NP-MRD: Showing NP-Card for (1r,10s,12r,13r,14r,16s,17s,18r)-14-hydroxy-13-[(1r)-1-methoxyethyl]-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-18-yl acetate (NP0309669)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 04:25:35 UTC

Updated at

2022-09-11 04:25:35 UTC

NP-MRD ID

NP0309669

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,10s,12r,13r,14r,16s,17s,18r)-14-hydroxy-13-[(1r)-1-methoxyethyl]-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-18-yl acetate

Description

(1R,10S,12R,13R,14R,16S,17S,18R)-14-hydroxy-13-[(1R)-1-methoxyethyl]-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]Nonadeca-2,4,6,8-tetraen-18-yl acetate belongs to the class of organic compounds known as ajmaline-sarpagine alkaloids. These are organic compounds containing either of the ajmalan, sarpagan skeleton, or derivative thereof. The Sarpagine (Akuammidine) group, based on the sarpagan nucleus, arises from bond formation between C-16 and C-5 of the corynantheine precursor. Ajmaline alkaloids are based on a 17,19-secoyohimban skeleton (oxayohimban) which is invariably present as an ether. (1r,10s,12r,13r,14r,16s,17s,18r)-14-hydroxy-13-[(1r)-1-methoxyethyl]-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-18-yl acetate is found in Alstonia yunnanensis. Based on a literature review very few articles have been published on (1R,10S,12R,13R,14R,16S,17S,18R)-14-hydroxy-13-[(1R)-1-methoxyethyl]-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]Nonadeca-2,4,6,8-tetraen-18-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112206252D          

 28 33  0  0  1  0            999 V2000
   -1.8603    1.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2724    0.6461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4772    0.8658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2699    1.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1106    0.2870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9791    0.1877    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9515    1.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5871    0.4291    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4498    0.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0204    1.2285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6572    0.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4211    0.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0729    0.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9608   -0.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1969   -0.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5451   -0.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6786   -0.2627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1182   -1.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3140   -1.1684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7535   -0.4514    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6022   -0.9752    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9651   -1.7161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7882   -1.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2484   -1.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1510   -2.5132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0676   -0.3823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2173   -0.5325    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2709   -1.1975    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  1  6  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  6  0  0  0
 19 18  1  6  0  0  0
 20 19  1  6  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 19 26  1  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  6  0  0  0
M  END

     RDKit          3D

 54 59  0  0  0  0  0  0  0  0999 V2000
   -5.3666   -0.1660   -1.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1373    0.3559   -0.8848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7666   -0.0826    0.3687 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7353    0.9601    1.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775   -0.9654    0.2389 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4435   -0.4620   -0.6190 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6413   -1.7452   -0.9024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0163   -2.0812    0.4073 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4290   -1.6599    0.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5302   -2.2267    0.0629 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6204   -1.3112    0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -1.4768   -0.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8596   -0.4067   -0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3622    0.8512    0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9983    0.9973    0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1215   -0.0541    0.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7013   -0.2133    0.4958 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1468    0.1170    1.8507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3254    0.0234    1.5515 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5252    0.4961    0.1377 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8403    0.6140   -0.4207 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3239    1.9005   -0.6346 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7408    2.4490   -1.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436    3.8422   -1.9315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6968    1.7450   -2.8237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6156   -1.4160    1.5443 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0477   -1.5223    1.5258 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3710   -2.8623    1.7319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2151   -1.2847   -1.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1376    0.0217   -0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6179    0.1170   -2.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6126   -0.7716    0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8845    0.4969    2.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9026    1.6366    1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6633    1.5873    1.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9631   -1.8767   -0.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7703   -0.0025   -1.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0006   -1.6825   -1.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3769   -2.5800   -1.1030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0114   -3.1653    0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3530   -2.4705   -0.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9253   -0.5773   -0.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0567    1.6815    0.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6438    1.9972    0.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4709    1.0651    2.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4668   -0.6879    2.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9608    0.4969    2.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.4874    0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8655    0.1226   -1.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3492    4.5024   -1.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8386    4.0066   -2.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8378    4.0579   -1.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4295   -0.9275    2.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3290   -2.9507    1.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5 27  1  0
 27 28  1  0
 27 26  1  0
 26 19  1  0
 19 18  1  0
 18 17  1  0
 17 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 21 20  1  0
 20  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  6  5  1  0
 16 11  1  0
  8 26  1  0
 20 19  1  0
  9 17  1  0
 17 16  1  1
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  1
  4 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  6
 27 53  1  1
 28 54  1  0
 19 47  1  1
 18 45  1  0
 18 46  1  0
 21 49  1  6
 24 50  1  0
 24 51  1  0
 24 52  1  0
 20 48  1  1
  6 37  1  6
  7 38  1  0
  7 39  1  0
  8 40  1  1
 12 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
M  END


  Mrv1652309112206252D          

 28 33  0  0  1  0            999 V2000
   -1.8603    1.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2724    0.6461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4772    0.8658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2699    1.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1106    0.2870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9791    0.1877    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9515    1.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5871    0.4291    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4498    0.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0204    1.2285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6572    0.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4211    0.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0729    0.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9608   -0.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1969   -0.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5451   -0.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6786   -0.2627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1182   -1.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3140   -1.1684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7535   -0.4514    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6022   -0.9752    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9651   -1.7161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7882   -1.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2484   -1.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1510   -2.5132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0676   -0.3823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2173   -0.5325    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2709   -1.1975    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  1  6  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  6  0  0  0
 19 18  1  6  0  0  0
 20 19  1  6  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 19 26  1  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0309669

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H](C)[C@@H]1[C@@H](O)N2[C@H]3C[C@]45[C@H](OC(C)=O)[C@H]3[C@H]1C[C@H]2C4=NC1=CC=CC=C51

> <INCHI_IDENTIFIER>
InChI=1S/C22H26N2O4/c1-10(27-3)17-12-8-15-19-22(13-6-4-5-7-14(13)23-19)9-16(24(15)21(17)26)18(12)20(22)28-11(2)25/h4-7,10,12,15-18,20-21,26H,8-9H2,1-3H3/t10-,12+,15+,16+,17+,18+,20-,21-,22-/m1/s1

> <INCHI_KEY>
XHABFDBTVXEZFH-ASMGYPJESA-N

> <FORMULA>
C22H26N2O4

> <MOLECULAR_WEIGHT>
382.46

> <EXACT_MASS>
382.189257325

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
41.26309055921669

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,10S,12R,13R,14R,16S,17S,18R)-14-hydroxy-13-[(1R)-1-methoxyethyl]-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6,8-tetraen-18-yl acetate

> <JCHEM_LOGP>
2.060723811666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.238190917458528

> <JCHEM_PKA_STRONGEST_BASIC>
5.629364636180522

> <JCHEM_POLAR_SURFACE_AREA>
71.36

> <JCHEM_REFRACTIVITY>
103.6829

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,10S,12R,13R,14R,16S,17S,18R)-14-hydroxy-13-[(1R)-1-methoxyethyl]-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6,8-tetraen-18-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.473   2.287   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.375   1.206   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.891   1.616   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.504   3.107   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.207   0.536   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.828   0.350   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.776   1.908   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.963   0.801   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.573   1.071   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       5.638   2.293   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       6.827   1.259   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.253   1.840   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.469   0.896   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.260  -0.629   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.834  -1.211   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.618  -0.267   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.000  -0.490   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.954  -2.009   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.453  -2.181   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.273  -0.843   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.857  -1.820   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.535  -3.203   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.071  -3.308   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.930  -2.030   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.749  -4.691   0.000  0.00  0.00           O+0
HETATM   26  N   UNK     0       1.993  -0.714   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       0.406  -0.994   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.506  -2.235   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   27                                                  
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   26                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16    9   18   21                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19    6   21                                                  
CONECT   21   20   17   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   19    8   27                                                  
CONECT   27   26    5   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   66    0
END

View in JSmol

Synonyms

Value	Source
(1R,10S,12R,13R,14R,16S,17S,18R)-14-Hydroxy-13-[(1R)-1-methoxyethyl]-8,15-diazahexacyclo[14.2.1.0,.0,.0,.0,]nonadeca-2,4,6,8-tetraen-18-yl acetic acid	Generator

Chemical Formula

C₂₂H₂₆N₂O₄

Average Mass

382.4600 Da

Monoisotopic Mass

382.18926 Da

IUPAC Name

(1R,10S,12R,13R,14R,16S,17S,18R)-14-hydroxy-13-[(1R)-1-methoxyethyl]-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6,8-tetraen-18-yl acetate

Traditional Name

(1R,10S,12R,13R,14R,16S,17S,18R)-14-hydroxy-13-[(1R)-1-methoxyethyl]-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6,8-tetraen-18-yl acetate

CAS Registry Number

Not Available

SMILES

CO[C@H](C)[C@@H]1[C@@H](O)N2[C@H]3C[C@]45[C@H](OC(C)=O)[C@H]3[C@H]1C[C@H]2C4=NC1=CC=CC=C51

InChI Identifier

InChI=1S/C22H26N2O4/c1-10(27-3)17-12-8-15-19-22(13-6-4-5-7-14(13)23-19)9-16(24(15)21(17)26)18(12)20(22)28-11(2)25/h4-7,10,12,15-18,20-21,26H,8-9H2,1-3H3/t10-,12+,15+,16+,17+,18+,20-,21-,22-/m1/s1

InChI Key

XHABFDBTVXEZFH-ASMGYPJESA-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
Alstonia yunnanensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ajmaline-sarpagine alkaloids. These are organic compounds containing either of the ajmalan, sarpagan skeleton, or derivative thereof. The Sarpagine (Akuammidine) group, based on the sarpagan nucleus, arises from bond formation between C-16 and C-5 of the corynantheine precursor. Ajmaline alkaloids are based on a 17,19-secoyohimban skeleton (oxayohimban) which is invariably present as an ether.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ajmaline-sarpagine alkaloids

Sub Class

Not Available

Direct Parent

Ajmaline-sarpagine alkaloids

Alternative Parents

Substituents

Sarpagine-skeleton
Quinolizidine
3-alkylindole
Indole or derivatives
Quinuclidine
Azepane
Piperidine
Benzenoid
Carboxylic acid ester
Hemiaminal
Ketimine
Alkanolamine
Carboxylic acid derivative
Dialkyl ether
Ether
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxide
Imine
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organopnictogen 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	2.06	ChemAxon
pKa (Strongest Acidic)	13.24	ChemAxon
pKa (Strongest Basic)	5.63	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	103.68 m³·mol⁻¹	ChemAxon
Polarizability	41.26 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

162970477

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,10s,12r,13r,14r,16s,17s,18r)-14-hydroxy-13-[(1r)-1-methoxyethyl]-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-18-yl acetate (NP0309669)

MOL for NP0309669 ((1r,10s,12r,13r,14r,16s,17s,18r)-14-hydroxy-13-[(1r)-1-methoxyethyl]-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-18-yl acetate)

3D MOL for NP0309669 ((1r,10s,12r,13r,14r,16s,17s,18r)-14-hydroxy-13-[(1r)-1-methoxyethyl]-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-18-yl acetate)

3D SDF for NP0309669 ((1r,10s,12r,13r,14r,16s,17s,18r)-14-hydroxy-13-[(1r)-1-methoxyethyl]-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-18-yl acetate)

3D-SDF for NP0309669 ((1r,10s,12r,13r,14r,16s,17s,18r)-14-hydroxy-13-[(1r)-1-methoxyethyl]-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-18-yl acetate)

PDB for NP0309669 ((1r,10s,12r,13r,14r,16s,17s,18r)-14-hydroxy-13-[(1r)-1-methoxyethyl]-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-18-yl acetate)

3D PDB for NP0309669 ((1r,10s,12r,13r,14r,16s,17s,18r)-14-hydroxy-13-[(1r)-1-methoxyethyl]-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-18-yl acetate)

SMILES for NP0309669 ((1r,10s,12r,13r,14r,16s,17s,18r)-14-hydroxy-13-[(1r)-1-methoxyethyl]-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-18-yl acetate)

INCHI for NP0309669 ((1r,10s,12r,13r,14r,16s,17s,18r)-14-hydroxy-13-[(1r)-1-methoxyethyl]-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-18-yl acetate)

Structure for NP0309669 ((1r,10s,12r,13r,14r,16s,17s,18r)-14-hydroxy-13-[(1r)-1-methoxyethyl]-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-18-yl acetate)

3D Structure for NP0309669 ((1r,10s,12r,13r,14r,16s,17s,18r)-14-hydroxy-13-[(1r)-1-methoxyethyl]-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-18-yl acetate)