NP-MRD: Showing NP-Card for 2,18-dimethyl 17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate (NP0184546)

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Record Information

Version

2.0

Created at

2022-09-03 23:42:15 UTC

Updated at

2022-09-03 23:42:15 UTC

NP-MRD ID

NP0184546

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,18-dimethyl 17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate

Description

2,18-Dimethyl 17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]Henicosa-3,5,7-triene-2,18-dicarboxylate belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. 2,18-dimethyl 17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate is found in Kopsia singapurensis. 2,18-Dimethyl 17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]Henicosa-3,5,7-triene-2,18-dicarboxylate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151518552D          

 31 36  0  0  0  0            999 V2000
    6.0919    3.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7841    3.1886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2930    2.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1098    2.6555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9852    1.7739    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3782    1.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1520    0.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2909   -0.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6562   -0.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8824   -0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7434    0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8791    0.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9355   -0.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4119   -0.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7506   -0.3655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286   -0.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2707   -0.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3496    0.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1693    1.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8319    1.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5395    1.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1776    1.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4232    2.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667    2.5613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5154    1.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0124    2.5878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1027    2.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6008    3.4629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2841    2.9077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9636    3.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9201    0.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 23 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 19 31  1  0  0  0  0
 12 31  1  0  0  0  0
 15 31  1  0  0  0  0
M  END

     RDKit          3D

 59 64  0  0  0  0  0  0  0  0999 V2000
    5.4361    1.0916    0.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2998    0.3325    0.1165 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9869    0.7191    0.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0018    1.8045    1.1377 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8761   -0.0686    0.2185 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471   -1.3198   -0.4702 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9803   -2.2158   -0.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -3.3868   -1.4088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5138   -3.7178   -1.8868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4744   -2.8132   -1.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7048   -1.6574   -0.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2378   -0.5636   -0.5966 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6369    0.1148   -1.8139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9259   -0.5953   -2.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4033   -1.1975   -1.1114 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7960   -1.1551   -0.8724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1608   -1.2450    0.5979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4085   -0.2429    1.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9473   -0.1861    1.0990 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1032   -0.6921    2.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2881   -0.8358    1.7256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042    0.1254    0.4980 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0026    1.4079    0.9745 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2918    1.4937    2.3766 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4359    2.6630    0.4118 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6601    3.6505    1.2209 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6659    3.0095   -0.9018 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0930    4.2771   -1.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5417    1.2601    0.9321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0406    1.9173    2.0851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5272   -1.0703   -0.0275 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2348    2.1834    0.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7969    0.8042    1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2222    0.8298   -0.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9861   -1.9926   -0.3540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5549   -4.0962   -1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3320   -4.6382   -2.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4905   -3.1265   -2.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8694    1.1546   -1.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0970   -0.0803   -2.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7111   -1.3578   -3.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6260    0.1183   -2.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2766   -0.2992   -1.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2533   -2.0733   -1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0671   -2.2809    0.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2492   -0.9912    0.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9191    0.7349    1.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5108   -0.5505    2.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5070   -1.6751    2.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2280   -0.0080    3.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9975   -0.4925    2.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4943   -1.8593    1.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263    2.4339    2.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4911    4.8127   -0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2327    4.8175   -1.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8811    4.1873   -2.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9943    1.7858    0.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7471    2.8604    2.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2931   -2.1049    0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
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 12 13  1  6
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 19 31  1  0
 22  5  1  6
 11  6  1  0
 22 12  1  0
 31 12  1  0
 31 15  1  0
 29 19  1  0
  1 32  1  0
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  7 35  1  0
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 10 38  1  0
 13 39  1  0
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 24 53  1  0
 29 57  1  6
 30 58  1  0
 28 54  1  0
 28 55  1  0
 28 56  1  0
 31 59  1  1
M  END


  Mrv1533004151518552D          

 31 36  0  0  0  0            999 V2000
    6.0919    3.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7841    3.1886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2930    2.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1098    2.6555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9852    1.7739    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3782    1.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1520    0.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2909   -0.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6562   -0.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8824   -0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7434    0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8791    0.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9355   -0.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4119   -0.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7506   -0.3655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286   -0.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2707   -0.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3496    0.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1693    1.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8319    1.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5395    1.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1776    1.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4232    2.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667    2.5613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5154    1.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0124    2.5878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1027    2.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6008    3.4629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2841    2.9077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9636    3.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9201    0.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  0  0  0  0
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 23 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 23 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 19 31  1  0  0  0  0
 12 31  1  0  0  0  0
 15 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0184546

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)N1C2=CC=CC=C2C23CCN4CCCC5(CCC12C(O)(C5O)C(=O)OC)C34

> <INCHI_IDENTIFIER>
InChI=1S/C23H28N2O6/c1-30-18(27)23(29)17(26)20-8-5-12-24-13-11-21(16(20)24)14-6-3-4-7-15(14)25(19(28)31-2)22(21,23)10-9-20/h3-4,6-7,16-17,26,29H,5,8-13H2,1-2H3

> <INCHI_KEY>
GMLJERYGIGLLSG-UHFFFAOYSA-N

> <FORMULA>
C23H28N2O6

> <MOLECULAR_WEIGHT>
428.485

> <EXACT_MASS>
428.19473663

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
43.8737636138678

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,18-dimethyl 17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate

> <ALOGPS_LOGP>
1.06

> <JCHEM_LOGP>
0.7494757072826176

> <ALOGPS_LOGS>
-2.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.023533552390113

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.776654215411948

> <JCHEM_PKA_STRONGEST_BASIC>
9.079437726046383

> <JCHEM_POLAR_SURFACE_AREA>
99.54

> <JCHEM_REFRACTIVITY>
109.05270000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,18-dimethyl 17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0      11.372   7.381   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.797   5.952   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.747   4.740   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      13.272   4.957   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      11.172   3.311   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      11.906   1.934   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.350   1.400   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.610  -0.118   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.425  -1.102   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.981  -0.568   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.721   0.950   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.108   1.124   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.213  -0.481   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.235  -1.690   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       7.001  -0.682   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       5.467  -1.110   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.239  -0.108   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.386   1.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.916   1.999   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.153   2.609   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.474   2.186   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.665   2.817   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.257   3.817   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.458   4.781   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.562   3.610   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.623   4.830   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.658   5.236   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.588   6.464   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       6.130   5.428   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.532   6.847   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.318   0.927   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   22                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11   13   22   31                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   31                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   25   31                                             
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    5   12   23                                             
CONECT   23   22   24   25   27                                             
CONECT   24   23                                                            
CONECT   25   23   19   26                                                  
CONECT   26   25                                                            
CONECT   27   23   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31   19   12   15                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Value	Source
2,18-Dimethyl 17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1,.0,.0,.0,]henicosa-3,5,7-triene-2,18-dicarboxylic acid	Generator
2,18-Dimethyl 17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylic acid	Generator

Chemical Formula

C₂₃H₂₈N₂O₆

Average Mass

428.4850 Da

Monoisotopic Mass

428.19474 Da

IUPAC Name

2,18-dimethyl 17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate

Traditional Name

2,18-dimethyl 17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)N1C2=CC=CC=C2C23CCN4CCCC5(CCC12C(O)(C5O)C(=O)OC)C34

InChI Identifier

InChI=1S/C23H28N2O6/c1-30-18(27)23(29)17(26)20-8-5-12-24-13-11-21(16(20)24)14-6-3-4-7-15(14)25(19(28)31-2)22(21,23)10-9-20/h3-4,6-7,16-17,26,29H,5,8-13H2,1-2H3

InChI Key

GMLJERYGIGLLSG-UHFFFAOYSA-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
Kopsia singapurensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

Triterpene saponin
Triterpenoid
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Disaccharide
Glycosyl compound
O-glycosyl compound
Pyran
Oxane
Cyclic alcohol
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid
Carboxylic acid derivative
Polyol
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	1.06	ALOGPS
logP	0.75	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	10.78	ChemAxon
pKa (Strongest Basic)	9.08	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.54 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	109.05 m³·mol⁻¹	ChemAxon
Polarizability	43.87 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74218056

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,18-dimethyl 17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate (NP0184546)

MOL for NP0184546 (2,18-dimethyl 17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate)

3D MOL for NP0184546 (2,18-dimethyl 17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate)

3D SDF for NP0184546 (2,18-dimethyl 17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate)

3D-SDF for NP0184546 (2,18-dimethyl 17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate)

PDB for NP0184546 (2,18-dimethyl 17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate)

3D PDB for NP0184546 (2,18-dimethyl 17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate)

SMILES for NP0184546 (2,18-dimethyl 17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate)

INCHI for NP0184546 (2,18-dimethyl 17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate)

Structure for NP0184546 (2,18-dimethyl 17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate)

3D Structure for NP0184546 (2,18-dimethyl 17,18-dihydroxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate)