NP-MRD: Showing NP-Card for (1s,12s,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaene-12-carboxylic acid (NP0207371)

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Record Information

Version

2.0

Created at

2022-09-05 03:57:19 UTC

Updated at

2022-09-05 03:57:19 UTC

NP-MRD ID

NP0207371

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,12s,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaene-12-carboxylic acid

Description

5|A-Carboxytetrahydroalstonine belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor. (1s,12s,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaene-12-carboxylic acid is found in Adina eurhyncha. Based on a literature review very few articles have been published on 5|A-Carboxytetrahydroalstonine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052205572D          

 29 33  0  0  1  0            999 V2000
    3.1037   -1.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8316   -1.8790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700   -2.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1805   -2.3503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0978   -3.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2873   -3.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0151   -4.2154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -4.8405    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2814   -5.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3641   -4.6868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9025   -5.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7131   -5.1582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2515   -5.7833    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9793   -6.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5177   -7.1872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1688   -6.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0620   -5.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3342   -4.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7957   -4.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2239   -3.5204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0269   -3.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7048   -3.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4509   -3.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5191   -4.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8411   -4.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0950   -4.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9852   -4.3793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4468   -3.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6362   -3.9080    0.0000 C   0  0  2  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  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 18 26  1  0  0  0  0
 21 26  1  0  0  0  0
 27 19  1  1  0  0  0
 12 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  1  0  0  0
  5 29  1  0  0  0  0
 10 29  1  0  0  0  0
M  END

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
    4.7269    3.4871   -0.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5003    2.0929   -1.0233 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4529    1.5644   -0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7664    2.3306    0.4441 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1620    0.1242   -0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8874   -0.6926   -1.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6198   -2.0439   -1.0917 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0209   -2.5994    0.0853 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9067   -2.4486    1.2744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7266   -1.8289    0.3116 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7773   -2.0563   -0.8581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4072   -1.3243   -0.5936 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6354   -1.9354   -0.9311 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1223   -1.3618   -2.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4817   -0.4767   -2.8397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3240   -1.7796   -2.7933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7135   -1.6701    0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7984   -0.1901    0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5856    0.4612    0.4147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7793    1.7888    0.5110 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1055    1.9761    0.3895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8505    3.1285    0.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2196    3.0479    0.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8666    1.8351    0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1233    0.6654    0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7592    0.7705    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3793   -0.4097    0.4641 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8363    0.5077    0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0522   -0.3860    0.5057 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2718    3.8892   -1.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7357    3.9792   -0.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2803    3.6657    0.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6946   -0.2319   -1.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8205   -3.6884   -0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9742   -2.2433    0.9732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9776   -3.4095    1.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6302   -1.6793    1.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2400   -2.2594    1.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2809   -1.6243   -1.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6692   -3.1303   -0.9994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6020   -3.0359   -1.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2124   -1.7056   -2.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2958   -2.0504    1.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6593   -2.1482   -0.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0356    2.5264    0.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3292    4.0754    0.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7864    3.9773    0.2857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9429    1.7624   -0.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5629   -0.3135   -0.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2803   -0.8980    1.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7614    1.3339    0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8154    0.8530   -0.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2709   -0.2216    1.6046 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  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 19 27  1  0
 27 28  1  0
 28 29  1  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
 29  5  1  0
 29 10  1  0
 27 12  1  0
 26 18  1  0
 26 21  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  6 33  1  0
  8 34  1  6
  9 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  1
 11 39  1  0
 11 40  1  0
 13 41  1  6
 17 43  1  0
 17 44  1  0
 20 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  0
 27 50  1  1
 28 51  1  0
 28 52  1  0
 29 53  1  1
 16 42  1  0
M  END


  Mrv1652309052205572D          

 29 33  0  0  1  0            999 V2000
    3.1037   -1.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8316   -1.8790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700   -2.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1805   -2.3503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0978   -3.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2873   -3.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0151   -4.2154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -4.8405    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2814   -5.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3641   -4.6868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9025   -5.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7131   -5.1582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2515   -5.7833    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9793   -6.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5177   -7.1872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1688   -6.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0620   -5.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3342   -4.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7957   -4.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2239   -3.5204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0269   -3.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7048   -3.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4509   -3.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5191   -4.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8411   -4.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0950   -4.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9852   -4.3793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4468   -3.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6362   -3.9080    0.0000 C   0  0  2  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  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 18 26  1  0  0  0  0
 21 26  1  0  0  0  0
 27 19  1  1  0  0  0
 12 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  1  0  0  0
  5 29  1  0  0  0  0
 10 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0207371

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](C)[C@@H]2CN3[C@@H](CC4=C(NC5=CC=CC=C45)[C@@H]3C[C@H]12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H24N2O5/c1-11-15-9-24-18(7-13(15)16(10-29-11)22(27)28-2)20-14(8-19(24)21(25)26)12-5-3-4-6-17(12)23-20/h3-6,10-11,13,15,18-19,23H,7-9H2,1-2H3,(H,25,26)/t11-,13-,15-,18-,19-/m0/s1

> <INCHI_KEY>
KLVJWWMEDXWHEI-UNPMYHOCSA-N

> <FORMULA>
C22H24N2O5

> <MOLECULAR_WEIGHT>
396.443

> <EXACT_MASS>
396.168521881

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
41.112147400232146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,12S,15S,16S,20S)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,18-pentaene-12-carboxylic acid

> <JCHEM_LOGP>
-0.45509066105919166

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.301904607341907

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4355647304793546

> <JCHEM_PKA_STRONGEST_BASIC>
7.855855353042379

> <JCHEM_POLAR_SURFACE_AREA>
91.86000000000001

> <JCHEM_REFRACTIVITY>
105.66630000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,12S,15S,16S,20S)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,18-pentaene-12-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       5.794  -2.054   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.286  -3.507   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.291  -4.674   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.804  -4.387   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.783  -6.128   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.270  -6.415   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.762  -7.869   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.767  -9.036   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.259 -10.489   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.280  -8.749   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.285  -9.916   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       8.798  -9.629   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       9.803 -10.795   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.295 -12.249   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.300 -13.416   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       7.782 -12.536   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.316 -10.508   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.824  -9.055   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.819  -7.888   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      11.618  -6.571   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      13.117  -6.925   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.382  -6.047   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.775  -6.704   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.902  -8.239   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.637  -9.117   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.244  -8.459   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.306  -8.175   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.301  -7.008   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.788  -7.295   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   29                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   29                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   27                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18                                                       
CONECT   18   17   19   26                                                  
CONECT   19   18   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   18   21                                                  
CONECT   27   19   12   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28    5   10                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₄N₂O₅

Average Mass

396.4430 Da

Monoisotopic Mass

396.16852 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](C)[C@@H]2CN3[C@@H](CC4=C(NC5=CC=CC=C45)[C@@H]3C[C@H]12)C(O)=O

InChI Identifier

InChI=1S/C22H24N2O5/c1-11-15-9-24-18(7-13(15)16(10-29-11)22(27)28-2)20-14(8-19(24)21(25)26)12-5-3-4-6-17(12)23-20/h3-6,10-11,13,15,18-19,23H,7-9H2,1-2H3,(H,25,26)/t11-,13-,15-,18-,19-/m0/s1

InChI Key

KLVJWWMEDXWHEI-UNPMYHOCSA-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
Adina eurhyncha	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Yohimbine alkaloids

Sub Class

Not Available

Direct Parent

Yohimbine alkaloids

Alternative Parents

Substituents

Ajmalicine-skeleton
18-oxayohimban
Corynanthean skeleton
Yohimbine alkaloid
Beta-carboline
Pyridoindole
Alpha-amino acid or derivatives
L-alpha-amino acid
Alpha-amino acid
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Dicarboxylic acid or derivatives
Benzenoid
Piperidine
Enoate ester
Methyl ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Heteroaromatic compound
Pyrrole
Amino acid
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organonitrogen compound
Organic nitrogen compound
Amine
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Organic oxide
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000134

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

137347447

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,12s,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaene-12-carboxylic acid (NP0207371)

MOL for NP0207371 ((1s,12s,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaene-12-carboxylic acid)

3D MOL for NP0207371 ((1s,12s,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaene-12-carboxylic acid)

3D SDF for NP0207371 ((1s,12s,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaene-12-carboxylic acid)

3D-SDF for NP0207371 ((1s,12s,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaene-12-carboxylic acid)

PDB for NP0207371 ((1s,12s,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaene-12-carboxylic acid)

3D PDB for NP0207371 ((1s,12s,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaene-12-carboxylic acid)

SMILES for NP0207371 ((1s,12s,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaene-12-carboxylic acid)

INCHI for NP0207371 ((1s,12s,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaene-12-carboxylic acid)

Structure for NP0207371 ((1s,12s,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaene-12-carboxylic acid)

3D Structure for NP0207371 ((1s,12s,15s,16s,20s)-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,18-pentaene-12-carboxylic acid)