NP-MRD: Showing NP-Card for methyl (1s,15s,18r,19s,20s)-18-hydroxy-8-methoxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate (NP0141799)

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Record Information

Version

2.0

Created at

2022-09-01 20:12:00 UTC

Updated at

2022-09-01 20:12:01 UTC

NP-MRD ID

NP0141799

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,15s,18r,19s,20s)-18-hydroxy-8-methoxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate

Description

Alstovenine 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. methyl (1s,15s,18r,19s,20s)-18-hydroxy-8-methoxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate is found in Alstonia venenata. methyl (1s,15s,18r,19s,20s)-18-hydroxy-8-methoxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate was first documented in 2013 (PMID: 23344433). Based on a literature review very few articles have been published on Alstovenine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309012222122D          

 28 32  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  1  0  0  0  0  0  0  0  0  0
    3.6362   -3.9080    0.0000 C   0  0  1  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
    4.9852   -4.3793    0.0000 C   0  0  1  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
    7.9093   -5.7061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6554   -6.0581    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
    6.3342   -4.8507    0.0000 C   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
    5.2515   -5.7833    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
    3.9025   -5.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3641   -4.6868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5535   -4.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0151   -4.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2873   -3.4366    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7489   -2.8115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  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  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  2  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
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  1  0  0  0
  6 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  1  0  0  0
M  END

     RDKit          3D

 56 60  0  0  0  0  0  0  0  0999 V2000
    3.9045   -1.5485    2.5160 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2321   -1.5317    1.2750 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8964   -0.9821    0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0544   -0.5380    0.3948 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3325   -0.8928   -1.1596 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0533   -0.1485   -1.2875 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9377   -0.7233   -0.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2801    0.1401   -0.7740 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5275   -0.5187   -0.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8871   -1.7936   -0.1842 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1502   -1.8919    0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9696   -2.9625    0.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2505   -2.7502    1.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7544   -1.4712    1.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9523   -0.3957    0.9315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3431    0.9213    1.0723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5909    1.3497    1.5267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6587   -0.6123    0.4601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6258    0.2196    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4798    1.6979    0.0291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0765    1.9966    0.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1261    1.4834   -0.3475 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2368    1.8658   -0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1387    1.3353   -1.1611 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5392    1.8575   -0.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5845    1.2071   -1.7477 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3436   -0.2275   -2.0648 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5353   -0.9756   -1.9913 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1335   -0.5124    2.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3251   -2.0661    3.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8960   -2.0252    2.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1565   -1.9153   -1.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6800   -0.3591   -2.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7237   -1.7428   -0.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1663   -0.6427    0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2623    0.1529   -1.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3029   -2.6344   -0.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6459   -3.9762    0.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9136   -3.5782    1.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7511   -1.2955    1.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4956    1.5558    2.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4063    0.6279    1.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9172    2.3104    1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2488    2.2320    0.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4606    1.9854   -1.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9707    1.6075    1.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9865    3.0859    0.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718    1.5819    0.9420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769    2.9792   -0.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7809    1.8721   -2.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5343    2.9538   -1.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7765    1.8788    0.1795 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5613    1.3199   -1.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7035    1.7645   -2.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9438   -0.3415   -3.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0150   -0.9288   -2.8430 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 27  1  0
 27 28  1  0
 27 26  1  0
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  6 24  1  0
  8 22  1  0
 18 19  1  0
 18 11  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  5 32  1  6
 27 55  1  6
 28 56  1  0
 26 53  1  0
 26 54  1  0
 25 51  1  0
 25 52  1  0
 24 50  1  6
 23 48  1  0
 23 49  1  0
 21 46  1  0
 21 47  1  0
 20 44  1  0
 20 45  1  0
 10 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
  8 36  1  6
  7 34  1  0
  7 35  1  0
  6 33  1  6
M  END


  Mrv1652309012222122D          

 28 32  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  1  0  0  0  0  0  0  0  0  0
    3.6362   -3.9080    0.0000 C   0  0  1  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
    4.9852   -4.3793    0.0000 C   0  0  1  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
    7.9093   -5.7061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6554   -6.0581    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
    6.3342   -4.8507    0.0000 C   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
    5.2515   -5.7833    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
    3.9025   -5.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3641   -4.6868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5535   -4.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0151   -4.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2873   -3.4366    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7489   -2.8115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  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  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  2  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
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  1  0  0  0
  6 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0141799

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H]1[C@H](O)CC[C@@H]2CN3CCC4=C(NC5=CC=CC(OC)=C45)[C@@H]3C[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C22H28N2O4/c1-27-18-5-3-4-15-19(18)13-8-9-24-11-12-6-7-17(25)20(22(26)28-2)14(12)10-16(24)21(13)23-15/h3-5,12,14,16-17,20,23,25H,6-11H2,1-2H3/t12-,14+,16+,17-,20+/m1/s1

> <INCHI_KEY>
WMMZYEBFJWWUJX-IFBQROQASA-N

> <FORMULA>
C22H28N2O4

> <MOLECULAR_WEIGHT>
384.476

> <EXACT_MASS>
384.20490739

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
42.44619361484568

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,15S,18R,19S,20S)-18-hydroxy-8-methoxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
1.9409869943333333

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.674985240737133

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.681301254266632

> <JCHEM_PKA_STRONGEST_BASIC>
6.981085431359744

> <JCHEM_POLAR_SURFACE_AREA>
74.79

> <JCHEM_REFRACTIVITY>
106.09419999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,15S,18R,19S,20S)-18-hydroxy-8-methoxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-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       6.788  -7.295   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.301  -7.008   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.306  -8.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.819  -7.888   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      11.618  -6.571   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      13.117  -6.925   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.382  -6.047   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.775  -6.704   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.902  -8.239   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.637  -9.117   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.764 -10.651   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      16.157 -11.308   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.244  -8.459   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.824  -9.055   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.316 -10.508   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.803 -10.795   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       8.798  -9.629   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       7.285  -9.916   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.280  -8.749   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.767  -9.036   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.762  -7.869   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.270  -6.415   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.265  -5.248   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   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   11   19                                                  
CONECT   19   18    9   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    8   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23    6   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    5   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₈N₂O₄

Average Mass

384.4760 Da

Monoisotopic Mass

384.20491 Da

IUPAC Name

methyl (1S,15S,18R,19S,20S)-18-hydroxy-8-methoxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate

Traditional Name

methyl (1S,15S,18R,19S,20S)-18-hydroxy-8-methoxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H]1[C@H](O)CC[C@@H]2CN3CCC4=C(NC5=CC=CC(OC)=C45)[C@@H]3C[C@H]12

InChI Identifier

InChI=1S/C22H28N2O4/c1-27-18-5-3-4-15-19(18)13-8-9-24-11-12-6-7-17(25)20(22(26)28-2)14(12)10-16(24)21(13)23-15/h3-5,12,14,16-17,20,23,25H,6-11H2,1-2H3/t12-,14+,16+,17-,20+/m1/s1

InChI Key

WMMZYEBFJWWUJX-IFBQROQASA-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 venenata	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

Yohimbine
Corynanthean skeleton
Yohimbine alkaloid
Beta-carboline
Pyridoindole
3-alkylindole
Indole
Indole or derivatives
Anisole
Alkyl aryl ether
Beta-hydroxy acid
Aralkylamine
Hydroxy acid
Piperidine
Benzenoid
Pyrrole
Methyl ester
Heteroaromatic compound
Cyclic alcohol
Tertiary amine
Secondary alcohol
Tertiary aliphatic amine
Amino acid or derivatives
Carboxylic acid ester
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Azacycle
Carboxylic acid derivative
Ether
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Amine
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	2.69	ALOGPS
logP	1.94	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	14.68	ChemAxon
pKa (Strongest Basic)	6.98	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.79 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	106.09 m³·mol⁻¹	ChemAxon
Polarizability	42.45 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

C00025767

Chemspider ID

172877

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

199742

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lebold TP, Wood JL, Deitch J, Lodewyk MW, Tantillo DJ, Sarpong R: A divergent approach to the synthesis of the yohimbinoid alkaloids venenatine and alstovenine. Nat Chem. 2013 Feb;5(2):126-31. doi: 10.1038/nchem.1528. Epub 2012 Dec 23. [PubMed:23344433 ]
LOTUS database [Link]

Showing NP-Card for methyl (1s,15s,18r,19s,20s)-18-hydroxy-8-methoxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate (NP0141799)

MOL for NP0141799 (methyl (1s,15s,18r,19s,20s)-18-hydroxy-8-methoxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate)

3D MOL for NP0141799 (methyl (1s,15s,18r,19s,20s)-18-hydroxy-8-methoxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate)

3D SDF for NP0141799 (methyl (1s,15s,18r,19s,20s)-18-hydroxy-8-methoxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate)

3D-SDF for NP0141799 (methyl (1s,15s,18r,19s,20s)-18-hydroxy-8-methoxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate)

PDB for NP0141799 (methyl (1s,15s,18r,19s,20s)-18-hydroxy-8-methoxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate)

3D PDB for NP0141799 (methyl (1s,15s,18r,19s,20s)-18-hydroxy-8-methoxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate)

SMILES for NP0141799 (methyl (1s,15s,18r,19s,20s)-18-hydroxy-8-methoxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate)

INCHI for NP0141799 (methyl (1s,15s,18r,19s,20s)-18-hydroxy-8-methoxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate)

Structure for NP0141799 (methyl (1s,15s,18r,19s,20s)-18-hydroxy-8-methoxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate)

3D Structure for NP0141799 (methyl (1s,15s,18r,19s,20s)-18-hydroxy-8-methoxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate)