NP-MRD: Showing NP-Card for methyl (1's,3r,4's,4'ar,5'as,10'as)-2-hydroxy-5,6-dimethoxy-1'-methyl-1',3',4',4'a,5',5'a,7',8',10',10'a-decahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate (NP0141358)

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Record Information

Version

1.0

Created at

2022-09-01 19:25:37 UTC

Updated at

2022-09-01 19:25:37 UTC

NP-MRD ID

NP0141358

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1's,3r,4's,4'ar,5'as,10'as)-2-hydroxy-5,6-dimethoxy-1'-methyl-1',3',4',4'a,5',5'a,7',8',10',10'a-decahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate

Description

Methyl (1'S,3R,4'S,4'aR,5'aS,10'aS)-2-hydroxy-5,6-dimethoxy-1'-methyl-1',3',4',4'a,5',5'a,7',8',10',10'a-decahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate 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. It was first documented in 1994 (PMID: 36044657). Based on a literature review a significant number of articles have been published on methyl (1'S,3R,4'S,4'aR,5'aS,10'aS)-2-hydroxy-5,6-dimethoxy-1'-methyl-1',3',4',4'a,5',5'a,7',8',10',10'a-decahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate (PMID: 36045005) (PMID: 36045004) (PMID: 36045003) (PMID: 36045002).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309012221252D          

 31 35  0  0  1  0            999 V2000
    3.4824   -0.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1601    0.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6566    0.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4754    0.6708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3342    1.5308    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5154    1.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1930    2.3907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6895    3.0496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3672    3.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5084    2.9491    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0049    3.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8237    3.5074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4464    4.0486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1535    3.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9679    2.8198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7898    2.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2147    3.5989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1122    2.1323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4751    0.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7535    0.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7391   -0.4586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4463   -0.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0464    0.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3248    0.3912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3104   -0.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0608    1.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7824    2.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1461    2.7480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6496    2.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8307    2.1896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  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 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  2  0  0  0  0
 19 28  1  0  0  0  0
 15 28  1  0  0  0  0
 15 29  1  0  0  0  0
 29 12  1  6  0  0  0
 29 30  1  0  0  0  0
 31 30  1  1  0  0  0
  5 31  1  0  0  0  0
 10 31  1  0  0  0  0
M  END

     RDKit          3D

 61 65  0  0  0  0  0  0  0  0999 V2000
   -4.7140   -0.2021    3.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0077    0.1629    2.0975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4880   -0.1714    0.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5735   -0.8092    0.8026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7681    0.1985   -0.4106 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5482   -0.3077   -1.5779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9175   -1.3750   -2.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7043   -0.9862   -2.7861 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8818    0.2095   -3.7105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7647   -0.5940   -1.6961 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6174   -1.5887   -1.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2738   -1.1167   -0.5181 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3747   -1.9753    0.6356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6990   -1.0971    1.8237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9219    0.2491    1.1873 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6626    1.3767    2.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4923    1.7023    2.7955 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062    2.1228    2.0947 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7492    1.6043    1.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441    2.0351    0.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8321    1.2959    0.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1159    1.7107   -0.1560 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5963    2.9025    0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3872    0.1305   -0.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -0.6161   -1.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7648   -1.8006   -1.9108 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1098   -0.2990   -0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2905    0.4412    0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0612    0.1871    0.0067 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4504    0.2852    0.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4109   -0.4521   -0.3536 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3454   -1.2126    3.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5841    0.5529    4.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7982   -0.3070    3.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7068    1.3146   -0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7301    0.5425   -2.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5700   -0.6818   -1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2956   -1.8534   -3.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8887    1.1560   -3.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0217    0.2793   -4.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8614    0.1669   -4.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2628    0.3901   -1.9210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0598   -1.6578   -2.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0265   -2.5758   -1.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1869   -2.7054    0.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5429   -2.5762    0.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5973   -1.4598    2.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1196   -1.0558    2.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9325    2.5891    2.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3751    2.9544    1.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8366    3.6901    0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6621    2.8124    1.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5922    3.1871    0.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7382   -1.7668   -2.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5009   -2.0332   -2.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8367   -2.6538   -1.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7405   -1.2228   -0.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2276    1.0096   -0.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5706   -0.0016    1.5879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7468    1.3735    0.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5514   -1.4777    0.0643 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  1  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 14  1  0
 14 15  1  0
 15 29  1  0
 29 30  1  0
 30 31  1  0
 15 16  1  1
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  2  0
 31  5  1  0
 28 19  1  0
 31 10  1  0
 29 12  1  0
 28 15  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  5 35  1  6
  6 36  1  0
  6 37  1  0
  8 38  1  6
  9 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  6
 11 43  1  0
 11 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 29 58  1  6
 30 59  1  0
 30 60  1  0
 31 61  1  1
 17 49  1  0
 20 50  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
 26 54  1  0
 26 55  1  0
 26 56  1  0
 27 57  1  0
M  END


  Mrv1652309012221252D          

 31 35  0  0  1  0            999 V2000
    3.4824   -0.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1601    0.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6566    0.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4754    0.6708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3342    1.5308    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5154    1.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1930    2.3907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6895    3.0496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3672    3.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5084    2.9491    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0049    3.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8237    3.5074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4464    4.0486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1535    3.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9679    2.8198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7898    2.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2147    3.5989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1122    2.1323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4751    0.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7535    0.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7391   -0.4586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4463   -0.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0464    0.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3248    0.3912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3104   -0.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0608    1.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7824    2.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1461    2.7480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6496    2.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8307    2.1896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  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 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  2  0  0  0  0
 19 28  1  0  0  0  0
 15 28  1  0  0  0  0
 15 29  1  0  0  0  0
 29 12  1  6  0  0  0
 29 30  1  0  0  0  0
 31 30  1  1  0  0  0
  5 31  1  0  0  0  0
 10 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0141358

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H]1CO[C@@H](C)[C@@H]2CN3CC[C@@]4([C@@H]3C[C@@H]12)C(O)=NC1=CC(OC)=C(OC)C=C41

> <INCHI_IDENTIFIER>
InChI=1S/C23H30N2O6/c1-12-14-10-25-6-5-23(20(25)7-13(14)15(11-31-12)21(26)30-4)16-8-18(28-2)19(29-3)9-17(16)24-22(23)27/h8-9,12-15,20H,5-7,10-11H2,1-4H3,(H,24,27)/t12-,13+,14-,15+,20-,23+/m0/s1

> <INCHI_KEY>
RZTBBIIHQWIBBU-LFBMRYBBSA-N

> <FORMULA>
C23H30N2O6

> <MOLECULAR_WEIGHT>
430.501

> <EXACT_MASS>
430.210386694

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
45.84353835070278

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1'S,3R,4'S,4'aR,5'aS,10'aS)-2-hydroxy-5,6-dimethoxy-1'-methyl-1',3',4',4'a,5',5'a,7',8',10',10'a-decahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
-0.9156436185828553

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.46191683733516

> <JCHEM_PKA_STRONGEST_BASIC>
10.758311544689168

> <JCHEM_POLAR_SURFACE_AREA>
89.82000000000001

> <JCHEM_REFRACTIVITY>
115.06749999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1'S,3R,4'S,4'aR,5'aS,10'aS)-2-hydroxy-5,6-dimethoxy-1'-methyl-1',3',4',4'a,5',5'a,7',8',10',10'a-decahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-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       6.500  -1.208   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.899   0.210   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.826   1.440   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.354   1.252   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.224   2.857   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.695   3.045   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.094   4.463   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.020   5.693   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.419   7.110   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.549   5.505   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.476   6.735   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       9.004   6.547   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      10.167   7.557   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.487   6.764   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.140   5.264   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.674   5.398   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      13.467   6.718   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      13.276   3.980   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      12.114   2.970   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.087   1.430   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.740   0.684   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.713  -0.856   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.033  -1.649   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.420   1.477   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.073   0.730   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.046  -0.810   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.447   3.017   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.794   3.763   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.606   5.130   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.679   3.900   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.151   4.087   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   31                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   31                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   29                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   28   29                                             
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27   19   15                                                  
CONECT   29   15   12   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30    5   10                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1's,3R,4's,4'ar,5'as,10'as)-2-hydroxy-5,6-dimethoxy-1'-methyl-1',3',4',4'a,5',5'a,7',8',10',10'a-decahydrospiro[indole-3,6'-pyrano[3,4-F]indolizine]-4'-carboxylic acid	Generator

Chemical Formula

C₂₃H₃₀N₂O₆

Average Mass

430.5010 Da

Monoisotopic Mass

430.21039 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H]1CO[C@@H](C)[C@@H]2CN3CC[C@@]4([C@@H]3C[C@@H]12)C(O)=NC1=CC(OC)=C(OC)C=C41

InChI Identifier

InChI=1S/C23H30N2O6/c1-12-14-10-25-6-5-23(20(25)7-13(14)15(11-31-12)21(26)30-4)16-8-18(28-2)19(29-3)9-17(16)24-22(23)27/h8-9,12-15,20H,5-7,10-11H2,1-4H3,(H,24,27)/t12-,13+,14-,15+,20-,23+/m0/s1

InChI Key

RZTBBIIHQWIBBU-LFBMRYBBSA-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

Not Available

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

Yohimban skeleton
Yohimbine alkaloid
3-alkylindole
Indole or derivatives
Indolizidine
Anisole
Alkyl aryl ether
Aralkylamine
Oxane
Piperidine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Cyclic carboximidic acid
Methyl ester
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Propargyl-type 1,3-dipolar organic compound
Azacycle
Oxacycle
Organic 1,3-dipolar compound
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Dialkyl ether
Ether
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Amine
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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

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

162937867

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Levonorgestrel (Plan B One-Step(R)). 1994. [PubMed:36044657 ]
Keenan RA, Rogers RN, Winn CB: Carbon Dioxide, Oxygen, and Ammonia Levels in Mouse and Rat Disposable IVC Removed from Mechanical Ventilation. J Am Assoc Lab Anim Sci. 2022 Sep 1;61(5):432-440. doi: 10.30802/AALAS-JAALAS-22-000028. Epub 2022 Aug 31. [PubMed:36045005 ]
Bailey KT, Jantre SR, Lawrence FR, Hankenson FC, Del Valle JM: Evaluation of Active Warming and Surgical Draping for Perioperative Thermal Support in Laboratory Mice. J Am Assoc Lab Anim Sci. 2022 Sep 1;61(5):482-494. doi: 10.30802/AALAS-JAALAS-21-000036. Epub 2022 Aug 31. [PubMed:36045004 ]
McGugin RW, Sunday MA, Gauthier I: The neural correlates of domain-general visual ability. Cereb Cortex. 2022 Aug 31. pii: 6679448. doi: 10.1093/cercor/bhac342. [PubMed:36045003 ]
Bailey KM, Giordano BL, Kaas AL, Smith FW: Decoding sounds depicting hand-object interactions in primary somatosensory cortex. Cereb Cortex. 2022 Aug 31. pii: 6679450. doi: 10.1093/cercor/bhac296. [PubMed:36045002 ]

Showing NP-Card for methyl (1's,3r,4's,4'ar,5'as,10'as)-2-hydroxy-5,6-dimethoxy-1'-methyl-1',3',4',4'a,5',5'a,7',8',10',10'a-decahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate (NP0141358)

MOL for NP0141358 (methyl (1's,3r,4's,4'ar,5'as,10'as)-2-hydroxy-5,6-dimethoxy-1'-methyl-1',3',4',4'a,5',5'a,7',8',10',10'a-decahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

3D MOL for NP0141358 (methyl (1's,3r,4's,4'ar,5'as,10'as)-2-hydroxy-5,6-dimethoxy-1'-methyl-1',3',4',4'a,5',5'a,7',8',10',10'a-decahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

3D SDF for NP0141358 (methyl (1's,3r,4's,4'ar,5'as,10'as)-2-hydroxy-5,6-dimethoxy-1'-methyl-1',3',4',4'a,5',5'a,7',8',10',10'a-decahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

3D-SDF for NP0141358 (methyl (1's,3r,4's,4'ar,5'as,10'as)-2-hydroxy-5,6-dimethoxy-1'-methyl-1',3',4',4'a,5',5'a,7',8',10',10'a-decahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

PDB for NP0141358 (methyl (1's,3r,4's,4'ar,5'as,10'as)-2-hydroxy-5,6-dimethoxy-1'-methyl-1',3',4',4'a,5',5'a,7',8',10',10'a-decahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

3D PDB for NP0141358 (methyl (1's,3r,4's,4'ar,5'as,10'as)-2-hydroxy-5,6-dimethoxy-1'-methyl-1',3',4',4'a,5',5'a,7',8',10',10'a-decahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

SMILES for NP0141358 (methyl (1's,3r,4's,4'ar,5'as,10'as)-2-hydroxy-5,6-dimethoxy-1'-methyl-1',3',4',4'a,5',5'a,7',8',10',10'a-decahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

INCHI for NP0141358 (methyl (1's,3r,4's,4'ar,5'as,10'as)-2-hydroxy-5,6-dimethoxy-1'-methyl-1',3',4',4'a,5',5'a,7',8',10',10'a-decahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

Structure for NP0141358 (methyl (1's,3r,4's,4'ar,5'as,10'as)-2-hydroxy-5,6-dimethoxy-1'-methyl-1',3',4',4'a,5',5'a,7',8',10',10'a-decahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)

3D Structure for NP0141358 (methyl (1's,3r,4's,4'ar,5'as,10'as)-2-hydroxy-5,6-dimethoxy-1'-methyl-1',3',4',4'a,5',5'a,7',8',10',10'a-decahydrospiro[indole-3,6'-pyrano[3,4-f]indolizine]-4'-carboxylate)