NP-MRD: Showing NP-Card for (-)-Lochnericine (NP0066813)

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Record Information

Version

2.0

Created at

2022-04-28 11:02:57 UTC

Updated at

2022-04-28 11:02:57 UTC

NP-MRD ID

NP0066813

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Lochnericine

Description

Lochnericine 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. Lochnericine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (-)-Lochnericine is found in Alstonia lanceolifera, Alstonia lenormandii var.lenormandii, Alstonia lenormandii var.minutifolia, Alstonia yunnanensis, Amsonia elliptica, Amsonia sinensis, Catharanthus pusillus (Vinca pusilla), Catharanthus roseus , Catharanthus trichophyllus, Tabernaemontana divaricata, Hazunta modesta var.modesta subvar montana, Melodinus aeneus, Melodinus scandens , Petchia ceylanica, Tabernaemontana alternifolia, Tabernaemontana citrifolia , Tabernaemontana coffeoides, Tabernaemontana coffeoides Boj., Tabernaemontana divaricata (L.)R.Br. , Tabernaemontana pachysiphon and Voacanga africana . (-)-Lochnericine was first documented in 2016 (PMID: 26351111). Based on a literature review a small amount of articles have been published on lochnericine (PMID: 33255314) (PMID: 29934299) (PMID: 29105731) (PMID: 28478314).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282213022D          

 26 31  0  0  1  0            999 V2000
    6.8780    2.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4398    1.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1975    0.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3933    0.4489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8315    1.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0738    1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0833    0.7054    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1827   -0.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5232   -0.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7642   -0.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6648    0.5333    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3244    1.0289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2250    1.8478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4660    2.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8065    1.6757    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9058    0.8567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1469    1.1801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2016    2.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6255    1.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0052    0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2463    0.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6226   -1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3815   -1.7515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9630   -1.9237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0624   -2.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9924   -0.2721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  1  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  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  1  0  0  0
 15 17  1  1  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 19  1  0  0  0  0
 11 20  1  1  0  0  0
 20 21  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 26  1  0  0  0  0
  4 26  1  0  0  0  0
M  END

     RDKit          3D

 50 55  0  0  0  0  0  0  0  0999 V2000
   -1.8022    1.9706   -2.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3933    0.6945   -1.7396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5343    0.7685   -0.2435 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6766    1.8769    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7531    1.6309    0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6121    2.6880   -0.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1389    3.8712   -0.5226 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9390    2.5537   -0.7361 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7212    3.6593   -1.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1788    0.3701    0.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4528   -0.1889   -0.0541 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3109   -1.6272   -0.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2472   -2.5955   -0.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -3.9119   -0.4728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5647   -4.2318   -0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6289   -3.2762    0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0000   -1.9385    0.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3129   -0.7098    0.6351 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3797   -0.8206    2.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0216   -1.3503    2.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8282   -0.6664    1.5835 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1536   -1.0452    1.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8193    0.1853    0.6879 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8714    0.2919   -0.6779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9633    1.1141    0.0710 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1163   -0.5806    0.3158 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0224    2.7520   -2.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9163    1.7082   -3.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7845    2.2948   -2.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0913   -0.0956   -2.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3809    0.3766   -2.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0601    2.8380    0.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7811    1.7966    1.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6623    3.6268   -0.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2269    4.6234   -0.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542    3.5593   -2.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3540    0.3217   -0.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2609   -2.3080   -0.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6101   -4.7013   -0.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3092   -5.2923   -0.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4043   -3.5596    0.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0946   -1.5598    2.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5719    0.1736    2.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2493   -0.9949    3.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0577   -2.4370    2.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7255   -1.4443    2.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1632   -1.8255    0.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6605    0.5595    1.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2177    2.2083    0.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4769   -1.3526   -0.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  5 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  1
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 21 26  1  0
 25  3  1  0
 26  3  1  0
 18 10  1  0
 26 18  1  0
 17 12  1  0
 25 23  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  4 32  1  0
  4 33  1  0
  9 34  1  0
  9 35  1  0
  9 36  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  1
 25 49  1  1
 26 50  1  6
M  END


  Mrv1652304282213022D          

 26 31  0  0  1  0            999 V2000
    6.8780    2.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4398    1.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1975    0.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3933    0.4489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8315    1.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0738    1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0833    0.7054    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1827   -0.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5232   -0.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7642   -0.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6648    0.5333    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3244    1.0289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2250    1.8478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4660    2.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8065    1.6757    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9058    0.8567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1469    1.1801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2016    2.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6255    1.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0052    0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2463    0.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6226   -1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3815   -1.7515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9630   -1.9237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0624   -2.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9924   -0.2721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  1  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  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  1  0  0  0
 15 17  1  1  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 19  1  0  0  0  0
 11 20  1  1  0  0  0
 20 21  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 26  1  0  0  0  0
  4 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066813

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]12CC(C(=O)OC)=C3NC4=CC=CC=C4[C@@]33CCN(C[C@@H]4O[C@H]14)[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C21H24N2O3/c1-3-20-10-12(18(24)25-2)16-21(13-6-4-5-7-14(13)22-16)8-9-23(19(20)21)11-15-17(20)26-15/h4-7,15,17,19,22H,3,8-11H2,1-2H3/t15-,17-,19-,20+,21-/m0/s1

> <INCHI_KEY>
AUVZFRDLRJQTQF-KXEYLTKFSA-N

> <FORMULA>
C21H24N2O3

> <MOLECULAR_WEIGHT>
352.434

> <EXACT_MASS>
352.178692641

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.16021653941577

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,12S,13R,15S,20R)-12-ethyl-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

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
1.961635491

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.072402555215909

> <JCHEM_PKA_STRONGEST_BASIC>
7.566430875223714

> <JCHEM_POLAR_SURFACE_AREA>
54.10000000000001

> <JCHEM_REFRACTIVITY>
99.34409999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,12S,13R,15S,20R)-12-ethyl-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                                 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      12.839   3.782   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.888   2.654   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.435   1.182   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.934   0.838   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.886   1.966   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.338   3.438   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.489   1.317   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.674  -0.212   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.443  -1.137   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.027  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.841   0.995   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.072   1.921   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       7.887   3.449   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       6.470   4.053   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.239   3.128   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.424   1.599   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.008   2.203   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.710   3.799   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.501   2.478   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.610   0.070   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.193   0.674   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.629  -2.666   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.046  -3.270   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.398  -3.591   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.583  -5.120   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      11.186  -0.508   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   26                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   12   19                                             
CONECT    8    7    9   26                                                  
CONECT    9    8   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16   20                                             
CONECT   12   11    7   13                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15   11   17                                                  
CONECT   17   16   15                                                       
CONECT   18   13   19                                                       
CONECT   19   18    7                                                       
CONECT   20   11   21                                                       
CONECT   21   20                                                            
CONECT   22    9   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26    8    4                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   62    0
END

View in JSmol

Synonyms

Value	Source
(-)-Lochnericine	ChEBI
(5alpha,6alpha,7alpha,12beta,19alpha)-2,3-Didehydro-6,7-epoxyaspidospermidine-3-carboxylic acid methyl ester	ChEBI
(5a,6a,7a,12b,19a)-2,3-Didehydro-6,7-epoxyaspidospermidine-3-carboxylate methyl ester	Generator
(5a,6a,7a,12b,19a)-2,3-Didehydro-6,7-epoxyaspidospermidine-3-carboxylic acid methyl ester	Generator
(5alpha,6alpha,7alpha,12beta,19alpha)-2,3-Didehydro-6,7-epoxyaspidospermidine-3-carboxylate methyl ester	Generator
(5Α,6α,7α,12β,19α)-2,3-didehydro-6,7-epoxyaspidospermidine-3-carboxylate methyl ester	Generator
(5Α,6α,7α,12β,19α)-2,3-didehydro-6,7-epoxyaspidospermidine-3-carboxylic acid methyl ester	Generator

Chemical Formula

C₂₁H₂₄N₂O₃

Average Mass

352.4340 Da

Monoisotopic Mass

352.17869 Da

IUPAC Name

methyl (1R,12S,13R,15S,20R)-12-ethyl-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,13R,15S,20R)-12-ethyl-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

CC[C@@]12CC(C(=O)OC)=C3NC4=CC=CC=C4[C@@]33CCN(C[C@@H]4O[C@H]14)[C@@H]23

InChI Identifier

InChI=1S/C21H24N2O3/c1-3-20-10-12(18(24)25-2)16-21(13-6-4-5-7-14(13)22-16)8-9-23(19(20)21)11-15-17(20)26-15/h4-7,15,17,19,22H,3,8-11H2,1-2H3/t15-,17-,19-,20+,21-/m0/s1

InChI Key

AUVZFRDLRJQTQF-KXEYLTKFSA-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
Alstonia lanceolifera	Plant	KNApSAcK
Alstonia lenormandii var.lenormandii	Plant	KNApSAcK
Alstonia lenormandii var.minutifolia	Plant	KNApSAcK
Alstonia yunnanensis	Plant	KNApSAcK
Amsonia elliptica	LOTUS Database	35616633
Amsonia sinensis	Plant	KNApSAcK
Catharanthus pusillus (Vinca pusilla)	Plant	KNApSAcK
Catharanthus roseus	Plant	KNApSAcK
Catharanthus trichophyllus	Plant	KNApSAcK
Ervatamia coronaria	LOTUS Database	35616633
Hazunta modesta var.modesta subvar montana	Plant	KNApSAcK
Melodinus aeneus	Plant	KNApSAcK
Melodinus scandens	Plant	KNApSAcK
Petchia ceylanica	Plant	KNApSAcK
Tabernaemontana alternifolia	LOTUS Database	35616633
Tabernaemontana citrifolia	Plant	KNApSAcK
Tabernaemontana coffeoides	LOTUS Database	35616633
Tabernaemontana coffeoides Boj.	Plant	KNApSAcK
Tabernaemontana divaricata (L.)R.Br.	Plant	KNApSAcK
Tabernaemontana pachysiphon	Plant	KNApSAcK
Voacanga africana	Plant	KNApSAcK

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
Methyl ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous amide
Pyrrolidine
Enoate ester
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Secondary amine
Carboxylic acid derivative
Dialkyl ether
Enamine
Oxirane
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Amine
Organooxygen compound
Organic nitrogen compound
Organonitrogen compound
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	2.43	ALOGPS
logP	1.96	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	14.07	ChemAxon
pKa (Strongest Basic)	7.57	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.1 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	99.34 m³·mol⁻¹	ChemAxon
Polarizability	38.16 Å³	ChemAxon
Number of Rings	6	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

C00024457

Chemspider ID

9557512

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lochnericine

METLIN ID

Not Available

PubChem Compound

11382599

PDB ID

Not Available

ChEBI ID

6510

Good Scents ID

Not Available

References

General References

Stander EA, Sepulveda LJ, Duge de Bernonville T, Carqueijeiro I, Koudounas K, Lemos Cruz P, Besseau S, Lanoue A, Papon N, Giglioli-Guivarc'h N, Dirks R, O'Connor SE, Atehortua L, Oudin A, Courdavault V: Identifying Genes Involved in alkaloid Biosynthesis in Vinca minor Through Transcriptomics and Gene Co-Expression Analysis. Biomolecules. 2020 Nov 24;10(12). pii: biom10121595. doi: 10.3390/biom10121595. [PubMed:33255314 ]
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 ]
Sun J, Zhao L, Shao Z, Shanks J, Peebles CAM: Expression of tabersonine 16-hydroxylase and 16-hydroxytabersonine-O-methyltransferase in Catharanthus roseus hairy roots. Biotechnol Bioeng. 2018 Mar;115(3):673-683. doi: 10.1002/bit.26487. Epub 2017 Nov 22. [PubMed:29105731 ]
Demessie Z, Woolfson KN, Yu F, Qu Y, De Luca V: The ATP binding cassette transporter, VmTPT2/VmABCG1, is involved in export of the monoterpenoid indole alkaloid, vincamine in Vinca minor leaves. Phytochemistry. 2017 Aug;140:118-124. doi: 10.1016/j.phytochem.2017.04.019. Epub 2017 May 4. [PubMed:28478314 ]
Sun J, Peebles CA: Engineering overexpression of ORCA3 and strictosidine glucosidase in Catharanthus roseus hairy roots increases alkaloid production. Protoplasma. 2016 Sep;253(5):1255-64. doi: 10.1007/s00709-015-0881-7. Epub 2015 Sep 8. [PubMed:26351111 ]

Showing NP-Card for (-)-Lochnericine (NP0066813)

MOL for NP0066813 ((-)-Lochnericine)

3D MOL for NP0066813 ((-)-Lochnericine)

3D SDF for NP0066813 ((-)-Lochnericine)

3D-SDF for NP0066813 ((-)-Lochnericine)

PDB for NP0066813 ((-)-Lochnericine)

3D PDB for NP0066813 ((-)-Lochnericine)

SMILES for NP0066813 ((-)-Lochnericine)

INCHI for NP0066813 ((-)-Lochnericine)

Structure for NP0066813 ((-)-Lochnericine)

3D Structure for NP0066813 ((-)-Lochnericine)