NP-MRD: Showing NP-Card for methyl (12s,13s,15r,17s,19s)-19-hydroxy-13-[(1s)-1-hydroxyethyl]-4-methoxy-1,11-diazapentacyclo[13.3.1.0²,⁷.0⁸,¹⁸.0¹²,¹⁷]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate (NP0255686)

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Record Information

Version

2.0

Created at

2022-09-07 20:15:32 UTC

Updated at

2022-09-07 20:15:32 UTC

NP-MRD ID

NP0255686

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (12s,13s,15r,17s,19s)-19-hydroxy-13-[(1s)-1-hydroxyethyl]-4-methoxy-1,11-diazapentacyclo[13.3.1.0²,⁷.0⁸,¹⁸.0¹²,¹⁷]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate

Description

Dippinine A belongs to the class of organic compounds known as pyrroloazepines. Pyrroloazepines are compounds containing a pyrroloazepine moiety, which is a bicyclic heterocycle which consists of a pyrrole ring fused to an azepine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Azepine is a 7-membered ring consisting of six carbon and one nitrogen atom. methyl (12s,13s,15r,17s,19s)-19-hydroxy-13-[(1s)-1-hydroxyethyl]-4-methoxy-1,11-diazapentacyclo[13.3.1.0²,⁷.0⁸,¹⁸.0¹²,¹⁷]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate is found in Tabernaemontana corymbosa. Based on a literature review very few articles have been published on Dippinine A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072222152D          

 29 33  0  0  1  0            999 V2000
    3.9630    3.5588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3614    2.6403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2249    2.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5806    3.6143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3307    1.7143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5946    0.9575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8074    0.3651    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5875    0.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6582    1.7182    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4786    2.0438    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8404    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2603    1.7017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9419    2.2257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6985    3.0655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9444    3.4588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1919    3.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9935    2.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5390    1.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2454    0.8420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4100    1.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7826    0.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0049    0.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3101    0.2400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4656    0.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8547    1.5763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4821    2.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2597    1.8365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9046    0.2107    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7971   -0.6381    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  6  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  1  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  1  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  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
 25 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
 19 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  6  0  0  0
M  END

     RDKit          3D

 57 61  0  0  0  0  0  0  0  0999 V2000
   -2.8976    3.8136   -2.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7125    2.7022   -1.3605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4779    2.1977   -1.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4771    2.7434   -1.5606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2704    1.0412   -0.1326 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7230    1.5160    1.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2025    0.5694    2.3000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4292   -0.8113    1.7892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4496   -0.9311    0.6864 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5785   -2.4043    0.3609 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5634   -2.6795   -0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9997   -3.0361    1.5491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0405   -0.1907   -0.5549 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2782   -1.0524   -1.4063 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8785   -0.3882   -2.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5735    0.0746   -2.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9358    0.2278   -1.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1497    0.6246   -0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8817    0.5774    1.0867 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932    0.1749    0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2219   -0.0378    1.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3936   -0.4661    0.9477 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4887   -0.6598    1.7809 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7503   -1.0959    1.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4712   -0.6936   -0.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3528   -0.4852   -1.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1748   -0.0530   -0.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2977    0.8914    2.3972 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5135    2.2373    2.6283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0475    3.9377   -2.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8799    3.7499   -2.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9150    4.7119   -1.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2291    2.4945    1.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006    1.6762    1.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6504    0.8306    3.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8431   -1.4115    2.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4969   -1.3392    1.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4370   -0.5553    1.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5710   -2.7673    0.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1862   -1.8075   -1.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0672   -3.0623   -1.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2938   -3.4658   -0.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9779   -3.1510    1.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9399    0.1157   -1.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4209   -1.4366   -0.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5638    0.4414   -2.8634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9294   -1.1525   -3.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2532   -0.7067   -2.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6862    0.9593   -3.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1779    0.1362    2.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2392   -0.2825    0.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3696   -1.2986    2.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6543   -2.0279    0.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4234   -1.0351   -0.8443 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3910   -0.6564   -2.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6930    0.2817    3.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0422    2.4142    3.4421 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  6
  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 28  1  0
 28 29  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  2  0
 25 26  1  0
 26 27  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  1
  8 36  1  0
  8 37  1  0
  9 38  1  1
 10 39  1  6
 11 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  6
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 28 56  1  1
 29 57  1  0
 21 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
 25 54  1  0
 26 55  1  0
M  END


  Mrv1652309072222152D          

 29 33  0  0  1  0            999 V2000
    3.9630    3.5588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3614    2.6403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2249    2.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5806    3.6143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3307    1.7143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5946    0.9575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8074    0.3651    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5875    0.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6582    1.7182    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4786    2.0438    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8404    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2603    1.7017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9419    2.2257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6985    3.0655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9444    3.4588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1919    3.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9935    2.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5390    1.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2454    0.8420    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4100    1.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7826    0.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0049    0.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3101    0.2400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4656    0.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8547    1.5763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4821    2.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2597    1.8365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9046    0.2107    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7971   -0.6381    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  6  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  1  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  1  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  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
 25 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
 19 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0255686

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]12C[C@H]3C[C@H]([C@H](C)O)[C@@H]1NCCC1=C2N([C@H]3O)C2=CC(OC)=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C22H28N2O5/c1-11(25)16-8-12-10-22(21(27)29-3)18(16)23-7-6-15-14-5-4-13(28-2)9-17(14)24(19(15)22)20(12)26/h4-5,9,11-12,16,18,20,23,25-26H,6-8,10H2,1-3H3/t11-,12+,16+,18-,20-,22-/m0/s1

> <INCHI_KEY>
QKYXTXFMWJYJDW-LMIFGVMKSA-N

> <FORMULA>
C22H28N2O5

> <MOLECULAR_WEIGHT>
400.475

> <EXACT_MASS>
400.19982201

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
42.247569956268926

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (12S,13S,15R,17S,19S)-19-hydroxy-13-[(1S)-1-hydroxyethyl]-4-methoxy-1,11-diazapentacyclo[13.3.1.0^{2,7}.0^{8,18}.0^{12,17}]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate

> <JCHEM_LOGP>
1.3001353520000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.221339480635613

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.07885336451687

> <JCHEM_PKA_STRONGEST_BASIC>
9.16397006522871

> <JCHEM_POLAR_SURFACE_AREA>
92.95

> <JCHEM_REFRACTIVITY>
106.73649999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (12S,13S,15R,17S,19S)-19-hydroxy-13-[(1S)-1-hydroxyethyl]-4-methoxy-1,11-diazapentacyclo[13.3.1.0^{2,7}.0^{8,18}.0^{12,17}]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       7.398   6.643   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.141   4.929   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.753   4.965   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.417   6.747   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.951   3.200   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.443   1.787   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.840   0.682   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.297   1.538   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.429   3.207   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.960   3.815   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.635   5.265   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      15.419   3.176   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.091   4.155   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      10.637   5.722   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       9.230   6.456   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.825   5.773   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.455   4.226   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.473   3.037   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       7.925   1.572   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       6.365   1.914   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.194   0.914   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.743   1.428   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.445   0.448   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.869   0.681   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.462   2.942   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.633   3.942   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.085   3.428   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.155   0.393   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.955  -1.191   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                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   27                                                  
CONECT   18   17    5   19                                                  
CONECT   19   18   20   28                                                  
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   17   20                                                  
CONECT   28   19    7   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₈N₂O₅

Average Mass

400.4750 Da

Monoisotopic Mass

400.19982 Da

IUPAC Name

methyl (12S,13S,15R,17S,19S)-19-hydroxy-13-[(1S)-1-hydroxyethyl]-4-methoxy-1,11-diazapentacyclo[13.3.1.0^{2,7}.0^{8,18}.0^{12,17}]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate

Traditional Name

methyl (12S,13S,15R,17S,19S)-19-hydroxy-13-[(1S)-1-hydroxyethyl]-4-methoxy-1,11-diazapentacyclo[13.3.1.0^{2,7}.0^{8,18}.0^{12,17}]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]12C[C@H]3C[C@H]([C@H](C)O)[C@@H]1NCCC1=C2N([C@H]3O)C2=CC(OC)=CC=C12

InChI Identifier

InChI=1S/C22H28N2O5/c1-11(25)16-8-12-10-22(21(27)29-3)18(16)23-7-6-15-14-5-4-13(28-2)9-17(14)24(19(15)22)20(12)26/h4-5,9,11-12,16,18,20,23,25-26H,6-8,10H2,1-3H3/t11-,12+,16+,18-,20-,22-/m0/s1

InChI Key

QKYXTXFMWJYJDW-LMIFGVMKSA-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 pyrroloazepines. Pyrroloazepines are compounds containing a pyrroloazepine moiety, which is a bicyclic heterocycle which consists of a pyrrole ring fused to an azepine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Azepine is a 7-membered ring consisting of six carbon and one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrroloazepines

Sub Class

Not Available

Direct Parent

Pyrroloazepines

Alternative Parents

Substituents

Pyrroloazepine
3-alkylindole
Indole
Indole or derivatives
Anisole
Phenol ether
Alkyl aryl ether
Azepine
Aralkylamine
Benzenoid
Methyl ester
Heteroaromatic compound
Pyrrole
1,3-aminoalcohol
Secondary alcohol
Amino acid or derivatives
Carboxylic acid ester
Secondary amine
Alkanolamine
Azacycle
Monocarboxylic acid or derivatives
Ether
Secondary aliphatic amine
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic nitrogen compound
Organic oxygen compound
Amine
Organic oxide
Organonitrogen compound
Organooxygen 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	1.3	ChemAxon
pKa (Strongest Acidic)	13.08	ChemAxon
pKa (Strongest Basic)	9.16	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.95 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	106.74 m³·mol⁻¹	ChemAxon
Polarizability	42.25 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

10220225

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21595540

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (12s,13s,15r,17s,19s)-19-hydroxy-13-[(1s)-1-hydroxyethyl]-4-methoxy-1,11-diazapentacyclo[13.3.1.0²,⁷.0⁸,¹⁸.0¹²,¹⁷]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate (NP0255686)

MOL for NP0255686 (methyl (12s,13s,15r,17s,19s)-19-hydroxy-13-[(1s)-1-hydroxyethyl]-4-methoxy-1,11-diazapentacyclo[13.3.1.0²,⁷.0⁸,¹⁸.0¹²,¹⁷]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate)

3D MOL for NP0255686 (methyl (12s,13s,15r,17s,19s)-19-hydroxy-13-[(1s)-1-hydroxyethyl]-4-methoxy-1,11-diazapentacyclo[13.3.1.0²,⁷.0⁸,¹⁸.0¹²,¹⁷]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate)

3D SDF for NP0255686 (methyl (12s,13s,15r,17s,19s)-19-hydroxy-13-[(1s)-1-hydroxyethyl]-4-methoxy-1,11-diazapentacyclo[13.3.1.0²,⁷.0⁸,¹⁸.0¹²,¹⁷]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate)

3D-SDF for NP0255686 (methyl (12s,13s,15r,17s,19s)-19-hydroxy-13-[(1s)-1-hydroxyethyl]-4-methoxy-1,11-diazapentacyclo[13.3.1.0²,⁷.0⁸,¹⁸.0¹²,¹⁷]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate)

PDB for NP0255686 (methyl (12s,13s,15r,17s,19s)-19-hydroxy-13-[(1s)-1-hydroxyethyl]-4-methoxy-1,11-diazapentacyclo[13.3.1.0²,⁷.0⁸,¹⁸.0¹²,¹⁷]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate)

3D PDB for NP0255686 (methyl (12s,13s,15r,17s,19s)-19-hydroxy-13-[(1s)-1-hydroxyethyl]-4-methoxy-1,11-diazapentacyclo[13.3.1.0²,⁷.0⁸,¹⁸.0¹²,¹⁷]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate)

SMILES for NP0255686 (methyl (12s,13s,15r,17s,19s)-19-hydroxy-13-[(1s)-1-hydroxyethyl]-4-methoxy-1,11-diazapentacyclo[13.3.1.0²,⁷.0⁸,¹⁸.0¹²,¹⁷]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate)

INCHI for NP0255686 (methyl (12s,13s,15r,17s,19s)-19-hydroxy-13-[(1s)-1-hydroxyethyl]-4-methoxy-1,11-diazapentacyclo[13.3.1.0²,⁷.0⁸,¹⁸.0¹²,¹⁷]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate)

Structure for NP0255686 (methyl (12s,13s,15r,17s,19s)-19-hydroxy-13-[(1s)-1-hydroxyethyl]-4-methoxy-1,11-diazapentacyclo[13.3.1.0²,⁷.0⁸,¹⁸.0¹²,¹⁷]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate)

3D Structure for NP0255686 (methyl (12s,13s,15r,17s,19s)-19-hydroxy-13-[(1s)-1-hydroxyethyl]-4-methoxy-1,11-diazapentacyclo[13.3.1.0²,⁷.0⁸,¹⁸.0¹²,¹⁷]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate)