NP-MRD: Showing NP-Card for methyl 4,17,18-trihydroxy-5-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-18-carboxylate (NP0328549)

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Record Information

Version

2.0

Created at

2022-09-12 12:07:24 UTC

Updated at

2022-09-12 12:07:25 UTC

NP-MRD ID

NP0328549

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4,17,18-trihydroxy-5-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-18-carboxylate

Description

Methyl 4,17,18-trihydroxy-5-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]Henicosa-3(8),4,6,14-tetraene-18-carboxylate belongs to the class of organic compounds known as aspidofractine alkaloids. These are alkaloids with a structure that is based on the hexacyclic aspidofractine core. These compounds are related to the Aspidosperma group by formation of a C-2 to C-18 bond. Methyl 4,17,18-trihydroxy-5-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]Henicosa-3(8),4,6,14-tetraene-18-carboxylate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191513482D          

 30 35  0  0  0  0            999 V2000
    3.2414   -2.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5355   -1.5531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0151   -0.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2005   -1.0436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3092   -0.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9731   -0.6320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3823   -0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8628   -0.6962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1050    0.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7556    0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3933    0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0361    0.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8508    0.1240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2531    0.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0468    1.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6385    0.5219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2488    1.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0425    2.1217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2446    2.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6571    2.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8634    2.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6613    1.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7822    1.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8205    2.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2641    2.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5942    2.3256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7615    2.4582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424    1.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2579    1.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8193    1.4584    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
  9 29  1  0  0  0  0
 26 30  1  0  0  0  0
  9 30  1  0  0  0  0
 23 30  1  0  0  0  0
M  END

     RDKit          3D

 56 61  0  0  0  0  0  0  0  0999 V2000
   -2.2056    4.5151    0.6284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0711    3.1201    0.4736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9311    2.6116   -0.0732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0492    3.4784   -0.4110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5905    1.2046   -0.3231 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6493    1.2009   -0.9807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5295    0.5015   -1.2869 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5715    1.4283   -1.5302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0939   -0.6770   -0.5258 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9670   -1.5395   -1.3234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7194   -2.8365   -1.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5928   -3.5555   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5195   -2.6682   -0.3572 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1187   -3.1321    0.9036 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1992   -1.8780    1.8227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0403   -0.8497    0.7839 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2421   -0.6081    0.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1063   -1.2075   -0.7179 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3410   -0.6875   -1.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7528    0.4605   -0.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9913    1.0255   -0.6444 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9101    0.4631   -1.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9458    1.1059    0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4019    2.2711    1.1412 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6840    0.5574    0.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6339    1.0375    1.6818 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5166    0.5098    1.0280 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8280    0.5315    1.6365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8553    0.0583    0.6168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1572   -1.5372    0.1488 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1961    4.9844    0.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7197    4.7789    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8073    4.9792   -0.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5840    1.8944   -1.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0418    0.2189   -2.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3989    0.9970   -1.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8170   -1.1373   -1.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3952   -3.4454   -2.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0054   -3.9935    0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2376   -4.3980   -1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4988   -3.8937    1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1449   -3.4772    0.6627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5632   -1.9443    2.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2129   -1.8434    2.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7801   -2.1115   -1.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0174   -1.1457   -1.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6815    1.1757   -1.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4133   -0.4385   -1.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3278    0.2139   -2.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7774    2.7153    1.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8238    1.5996    2.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1049    1.5114    2.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8901   -0.2429    2.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5264   -0.7357    1.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5141    0.8307    0.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7845   -1.9963    1.0054 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  6
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 29  1  0
 29 28  1  0
 28 27  1  0
 27 26  1  1
 26 25  1  0
 25 23  2  0
 23 24  1  0
 23 20  1  0
 20 21  1  0
 21 22  1  0
 20 19  2  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  1  1
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  2  0
 13 30  1  0
 27  5  1  0
 16 27  1  0
 30 16  1  0
  9 10  1  6
 30  9  1  0
 17 25  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  6 34  1  0
  7 35  1  6
  8 36  1  0
 29 54  1  0
 29 55  1  0
 28 52  1  0
 28 53  1  0
 26 51  1  0
 24 50  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 19 46  1  0
 18 45  1  0
 15 43  1  0
 15 44  1  0
 14 41  1  0
 14 42  1  0
 12 39  1  0
 12 40  1  0
 11 38  1  0
 10 37  1  0
 30 56  1  1
M  END


  Mrv1533004191513482D          

 30 35  0  0  0  0            999 V2000
    3.2414   -2.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5355   -1.5531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0151   -0.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2005   -1.0436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3092   -0.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9731   -0.6320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3823   -0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8628   -0.6962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1050    0.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7556    0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3933    0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0361    0.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8508    0.1240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2531    0.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0468    1.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6385    0.5219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2488    1.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0425    2.1217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2446    2.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6571    2.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8634    2.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6613    1.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7822    1.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8205    2.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2641    2.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5942    2.3256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7615    2.4582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424    1.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2579    1.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8193    1.4584    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
  9 29  1  0  0  0  0
 26 30  1  0  0  0  0
  9 30  1  0  0  0  0
 23 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328549

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(O)C(O)C23CCC11NC4=C(O)C(OC)=CC=C4C11CCN(CC=C2)C31

> <INCHI_IDENTIFIER>
InChI=1S/C22H26N2O6/c1-29-13-5-4-12-14(15(13)25)23-21-8-7-19(17(26)22(21,28)18(27)30-2)6-3-10-24-11-9-20(12,21)16(19)24/h3-6,16-17,23,25-26,28H,7-11H2,1-2H3

> <INCHI_KEY>
XWCPEWKDCBONQW-UHFFFAOYSA-N

> <FORMULA>
C22H26N2O6

> <MOLECULAR_WEIGHT>
414.458

> <EXACT_MASS>
414.179086565

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
42.71961849777461

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 4,17,18-trihydroxy-5-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-18-carboxylate

> <ALOGPS_LOGP>
1.31

> <JCHEM_LOGP>
-0.047083178333333496

> <ALOGPS_LOGS>
-1.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.035458139026684

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.427120845800149

> <JCHEM_PKA_STRONGEST_BASIC>
8.014046901132694

> <JCHEM_POLAR_SURFACE_AREA>
111.49000000000001

> <JCHEM_REFRACTIVITY>
109.05069999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.52e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4,17,18-trihydroxy-5-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-18-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       6.051  -4.338   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.600  -2.899   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.628  -1.704   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.108  -1.948   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.177  -0.265   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.416  -1.180   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.447  -0.103   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.477  -1.300   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.929   1.559   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.144   0.774   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.334   1.536   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.534   0.797   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       9.055   0.231   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       9.806   1.627   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.287   2.047   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.392   0.974   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.664   3.541   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      13.146   3.960   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      13.523   5.454   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.560   4.614   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.078   4.194   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.701   2.701   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.060   2.516   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.132   4.122   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.093   5.297   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       4.843   4.341   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       3.288   4.589   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.132   3.534   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.348   1.978   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.263   2.722   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    7   12                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   29   30                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    5   13   23                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   14   23                                                  
CONECT   23   22   12   24   30                                             
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    9                                                       
CONECT   30   26    9   23                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

View in JSmol

Synonyms

Value	Source
Methyl 4,17,18-trihydroxy-5-methoxy-2,12-diazahexacyclo[14.2.2.1,.0,.0,.0,]henicosa-3(8),4,6,14-tetraene-18-carboxylic acid	Generator
Methyl 4,17,18-trihydroxy-5-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3(8),4,6,14-tetraene-18-carboxylic acid	Generator

Chemical Formula

C₂₂H₂₆N₂O₆

Average Mass

414.4580 Da

Monoisotopic Mass

414.17909 Da

IUPAC Name

methyl 4,17,18-trihydroxy-5-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-18-carboxylate

Traditional Name

methyl 4,17,18-trihydroxy-5-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-18-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(O)C(O)C23CCC11NC4=C(O)C(OC)=CC=C4C11CCN(CC=C2)C31

InChI Identifier

InChI=1S/C22H26N2O6/c1-29-13-5-4-12-14(15(13)25)23-21-8-7-19(17(26)22(21,28)18(27)30-2)6-3-10-24-11-9-20(12,21)16(19)24/h3-6,16-17,23,25-26,28H,7-11H2,1-2H3

InChI Key

XWCPEWKDCBONQW-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspidofractine alkaloids. These are alkaloids with a structure that is based on the hexacyclic aspidofractine core. These compounds are related to the Aspidosperma group by formation of a C-2 to C-18 bond.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aspidofractine alkaloids

Sub Class

Not Available

Direct Parent

Aspidofractine alkaloids

Alternative Parents

Substituents

Aspidofractine skeleton
Carbazole
Dihydroindole
Indole or derivatives
Anisole
1-hydroxy-4-unsubstituted benzenoid
Secondary aliphatic/aromatic amine
Alkyl aryl ether
Aralkylamine
Beta-hydroxy acid
Benzenoid
N-alkylpyrrolidine
Hydroxy acid
Methyl ester
Tertiary alcohol
Cyclic alcohol
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
1,2-diol
Carboxylic acid ester
Amino acid or derivatives
Secondary alcohol
Azacycle
Carboxylic acid derivative
Organoheterocyclic compound
Secondary amine
Ether
Polyol
Monocarboxylic acid or derivatives
Alcohol
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Amine
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	1.31	ALOGPS
logP	-0.047	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	10.43	ChemAxon
pKa (Strongest Basic)	8.01	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	111.49 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	109.05 m³·mol⁻¹	ChemAxon
Polarizability	42.72 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 4,17,18-trihydroxy-5-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-18-carboxylate (NP0328549)

MOL for NP0328549 (methyl 4,17,18-trihydroxy-5-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-18-carboxylate)

3D MOL for NP0328549 (methyl 4,17,18-trihydroxy-5-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-18-carboxylate)

3D SDF for NP0328549 (methyl 4,17,18-trihydroxy-5-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-18-carboxylate)

3D-SDF for NP0328549 (methyl 4,17,18-trihydroxy-5-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-18-carboxylate)

PDB for NP0328549 (methyl 4,17,18-trihydroxy-5-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-18-carboxylate)

3D PDB for NP0328549 (methyl 4,17,18-trihydroxy-5-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-18-carboxylate)

SMILES for NP0328549 (methyl 4,17,18-trihydroxy-5-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-18-carboxylate)

INCHI for NP0328549 (methyl 4,17,18-trihydroxy-5-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-18-carboxylate)

Structure for NP0328549 (methyl 4,17,18-trihydroxy-5-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-18-carboxylate)

3D Structure for NP0328549 (methyl 4,17,18-trihydroxy-5-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7,14-tetraene-18-carboxylate)