NP-MRD: Showing NP-Card for (1r,2r,3r,6r,12s,13s,15r)-2,3,12,15,16-pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione (NP0302522)

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Record Information

Version

2.0

Created at

2022-09-10 16:10:34 UTC

Updated at

2022-09-10 16:10:34 UTC

NP-MRD ID

NP0302522

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,3r,6r,12s,13s,15r)-2,3,12,15,16-pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione

Description

(1R,2R,3R,6R,12S,13S,15R)-2,3,12,15,16-pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]Nonadec-9-ene-4,11-dione 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,2r,3r,6r,12s,13s,15r)-2,3,12,15,16-pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione is found in Brucea javanica. Based on a literature review very few articles have been published on (1R,2R,3R,6R,12S,13S,15R)-2,3,12,15,16-pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]Nonadec-9-ene-4,11-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102218102D          

 30 34  0  0  1  0            999 V2000
    4.0957   -1.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8032   -1.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3250   -0.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0324    0.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542    0.8587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2181    0.3520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9255    1.1234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6963   -0.2871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3965    0.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9889   -1.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4438   -1.6714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6243   -1.4971    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1762   -2.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3527   -2.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1064   -2.8377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0058   -1.4126    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8122   -1.3052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5993   -0.7073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2019   -0.5108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883    0.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1085    0.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9273    0.8009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3275   -0.0798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1001   -0.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1996   -0.7440    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8734   -0.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7055    0.6329    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3190    1.1846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9300    0.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7035    1.6767    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  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  6  0  0  0
 12 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
  8 26  1  0  0  0  0
 26 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  0  0  0  0
M  END

     RDKit          3D

 56 60  0  0  0  0  0  0  0  0999 V2000
   -3.9785    0.4007    2.5443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4264    0.1603    1.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2623   -0.0166    0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7315   -0.2510   -1.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5105   -0.4342   -2.0957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2816   -0.2885   -1.4225 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1074    0.3591   -2.6553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4789    0.4467   -0.3420 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8024    1.9276   -0.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9649    0.1363    1.0339 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4152   -1.1756    1.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0932   -1.0121    1.7102 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5754   -2.3473    1.6820 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3214   -2.8939    0.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3674   -4.1311    0.5528 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0793   -2.0100   -0.2334 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4119   -2.4396   -0.3617 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0976   -0.6823    0.3900 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8747   -0.7795    1.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6482    0.4653   -0.3558 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1223    0.2949   -0.5585 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7222    1.4238   -1.1110 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3577    1.5421    0.5050 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    1.1785    1.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7221   -0.1102    0.7466 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0402    0.1361   -0.5203 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5804    1.1977   -1.3738 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6449    2.4418   -0.8022 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0066    0.7571   -1.6658 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0734   -0.2625   -2.5869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0086    0.8423    2.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1542   -0.6100    2.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3256    1.0150    3.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3443    0.0023    0.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8811   -1.3019   -1.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2566   -0.2229   -3.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371    2.2382   -1.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4552    2.5712    0.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9317    1.9668   -0.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5621    0.9164    1.7194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4841   -1.8821    0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9168   -1.6175    2.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1843   -0.6066    2.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6276   -2.1022   -1.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4970   -3.1092   -1.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3562   -0.9978    2.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2437   -0.5039   -1.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6287   -0.0807    0.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8556    2.0645   -0.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7344    0.9426    2.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5663    1.9683    1.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0446   -0.8226   -1.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0520    1.1939   -2.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4030    2.9546   -1.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5118    1.6492   -2.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1711   -0.5018   -2.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  6
 21 22  1  0
 20 23  1  0
 23 24  1  0
 25 24  1  1
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 10  2  1  0
 25 12  1  0
 26  8  1  0
 25 18  1  0
 29 20  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  6 35  1  6
  7 36  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
 10 40  1  1
 11 41  1  0
 11 42  1  0
 12 43  1  1
 16 44  1  6
 17 45  1  0
 19 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 24 50  1  0
 24 51  1  0
 26 52  1  6
 27 53  1  6
 28 54  1  0
 29 55  1  6
 30 56  1  0
M  END


  Mrv1652309102218102D          

 30 34  0  0  1  0            999 V2000
    4.0957   -1.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8032   -1.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3250   -0.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0324    0.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542    0.8587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2181    0.3520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9255    1.1234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6963   -0.2871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3965    0.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9889   -1.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4438   -1.6714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6243   -1.4971    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1762   -2.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3527   -2.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1064   -2.8377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0058   -1.4126    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8122   -1.3052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5993   -0.7073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2019   -0.5108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883    0.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1085    0.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9273    0.8009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3275   -0.0798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1001   -0.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1996   -0.7440    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8734   -0.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7055    0.6329    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3190    1.1846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9300    0.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7035    1.6767    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  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  6  0  0  0
 12 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
  8 26  1  0  0  0  0
 26 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  0  0  0  0
M  END
> <DATABASE_ID>
NP0302522

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=O)[C@@H](O)[C@@]2(C)C1C[C@H]1OC(=O)[C@H](O)[C@@]3(O)C4(CO)OC[C@]13C2[C@@H](O)C4O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O10/c1-7-3-9(22)13(24)17(2)8(7)4-10-18-6-29-19(5-21,14(25)11(23)12(17)18)20(18,28)15(26)16(27)30-10/h3,8,10-15,21,23-26,28H,4-6H2,1-2H3/t8?,10-,11-,12?,13-,14?,15+,17+,18-,19?,20+/m1/s1

> <INCHI_KEY>
QXKKRGMRXXMDDP-YIHGHLGWSA-N

> <FORMULA>
C20H26O10

> <MOLECULAR_WEIGHT>
426.418

> <EXACT_MASS>
426.152597037

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
40.09649594215987

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3R,6R,12S,13S,15R)-2,3,12,15,16-pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-9-ene-4,11-dione

> <JCHEM_LOGP>
-3.29248864

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.411427707006048

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.31634804576265

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1551486441103123

> <JCHEM_POLAR_SURFACE_AREA>
173.98

> <JCHEM_REFRACTIVITY>
96.9097

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3R,6R,12S,13S,15R)-2,3,12,15,16-pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-9-ene-4,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       7.645  -3.663   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.099  -2.223   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.073  -1.030   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.527   0.410   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.501   1.603   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.007   0.657   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.461   2.097   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.033  -0.536   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.473   0.899   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.579  -1.976   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.562  -3.120   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.032  -2.795   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.196  -4.091   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.658  -4.017   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.199  -5.297   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.011  -2.637   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.516  -2.436   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.119  -1.320   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.377  -0.954   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.725   0.454   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.203   1.683   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.731   1.495   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.611  -0.149   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.187  -1.510   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.239  -1.389   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.497  -0.316   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.184   1.182   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.329   2.211   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.736   1.649   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.313   3.130   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    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   26                                             
CONECT    9    8                                                            
CONECT   10    8    2   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   25                                             
CONECT   19   18                                                            
CONECT   20   18   21   23   29                                             
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   12   18   26                                             
CONECT   26   25    8   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   20   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₁₀

Average Mass

426.4180 Da

Monoisotopic Mass

426.15260 Da

IUPAC Name

(1R,2R,3R,6R,12S,13S,15R)-2,3,12,15,16-pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-9-ene-4,11-dione

Traditional Name

(1R,2R,3R,6R,12S,13S,15R)-2,3,12,15,16-pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-9-ene-4,11-dione

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)[C@@H](O)[C@@]2(C)C1C[C@H]1OC(=O)[C@H](O)[C@@]3(O)C4(CO)OC[C@]13C2[C@@H](O)C4O

InChI Identifier

InChI=1S/C20H26O10/c1-7-3-9(22)13(24)17(2)8(7)4-10-18-6-29-19(5-21,14(25)11(23)12(17)18)20(18,28)15(26)16(27)30-10/h3,8,10-15,21,23-26,28H,4-6H2,1-2H3/t8?,10-,11-,12?,13-,14?,15+,17+,18-,19?,20+/m1/s1

InChI Key

QXKKRGMRXXMDDP-YIHGHLGWSA-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
Brucea javanica	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
Furopyran
Cyclohexenone
Oxepane
Delta_valerolactone
Delta valerolactone
Pyran
Oxane
Tetrahydrofuran
Tertiary alcohol
Furan
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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
logP	-3.3	ChemAxon
pKa (Strongest Acidic)	11.32	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	173.98 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	96.91 m³·mol⁻¹	ChemAxon
Polarizability	40.1 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

4474800

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5315514

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,3r,6r,12s,13s,15r)-2,3,12,15,16-pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione (NP0302522)

MOL for NP0302522 ((1r,2r,3r,6r,12s,13s,15r)-2,3,12,15,16-pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione)

3D MOL for NP0302522 ((1r,2r,3r,6r,12s,13s,15r)-2,3,12,15,16-pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione)

3D SDF for NP0302522 ((1r,2r,3r,6r,12s,13s,15r)-2,3,12,15,16-pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione)

3D-SDF for NP0302522 ((1r,2r,3r,6r,12s,13s,15r)-2,3,12,15,16-pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione)

PDB for NP0302522 ((1r,2r,3r,6r,12s,13s,15r)-2,3,12,15,16-pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione)

3D PDB for NP0302522 ((1r,2r,3r,6r,12s,13s,15r)-2,3,12,15,16-pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione)

SMILES for NP0302522 ((1r,2r,3r,6r,12s,13s,15r)-2,3,12,15,16-pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione)

INCHI for NP0302522 ((1r,2r,3r,6r,12s,13s,15r)-2,3,12,15,16-pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione)

Structure for NP0302522 ((1r,2r,3r,6r,12s,13s,15r)-2,3,12,15,16-pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione)

3D Structure for NP0302522 ((1r,2r,3r,6r,12s,13s,15r)-2,3,12,15,16-pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione)