NP-MRD: Showing NP-Card for (1r,4r,5r,7r,8r,11r,13s,16s,17s,18s,19r)-4,5,7,8,16,17-hexahydroxy-14,18-dimethyl-6-methylidene-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one (NP0328882)

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Record Information

Version

2.0

Created at

2022-09-12 12:44:45 UTC

Updated at

2022-09-12 12:44:45 UTC

NP-MRD ID

NP0328882

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4r,5r,7r,8r,11r,13s,16s,17s,18s,19r)-4,5,7,8,16,17-hexahydroxy-14,18-dimethyl-6-methylidene-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one

Description

Eurycomanol belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. (1r,4r,5r,7r,8r,11r,13s,16s,17s,18s,19r)-4,5,7,8,16,17-hexahydroxy-14,18-dimethyl-6-methylidene-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one is found in Eurycoma longifolia. It was first documented in 2019 (PMID: 31920654). Based on a literature review a significant number of articles have been published on Eurycomanol (PMID: 31223329) (PMID: 36054770) (PMID: 34785103) (PMID: 33876232).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122214442D          

 29 33  0  0  1  0            999 V2000
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2180   -2.2343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369   -2.5432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3268   -1.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3984   -2.0221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    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  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  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  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22  5  1  1  0  0  0
  9 22  1  0  0  0  0
 10 23  1  6  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  1  1  0  0  0
 26 28  1  0  0  0  0
  2 28  1  0  0  0  0
  9 28  1  0  0  0  0
 28 29  1  1  0  0  0
M  END

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
   -4.3856   -0.3653   -0.6116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1127   -0.4619   -0.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4842   -1.7857   -0.2121 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3788   -2.2522   -1.5308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1316   -1.7930    0.4653 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4892   -2.9556    0.1739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3637   -1.6025    1.8243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5171   -0.2622    2.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1135    0.4871    0.8224 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4016    1.7286    1.1482 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0369    1.4190    1.5577 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6668    0.8018    0.3606 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1166    0.8035    0.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8700    1.8733    1.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7780   -0.1361   -0.3301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -1.2530   -1.0544 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7140   -1.3039   -2.3418 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6733   -1.0160   -1.2109 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9948   -2.0484   -1.7972 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0679   -0.5939    0.1383 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6139   -1.5304    1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3938   -0.5384    0.0339 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3417    2.6577    0.0783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9808    2.4455   -1.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6054    2.9954   -2.1994 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1456    1.5496   -1.1952 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3268    2.2444   -1.5353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4110    0.8171    0.0797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2690    1.5405    0.9027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9419   -1.2463   -0.8634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9173    0.5835   -0.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1673   -2.4860    0.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2687   -2.6033   -1.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0461   -3.5509   -0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9187    0.0955    2.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5832   -0.0402    2.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9036    2.2460    1.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0782    0.7992    2.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5129    2.4013    1.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3047    1.3914   -0.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5697    1.9764    2.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7291    2.8361    0.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9629    1.6865    1.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8613   -0.0884   -0.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3945   -2.2107   -0.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6953   -1.4542   -2.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5615   -0.1078   -1.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1233   -1.9820   -2.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8769   -2.5429    0.7438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5698   -1.1307    1.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9558   -1.6483    2.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6621   -0.4046   -1.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0315    0.7818   -2.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6488    2.7849   -0.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9252    2.4485    1.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  1
 20 22  1  0
 22  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  1  0
  9  8  1  1
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  1
 28  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
 12 13  1  0
 12 20  1  0
  9 22  1  0
 28  9  1  0
  3  5  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  1
 17 46  1  0
 18 47  1  6
 19 48  1  0
 21 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  6
  6 34  1  0
  8 35  1  0
  8 36  1  0
 10 37  1  1
 11 38  1  0
 11 39  1  0
 12 40  1  6
 26 53  1  6
 27 54  1  0
 29 55  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  1
  4 33  1  0
M  END


  Mrv1652309122214442D          

 29 33  0  0  1  0            999 V2000
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2180   -2.2343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369   -2.5432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3268   -1.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3984   -2.0221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    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  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  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  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22  5  1  1  0  0  0
  9 22  1  0  0  0  0
 10 23  1  6  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  1  1  0  0  0
 26 28  1  0  0  0  0
  2 28  1  0  0  0  0
  9 28  1  0  0  0  0
 28 29  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0328882

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C[C@H](O)[C@@H](O)[C@]2(C)[C@H]3[C@@]4(O)OC[C@@]33[C@@H](C[C@@H]12)OC(=O)[C@H](O)[C@@]3(O)C(=C)[C@H]4O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O9/c1-7-4-10(21)13(23)17(3)9(7)5-11-18-6-28-20(27,16(17)18)12(22)8(2)19(18,26)14(24)15(25)29-11/h4,9-14,16,21-24,26-27H,2,5-6H2,1,3H3/t9-,10-,11+,12+,13+,14-,16+,17+,18+,19-,20-/m0/s1

> <INCHI_KEY>
QPHFGJSVJHRLFM-KKSWBDSZSA-N

> <FORMULA>
C20H26O9

> <MOLECULAR_WEIGHT>
410.419

> <EXACT_MASS>
410.157682417

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
39.66646772888182

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4R,5R,7R,8R,11R,13S,16S,17S,18S,19R)-4,5,7,8,16,17-hexahydroxy-14,18-dimethyl-6-methylidene-3,10-dioxapentacyclo[9.8.0.0^{1,7}.0^{4,19}.0^{13,18}]nonadec-14-en-9-one

> <JCHEM_LOGP>
-2.4310893983333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.535326235888284

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.723452502488474

> <JCHEM_PKA_STRONGEST_BASIC>
-3.318519427465924

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
95.98159999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R,5R,7R,8R,11R,13S,16S,17S,18S,19R)-4,5,7,8,16,17-hexahydroxy-14,18-dimethyl-6-methylidene-3,10-dioxapentacyclo[9.8.0.0^{1,7}.0^{4,19}.0^{13,18}]nonadec-14-en-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.140  -4.171   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.816  -4.747   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.610  -3.453   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.477  -3.775   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.334  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   22                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   22   28                                             
CONECT   10    9   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   12   21   22                                             
CONECT   21   20                                                            
CONECT   22   20    5    9                                                  
CONECT   23   10   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    2    9   29                                             
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₉

Average Mass

410.4190 Da

Monoisotopic Mass

410.15768 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1=C[C@H](O)[C@@H](O)[C@]2(C)[C@H]3[C@@]4(O)OC[C@@]33[C@@H](C[C@@H]12)OC(=O)[C@H](O)[C@@]3(O)C(=C)[C@H]4O

InChI Identifier

InChI=1S/C20H26O9/c1-7-4-10(21)13(23)17(3)9(7)5-11-18-6-28-20(27,16(17)18)12(22)8(2)19(18,26)14(24)15(25)29-11/h4,9-14,16,21-24,26-27H,2,5-6H2,1,3H3/t9-,10-,11+,12+,13+,14-,16+,17+,18+,19-,20-/m0/s1

InChI Key

QPHFGJSVJHRLFM-KKSWBDSZSA-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
Eurycoma longifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Quassinoids

Alternative Parents

Substituents

Polycyclic triterpenoid
Triterpenoid
C-20 quassinoid skeleton
Quassinoid
Naphthopyran
Naphthalene
Delta valerolactone
Delta_valerolactone
Oxepane
Oxane
Pyran
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Lactone
Hemiacetal
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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

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

19981985

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14396865

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ezzat SM, Okba MM, Ezzat MI, Aborehab NM, Mohamed SO: Rho-Kinase II Inhibitory Potential of Eurycoma longifolia New Isolate for the Management of Erectile Dysfunction. Evid Based Complement Alternat Med. 2019 May 15;2019:4341592. doi: 10.1155/2019/4341592. eCollection 2019. [PubMed:31223329 ]
Okba MM, Ezzat MI, Shehabeldine AM, Ezzat SM: Eurycomanol and eurycomanone as potent inducers for cell-cycle arrest and apoptosis in small and large human lung cancer cell lines. Nat Prod Res. 2022 Sep 2:1-7. doi: 10.1080/14786419.2022.2119387. [PubMed:36054770 ]
Bao R, Chen Q, Li Z, Wang D, Wu Y, Liu M, Zhang Y, Wang T: Eurycomanol alleviates hyperuricemia by promoting uric acid excretion and reducing purine synthesis. Phytomedicine. 2022 Feb;96:153850. doi: 10.1016/j.phymed.2021.153850. Epub 2021 Nov 6. [PubMed:34785103 ]
Chua LS, Segaran A, Wong HJ: LC-PDA-MS/MS-Based Characterization of Key Phytochemicals in Eurycoma Longifolia Roots. J Chromatogr Sci. 2021 Jun 21;59(7):659-669. doi: 10.1093/chromsci/bmab041. [PubMed:33876232 ]
Bao R, Liu M, Wang D, Wen S, Yu H, Zhong Y, Li Z, Zhang Y, Wang T: Effect of Eurycoma longifolia Stem Extract on Uric Acid Excretion in Hyperuricemia Mice. Front Pharmacol. 2019 Dec 10;10:1464. doi: 10.3389/fphar.2019.01464. eCollection 2019. [PubMed:31920654 ]
LOTUS database [Link]

Showing NP-Card for (1r,4r,5r,7r,8r,11r,13s,16s,17s,18s,19r)-4,5,7,8,16,17-hexahydroxy-14,18-dimethyl-6-methylidene-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one (NP0328882)

MOL for NP0328882 ((1r,4r,5r,7r,8r,11r,13s,16s,17s,18s,19r)-4,5,7,8,16,17-hexahydroxy-14,18-dimethyl-6-methylidene-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one)

3D MOL for NP0328882 ((1r,4r,5r,7r,8r,11r,13s,16s,17s,18s,19r)-4,5,7,8,16,17-hexahydroxy-14,18-dimethyl-6-methylidene-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one)

3D SDF for NP0328882 ((1r,4r,5r,7r,8r,11r,13s,16s,17s,18s,19r)-4,5,7,8,16,17-hexahydroxy-14,18-dimethyl-6-methylidene-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one)

3D-SDF for NP0328882 ((1r,4r,5r,7r,8r,11r,13s,16s,17s,18s,19r)-4,5,7,8,16,17-hexahydroxy-14,18-dimethyl-6-methylidene-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one)

PDB for NP0328882 ((1r,4r,5r,7r,8r,11r,13s,16s,17s,18s,19r)-4,5,7,8,16,17-hexahydroxy-14,18-dimethyl-6-methylidene-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one)

3D PDB for NP0328882 ((1r,4r,5r,7r,8r,11r,13s,16s,17s,18s,19r)-4,5,7,8,16,17-hexahydroxy-14,18-dimethyl-6-methylidene-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one)

SMILES for NP0328882 ((1r,4r,5r,7r,8r,11r,13s,16s,17s,18s,19r)-4,5,7,8,16,17-hexahydroxy-14,18-dimethyl-6-methylidene-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one)

INCHI for NP0328882 ((1r,4r,5r,7r,8r,11r,13s,16s,17s,18s,19r)-4,5,7,8,16,17-hexahydroxy-14,18-dimethyl-6-methylidene-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one)

Structure for NP0328882 ((1r,4r,5r,7r,8r,11r,13s,16s,17s,18s,19r)-4,5,7,8,16,17-hexahydroxy-14,18-dimethyl-6-methylidene-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one)

3D Structure for NP0328882 ((1r,4r,5r,7r,8r,11r,13s,16s,17s,18s,19r)-4,5,7,8,16,17-hexahydroxy-14,18-dimethyl-6-methylidene-3,10-dioxapentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadec-14-en-9-one)