    1.3315    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0360    2.0566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6319    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7468    0.9102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 10 19  1  6  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0310452

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\[C@@]1(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(C)=CC(=O)CC1(C)C)=C\C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O9/c1-11(7-15(24)25)5-6-21(12(2)8-13(23)9-20(21,3)4)30-19-18(28)17(27)16(26)14(10-22)29-19/h5-8,14,16-19,22,26-28H,9-10H2,1-4H3,(H,24,25)/b6-5+,11-7-/t14-,16-,17+,18-,19+,21-/m1/s1

> <INCHI_KEY>
IZIIGYFDADLHAJ-VTEUUMMASA-N

> <FORMULA>
C21H30O9

> <MOLECULAR_WEIGHT>
426.462

> <EXACT_MASS>
426.188982546

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
43.04463414151932

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z,4E)-3-methyl-5-[(1S)-2,6,6-trimethyl-4-oxo-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-yl]penta-2,4-dienoic acid

> <JCHEM_LOGP>
0.32243984766666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.209021142544604

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.354255373089088

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810840578499462

> <JCHEM_POLAR_SURFACE_AREA>
153.75

> <JCHEM_REFRACTIVITY>
107.38969999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,4E)-3-methyl-5-[(1S)-2,6,6-trimethyl-4-oxo-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-yl]penta-2,4-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       2.131  -3.405   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.518  -3.616   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.518  -5.156   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.816  -5.926   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.665  -7.528   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.150  -5.156   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.150  -3.616   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.617  -4.473   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.561  -2.862   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.816  -2.846   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.977  -1.479   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.121  -1.910   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.341  -0.739   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.186   0.473   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.986  -0.500   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -7.940  -1.709   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -9.464  -1.488   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -7.370  -3.140   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.117  -1.437   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.909  -0.180   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.448  -0.234   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.264   1.072   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.763   1.985   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.720   3.291   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.541   2.432   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.870   4.011   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.002   2.485   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.067   3.839   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.186   1.179   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.394   1.699   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7    2   11   19                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   10   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   20   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Value	Source
(2Z,4E)-3-Methyl-5-[(1S)-2,6,6-trimethyl-4-oxo-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-yl]penta-2,4-dienoate	Generator

Chemical Formula

C₂₁H₃₀O₉

Average Mass

426.4620 Da

Monoisotopic Mass

426.18898 Da

IUPAC Name

(2Z,4E)-3-methyl-5-[(1S)-2,6,6-trimethyl-4-oxo-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-yl]penta-2,4-dienoic acid

Traditional Name

(2Z,4E)-3-methyl-5-[(1S)-2,6,6-trimethyl-4-oxo-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-yl]penta-2,4-dienoic acid

CAS Registry Number

Not Available

SMILES

C\C(\C=C\[C@@]1(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(C)=CC(=O)CC1(C)C)=C\C(O)=O

InChI Identifier

InChI=1S/C21H30O9/c1-11(7-15(24)25)5-6-21(12(2)8-13(23)9-20(21,3)4)30-19-18(28)17(27)16(26)14(10-22)29-19/h5-8,14,16-19,22,26-28H,9-10H2,1-4H3,(H,24,25)/b6-5+,11-7-/t14-,16-,17+,18-,19+,21-/m1/s1

InChI Key

IZIIGYFDADLHAJ-VTEUUMMASA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Nicotiana tabacum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as abscisic acids and derivatives. These are terpene compounds containing the abscisic acid moiety, which is characterized by a 3-methylpenta-2,4-dienoic acid attached to the C1 carbon of a 4-oxocyclohex-2-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Abscisic acids and derivatives

Alternative Parents

Substituents

Abscisic acid
Saccharolipid
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Medium-chain fatty acid
Branched fatty acid
Hydroxy fatty acid
Cyclohexenone
Methyl-branched fatty acid
Heterocyclic fatty acid
Oxane
Unsaturated fatty acid
Monosaccharide
Fatty acid
Fatty acyl
Secondary alcohol
Cyclic ketone
Ketone
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Aldehyde
Primary alcohol
Organic oxide
Carbonyl group
Organooxygen compound
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	0.32	ChemAxon
pKa (Strongest Acidic)	4.35	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	107.39 m³·mol⁻¹	ChemAxon
Polarizability	43.04 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162985762

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2z,4e)-3-methyl-5-[(1s)-2,6,6-trimethyl-4-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-yl]penta-2,4-dienoic acid (NP0310452)

MOL for NP0310452 ((2z,4e)-3-methyl-5-[(1s)-2,6,6-trimethyl-4-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-yl]penta-2,4-dienoic acid)

3D MOL for NP0310452 ((2z,4e)-3-methyl-5-[(1s)-2,6,6-trimethyl-4-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-yl]penta-2,4-dienoic acid)

3D SDF for NP0310452 ((2z,4e)-3-methyl-5-[(1s)-2,6,6-trimethyl-4-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-yl]penta-2,4-dienoic acid)

3D-SDF for NP0310452 ((2z,4e)-3-methyl-5-[(1s)-2,6,6-trimethyl-4-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-yl]penta-2,4-dienoic acid)

PDB for NP0310452 ((2z,4e)-3-methyl-5-[(1s)-2,6,6-trimethyl-4-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-yl]penta-2,4-dienoic acid)

3D PDB for NP0310452 ((2z,4e)-3-methyl-5-[(1s)-2,6,6-trimethyl-4-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-yl]penta-2,4-dienoic acid)

SMILES for NP0310452 ((2z,4e)-3-methyl-5-[(1s)-2,6,6-trimethyl-4-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-yl]penta-2,4-dienoic acid)

INCHI for NP0310452 ((2z,4e)-3-methyl-5-[(1s)-2,6,6-trimethyl-4-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-yl]penta-2,4-dienoic acid)

Structure for NP0310452 ((2z,4e)-3-methyl-5-[(1s)-2,6,6-trimethyl-4-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-yl]penta-2,4-dienoic acid)

3D Structure for NP0310452 ((2z,4e)-3-methyl-5-[(1s)-2,6,6-trimethyl-4-oxo-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-yl]penta-2,4-dienoic acid)