NP-MRD: Showing NP-Card for Mitraphylline (NP0050890)

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Record Information

Version

2.0

Created at

2022-04-27 22:21:07 UTC

Updated at

2022-04-27 22:21:07 UTC

NP-MRD ID

NP0050890

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Mitraphylline

Description

Mitraphylline belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen. Mitraphylline is found in Catharanthus roseus , Cephalanthus glabratus, Mitragyna hirsuta, Mitragyna macrophylla, Mitragyna parvifolia , Mitragyna rubrostipula, Rauvolfia caffra, Uncaria africana , Uncaria attenuata, Uncaria callophylla, Uncaria elliptica, Uncaria gambir , Uncaria guianensis , Uncaria hirsuta , Uncaria homomalla, Uncaria kawakamii, Uncaria laevigata, Uncaria lancifolia, Uncaria lanosa, Uncaria longiflora, Uncaria orientalis, Uncaria rhynchophylla, Uncaria scandens , Uncaria sessilifructus , Uncaria tomentosa and Uncaria veluntina. Mitraphylline was first documented in 2020 (PMID: 33408731). Based on a literature review a small amount of articles have been published on Mitraphylline (PMID: 33620222) (PMID: 35472200) (PMID: 34956811) (PMID: 35037838).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200212D          

 27 31  0  0  1  0            999 V2000
    2.9933   -1.3568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6710   -0.5974    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1675    0.0615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9863   -0.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087   -0.7985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8122   -1.4574    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1345   -2.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8451    0.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0263    0.9215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417    1.4798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0193    2.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8521   -0.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.1557    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6780   -1.9151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4968   -2.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0553   -2.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3482   -2.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5338   -1.2276    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7194   -0.4237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122    0.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6104   -0.5401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2881   -1.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7130   -2.0066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0266    0.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7482    1.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4553    0.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4409   -0.0238    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  6  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  3  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
  1 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
 13 18  1  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
 18 22  1  0  0  0  0
 22 23  2  0  0  0  0
 20 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 19 27  1  0  0  0  0
M  END

     RDKit          3D

 51 55  0  0  0  0  0  0  0  0999 V2000
   -3.6775    4.4575    1.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6882    3.1659    0.6152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5495    2.3550    0.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4976    2.8534    0.9611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6838    1.0522   -0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8963    0.6398   -0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8985   -0.6418   -1.0116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3078   -1.7224   -0.2692 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1113   -2.8658   -1.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0364   -1.2777    0.3970 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9033   -2.2131    0.2636 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1355   -1.8304   -0.6309 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2041   -2.7766   -0.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4218   -2.0949   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0159   -0.6593    0.2280 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0740   -0.3325    1.6526 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4167   -0.8184    2.6073 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0531    0.6915    1.8283 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6310    1.0349    0.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6008    1.9383    0.2098 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0015    2.0860   -1.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4297    1.3188   -2.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4443    0.3979   -1.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0360    0.2426   -0.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6889   -0.5470   -0.4180 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2806    0.3955    0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6330    0.0625   -0.2408 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2826    4.4345    2.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6407    4.7666    1.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1402    5.1696    0.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7738    1.2625   -0.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0769   -2.0310    0.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2711   -2.6935   -1.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0282   -2.9244   -1.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0477   -3.8481   -0.7050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2633   -1.0503    1.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2155   -3.2578   -0.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4258   -2.3634    1.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3771   -3.0636   -1.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8932   -3.6620   -0.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7520   -2.6160    0.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2322   -2.1626   -0.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3338    1.1512    2.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0743    2.5607    0.9513 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7662    2.8105   -1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7290    1.4187   -3.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0127   -0.1933   -2.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8275   -0.0572   -1.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0317    1.4512    0.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3121    0.1777    1.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5413   -0.1920   -1.3459 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 14  1  0
 14 15  1  0
 15 25  1  0
 25 26  1  0
 26 27  1  0
 15 16  1  1
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 24  2  0
 24 23  1  0
 23 22  2  0
 22 21  1  0
 21 20  2  0
 27  5  1  0
 20 19  1  0
 27 10  1  0
 25 12  1  0
 24 15  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  6 31  1  0
  8 32  1  1
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  1
 11 37  1  0
 11 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 25 48  1  6
 26 49  1  0
 26 50  1  0
 27 51  1  6
 18 43  1  0
 23 47  1  0
 22 46  1  0
 21 45  1  0
 20 44  1  0
M  END


  Mrv1652304282200212D          

 27 31  0  0  1  0            999 V2000
    2.9933   -1.3568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6710   -0.5974    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1675    0.0615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9863   -0.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087   -0.7985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8122   -1.4574    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1345   -2.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8451    0.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0263    0.9215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417    1.4798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0193    2.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8521   -0.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.1557    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6780   -1.9151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4968   -2.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0553   -2.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3482   -2.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5338   -1.2276    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7194   -0.4237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122    0.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6104   -0.5401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2881   -1.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7130   -2.0066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0266    0.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7482    1.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4553    0.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4409   -0.0238    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  6  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  3  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
  1 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
 13 18  1  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
 18 22  1  0  0  0  0
 22 23  2  0  0  0  0
 20 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 19 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050890

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](C)[C@H]2CN3CC[C@@]4([C@@H]3C[C@H]12)C(=O)NC1=C4C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H24N2O4/c1-12-14-10-23-8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-27-12)19(24)26-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)/t12-,13-,14+,18-,21+/m0/s1

> <INCHI_KEY>
JMIAZDVHNCCPDM-DAFCLMLCSA-N

> <FORMULA>
C21H24N2O4

> <MOLECULAR_WEIGHT>
368.433

> <EXACT_MASS>
368.173607261

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
39.467961341778285

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.31

> <JCHEM_LOGP>
1.7049254469999995

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.167255479052887

> <JCHEM_PKA_STRONGEST_BASIC>
10.747925133916343

> <JCHEM_POLAR_SURFACE_AREA>
67.87

> <JCHEM_REFRACTIVITY>
101.39240000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mitraphylline

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.588  -2.533   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.986  -1.115   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.913   0.115   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.441  -0.073   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.043  -1.491   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.116  -2.720   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.718  -4.138   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.311   1.532   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.782   1.720   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       6.238   2.762   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.636   4.180   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.457  -0.927   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.530  -2.157   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       3.132  -3.575   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       4.661  -3.763   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.970  -4.585   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.650  -3.792   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.996  -2.292   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.343  -0.791   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.023   0.002   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      -1.139  -1.008   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      -0.538  -2.426   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.331  -3.746   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.050   1.542   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.397   2.289   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.717   1.495   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.690  -0.044   0.000  0.00  0.00           C+0
CONECT    1    2    6   15                                                  
CONECT    2    1    3   12                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    3    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10                                                            
CONECT   12    2   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14    1                                                       
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19   22                                             
CONECT   19   18   20   27                                                  
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   18   23                                                  
CONECT   23   22                                                            
CONECT   24   20   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   19                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Value	Source
Methyl (19alpha)-19-methyl-2-oxoformosanan-16-carboxylate	MeSH

Chemical Formula

C₂₁H₂₄N₂O₄

Average Mass

368.4330 Da

Monoisotopic Mass

368.17361 Da

IUPAC Name

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

Traditional Name

mitraphylline

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](C)[C@H]2CN3CC[C@@]4([C@@H]3C[C@H]12)C(=O)NC1=C4C=CC=C1

InChI Identifier

InChI=1S/C21H24N2O4/c1-12-14-10-23-8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-27-12)19(24)26-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)/t12-,13-,14+,18-,21+/m0/s1

InChI Key

JMIAZDVHNCCPDM-DAFCLMLCSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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	Plant	KNApSAcK
Cephalanthus glabratus	LOTUS Database	35616633
Mitragyna hirsuta	Plant	KNApSAcK
Mitragyna macrophylla	Plant	KNApSAcK
Mitragyna parvifolia	Plant	KNApSAcK
Mitragyna rubrostipula	Plant	KNApSAcK
Rauvolfia caffra	LOTUS Database	35616633
Uncaria africana	Plant	KNApSAcK
Uncaria attenuata	Plant	KNApSAcK
Uncaria callophylla	Plant	KNApSAcK
Uncaria elliptica	Plant	KNApSAcK
Uncaria gambir	Plant	KNApSAcK
Uncaria guianensis	Plant	KNApSAcK
Uncaria hirsuta	Plant	KNApSAcK
Uncaria homomalla	Plant	KNApSAcK
Uncaria kawakamii	Plant	KNApSAcK
Uncaria laevigata	Plant	KNApSAcK
Uncaria lancifolia	Plant	KNApSAcK
Uncaria lanosa	Plant	KNApSAcK
Uncaria longiflora	Plant	KNApSAcK
Uncaria orientalis	Plant	KNApSAcK
Uncaria rhynchophylla	LOTUS Database	35616633
Uncaria scandens	Plant	KNApSAcK
Uncaria sessilifructus	Plant	KNApSAcK
Uncaria tomentosa	Plant	KNApSAcK
Uncaria veluntina	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indolizidines

Sub Class

Not Available

Direct Parent

Indolizidines

Alternative Parents

Substituents

Indole or derivatives
Dihydroindole
Indolizidine
Aralkylamine
Piperidine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Carboxamide group
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Carboxylic acid ester
Lactam
Azacycle
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indolizines (CHEBI:6957 )

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	2.31	ALOGPS
logP	1.7	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	13.17	ChemAxon
pKa (Strongest Basic)	10.75	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	67.87 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	101.39 m³·mol⁻¹	ChemAxon
Polarizability	39.47 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

C00001752

Chemspider ID

84977

KEGG Compound ID

C09227

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mitraphylline

METLIN ID

Not Available

PubChem Compound

94160

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kamble SH, Berthold EC, King TI, Raju Kanumuri SR, Popa R, Herting JR, Leon F, Sharma A, McMahon LR, Avery BA, McCurdy CR: Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats. J Nat Prod. 2021 Apr 23;84(4):1104-1112. doi: 10.1021/acs.jnatprod.0c01163. Epub 2021 Feb 23. [PubMed:33620222 ]
Zhang M, Sharma A, Leon F, Avery B, Kjelgren R, McCurdy CR, Pearson BJ: Plant growth and phytoactive alkaloid synthesis in kratom [Mitragyna speciosa (Korth.)] in response to varying radiance. PLoS One. 2022 Apr 26;17(4):e0259326. doi: 10.1371/journal.pone.0259326. eCollection 2022. [PubMed:35472200 ]
Pinto GHT, Lopes AA, de Freitas Morel LJ, Crevelin EJ, Miranda CES, Contini SHT, de Castro Franca S, Bertoni BW, Pereira AMS: Genetic diversity among genotypes of Uncaria guianensis (Aubl.) J.F. Gmel. maintained in an in vitro germplasm bank. 3 Biotech. 2022 Jan;12(1):8. doi: 10.1007/s13205-021-03016-y. Epub 2021 Dec 7. [PubMed:34956811 ]
Alam MS, Sharma M, Kumar R, Das J, Rode S, Kumar P, Prasad R, Sharma AK: In silico identification of potential phytochemical inhibitors targeting farnesyl diphosphate synthase of cotton bollworm (Helicoverpa armigera). J Biomol Struct Dyn. 2022 Jan 17:1-10. doi: 10.1080/07391102.2022.2025904. [PubMed:35037838 ]
Zhang M, Sharma A, Leon F, Avery B, Kjelgren R, McCurdy CR, Pearson BJ: Effects of Nutrient Fertility on Growth and Alkaloidal Content in Mitragyna speciosa (Kratom). Front Plant Sci. 2020 Dec 21;11:597696. doi: 10.3389/fpls.2020.597696. eCollection 2020. [PubMed:33408731 ]

Showing NP-Card for Mitraphylline (NP0050890)

MOL for NP0050890 (Mitraphylline)

3D MOL for NP0050890 (Mitraphylline)

3D SDF for NP0050890 (Mitraphylline)

3D-SDF for NP0050890 (Mitraphylline)

PDB for NP0050890 (Mitraphylline)

3D PDB for NP0050890 (Mitraphylline)

SMILES for NP0050890 (Mitraphylline)

INCHI for NP0050890 (Mitraphylline)

Structure for NP0050890 (Mitraphylline)

3D Structure for NP0050890 (Mitraphylline)