NP-MRD: Showing NP-Card for (1r,2r,3r,6r,8s,12s,13s,14r,15r,16s,17s)-2,3,12,15,16-pentahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione (NP0300756)

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Record Information

Version

2.0

Created at

2022-09-10 13:19:48 UTC

Updated at

2022-09-10 13:19:48 UTC

NP-MRD ID

NP0300756

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,3r,6r,8s,12s,13s,14r,15r,16s,17s)-2,3,12,15,16-pentahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione

Description

Bruceine D 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,8s,12s,13s,14r,15r,16s,17s)-2,3,12,15,16-pentahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione is found in Brucea javanica and Brucea mollis. (1r,2r,3r,6r,8s,12s,13s,14r,15r,16s,17s)-2,3,12,15,16-pentahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione was first documented in 2021 (PMID: 34900531). Based on a literature review a small amount of articles have been published on Bruceine D (PMID: 35215292) (PMID: 34761661) (PMID: 35999761) (PMID: 35990425).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102215192D          

 29 33  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  1  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  1  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
   -0.3275   -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  2  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  2  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
 10  2  1  6  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  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  6  0  0  0
 12 24  1  0  0  0  0
 18 24  1  0  0  0  0
 25 24  1  6  0  0  0
  8 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  1  0  0  0
M  END

     RDKit          2D

 55 59  0  0  0  0  0  0  0  0999 V2000
   -2.3313   -6.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323   -5.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2668   -6.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5658   -5.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8648   -6.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5658   -3.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0430   -4.0105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2668   -3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5658   -2.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323   -3.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3313   -3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3313   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6304   -0.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6304    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9294    1.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3313    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3671    2.6491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8755    2.2418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943    1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8578    2.6401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2760    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943   -1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2668   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5863   -1.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0741   -0.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6567    0.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2353    1.7873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6304   -6.7500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5813   -7.2990    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3734   -4.9210    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2668   -7.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6806   -2.7464    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0072   -2.8614    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0077   -1.8366    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8379   -3.0447    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0544   -0.8318    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3313   -4.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8293   -2.9215    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1702   -4.2435    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7121   -2.0861    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2955    2.6491    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8802    4.0586    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3065    3.1653    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3213    4.0667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542    2.5356    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5688    3.1036    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8362   -1.6269    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1339   -2.6908    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4647   -0.5972    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6527   -2.1498    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8171    0.3989    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1493    0.2547    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7231    1.9781    0.0000 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  6
 18 20  1  0
 20 21  1  1
 20 22  1  0
 22 23  1  0
 24 23  1  6
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 10  2  1  0
 24 12  1  0
 25  8  1  0
 24 18  1  0
 28 20  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  6 34  1  1
  7 35  1  0
  9 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  1
 11 40  1  0
 11 41  1  0
 12 42  1  6
 16 43  1  1
 17 44  1  0
 19 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 23 49  1  0
 23 50  1  0
 25 51  1  1
 26 52  1  1
 27 53  1  0
 28 54  1  6
 29 55  1  0
M  END


  Mrv1652309102215192D          

 29 33  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  1  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  1  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
   -0.3275   -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  2  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  2  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
 10  2  1  6  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  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  6  0  0  0
 12 24  1  0  0  0  0
 18 24  1  0  0  0  0
 25 24  1  6  0  0  0
  8 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0300756

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=O)[C@@H](O)[C@@]2(C)[C@H]1C[C@H]1OC(=O)[C@H](O)[C@@]3(O)[C@@]4(C)OC[C@]13[C@@H]2[C@@H](O)[C@@H]4O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O9/c1-7-4-9(21)13(23)17(2)8(7)5-10-19-6-28-18(3,14(24)11(22)12(17)19)20(19,27)15(25)16(26)29-10/h4,8,10-15,22-25,27H,5-6H2,1-3H3/t8-,10+,11+,12+,13+,14-,15-,17-,18-,19+,20+/m0/s1

> <INCHI_KEY>
JBDMZGKDLMGOFR-DFEKUIMESA-N

> <FORMULA>
C20H26O9

> <MOLECULAR_WEIGHT>
410.419

> <EXACT_MASS>
410.157682417

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
78.87683590249188

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3R,6R,8S,12S,13S,14R,15R,16S,17S)-2,3,12,15,16-pentahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-9-ene-4,11-dione

> <JCHEM_LOGP>
-2.245578673333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.462281172312387

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.341061395937517

> <JCHEM_PKA_STRONGEST_BASIC>
-3.31820228019848

> <JCHEM_POLAR_SURFACE_AREA>
153.75

> <JCHEM_REFRACTIVITY>
95.366

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3R,6R,8S,12S,13S,14R,15R,16S,17S)-2,3,12,15,16-pentahydroxy-9,13,17-trimethyl-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      -0.611  -0.149   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.187  -1.510   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.239  -1.389   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.497  -0.316   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.184   1.182   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.329   2.211   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.736   1.649   0.000  0.00  0.00           C+0
HETATM   29  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   25                                             
CONECT    9    8                                                            
CONECT   10    8    2   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   24                                                  
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   24                                             
CONECT   19   18                                                            
CONECT   20   18   21   22   28                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   12   18   25                                             
CONECT   25   24    8   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   20   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=CC(=O)[C@@H](O)[C@@]2(C)[C@H]1C[C@H]1OC(=O)[C@H](O)[C@@]3(O)[C@@]4(C)OC[C@]13[C@@H]2[C@@H](O)[C@@H]4O

InChI Identifier

InChI=1S/C20H26O9/c1-7-4-9(21)13(23)17(2)8(7)5-10-19-6-28-18(3,14(24)11(22)12(17)19)20(19,27)15(25)16(26)29-10/h4,8,10-15,22-25,27H,5-6H2,1-3H3/t8-,10+,11+,12+,13+,14-,15-,17-,18-,19+,20+/m0/s1

InChI Key

JBDMZGKDLMGOFR-DFEKUIMESA-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
Brucea mollis	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
Delta valerolactone
Cyclohexenone
Delta_valerolactone
Oxepane
Oxane
Pyran
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Furan
Secondary alcohol
Carboxylic acid ester
Cyclic ketone
Ketone
Lactone
Carboxylic acid derivative
Ether
Dialkyl ether
Polyol
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003702

Chemspider ID

109456

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122784

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cipriani C, Pacheco MP, Kishk A, Wachich M, Abankwa D, Schaffner-Reckinger E, Sauter T: Bruceine D Identified as a Drug Candidate against Breast Cancer by a Novel Drug Selection Pipeline and Cell Viability Assay. Pharmaceuticals (Basel). 2022 Jan 31;15(2). pii: ph15020179. doi: 10.3390/ph15020179. [PubMed:35215292 ]
Huang R, Zhang L, Jin J, Zhou Y, Zhang H, Lv C, Lu D, Wu Y, Zhang H, Liu S, Chen H, Luan X, Zhang W: Bruceine D inhibits HIF-1alpha-mediated glucose metabolism in hepatocellular carcinoma by blocking ICAT/beta-catenin interaction. Acta Pharm Sin B. 2021 Nov;11(11):3481-3492. doi: 10.1016/j.apsb.2021.05.009. Epub 2021 May 20. [PubMed:34900531 ]
Nie Y, Yang B, Hu J, Zhang L, Ma Z: Bruceine D ameliorates the balance of Th1/Th2 in a mouse model of ovalbumin-induced allergic asthma via inhibiting the NOTCH pathway. Allergol Immunopathol (Madr). 2021 Nov 4;49(6):73-79. doi: 10.15586/aei.v49i6.499. eCollection 2021. [PubMed:34761661 ]
Tong Y, Yi SC, Liu SY, Xu L, Qiu ZX, Zeng DQ, Tang WW: Bruceine D may affect the phenylpropanoid biosynthesis by acting on ADTs thus inhibiting Bidens pilosa L. seed germination. Ecotoxicol Environ Saf. 2022 Sep 1;242:113943. doi: 10.1016/j.ecoenv.2022.113943. Epub 2022 Aug 4. [PubMed:35999761 ]
Jia XN, Wang WJ, Yin B, Zhou LJ, Zhen YQ, Zhang L, Zhou XL, Song HN, Tang Y, Gao F: Deep Learning Promotes the Screening of Natural Products with Potential Microtubule Inhibition Activity. ACS Omega. 2022 Aug 5;7(32):28334-28341. doi: 10.1021/acsomega.2c02854. eCollection 2022 Aug 16. [PubMed:35990425 ]
LOTUS database [Link]

Showing NP-Card for (1r,2r,3r,6r,8s,12s,13s,14r,15r,16s,17s)-2,3,12,15,16-pentahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione (NP0300756)

MOL for NP0300756 ((1r,2r,3r,6r,8s,12s,13s,14r,15r,16s,17s)-2,3,12,15,16-pentahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione)

3D MOL for NP0300756 ((1r,2r,3r,6r,8s,12s,13s,14r,15r,16s,17s)-2,3,12,15,16-pentahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione)

3D SDF for NP0300756 ((1r,2r,3r,6r,8s,12s,13s,14r,15r,16s,17s)-2,3,12,15,16-pentahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione)

3D-SDF for NP0300756 ((1r,2r,3r,6r,8s,12s,13s,14r,15r,16s,17s)-2,3,12,15,16-pentahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione)

PDB for NP0300756 ((1r,2r,3r,6r,8s,12s,13s,14r,15r,16s,17s)-2,3,12,15,16-pentahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione)

3D PDB for NP0300756 ((1r,2r,3r,6r,8s,12s,13s,14r,15r,16s,17s)-2,3,12,15,16-pentahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione)

SMILES for NP0300756 ((1r,2r,3r,6r,8s,12s,13s,14r,15r,16s,17s)-2,3,12,15,16-pentahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione)

INCHI for NP0300756 ((1r,2r,3r,6r,8s,12s,13s,14r,15r,16s,17s)-2,3,12,15,16-pentahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione)

Structure for NP0300756 ((1r,2r,3r,6r,8s,12s,13s,14r,15r,16s,17s)-2,3,12,15,16-pentahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione)

3D Structure for NP0300756 ((1r,2r,3r,6r,8s,12s,13s,14r,15r,16s,17s)-2,3,12,15,16-pentahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.0¹,⁶.0²,¹⁷.0⁸,¹³]nonadec-9-ene-4,11-dione)