NP-MRD: Showing NP-Card for horhammericine (NP0239711)

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Record Information

Version

2.0

Created at

2022-09-06 23:21:48 UTC

Updated at

2022-09-06 23:21:48 UTC

NP-MRD ID

NP0239711

Secondary Accession Numbers

None

Natural Product Identification

Common Name

horhammericine

Description

Horhammericine belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids. Horhammericine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. horhammericine is found in Catharanthus roseus and Catharanthus trichophyllus. horhammericine was first documented in 2018 (PMID: 29934299). Based on a literature review a small amount of articles have been published on Horhammericine (PMID: 31009114) (PMID: 29438577) (PMID: 35660549) (PMID: 32303816).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072201212D          

 27 32  0  0  1  0            999 V2000
    3.8242    5.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7248    4.8112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3844    4.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1434    4.6390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2850    3.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9446    3.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542    3.1596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1552    2.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9593    2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2016    1.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6398    0.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8357    1.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5934    1.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8452    2.1821    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3873    1.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9634    0.8524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868    1.0397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2279    0.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5683    1.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9087    1.7074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6677    2.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4267    2.3542    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7671    2.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8665    3.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0081    2.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5260    3.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0862    1.8586    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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 14 13  1  6  0  0  0
  6 14  1  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
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 22 26  1  0  0  0  0
  5 26  1  0  0  0  0
 22 27  1  0  0  0  0
 27 17  1  1  0  0  0
 14 27  1  0  0  0  0
M  END

     RDKit          3D

 51 56  0  0  0  0  0  0  0  0999 V2000
    1.2583    5.3069   -0.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7110    4.0776   -0.3466 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3972    2.8753   -0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5497    2.9148   -0.9030 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8122    1.6282    0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4424    0.4669   -0.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7156    0.1321   -0.4906 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7741   -1.2944   -0.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8012   -2.1120   -1.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125   -3.4748   -1.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4335   -4.0208   -0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4129   -3.2003   -0.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5926   -1.8345   -0.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7693   -0.7248    0.4719 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8615   -0.8017    2.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4569   -1.3781    2.4492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1437   -1.6412    1.2448 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5633   -1.7743    1.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2966   -0.4690    1.3575 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7121    0.5103    2.1805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7072    0.5940    0.7553 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3906    0.4849    0.0349 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6797    0.7925   -1.4216 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6625   -0.1475   -2.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1744    2.0878   -1.5667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5722    1.6604    0.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6921   -0.8230    0.1807 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0601    5.4478   -1.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3311    5.2843   -0.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8359    6.1676   -0.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4927    0.8021   -0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7380   -1.7014   -1.3611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3999   -4.0949   -1.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3060   -5.0930   -0.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4774   -3.6001    0.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0804    0.1897    2.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6886   -1.5273    2.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2551   -2.3231    3.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9475   -0.6461    3.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7719   -2.3419    2.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9362   -2.3894    0.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4074   -0.5901    1.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2768    1.5149    0.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7471    0.7490   -2.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1532   -1.0624   -2.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5358   -0.3689   -1.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0581    0.3675   -2.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0432    2.4437   -2.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0317    2.6098    0.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5345    1.7153    1.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8039   -1.3888   -0.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  1
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 26  1  1
 22 23  1  0
 23 24  1  0
 23 25  1  0
 22 27  1  0
 26  5  1  0
 14  6  1  0
 27 14  1  0
 13  8  1  0
 27 17  1  0
 21 19  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  1
 21 43  1  1
 26 49  1  0
 26 50  1  0
 23 44  1  6
 24 45  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  0
 27 51  1  6
M  END


  Mrv1652309072201212D          

 27 32  0  0  1  0            999 V2000
    3.8242    5.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7248    4.8112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3844    4.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1434    4.6390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2850    3.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9446    3.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542    3.1596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1552    2.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9593    2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2016    1.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6398    0.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8357    1.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5934    1.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8452    2.1821    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3873    1.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9634    0.8524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868    1.0397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2279    0.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5683    1.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9087    1.7074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6677    2.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4267    2.3542    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7671    2.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8665    3.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0081    2.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5260    3.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0862    1.8586    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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 14 13  1  6  0  0  0
  6 14  1  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
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 22 26  1  0  0  0  0
  5 26  1  0  0  0  0
 22 27  1  0  0  0  0
 27 17  1  1  0  0  0
 14 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0239711

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C2NC3=CC=CC=C3[C@@]22CCN3CC4OC4[C@](C1)(C(C)O)[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C21H24N2O4/c1-11(24)21-9-12(18(25)26-2)16-20(13-5-3-4-6-14(13)22-16)7-8-23(19(20)21)10-15-17(21)27-15/h3-6,11,15,17,19,22,24H,7-10H2,1-2H3/t11?,15?,17?,19-,20+,21+/m1/s1

> <INCHI_KEY>
QVNXPWJNUKKMHP-SJSDVCPDSA-N

> <FORMULA>
C21H24N2O4

> <MOLECULAR_WEIGHT>
368.433

> <EXACT_MASS>
368.173607261

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
38.786068516495575

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,12S,20R)-12-(1-hydroxyethyl)-14-oxa-8,17-diazahexacyclo[10.7.1.0^{1,9}.0^{2,7}.0^{13,15}.0^{17,20}]icosa-2,4,6,9-tetraene-10-carboxylate

> <JCHEM_LOGP>
0.652870694

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.915988394226751

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.998712355000809

> <JCHEM_PKA_STRONGEST_BASIC>
8.636248911809338

> <JCHEM_POLAR_SURFACE_AREA>
74.33

> <JCHEM_REFRACTIVITY>
100.9366

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,12S,20R)-12-(1-hydroxyethyl)-14-oxa-8,17-diazahexacyclo[10.7.1.0^{1,9}.0^{2,7}.0^{13,15}.0^{17,20}]icosa-2,4,6,9-tetraene-10-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       7.139  10.510   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.953   8.981   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.184   8.056   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.601   8.660   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.999   6.527   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.230   5.602   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      10.741   5.898   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      11.490   4.552   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.991   4.208   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.443   2.736   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.394   1.608   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.893   1.952   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.441   3.424   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.044   4.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.056   2.912   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.265   1.591   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       7.442   1.941   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       6.025   1.337   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.794   2.262   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.563   3.187   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.980   3.791   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.396   4.395   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.165   5.320   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.351   6.848   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.748   4.716   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.582   5.923   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.628   3.469   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   26                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13    6   15   27                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   27                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19   21                                                       
CONECT   21   20   19   22                                                  
CONECT   22   21   23   26   27                                             
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   22    5                                                       
CONECT   27   22   17   14                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₄N₂O₄

Average Mass

368.4330 Da

Monoisotopic Mass

368.17361 Da

IUPAC Name

methyl (1R,12S,20R)-12-(1-hydroxyethyl)-14-oxa-8,17-diazahexacyclo[10.7.1.0^{1,9}.0^{2,7}.0^{13,15}.0^{17,20}]icosa-2,4,6,9-tetraene-10-carboxylate

Traditional Name

methyl (1R,12S,20R)-12-(1-hydroxyethyl)-14-oxa-8,17-diazahexacyclo[10.7.1.0^{1,9}.0^{2,7}.0^{13,15}.0^{17,20}]icosa-2,4,6,9-tetraene-10-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C2NC3=CC=CC=C3[C@@]22CCN3CC4OC4[C@](C1)(C(C)O)[C@@H]23

InChI Identifier

InChI=1S/C21H24N2O4/c1-11(24)21-9-12(18(25)26-2)16-20(13-5-3-4-6-14(13)22-16)7-8-23(19(20)21)10-15-17(21)27-15/h3-6,11,15,17,19,22,24H,7-10H2,1-2H3/t11?,15?,17?,19-,20+,21+/m1/s1

InChI Key

QVNXPWJNUKKMHP-SJSDVCPDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Catharanthus roseus	LOTUS Database	35616633
Catharanthus trichophyllus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aspidospermatan-type alkaloids

Sub Class

Not Available

Direct Parent

Aspidospermatan-type alkaloids

Alternative Parents

Substituents

Aspidosperma alkaloid
Carbazole
Indole or derivatives
Dihydroindole
Indolizidine
Para-oxazepine
Epoxypiperidine
Aralkylamine
Secondary aliphatic/aromatic amine
Piperidine
N-alkylpyrrolidine
Benzenoid
Enoate ester
Vinylogous amide
Methyl ester
Pyrrolidine
1,3-aminoalcohol
Alpha,beta-unsaturated carboxylic ester
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Amino acid or derivatives
Secondary alcohol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Azacycle
Oxacycle
Carboxylic acid derivative
Ether
Secondary amine
Oxirane
Enamine
Dialkyl ether
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Amine
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carbazoles (CHEBI:5765 )

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	0.65	ChemAxon
pKa (Strongest Acidic)	14	ChemAxon
pKa (Strongest Basic)	8.64	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.33 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	100.94 m³·mol⁻¹	ChemAxon
Polarizability	38.79 Å³	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00060620

Chemspider ID

391594

KEGG Compound ID

C11677

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443358

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Carqueijeiro I, Brown S, Chung K, Dang TT, Walia M, Besseau S, Duge de Bernonville T, Oudin A, Lanoue A, Billet K, Munsch T, Koudounas K, Melin C, Godon C, Razafimandimby B, de Craene JO, Glevarec G, Marc J, Giglioli-Guivarc'h N, Clastre M, St-Pierre B, Papon N, Andrade RB, O'Connor SE, Courdavault V: Two Tabersonine 6,7-Epoxidases Initiate Lochnericine-Derived Alkaloid Biosynthesis in Catharanthus roseus. Plant Physiol. 2018 Aug;177(4):1473-1486. doi: 10.1104/pp.18.00549. Epub 2018 Jun 22. [PubMed:29934299 ]
Williams D, Qu Y, Simionescu R, De Luca V: The assembly of (+)-vincadifformine- and (-)-tabersonine-derived monoterpenoid indole alkaloids in Catharanthus roseus involves separate branch pathways. Plant J. 2019 Aug;99(4):626-636. doi: 10.1111/tpj.14346. Epub 2019 May 21. [PubMed:31009114 ]
Carqueijeiro I, Duge de Bernonville T, Lanoue A, Dang TT, Teijaro CN, Paetz C, Billet K, Mosquera A, Oudin A, Besseau S, Papon N, Glevarec G, Atehortua L, Clastre M, Giglioli-Guivarc'h N, Schneider B, St-Pierre B, Andrade RB, O'Connor SE, Courdavault V: A BAHD acyltransferase catalyzing 19-O-acetylation of tabersonine derivatives in roots of Catharanthus roseus enables combinatorial synthesis of monoterpene indole alkaloids. Plant J. 2018 May;94(3):469-484. doi: 10.1111/tpj.13868. Epub 2018 Mar 27. [PubMed:29438577 ]
Williams D, Brzezinski W, Gordon H, De Luca V: Site directed mutagenesis of Catharanthus roseus (+)-vincadifformine 19-hydroxylase (CYP71BY3) results in two distinct enzymatic functions. Phytochemistry. 2022 Sep;201:113265. doi: 10.1016/j.phytochem.2022.113265. Epub 2022 Jun 2. [PubMed:35660549 ]
Das A, Sarkar S, Bhattacharyya S, Gantait S: Biotechnological advancements in Catharanthus roseus (L.) G. Don. Appl Microbiol Biotechnol. 2020 Jun;104(11):4811-4835. doi: 10.1007/s00253-020-10592-1. Epub 2020 Apr 17. [PubMed:32303816 ]
LOTUS database [Link]

Showing NP-Card for horhammericine (NP0239711)

MOL for NP0239711 (horhammericine)

3D MOL for NP0239711 (horhammericine)

3D SDF for NP0239711 (horhammericine)

3D-SDF for NP0239711 (horhammericine)

PDB for NP0239711 (horhammericine)

3D PDB for NP0239711 (horhammericine)

SMILES for NP0239711 (horhammericine)

INCHI for NP0239711 (horhammericine)

Structure for NP0239711 (horhammericine)

3D Structure for NP0239711 (horhammericine)