NP-MRD: Showing NP-Card for (18s,19r)-13,16,17-trihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-12-yl acetate (NP0247022)

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Record Information

Version

2.0

Created at

2022-09-07 08:41:14 UTC

Updated at

2022-09-07 08:41:14 UTC

NP-MRD ID

NP0247022

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(18s,19r)-13,16,17-trihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-12-yl acetate

Description

(18S,19R)-13,16,17-trihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]Nonadeca-3(7),5-dien-12-yl acetate 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. (18s,19r)-13,16,17-trihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-12-yl acetate is found in Caesalpinia minax. Based on a literature review very few articles have been published on (18S,19R)-13,16,17-trihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]Nonadeca-3(7),5-dien-12-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072210412D          

 30 34  0  0  1  0            999 V2000
    4.1871    1.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3646    1.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    2.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0081    0.9876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4741    0.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2967    0.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8001    1.0238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5773    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2580    1.2131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -0.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1516   -0.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9742   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2886   -1.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6603   -1.8808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9576   -1.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662   -1.6814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4063   -1.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7628   -0.3106    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5837   -1.1178    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0498   -1.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2272   -1.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6933   -2.5426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4046   -1.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0481   -2.6691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9386   -1.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2951   -0.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5005   -0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3756    0.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1176   -0.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6516    0.2436    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 10  1  1  0  0  0
  6 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
  5 29  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 58 62  0  0  0  0  0  0  0  0999 V2000
    0.2457    4.9760   -1.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1464    3.8848   -0.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8571    4.1507    0.8682 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2094    2.5600   -0.3285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1726    1.5257    0.5590 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9903    0.9532    1.2452 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1896    1.7333    1.2677 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1907    0.7692    1.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3627    1.0970    1.8713 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5843   -0.6038    1.4931 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3592   -1.6212    0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6096   -2.1711    1.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8538   -3.1453    0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8183   -3.1638   -0.6357 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8926   -2.2813   -0.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5858   -2.0623   -0.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6907   -1.2291   -0.0467 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5255   -0.1753    0.4605 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4215   -0.5526   -0.8645 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1874    0.1819   -2.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3738   -1.5179   -1.4632 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6861   -1.2255   -2.8171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6480   -1.7713   -0.7660 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6306   -2.1611   -1.7145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2412   -0.6091   -0.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1779    0.0196    0.8516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8458    1.2626    1.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8630   -0.9049    1.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1080    0.5201   -0.0541 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8312    1.2532   -1.0427 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6035    5.8169   -0.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0859    4.6667   -1.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302    5.3496   -1.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7891    2.0505    1.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8423    0.7398    2.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0969   -0.8855    2.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2828   -1.9077    1.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7227   -3.7762   -0.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8694   -1.5047   -1.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1420   -3.0444   -1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2140   -1.9074    0.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1745    0.2173   -0.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4334   -0.5142   -2.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9361    0.9162   -1.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6856    0.7688   -2.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8390   -2.5137   -1.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4724   -0.6019   -2.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5647   -2.6972   -0.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5352   -3.1294   -1.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0192   -1.0208    0.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6651    0.0890   -0.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4136    1.4905    2.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8465    2.1151    0.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9143    0.9960    1.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9584   -2.0036    1.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328   -0.8228    2.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6676   -0.7870    2.7260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7620    2.2087   -0.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 17 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 29 30  1  6
 29  5  1  0
 18  6  1  0
 14 15  1  0
 29 19  1  0
 11 10  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  5 34  1  1
  6 35  1  1
 10 36  1  1
 18 42  1  6
 17 41  1  1
 16 39  1  0
 16 40  1  0
 12 37  1  0
 13 38  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  6
 22 47  1  0
 23 48  1  1
 24 49  1  0
 25 50  1  0
 25 51  1  0
 27 52  1  0
 27 53  1  0
 27 54  1  0
 28 55  1  0
 28 56  1  0
 28 57  1  0
 30 58  1  0
M  END


  Mrv1652309072210412D          

 30 34  0  0  1  0            999 V2000
    4.1871    1.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3646    1.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    2.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0081    0.9876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4741    0.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2967    0.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8001    1.0238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5773    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2580    1.2131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -0.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1516   -0.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9742   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2886   -1.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6603   -1.8808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9576   -1.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662   -1.6814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4063   -1.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7628   -0.3106    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5837   -1.1178    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0498   -1.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2272   -1.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6933   -2.5426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4046   -1.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0481   -2.6691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9386   -1.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2951   -0.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5005   -0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3756    0.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1176   -0.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6516    0.2436    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 10  1  1  0  0  0
  6 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
  5 29  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247022

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1C2OC(=O)C3[C@H]2C(CC2=C3C=CO2)[C@@]2(C)C(O)C(O)CC(C)(C)C12O

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O8/c1-9(23)29-18-16-15-11(7-13-10(5-6-28-13)14(15)19(26)30-16)21(4)17(25)12(24)8-20(2,3)22(18,21)27/h5-6,11-12,14-18,24-25,27H,7-8H2,1-4H3/t11?,12?,14?,15-,16?,17?,18?,21+,22?/m1/s1

> <INCHI_KEY>
PNGGBDIIVKKALA-LLLCQXNSSA-N

> <FORMULA>
C22H28O8

> <MOLECULAR_WEIGHT>
420.458

> <EXACT_MASS>
420.178417862

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
42.847927631502515

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(18S,19R)-13,16,17-trihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0^{3,7}.0^{8,19}.0^{13,18}]nonadeca-3(7),5-dien-12-yl acetate

> <JCHEM_LOGP>
0.1632323676666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.727425570562865

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.894644219088761

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8238260134273605

> <JCHEM_POLAR_SURFACE_AREA>
126.43000000000002

> <JCHEM_REFRACTIVITY>
101.37420000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(18S,19R)-13,16,17-trihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0^{3,7}.0^{8,19}.0^{13,18}]nonadeca-3(7),5-dien-12-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       7.816   3.350   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.281   3.232   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.411   4.503   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.615   1.844   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.485   0.573   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.021   0.691   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.960   1.911   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.411   1.394   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.682   2.264   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.368  -0.145   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.483  -1.207   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.019  -1.089   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.605  -2.513   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.433  -3.511   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      11.121  -2.704   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.644  -3.139   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.225  -1.969   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.891  -0.580   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.690  -2.087   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.560  -3.357   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.024  -3.475   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.894  -4.746   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.489  -3.593   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.823  -4.982   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.619  -2.323   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.284  -0.934   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.801  -0.520   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.434   0.599   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.820  -0.816   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.950   0.455   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   18                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   10    6                                                  
CONECT   19   17   20   21   29                                             
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26    5   19   30                                             
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Value	Source
(18S,19R)-13,16,17-Trihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0,.0,.0,]nonadeca-3(7),5-dien-12-yl acetic acid	Generator

Chemical Formula

C₂₂H₂₈O₈

Average Mass

420.4580 Da

Monoisotopic Mass

420.17842 Da

IUPAC Name

(18S,19R)-13,16,17-trihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0^{3,7}.0^{8,19}.0^{13,18}]nonadeca-3(7),5-dien-12-yl acetate

Traditional Name

(18S,19R)-13,16,17-trihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0^{3,7}.0^{8,19}.0^{13,18}]nonadeca-3(7),5-dien-12-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1C2OC(=O)C3[C@H]2C(CC2=C3C=CO2)[C@@]2(C)C(O)C(O)CC(C)(C)C12O

InChI Identifier

InChI=1S/C22H28O8/c1-9(23)29-18-16-15-11(7-13-10(5-6-28-13)14(15)19(26)30-16)21(4)17(25)12(24)8-20(2,3)22(18,21)27/h5-6,11-12,14-18,24-25,27H,7-8H2,1-4H3/t11?,12?,14?,15-,16?,17?,18?,21+,22?/m1/s1

InChI Key

PNGGBDIIVKKALA-LLLCQXNSSA-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
Caesalpinia minax	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
Eudesmanolide
Terpene lactone
Naphthofuran
Benzofuran
Gamma butyrolactone
Dicarboxylic acid or derivatives
Heteroaromatic compound
Tetrahydrofuran
Tertiary alcohol
Furan
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.16	ChemAxon
pKa (Strongest Acidic)	12.89	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	126.43 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	101.37 m³·mol⁻¹	ChemAxon
Polarizability	42.85 Å³	ChemAxon
Number of Rings	5	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

4474870

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5315595

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (18s,19r)-13,16,17-trihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-12-yl acetate (NP0247022)

MOL for NP0247022 ((18s,19r)-13,16,17-trihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-12-yl acetate)

3D MOL for NP0247022 ((18s,19r)-13,16,17-trihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-12-yl acetate)

3D SDF for NP0247022 ((18s,19r)-13,16,17-trihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-12-yl acetate)

3D-SDF for NP0247022 ((18s,19r)-13,16,17-trihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-12-yl acetate)

PDB for NP0247022 ((18s,19r)-13,16,17-trihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-12-yl acetate)

3D PDB for NP0247022 ((18s,19r)-13,16,17-trihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-12-yl acetate)

SMILES for NP0247022 ((18s,19r)-13,16,17-trihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-12-yl acetate)

INCHI for NP0247022 ((18s,19r)-13,16,17-trihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-12-yl acetate)

Structure for NP0247022 ((18s,19r)-13,16,17-trihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-12-yl acetate)

3D Structure for NP0247022 ((18s,19r)-13,16,17-trihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-12-yl acetate)