NP-MRD: Showing NP-Card for methyl (1s,15r,17r,18s)-17-[(1r)-1-hydroxyethyl]-7-methoxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate (NP0272702)

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Record Information

Version

2.0

Created at

2022-09-08 19:25:54 UTC

Updated at

2022-09-08 19:25:54 UTC

NP-MRD ID

NP0272702

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,15r,17r,18s)-17-[(1r)-1-hydroxyethyl]-7-methoxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate

Description

Methyl (1S,15R,17R,18S)-17-[(1R)-1-hydroxyethyl]-7-methoxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]Nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate belongs to the class of organic compounds known as ibogan-type alkaloids. These are indole alkaloids with a structure based on the ibogamine skeleton or a derivative thereof. Ibogamine is a pentacyclic heterocyclic compound consisting of an indole fused to an azepane-containing tricyclic moiety ring. Iboga alkaloids arise from the cyclization of a secodine-type precursor through the formation of a 16,21 bond. methyl (1s,15r,17r,18s)-17-[(1r)-1-hydroxyethyl]-7-methoxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate is found in Tabernaemontana calcarea. Based on a literature review very few articles have been published on methyl (1S,15R,17R,18S)-17-[(1R)-1-hydroxyethyl]-7-methoxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]Nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082221252D          

 29 33  0  0  1  0            999 V2000
   -0.7563   -2.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0697   -2.4747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7028   -1.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4940   -2.3284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9323   -0.6568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1432   -0.8620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6447   -0.4036    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3031   -1.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6532   -1.1684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2466   -1.8507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0415   -2.7855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0489   -1.5758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6785   -0.1268    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3836    0.6820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0446    1.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8695    1.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2245    0.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8283   -0.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3942   -1.0040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1400   -0.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9011   -0.9697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5574   -0.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4525    0.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1713    0.8431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0164    0.7370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6914    0.6669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0351    0.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4494    0.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1036    1.0052    0.0000 O   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
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 10 12  1  6  0  0  0
  9 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  6  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  2  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 17 27  1  0  0  0  0
 20 27  1  0  0  0  0
 14 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
    1.8974    3.9103    1.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705    2.8162    0.4582 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5970    1.4889    0.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2790    1.3748    1.9023 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9951    0.4619    0.0739 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2176    0.8560   -1.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1797   -0.1288   -1.9996 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3167   -0.3035   -0.9647 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7862   -1.3391   -0.0123 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6777   -1.8163    1.0515 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9319   -2.4918    0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2183   -0.7724    1.7827 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3703   -0.9695    0.3158 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6367   -1.6123   -0.8332 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6057   -2.2915   -0.9184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6510   -1.2014   -1.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5480   -0.0984   -0.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4982    0.5761    0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0485    1.4806    1.1600 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3722    1.4007    1.1809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3283    2.0992    1.8921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6703    1.8209    1.7317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0351    0.8432    0.8577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3700    0.5435    0.6770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7771   -0.4663   -0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0616    0.1485    0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7253    0.4215    0.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3817   -1.4300   -2.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4047   -2.2003   -3.0029 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3813    4.0988    2.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7243    4.8133    0.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9815    3.7943    1.2714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2677    0.9161   -1.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6763    1.8708   -1.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5433    0.1583   -2.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4938    0.6496   -0.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2463   -0.5827   -1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7367   -2.2787   -0.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2509   -2.6117    1.6791 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6352   -3.4057   -0.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4008   -1.8047   -0.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6217   -2.7314    1.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0342   -0.9279    2.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9889   -1.3260    1.2642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8599   -2.7180    0.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6167   -2.9978   -1.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6185   -1.7204   -1.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4988   -0.8741   -2.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4698    2.1270    1.7147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0574    2.8751    2.5871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4297    2.3818    2.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1689   -1.3819   -0.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6487   -0.0884   -1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8417   -0.7294   -0.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3420   -0.6272   -0.5453 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
  5  3  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  2  0
 14 28  1  0
 28 29  2  0
 13  5  1  0
 27 17  1  0
 18  5  1  0
 27 20  1  0
 28  7  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  6
  8 36  1  0
  8 37  1  0
  9 38  1  6
 10 39  1  1
 11 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  1
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 19 49  1  0
 21 50  1  0
 22 51  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
 26 55  1  0
M  END


  Mrv1652309082221252D          

 29 33  0  0  1  0            999 V2000
   -0.7563   -2.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0697   -2.4747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7028   -1.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4940   -2.3284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9323   -0.6568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1432   -0.8620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6447   -0.4036    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3031   -1.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6532   -1.1684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2466   -1.8507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0415   -2.7855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0489   -1.5758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6785   -0.1268    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3836    0.6820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0446    1.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8695    1.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2245    0.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8283   -0.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3942   -1.0040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1400   -0.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9011   -0.9697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5574   -0.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4525    0.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1713    0.8431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0164    0.7370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6914    0.6669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0351    0.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4494    0.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1036    1.0052    0.0000 O   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
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 10 12  1  6  0  0  0
  9 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  6  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  2  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 17 27  1  0  0  0  0
 20 27  1  0  0  0  0
 14 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0272702

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]12C[C@H]3C[C@@H]([C@@H](C)O)[C@@H]1N(CCC1=C2NC2=CC=C(OC)C=C12)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H26N2O5/c1-11(25)15-8-12-10-22(21(27)29-3)18-14(6-7-24(19(15)22)20(12)26)16-9-13(28-2)4-5-17(16)23-18/h4-5,9,11-12,15,19,23,25H,6-8,10H2,1-3H3/t11-,12-,15+,19+,22-/m1/s1

> <INCHI_KEY>
OZUSKNIPJRUWKJ-JYCQGSJXSA-N

> <FORMULA>
C22H26N2O5

> <MOLECULAR_WEIGHT>
398.459

> <EXACT_MASS>
398.184171945

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
42.48416451752252

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,15R,17R,18S)-17-[(1R)-1-hydroxyethyl]-7-methoxy-14-oxo-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene-1-carboxylate

> <JCHEM_LOGP>
1.1641951853333339

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.774883794801152

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.075760666710266

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5694314983480814

> <JCHEM_POLAR_SURFACE_AREA>
91.86000000000001

> <JCHEM_REFRACTIVITY>
105.77780000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,15R,17R,18S)-17-[(1R)-1-hydroxyethyl]-7-methoxy-14-oxo-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.412  -5.243   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.130  -4.619   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.312  -3.251   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.789  -4.346   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.740  -1.226   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.267  -1.609   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.204  -0.753   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.566  -2.464   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.219  -2.181   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.327  -3.455   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.944  -5.200   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.825  -2.942   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.266  -0.237   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       0.716   1.273   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       1.950   2.339   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.490   2.030   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.152   0.597   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.413  -0.753   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       4.469  -1.874   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       5.861  -1.216   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.282  -1.810   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.507  -0.877   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.311   0.651   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.653   1.574   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      11.231   1.376   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.891   1.245   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.666   0.312   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.839   0.857   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.060   1.876   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   13   18                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   28                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    9    5   14                                                  
CONECT   14   13   15   28                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   27                                                  
CONECT   18   17    5   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27                                                       
CONECT   27   26   17   20                                                  
CONECT   28   14    7   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1S,15R,17R,18S)-17-[(1R)-1-hydroxyethyl]-7-methoxy-14-oxo-3,13-diazapentacyclo[13.3.1.0,.0,.0,]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylic acid	Generator

Chemical Formula

C₂₂H₂₆N₂O₅

Average Mass

398.4590 Da

Monoisotopic Mass

398.18417 Da

IUPAC Name

methyl (1S,15R,17R,18S)-17-[(1R)-1-hydroxyethyl]-7-methoxy-14-oxo-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene-1-carboxylate

Traditional Name

methyl (1S,15R,17R,18S)-17-[(1R)-1-hydroxyethyl]-7-methoxy-14-oxo-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]12C[C@H]3C[C@@H]([C@@H](C)O)[C@@H]1N(CCC1=C2NC2=CC=C(OC)C=C12)C3=O

InChI Identifier

InChI=1S/C22H26N2O5/c1-11(25)15-8-12-10-22(21(27)29-3)18-14(6-7-24(19(15)22)20(12)26)16-9-13(28-2)4-5-17(16)23-18/h4-5,9,11-12,15,19,23,25H,6-8,10H2,1-3H3/t11-,12-,15+,19+,22-/m1/s1

InChI Key

OZUSKNIPJRUWKJ-JYCQGSJXSA-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 calcarea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ibogan-type alkaloids. These are indole alkaloids with a structure based on the ibogamine skeleton or a derivative thereof. Ibogamine is a pentacyclic heterocyclic compound consisting of an indole fused to an azepane-containing tricyclic moiety ring. Iboga alkaloids arise from the cyclization of a secodine-type precursor through the formation of a 16,21 bond.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ibogan-type alkaloids

Sub Class

Not Available

Direct Parent

Ibogan-type alkaloids

Alternative Parents

Substituents

Ibogan skeleton
Catharanthine skeleton
3-alkylindole
Pyrroloazepine
Indole
Indole or derivatives
Piperidinecarboxylic acid
Anisole
Phenol ether
Alkyl aryl ether
Azepine
Delta-lactam
Piperidinone
Benzenoid
Piperidine
Heteroaromatic compound
Methyl ester
Tertiary carboxylic acid amide
Pyrrole
Secondary alcohol
Lactam
Carboxamide group
Carboxylic acid ester
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Ether
Organonitrogen compound
Hydrocarbon derivative
Alcohol
Organic nitrogen compound
Carbonyl group
Organic oxide
Organooxygen compound
Organic oxygen 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	1.16	ChemAxon
pKa (Strongest Acidic)	15.08	ChemAxon
pKa (Strongest Basic)	-0.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.86 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	105.78 m³·mol⁻¹	ChemAxon
Polarizability	42.48 Å³	ChemAxon
Number of Rings	5	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

4481128

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5323585

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1s,15r,17r,18s)-17-[(1r)-1-hydroxyethyl]-7-methoxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate (NP0272702)

MOL for NP0272702 (methyl (1s,15r,17r,18s)-17-[(1r)-1-hydroxyethyl]-7-methoxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

3D MOL for NP0272702 (methyl (1s,15r,17r,18s)-17-[(1r)-1-hydroxyethyl]-7-methoxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

3D SDF for NP0272702 (methyl (1s,15r,17r,18s)-17-[(1r)-1-hydroxyethyl]-7-methoxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

3D-SDF for NP0272702 (methyl (1s,15r,17r,18s)-17-[(1r)-1-hydroxyethyl]-7-methoxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

PDB for NP0272702 (methyl (1s,15r,17r,18s)-17-[(1r)-1-hydroxyethyl]-7-methoxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

3D PDB for NP0272702 (methyl (1s,15r,17r,18s)-17-[(1r)-1-hydroxyethyl]-7-methoxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

SMILES for NP0272702 (methyl (1s,15r,17r,18s)-17-[(1r)-1-hydroxyethyl]-7-methoxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

INCHI for NP0272702 (methyl (1s,15r,17r,18s)-17-[(1r)-1-hydroxyethyl]-7-methoxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

Structure for NP0272702 (methyl (1s,15r,17r,18s)-17-[(1r)-1-hydroxyethyl]-7-methoxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

3D Structure for NP0272702 (methyl (1s,15r,17r,18s)-17-[(1r)-1-hydroxyethyl]-7-methoxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)