NP-MRD: Showing NP-Card for methyl 2-[(3as,4r,5s,6s)-4-hydroxy-3-(hydroxymethyl)-6-{[2-(4-hydroxyphenyl)acetyl]oxy}-8-methyl-1-oxo-4,5,6,7-tetrahydro-3ah-azulen-5-yl]prop-2-enoate (NP0238508)

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Record Information

Version

2.0

Created at

2022-09-06 21:54:55 UTC

Updated at

2022-09-06 21:54:55 UTC

NP-MRD ID

NP0238508

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[(3as,4r,5s,6s)-4-hydroxy-3-(hydroxymethyl)-6-{[2-(4-hydroxyphenyl)acetyl]oxy}-8-methyl-1-oxo-4,5,6,7-tetrahydro-3ah-azulen-5-yl]prop-2-enoate

Description

ZINC225414948 belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. methyl 2-[(3as,4r,5s,6s)-4-hydroxy-3-(hydroxymethyl)-6-{[2-(4-hydroxyphenyl)acetyl]oxy}-8-methyl-1-oxo-4,5,6,7-tetrahydro-3ah-azulen-5-yl]prop-2-enoate is found in Cichorium intybus and Lactuca serriola. Based on a literature review very few articles have been published on ZINC225414948.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062223542D          

 32 34  0  0  1  0            999 V2000
    4.3699    3.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6713    2.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4871    2.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7885    1.5279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0015    2.9409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8172    2.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    1.7738    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5149    1.0305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3399    1.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7524    0.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -0.3985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5774    0.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9899   -0.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8149   -0.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2274   -1.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8149   -1.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2274   -2.5419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9899   -1.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5774   -1.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690   -0.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6680   -0.4216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    1.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6680    2.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8611    2.6541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    1.4430    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3526    1.9574    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1690    2.7617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 13 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 27  1  6  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
  7 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
   -1.1480    2.9799    1.6864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1069    2.2530    0.5633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9010    2.9380   -0.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7602    4.1790   -0.7128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8460    2.2876   -1.9187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6412    3.0136   -3.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2732    0.7765    0.6630 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0654    0.0497    0.1638 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1093    0.8169    0.1959 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9776    0.9068   -0.8619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6877    0.2528   -1.8998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2319    1.7474   -0.7863 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2910    0.7649   -0.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6604    0.7284    0.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5943   -0.1601    1.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2095   -1.0621    0.5727 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1540   -1.9721    1.0312 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8342   -1.0166   -0.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8955   -0.1236   -1.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1075   -1.2262    1.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8759   -2.2069    0.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3379   -3.4665   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1988   -2.0904    0.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1020   -3.0984   -0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7172   -4.1821   -0.6842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4286   -2.5485   -0.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3958   -1.3499    0.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6251   -0.5674    0.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7444   -0.3114    2.1998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0083   -0.9447    0.8433 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5631    0.2871    0.0674 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5368    1.2626    0.1443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3021    2.4842    2.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0286    4.0468    1.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1725    2.5400   -3.9780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0690    4.0443   -3.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4222    3.1375   -3.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3454    0.5436    1.7674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2143   -0.3207   -0.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4884    2.1425   -1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1258    2.5771   -0.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1664    1.4473    1.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8586   -0.1583    2.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1197   -1.6880    1.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3096   -1.7240   -1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6126   -0.0954   -2.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0894   -0.9953    2.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1155   -1.6181    0.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6647   -4.3561    0.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5574   -3.4854   -1.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7760   -3.4174   -0.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3079   -3.0777   -0.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6781    0.3770    0.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5351   -1.2057    0.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7846   -1.1520    2.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8803   -0.8002    1.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3934    0.0110   -0.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4490    1.8256   -0.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2  7  1  0
  7 31  1  0
 31 32  1  0
 31 30  1  0
 30 27  1  0
 27 28  1  0
 28 29  1  0
 27 26  2  0
 26 24  1  0
 24 25  2  0
 24 23  1  0
 23 21  2  0
 21 22  1  0
 21 20  1  0
 20  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  8  7  1  0
 19 13  1  0
 23 30  1  0
  6 35  1  0
  6 36  1  0
  6 37  1  0
  1 33  1  0
  1 34  1  0
  7 38  1  1
 31 57  1  6
 32 58  1  0
 30 56  1  1
 28 53  1  0
 28 54  1  0
 29 55  1  0
 26 52  1  0
 22 49  1  0
 22 50  1  0
 22 51  1  0
 20 47  1  0
 20 48  1  0
  8 39  1  6
 12 40  1  0
 12 41  1  0
 14 42  1  0
 15 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
M  END


  Mrv1652309062223542D          

 32 34  0  0  1  0            999 V2000
    4.3699    3.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6713    2.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4871    2.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7885    1.5279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0015    2.9409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8172    2.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    1.7738    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5149    1.0305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3399    1.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7524    0.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -0.3985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5774    0.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9899   -0.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8149   -0.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2274   -1.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8149   -1.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2274   -2.5419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9899   -1.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5774   -1.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690   -0.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6680   -0.4216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    1.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6680    2.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8611    2.6541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    1.4430    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3526    1.9574    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1690    2.7617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 13 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 27  1  6  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
  7 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0238508

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(=C)[C@H]1[C@H](O)[C@H]2C(CO)=CC(=O)C2=C(C)C[C@@H]1OC(=O)CC1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H26O8/c1-12-8-18(32-19(28)9-14-4-6-16(26)7-5-14)21(13(2)24(30)31-3)23(29)22-15(11-25)10-17(27)20(12)22/h4-7,10,18,21-23,25-26,29H,2,8-9,11H2,1,3H3/t18-,21+,22-,23-/m0/s1

> <INCHI_KEY>
DDNQXWHGQQEAOE-AWDZXFJFSA-N

> <FORMULA>
C24H26O8

> <MOLECULAR_WEIGHT>
442.464

> <EXACT_MASS>
442.162767797

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
45.7111307522213

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-[(3aS,4R,5S,6S)-4-hydroxy-3-(hydroxymethyl)-6-{[2-(4-hydroxyphenyl)acetyl]oxy}-8-methyl-1-oxo-1,3a,4,5,6,7-hexahydroazulen-5-yl]prop-2-enoate

> <JCHEM_LOGP>
1.4355817200000012

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.159752126994086

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.496329457324187

> <JCHEM_PKA_STRONGEST_BASIC>
-2.760550637095066

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
115.9807

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-[(3aS,4R,5S,6S)-4-hydroxy-3-(hydroxymethyl)-6-{[2-(4-hydroxyphenyl)acetyl]oxy}-8-methyl-1-oxo-4,5,6,7-tetrahydro-3aH-azulen-5-yl]prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       8.157   5.949   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.720   4.515   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.243   4.286   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.805   2.852   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      11.203   5.490   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      12.726   5.260   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.760   3.311   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.428   1.924   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.968   1.924   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.738   0.590   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.968  -0.744   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      12.278   0.590   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.048  -0.744   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.588  -0.744   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.358  -2.077   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.588  -3.411   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      15.358  -4.745   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      13.048  -3.411   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.278  -2.077   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.760   0.536   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.258   0.193   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.916  -1.308   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.054   1.154   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.590   0.678   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.114  -0.787   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.684   1.924   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.590   3.169   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.114   4.634   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.607   4.954   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.054   2.694   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.258   3.654   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.916   5.155   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5                                                            
CONECT    7    2    8   31                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13                                                       
CONECT   20    8   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   30                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   23   31                                                  
CONECT   31   30    7   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₆O₈

Average Mass

442.4640 Da

Monoisotopic Mass

442.16277 Da

IUPAC Name

methyl 2-[(3aS,4R,5S,6S)-4-hydroxy-3-(hydroxymethyl)-6-{[2-(4-hydroxyphenyl)acetyl]oxy}-8-methyl-1-oxo-1,3a,4,5,6,7-hexahydroazulen-5-yl]prop-2-enoate

Traditional Name

methyl 2-[(3aS,4R,5S,6S)-4-hydroxy-3-(hydroxymethyl)-6-{[2-(4-hydroxyphenyl)acetyl]oxy}-8-methyl-1-oxo-4,5,6,7-tetrahydro-3aH-azulen-5-yl]prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(=C)[C@H]1[C@H](O)[C@H]2C(CO)=CC(=O)C2=C(C)C[C@@H]1OC(=O)CC1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C24H26O8/c1-12-8-18(32-19(28)9-14-4-6-16(26)7-5-14)21(13(2)24(30)31-3)23(29)22-15(11-25)10-17(27)20(12)22/h4-7,10,18,21-23,25-26,29H,2,8-9,11H2,1,3H3/t18-,21+,22-,23-/m0/s1

InChI Key

DDNQXWHGQQEAOE-AWDZXFJFSA-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
Cichorium intybus	LOTUS Database	35616633
Lactuca serriola	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Ketone
Secondary alcohol
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Alcohol
Carbonyl group
Hydrocarbon derivative
Primary alcohol
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.44	ChemAxon
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	115.98 m³·mol⁻¹	ChemAxon
Polarizability	45.71 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

65104637

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100622832

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-[(3as,4r,5s,6s)-4-hydroxy-3-(hydroxymethyl)-6-{[2-(4-hydroxyphenyl)acetyl]oxy}-8-methyl-1-oxo-4,5,6,7-tetrahydro-3ah-azulen-5-yl]prop-2-enoate (NP0238508)

MOL for NP0238508 (methyl 2-[(3as,4r,5s,6s)-4-hydroxy-3-(hydroxymethyl)-6-{[2-(4-hydroxyphenyl)acetyl]oxy}-8-methyl-1-oxo-4,5,6,7-tetrahydro-3ah-azulen-5-yl]prop-2-enoate)

3D MOL for NP0238508 (methyl 2-[(3as,4r,5s,6s)-4-hydroxy-3-(hydroxymethyl)-6-{[2-(4-hydroxyphenyl)acetyl]oxy}-8-methyl-1-oxo-4,5,6,7-tetrahydro-3ah-azulen-5-yl]prop-2-enoate)

3D SDF for NP0238508 (methyl 2-[(3as,4r,5s,6s)-4-hydroxy-3-(hydroxymethyl)-6-{[2-(4-hydroxyphenyl)acetyl]oxy}-8-methyl-1-oxo-4,5,6,7-tetrahydro-3ah-azulen-5-yl]prop-2-enoate)

3D-SDF for NP0238508 (methyl 2-[(3as,4r,5s,6s)-4-hydroxy-3-(hydroxymethyl)-6-{[2-(4-hydroxyphenyl)acetyl]oxy}-8-methyl-1-oxo-4,5,6,7-tetrahydro-3ah-azulen-5-yl]prop-2-enoate)

PDB for NP0238508 (methyl 2-[(3as,4r,5s,6s)-4-hydroxy-3-(hydroxymethyl)-6-{[2-(4-hydroxyphenyl)acetyl]oxy}-8-methyl-1-oxo-4,5,6,7-tetrahydro-3ah-azulen-5-yl]prop-2-enoate)

3D PDB for NP0238508 (methyl 2-[(3as,4r,5s,6s)-4-hydroxy-3-(hydroxymethyl)-6-{[2-(4-hydroxyphenyl)acetyl]oxy}-8-methyl-1-oxo-4,5,6,7-tetrahydro-3ah-azulen-5-yl]prop-2-enoate)

SMILES for NP0238508 (methyl 2-[(3as,4r,5s,6s)-4-hydroxy-3-(hydroxymethyl)-6-{[2-(4-hydroxyphenyl)acetyl]oxy}-8-methyl-1-oxo-4,5,6,7-tetrahydro-3ah-azulen-5-yl]prop-2-enoate)

INCHI for NP0238508 (methyl 2-[(3as,4r,5s,6s)-4-hydroxy-3-(hydroxymethyl)-6-{[2-(4-hydroxyphenyl)acetyl]oxy}-8-methyl-1-oxo-4,5,6,7-tetrahydro-3ah-azulen-5-yl]prop-2-enoate)

Structure for NP0238508 (methyl 2-[(3as,4r,5s,6s)-4-hydroxy-3-(hydroxymethyl)-6-{[2-(4-hydroxyphenyl)acetyl]oxy}-8-methyl-1-oxo-4,5,6,7-tetrahydro-3ah-azulen-5-yl]prop-2-enoate)

3D Structure for NP0238508 (methyl 2-[(3as,4r,5s,6s)-4-hydroxy-3-(hydroxymethyl)-6-{[2-(4-hydroxyphenyl)acetyl]oxy}-8-methyl-1-oxo-4,5,6,7-tetrahydro-3ah-azulen-5-yl]prop-2-enoate)