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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:20 UTC

Update Date

2022-03-07 02:52:31 UTC

HMDB ID

HMDB0030360

Secondary Accession Numbers

HMDB30360

Metabolite Identification

Common Name

(+)-Aspidospermidine

Description

(+)-Aspidospermidine 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. Based on a literature review a significant number of articles have been published on (+)-Aspidospermidine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0030360
     RDKit          3D
(+)-Aspidospermidine
 47 51  0  0  0  0  0  0  0  0999 V2000
   -2.4008   -2.7368   -0.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3258   -1.7449   -0.9028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4596   -0.4495   -0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8140    0.1343   -0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0892    1.4349    0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346    2.2773    0.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8341    1.8465   -0.7207 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3234    2.6945   -0.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0764    2.0592    0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8207    0.5824    0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0433    0.0386   -0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3974    0.1723   -1.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5655   -0.4003   -2.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3509   -1.0899   -1.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0008   -1.2204    0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8153   -0.6422    0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1897   -0.5956    1.8136 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8398   -0.1242    1.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1584   -1.2204    1.7926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5226   -0.7341    1.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3753    0.4861   -0.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9422   -3.7072   -0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9555   -3.0278   -1.5848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1571   -2.4794    0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3013   -2.1629   -0.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4186   -1.4293   -1.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7171    0.3553   -1.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6346   -0.5668   -0.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4395    1.2946    1.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9255    1.9265   -0.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1567    3.3044   -0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4674    2.4569    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9415    2.7616   -1.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0052    3.7068   -0.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7624    2.3886    1.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1536    2.3032    0.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7787    0.7125   -2.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8754   -0.3167   -3.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2575   -1.5309   -1.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5897   -1.7501    0.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6484   -0.8612    2.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6575    0.6255    2.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1283   -2.1758    1.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2666   -1.4573    2.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396    0.1771    1.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2542   -1.4874    1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0312    0.1719   -1.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 10 21  1  0
 20  3  1  0
 21  3  1  0
 21  7  1  0
 18 10  1  0
 16 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
M  END


  Mrv0541 05061305112D          

 21 25  0  0  0  0            999 V2000
    0.8622    1.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6327    1.7471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4285   -0.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0125    0.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3729    0.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6318   -0.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7998    0.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1738    2.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5028    0.9324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4032    2.0419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2030    0.3605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0135   -0.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7529   -0.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4191    0.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0031    1.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8144    1.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9139    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2733    1.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6844    1.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6293    1.9451    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7840   -0.1074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  8  1  0  0  0  0
 12  5  1  0  0  0  0
 13 11  1  0  0  0  0
 14  6  2  0  0  0  0
 15  7  2  0  0  0  0
 15 14  1  0  0  0  0
 16  8  1  0  0  0  0
 18  2  1  0  0  0  0
 18  9  1  0  0  0  0
 18 10  1  0  0  0  0
 18 17  1  0  0  0  0
 19 11  1  0  0  0  0
 19 14  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 15  1  0  0  0  0
 20 16  1  0  0  0  0
 21 12  1  0  0  0  0
 21 13  1  0  0  0  0
 21 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030360

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC12CCCN3CCC4(C(CC1)NC1=CC=CC=C41)C23

> <INCHI_IDENTIFIER>
InChI=1S/C19H26N2/c1-2-18-9-5-12-21-13-11-19(17(18)21)14-6-3-4-7-15(14)20-16(19)8-10-18/h3-4,6-7,16-17,20H,2,5,8-13H2,1H3

> <INCHI_KEY>
YAAIPCQYJYPITK-UHFFFAOYSA-N

> <FORMULA>
C19H26N2

> <MOLECULAR_WEIGHT>
282.4231

> <EXACT_MASS>
282.209598842

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
34.57415609231129

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12-ethyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-triene

> <ALOGPS_LOGP>
4.59

> <JCHEM_LOGP>
3.3118070156666666

> <ALOGPS_LOGS>
-4.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.765517373742075

> <JCHEM_POLAR_SURFACE_AREA>
15.27

> <JCHEM_REFRACTIVITY>
88.02349999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-ethyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-triene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0030360
     RDKit          3D
(+)-Aspidospermidine
 47 51  0  0  0  0  0  0  0  0999 V2000
   -2.4008   -2.7368   -0.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3258   -1.7449   -0.9028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4596   -0.4495   -0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8140    0.1343   -0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0892    1.4349    0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346    2.2773    0.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8341    1.8465   -0.7207 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3234    2.6945   -0.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0764    2.0592    0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8207    0.5824    0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0433    0.0386   -0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3974    0.1723   -1.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5655   -0.4003   -2.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3509   -1.0899   -1.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0008   -1.2204    0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8153   -0.6422    0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1897   -0.5956    1.8136 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8398   -0.1242    1.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1584   -1.2204    1.7926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5226   -0.7341    1.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3753    0.4861   -0.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9422   -3.7072   -0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9555   -3.0278   -1.5848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1571   -2.4794    0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3013   -2.1629   -0.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4186   -1.4293   -1.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7171    0.3553   -1.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6346   -0.5668   -0.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4395    1.2946    1.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9255    1.9265   -0.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1567    3.3044   -0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4674    2.4569    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9415    2.7616   -1.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0052    3.7068   -0.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7624    2.3886    1.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1536    2.3032    0.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7787    0.7125   -2.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8754   -0.3167   -3.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2575   -1.5309   -1.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5897   -1.7501    0.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6484   -0.8612    2.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6575    0.6255    2.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1283   -2.1758    1.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2666   -1.4573    2.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396    0.1771    1.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2542   -1.4874    1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0312    0.1719   -1.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 10 21  1  0
 20  3  1  0
 21  3  1  0
 21  7  1  0
 18 10  1  0
 16 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.609   2.711   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.048   3.261   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.133  -0.718   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.223   0.370   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.563   0.220   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.646  -0.318   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.826   1.858   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.924   4.362   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.805   1.740   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.486   3.812   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.846   0.673   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.759  -0.751   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.005  -0.618   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.249   1.170   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.339   2.258   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.120   3.392   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.439   1.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.243   2.291   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.878   1.871   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       8.641   3.631   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       5.197  -0.200   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1   18                                                       
CONECT    3    4    6                                                       
CONECT    4    3    7                                                       
CONECT    5    9   12                                                       
CONECT    6    3   14                                                       
CONECT    7    4   15                                                       
CONECT    8   10   16                                                       
CONECT    9    5   18                                                       
CONECT   10    8   18                                                       
CONECT   11   13   19                                                       
CONECT   12    5   21                                                       
CONECT   13   11   21                                                       
CONECT   14    6   15   19                                                  
CONECT   15    7   14   20                                                  
CONECT   16    8   19   20                                                  
CONECT   17   18   19   21                                                  
CONECT   18    2    9   10   17                                             
CONECT   19   11   14   16   17                                             
CONECT   20   15   16                                                       
CONECT   21   12   13   17                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   50    0
END

COMPND    HMDB0030360
HETATM    1  C1  UNL     1      -2.401  -2.737  -0.645  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.326  -1.745  -0.903  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.460  -0.449  -0.115  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.814   0.134  -0.551  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.089   1.435   0.157  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.835   2.277   0.192  1.00  0.00           C  
HETATM    7  N1  UNL     1      -0.834   1.846  -0.721  1.00  0.00           N  
HETATM    8  C7  UNL     1       0.323   2.694  -0.577  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.076   2.059   0.536  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.821   0.582   0.332  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.043   0.039  -0.353  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.397   0.172  -1.704  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.565  -0.400  -2.152  1.00  0.00           C  
HETATM   14  C13 UNL     1       4.351  -1.090  -1.249  1.00  0.00           C  
HETATM   15  C14 UNL     1       4.001  -1.220   0.080  1.00  0.00           C  
HETATM   16  C15 UNL     1       2.815  -0.642   0.547  1.00  0.00           C  
HETATM   17  N2  UNL     1       2.190  -0.596   1.814  1.00  0.00           N  
HETATM   18  C16 UNL     1       0.840  -0.124   1.626  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.158  -1.220   1.793  1.00  0.00           C  
HETATM   20  C18 UNL     1      -1.523  -0.734   1.341  1.00  0.00           C  
HETATM   21  C19 UNL     1      -0.375   0.486  -0.508  1.00  0.00           C  
HETATM   22  H1  UNL     1      -1.942  -3.707  -0.302  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.955  -3.028  -1.585  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.157  -2.479   0.086  1.00  0.00           H  
HETATM   25  H4  UNL     1      -0.301  -2.163  -0.825  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.419  -1.429  -1.986  1.00  0.00           H  
HETATM   27  H6  UNL     1      -2.717   0.355  -1.634  1.00  0.00           H  
HETATM   28  H7  UNL     1      -3.635  -0.567  -0.418  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.440   1.295   1.202  1.00  0.00           H  
HETATM   30  H9  UNL     1      -3.926   1.927  -0.383  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.157   3.304  -0.158  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.467   2.457   1.231  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.942   2.762  -1.494  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.005   3.707  -0.233  1.00  0.00           H  
HETATM   35  H14 UNL     1       0.762   2.389   1.549  1.00  0.00           H  
HETATM   36  H15 UNL     1       2.154   2.303   0.454  1.00  0.00           H  
HETATM   37  H16 UNL     1       1.779   0.713  -2.408  1.00  0.00           H  
HETATM   38  H17 UNL     1       3.875  -0.317  -3.203  1.00  0.00           H  
HETATM   39  H18 UNL     1       5.257  -1.531  -1.610  1.00  0.00           H  
HETATM   40  H19 UNL     1       4.590  -1.750   0.807  1.00  0.00           H  
HETATM   41  H20 UNL     1       2.648  -0.861   2.707  1.00  0.00           H  
HETATM   42  H21 UNL     1       0.657   0.626   2.449  1.00  0.00           H  
HETATM   43  H22 UNL     1       0.128  -2.176   1.304  1.00  0.00           H  
HETATM   44  H23 UNL     1      -0.267  -1.457   2.878  1.00  0.00           H  
HETATM   45  H24 UNL     1      -1.740   0.177   1.921  1.00  0.00           H  
HETATM   46  H25 UNL     1      -2.254  -1.487   1.615  1.00  0.00           H  
HETATM   47  H26 UNL     1      -0.031   0.172  -1.545  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   20   21
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8   21
CONECT    8    9   33   34
CONECT    9   10   35   36
CONECT   10   11   18   21
CONECT   11   12   12   16
CONECT   12   13   37
CONECT   13   14   14   38
CONECT   14   15   39
CONECT   15   16   16   40
CONECT   16   17
CONECT   17   18   41
CONECT   18   19   42
CONECT   19   20   43   44
CONECT   20   45   46
CONECT   21   47
END

HMDB0030360
     RDKit          3D
(+)-Aspidospermidine
 47 51  0  0  0  0  0  0  0  0999 V2000
   -2.4008   -2.7368   -0.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3258   -1.7449   -0.9028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4596   -0.4495   -0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8140    0.1343   -0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0892    1.4349    0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346    2.2773    0.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8341    1.8465   -0.7207 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3234    2.6945   -0.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0764    2.0592    0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8207    0.5824    0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0433    0.0386   -0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3974    0.1723   -1.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5655   -0.4003   -2.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3509   -1.0899   -1.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0008   -1.2204    0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8153   -0.6422    0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1897   -0.5956    1.8136 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8398   -0.1242    1.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1584   -1.2204    1.7926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5226   -0.7341    1.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3753    0.4861   -0.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9422   -3.7072   -0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9555   -3.0278   -1.5848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1571   -2.4794    0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3013   -2.1629   -0.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4186   -1.4293   -1.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7171    0.3553   -1.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6346   -0.5668   -0.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4395    1.2946    1.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9255    1.9265   -0.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1567    3.3044   -0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4674    2.4569    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9415    2.7616   -1.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0052    3.7068   -0.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7624    2.3886    1.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1536    2.3032    0.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7787    0.7125   -2.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8754   -0.3167   -3.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2575   -1.5309   -1.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5897   -1.7501    0.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6484   -0.8612    2.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6575    0.6255    2.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1283   -2.1758    1.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2666   -1.4573    2.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396    0.1771    1.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2542   -1.4874    1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0312    0.1719   -1.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 10 21  1  0
 20  3  1  0
 21  3  1  0
 21  7  1  0
 18 10  1  0
 16 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Dehydrodivanillyl alcohol	HMDB
Aspidospermidine	HMDB

Chemical Formula

C₁₉H₂₆N₂

Average Molecular Weight

282.4231

Monoisotopic Molecular Weight

282.209598842

IUPAC Name

12-ethyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-triene

Traditional Name

12-ethyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-triene

CAS Registry Number

2912-09-6

SMILES

CCC12CCCN3CCC4(C(CC1)NC1=CC=CC=C41)C23

InChI Identifier

InChI=1S/C19H26N2/c1-2-18-9-5-12-21-13-11-19(17(18)21)14-6-3-4-7-15(14)20-16(19)8-10-18/h3-4,6-7,16-17,20H,2,5,8-13H2,1H3

InChI Key

YAAIPCQYJYPITK-UHFFFAOYSA-N

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
Plumeran-type alkaloid
Carbazole
Quinolidine
Indole or derivatives
Dihydroindole
Indolizidine
Aralkylamine
Secondary aliphatic/aromatic amine
Benzenoid
N-alkylpyrrolidine
Piperidine
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Secondary amine
Amine
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0030360)

Cellular substructure

Membrane (HMDB: HMDB0030360)

Source

Endogenous

Endogenous (HMDB: HMDB0030360)

Exogenous

Food

Food (HMDB: HMDB0030360)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	119.5 - 121 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.024 g/L	ALOGPS
logP	4.59	ALOGPS
logP	3.31	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	10.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	15.27 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.02 m³·mol⁻¹	ChemAxon
Polarizability	34.57 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	165.325	31661259
DarkChem	[M-H]-	164.779	31661259
DeepCCS	[M-2H]-	203.64	30932474
DeepCCS	[M+Na]+	178.88	30932474
AllCCS	[M+H]+	171.7	32859911
AllCCS	[M+H-H2O]+	168.4	32859911
AllCCS	[M+NH4]+	174.8	32859911
AllCCS	[M+Na]+	175.7	32859911
AllCCS	[M-H]-	180.3	32859911
AllCCS	[M+Na-2H]-	180.0	32859911
AllCCS	[M+HCOO]-	179.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(+)-Aspidospermidine	CCC12CCCN3CCC4(C(CC1)NC1=CC=CC=C41)C23	3312.8	Standard polar	33892256
(+)-Aspidospermidine	CCC12CCCN3CCC4(C(CC1)NC1=CC=CC=C41)C23	2527.3	Standard non polar	33892256
(+)-Aspidospermidine	CCC12CCCN3CCC4(C(CC1)NC1=CC=CC=C41)C23	2428.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(+)-Aspidospermidine,1TMS,isomer #1	CCC12CCCN3CCC4(C5=CC=CC=C5N([Si](C)(C)C)C4CC1)C32	2435.6	Semi standard non polar	33892256
(+)-Aspidospermidine,1TMS,isomer #1	CCC12CCCN3CCC4(C5=CC=CC=C5N([Si](C)(C)C)C4CC1)C32	2457.8	Standard non polar	33892256
(+)-Aspidospermidine,1TBDMS,isomer #1	CCC12CCCN3CCC4(C5=CC=CC=C5N([Si](C)(C)C(C)(C)C)C4CC1)C32	2658.2	Semi standard non polar	33892256
(+)-Aspidospermidine,1TBDMS,isomer #1	CCC12CCCN3CCC4(C5=CC=CC=C5N([Si](C)(C)C(C)(C)C)C4CC1)C32	2779.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Aspidospermidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-1090000000-c7bb8d6d49a21a981379	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Aspidospermidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Aspidospermidine 10V, Positive-QTOF	splash10-001i-0090000000-753254926ca73b72c086	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Aspidospermidine 20V, Positive-QTOF	splash10-001i-0090000000-2d7e9eab8bc37eaeec6c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Aspidospermidine 40V, Positive-QTOF	splash10-066u-0690000000-716fdd0d3058d52a0b96	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Aspidospermidine 10V, Negative-QTOF	splash10-001i-0090000000-d5dae2723d86ad3781cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Aspidospermidine 20V, Negative-QTOF	splash10-001i-0090000000-6510ef744feb6b1c41a9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Aspidospermidine 40V, Negative-QTOF	splash10-0gbi-1090000000-a528bcd16e1da0dca7d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Aspidospermidine 10V, Negative-QTOF	splash10-001i-0090000000-4af417b6c8cdf87c31f7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Aspidospermidine 20V, Negative-QTOF	splash10-001i-0090000000-4af417b6c8cdf87c31f7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Aspidospermidine 40V, Negative-QTOF	splash10-001i-0090000000-ee911222c1051ced6521	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Aspidospermidine 10V, Positive-QTOF	splash10-001i-0090000000-48c8d6d60cf70e82e98f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Aspidospermidine 20V, Positive-QTOF	splash10-001i-0090000000-8a1139910294cabb38b1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Aspidospermidine 40V, Positive-QTOF	splash10-001l-2590000000-0841c2cbd400320fd4b4	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002206

KNApSAcK ID

C00024464

Chemspider ID

504390

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11237396

PDB ID

Not Available

ChEBI ID

544590

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Stevens MM, Ali A, Helliwell S, Schiller LJ, Hansen S: Comparison of two bioassay techniques for assessing the acute toxicity of pesticides to chironomid larvae (Diptera: Chironomidae). J Am Mosq Control Assoc. 2002 Jun;18(2):119-25. [PubMed:12083354 ]
Wang L, Xu K, Bei F, Gao FS: [Effects of bagging on the microenvironment, yield and quality of overwintering tomato]. Ying Yong Sheng Tai Xue Bao. 2007 Apr;18(4):837-42. [PubMed:17615881 ]
Laskowski DA: Physical and chemical properties of pyrethroids. Rev Environ Contam Toxicol. 2002;174:49-170. [PubMed:12132343 ]
Rodriguez MM, Bisset JA, Fernandez D: Levels of insecticide resistance and resistance mechanisms in Aedes aegypti from some Latin American countries. J Am Mosq Control Assoc. 2007 Dec;23(4):420-9. [PubMed:18240518 ]
Ahmad M, Arif MI, Denholm I: High resistance of field populations of the cotton aphid Aphis gossypii Glover (Homoptera: Aphididae) to pyrethroid insecticides in Pakistan. J Econ Entomol. 2003 Jun;96(3):875-8. [PubMed:12852630 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (+)-Aspidospermidine (HMDB0030360)

MOL for HMDB0030360 ((+)-Aspidospermidine)

3D MOL for HMDB0030360 ((+)-Aspidospermidine)

3D SDF for HMDB0030360 ((+)-Aspidospermidine)

3D-SDF for HMDB0030360 ((+)-Aspidospermidine)

PDB for HMDB0030360 ((+)-Aspidospermidine)

3D PDB for HMDB0030360 ((+)-Aspidospermidine)

SMILES for HMDB0030360 ((+)-Aspidospermidine)

INCHI for HMDB0030360 ((+)-Aspidospermidine)

Structure for HMDB0030360 ((+)-Aspidospermidine)

3D Structure for HMDB0030360 ((+)-Aspidospermidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra