NP-MRD: Showing NP-Card for methyl 12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate (NP0275210)

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Record Information

Version

2.0

Created at

2022-09-08 22:52:40 UTC

Updated at

2022-09-08 22:52:40 UTC

NP-MRD ID

NP0275210

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate

Description

Methyl 12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]Icosa-2,4,6,9-tetraene-10-carboxylate belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids. methyl 12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate is found in Tabernaemontana corymbosa. Methyl 12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]Icosa-2,4,6,9-tetraene-10-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241508332D          

 30 35  0  0  0  0            999 V2000
    0.5792   -0.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3381   -0.4502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9977   -0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0971   -0.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8561    0.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5156   -0.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3253   -0.1404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7262   -0.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304   -1.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7727   -1.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5768   -2.0189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1386   -1.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2109   -2.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4532   -3.2272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4067   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1644   -1.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4162   -1.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9584   -1.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5345   -2.4476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5579   -2.2603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6573   -1.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7989   -2.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6995   -3.4028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1394   -2.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798   -1.5926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2387   -1.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9555    1.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7144    1.3390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2959    1.5112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3953    2.3302    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  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  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 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
  3 21  1  0  0  0  0
 17 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
 24 26  1  0  0  0  0
  5 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
M  END

     RDKit          3D

 54 59  0  0  0  0  0  0  0  0999 V2000
   -4.6593   -0.1123   -0.6190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5935   -0.8564    0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2396   -0.3346   -0.4075 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2996    1.1300   -0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9901    1.7249    0.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9532    3.1720    0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1070    3.7394    0.7247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0262    3.9981    0.0874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9115    5.3957    0.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1072    1.0587    0.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4440    1.3699    1.0237 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2787    0.2916    0.5111 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6454    0.2596    0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1617   -0.7169   -0.4678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5127   -0.7896   -0.6426 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3826    0.0946   -0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3579   -1.5986   -1.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9401   -2.5531   -1.9445 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9877   -1.5302   -0.9322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4118   -0.5954   -0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1341   -0.3646    0.5229 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4009   -1.1710    1.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1242   -2.5762    1.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7844   -2.3173    0.1066 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3304   -2.9368   -1.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3600   -4.1828   -1.0406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8554   -2.1039   -2.1201 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1788   -1.8025   -2.2399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2259   -0.7342   -1.8406 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1498   -0.9400    0.3517 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0410    0.7064    0.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3064    0.3769   -1.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5188   -0.7509   -0.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6100   -0.6266    1.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6781   -1.9477   -0.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0319    1.4360    0.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5921    1.6452   -1.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7307    5.8628   -0.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0616    5.7144    0.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8405    5.8312    0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7013    2.2170    1.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3002    0.9522    0.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4255   -0.3014   -0.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1695    0.1594    1.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2775    1.0907   -0.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9217   -2.6280   -2.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3791   -2.2272   -1.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4203   -1.0696    2.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3985   -0.9797    2.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3034   -3.2451    1.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1165   -2.9327    0.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3370   -2.2930   -3.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0889    0.0294   -2.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6107   -1.0376    1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  5 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  1
 22 23  1  0
 23 24  1  0
 24 30  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 30  3  1  0
 29 27  1  0
 29  3  1  0
 21 10  1  0
 30 21  1  0
 20 12  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  9 38  1  0
  9 39  1  0
  9 40  1  0
 11 41  1  0
 13 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 18 46  1  0
 19 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
 30 54  1  1
 27 52  1  6
 29 53  1  6
M  END


  Mrv1533004241508332D          

 30 35  0  0  0  0            999 V2000
    0.5792   -0.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3381   -0.4502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9977   -0.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0971   -0.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8561    0.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5156   -0.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3253   -0.1404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7262   -0.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304   -1.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7727   -1.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5768   -2.0189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1386   -1.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2109   -2.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4532   -3.2272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4067   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1644   -1.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4162   -1.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9584   -1.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5345   -2.4476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5579   -2.2603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6573   -1.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7989   -2.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6995   -3.4028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1394   -2.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798   -1.5926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2387   -1.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9555    1.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7144    1.3390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2959    1.5112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3953    2.3302    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  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  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 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
  3 21  1  0  0  0  0
 17 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
 24 26  1  0  0  0  0
  5 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
M  END
> <DATABASE_ID>
NP0275210

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC12CC(C(=O)OC)=C3NC4=CC(OC)=C(O)C=C4C33CCN(C13)C(=O)C1OC21

> <INCHI_IDENTIFIER>
InChI=1S/C22H24N2O6/c1-4-21-9-10(19(27)29-3)16-22(11-7-13(25)14(28-2)8-12(11)23-16)5-6-24(20(21)22)18(26)15-17(21)30-15/h7-8,15,17,20,23,25H,4-6,9H2,1-3H3

> <INCHI_KEY>
NCDJGOXCXAXUIG-UHFFFAOYSA-N

> <FORMULA>
C22H24N2O6

> <MOLECULAR_WEIGHT>
412.442

> <EXACT_MASS>
412.163436501

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.46331600916524

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
0.7523364249999993

> <ALOGPS_LOGS>
-2.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.136486108317865

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.830737655467686

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1016046360460292

> <JCHEM_POLAR_SURFACE_AREA>
100.63000000000001

> <JCHEM_REFRACTIVITY>
107.54439999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       1.081  -1.444   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.498  -0.840   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.729  -1.765   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.915  -0.237   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.331   0.367   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.563  -0.558   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       8.074  -0.262   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       8.822  -1.608   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.323  -1.952   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.776  -3.424   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.277  -3.769   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      13.325  -2.641   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.727  -4.552   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.179  -6.024   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.226  -4.208   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.774  -2.736   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.377  -2.087   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.389  -3.248   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.598  -4.569   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       4.775  -4.219   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       4.960  -2.691   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.358  -4.823   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.172  -6.352   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.127  -3.898   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.896  -2.973   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.312  -2.369   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.517   1.896   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.934   2.500   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.286   2.821   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.471   4.350   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21   26                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    8   17                                                  
CONECT   17   16    6   18   21                                             
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20    3   17                                                  
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24   26                                                       
CONECT   26   25    3   24                                                  
CONECT   27    5   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

View in JSmol

Synonyms

Value	Source
Methyl 12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0,.0,.0,.0,]icosa-2,4,6,9-tetraene-10-carboxylic acid	Generator
Methyl 12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylic acid	Generator

Chemical Formula

C₂₂H₂₄N₂O₆

Average Mass

412.4420 Da

Monoisotopic Mass

412.16344 Da

IUPAC Name

methyl 12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate

Traditional Name

methyl 12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate

CAS Registry Number

Not Available

SMILES

CCC12CC(C(=O)OC)=C3NC4=CC(OC)=C(O)C=C4C33CCN(C13)C(=O)C1OC21

InChI Identifier

InChI=1S/C22H24N2O6/c1-4-21-9-10(19(27)29-3)16-22(11-7-13(25)14(28-2)8-12(11)23-16)5-6-24(20(21)22)18(26)15-17(21)30-15/h7-8,15,17,20,23,25H,4-6,9H2,1-3H3

InChI Key

NCDJGOXCXAXUIG-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
Tabernaemontana corymbosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aspidospermatan-type alkaloids

Sub Class

Not Available

Direct Parent

Aspidospermatan-type alkaloids

Alternative Parents

Substituents

Aspidosperma alkaloid
Carbazole
Indolizidine
Dihydroindole
Indole or derivatives
Phenol ether
Anisole
Para-oxazepine
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Piperidinone
Secondary aliphatic/aromatic amine
Delta-lactam
Epoxypiperidine
Benzenoid
Piperidine
Pyrrolidine
Tertiary carboxylic acid amide
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous amide
Amino acid or derivatives
Carboxamide group
Carboxylic acid ester
Lactam
Secondary amine
Ether
Organoheterocyclic compound
Oxirane
Enamine
Dialkyl ether
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Amine
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen 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	2.39	ALOGPS
logP	0.75	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	10.83	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.63 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.54 m³·mol⁻¹	ChemAxon
Polarizability	42.46 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 12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate (NP0275210)

MOL for NP0275210 (methyl 12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate)

3D MOL for NP0275210 (methyl 12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate)

3D SDF for NP0275210 (methyl 12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate)

3D-SDF for NP0275210 (methyl 12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate)

PDB for NP0275210 (methyl 12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate)

3D PDB for NP0275210 (methyl 12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate)

SMILES for NP0275210 (methyl 12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate)

INCHI for NP0275210 (methyl 12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate)

Structure for NP0275210 (methyl 12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate)

3D Structure for NP0275210 (methyl 12-ethyl-4-hydroxy-5-methoxy-16-oxo-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate)