NP-MRD: Showing NP-Card for methyl 12-(1-hydroxyethyl)-5-methoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate (NP0253758)

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Record Information

Version

2.0

Created at

2022-09-07 17:43:31 UTC

Updated at

2022-09-07 17:43:31 UTC

NP-MRD ID

NP0253758

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 12-(1-hydroxyethyl)-5-methoxy-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-(1-hydroxyethyl)-5-methoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]Icosa-2(7),3,5,9-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-(1-hydroxyethyl)-5-methoxy-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 Catharanthus roseus. Methyl 12-(1-hydroxyethyl)-5-methoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]Icosa-2(7),3,5,9-tetraene-10-carboxylate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171507082D          

 29 34  0  0  0  0            999 V2000
    3.8242    5.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7248    4.8112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3844    4.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1434    4.6390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2850    3.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9446    3.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542    3.1596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1552    2.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9593    2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2016    1.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0057    1.2811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5675    1.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6398    0.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8357    1.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5934    1.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8452    2.1821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3873    1.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9634    0.8524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868    1.0397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2279    0.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5683    1.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9087    1.7074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6677    2.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4267    2.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5260    3.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7671    2.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8665    3.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0081    2.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0862    1.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  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
 14 15  2  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
  6 16  1  0  0  0  0
 16 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
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  5 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 24 29  1  0  0  0  0
 16 29  1  0  0  0  0
 19 29  1  0  0  0  0
M  END

     RDKit          3D

 55 60  0  0  0  0  0  0  0  0999 V2000
    0.0472    5.5204   -0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1347    4.1349    0.1073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7948    3.3202    0.7263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8067    3.9118    1.2185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6579    1.8630    0.8287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3978    1.2573    0.3139 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5515    1.7570   -0.3955 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2297    0.6081   -0.9159 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3360    0.5319   -1.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7779   -0.6779   -2.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9012   -0.7354   -3.0826 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3912   -1.9349   -3.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1136   -1.8301   -1.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0039   -1.7409   -1.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5644   -0.5315   -0.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4975   -0.1796    0.4222 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9356   -0.5956    1.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3938   -1.9802    1.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4356   -2.2111    0.7368 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4539   -3.1086    1.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4358   -2.4507    1.9969 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6199   -2.0819    1.3656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7560   -1.0761    1.8000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9909   -0.2713    0.7874 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8968    0.1315   -0.3887 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0737    0.9493   -0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2779   -1.0279   -1.1046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6926    1.0705    1.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7924   -0.9288    0.2163 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8599    5.9154    0.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1634    5.8394   -1.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9164    5.9560    0.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492    2.7285   -0.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8733    1.4178   -2.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6640   -2.5936   -2.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3105   -1.7034   -4.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6602   -2.4329   -4.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4742   -2.7715   -2.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250   -2.6830   -0.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6529    0.0958    2.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0603   -0.7083    1.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1959   -2.0778    2.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1648   -2.7692    1.9488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9614   -3.9314    1.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9243   -3.6587    0.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6246   -2.8972    3.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2235   -0.5278    2.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3060    0.7134   -1.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9377    0.7521   -0.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8952    2.0386   -0.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3930    0.7938    1.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5547   -0.7971   -2.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6372    1.7103    1.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5038    0.9418    2.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8885   -1.0442   -0.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  1
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 28  1  1
 24 25  1  0
 25 26  1  0
 25 27  1  0
 24 29  1  0
 28  5  1  0
 16  6  1  0
 29 16  1  0
 15  8  1  0
 29 19  1  0
 23 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  7 33  1  0
  9 34  1  0
 12 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  1
 23 47  1  1
 28 53  1  0
 28 54  1  0
 25 48  1  6
 26 49  1  0
 26 50  1  0
 26 51  1  0
 27 52  1  0
 29 55  1  6
M  END


  Mrv1533004171507082D          

 29 34  0  0  0  0            999 V2000
    3.8242    5.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7248    4.8112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3844    4.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1434    4.6390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2850    3.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9446    3.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542    3.1596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1552    2.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9593    2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2016    1.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0057    1.2811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5675    1.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6398    0.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8357    1.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5934    1.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8452    2.1821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3873    1.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9634    0.8524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868    1.0397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2279    0.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5683    1.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9087    1.7074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6677    2.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4267    2.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5260    3.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7671    2.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8665    3.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0081    2.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0862    1.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  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
 14 15  2  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
  6 16  1  0  0  0  0
 16 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
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  5 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 24 29  1  0  0  0  0
 16 29  1  0  0  0  0
 19 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0253758

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C2NC3=CC(OC)=CC=C3C22CCN3CC4OC4C(C1)(C(C)O)C23

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

> <INCHI_KEY>
JHLKAIJXPRFWJH-UHFFFAOYSA-N

> <FORMULA>
C22H26N2O5

> <MOLECULAR_WEIGHT>
398.459

> <EXACT_MASS>
398.184171945

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
42.191148105945885

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 12-(1-hydroxyethyl)-5-methoxy-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>
1.62

> <JCHEM_LOGP>
0.49519942833333347

> <ALOGPS_LOGS>
-2.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.87020176810687

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.56870567224086

> <JCHEM_PKA_STRONGEST_BASIC>
8.501015056811344

> <JCHEM_POLAR_SURFACE_AREA>
83.56

> <JCHEM_REFRACTIVITY>
107.3998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 12-(1-hydroxyethyl)-5-methoxy-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                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       7.139  10.510   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.953   8.981   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.184   8.056   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.601   8.660   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.999   6.527   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.230   5.602   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      10.741   5.898   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      11.490   4.552   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.991   4.208   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.443   2.736   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      14.944   2.391   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      15.993   3.519   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.394   1.608   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.893   1.952   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.441   3.424   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.044   4.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.056   2.912   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.265   1.591   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       7.442   1.941   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       6.025   1.337   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.794   2.262   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.563   3.187   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.980   3.791   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.396   4.395   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.582   5.923   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.165   5.320   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.351   6.848   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.748   4.716   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.628   3.469   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   25                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    8   16                                                  
CONECT   16   15    6   17   29                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   29                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21   23                                                       
CONECT   23   22   21   24                                                  
CONECT   24   23   25   26   29                                             
CONECT   25   24    5                                                       
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24   16   19                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   68    0
END

View in JSmol

Synonyms

Value	Source
Methyl 12-(1-hydroxyethyl)-5-methoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0,.0,.0,.0,]icosa-2(7),3,5,9-tetraene-10-carboxylic acid	Generator

Chemical Formula

C₂₂H₂₆N₂O₅

Average Mass

398.4590 Da

Monoisotopic Mass

398.18417 Da

IUPAC Name

methyl 12-(1-hydroxyethyl)-5-methoxy-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-(1-hydroxyethyl)-5-methoxy-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

COC(=O)C1=C2NC3=CC(OC)=CC=C3C22CCN3CC4OC4C(C1)(C(C)O)C23

InChI Identifier

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

InChI Key

JHLKAIJXPRFWJH-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
Catharanthus roseus	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
Anisole
Para-oxazepine
Alkyl aryl ether
Secondary aliphatic/aromatic amine
Epoxypiperidine
Aralkylamine
N-alkylpyrrolidine
Piperidine
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
1,3-aminoalcohol
Vinylogous amide
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Enamine
Oxirane
Secondary amine
Ether
Monocarboxylic acid or derivatives
Carbonyl group
Alcohol
Organopnictogen compound
Amine
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
Organonitrogen 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	1.62	ALOGPS
logP	0.5	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	13.57	ChemAxon
pKa (Strongest Basic)	8.5	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.56 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.4 m³·mol⁻¹	ChemAxon
Polarizability	42.19 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

269014

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-(1-hydroxyethyl)-5-methoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate (NP0253758)

MOL for NP0253758 (methyl 12-(1-hydroxyethyl)-5-methoxy-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 NP0253758 (methyl 12-(1-hydroxyethyl)-5-methoxy-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 NP0253758 (methyl 12-(1-hydroxyethyl)-5-methoxy-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 NP0253758 (methyl 12-(1-hydroxyethyl)-5-methoxy-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 NP0253758 (methyl 12-(1-hydroxyethyl)-5-methoxy-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 NP0253758 (methyl 12-(1-hydroxyethyl)-5-methoxy-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 NP0253758 (methyl 12-(1-hydroxyethyl)-5-methoxy-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 NP0253758 (methyl 12-(1-hydroxyethyl)-5-methoxy-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 NP0253758 (methyl 12-(1-hydroxyethyl)-5-methoxy-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 NP0253758 (methyl 12-(1-hydroxyethyl)-5-methoxy-14-oxa-8,17-diazahexacyclo[10.7.1.0¹,⁹.0²,⁷.0¹³,¹⁵.0¹⁷,²⁰]icosa-2,4,6,9-tetraene-10-carboxylate)