Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:01 UTC

Update Date

2022-03-07 02:52:30 UTC

HMDB ID

HMDB0030304

Secondary Accession Numbers

HMDB30304

Metabolite Identification

Common Name

Atherosperminine

Description

Atherosperminine belongs to the class of organic compounds known as 6,6a-secoaporphines. These are alkaloids with a structure that contains an aminoethylphenanthrene moiety. Based on a literature review very few articles have been published on Atherosperminine.

Structure

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

HMDB0030304
     RDKit          3D
Atherosperminine
 46 48  0  0  0  0  0  0  0  0999 V2000
   -1.3281    4.4203    0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9357    3.1683    0.0366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3030    1.9600    0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0356    1.8403    0.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6534    0.6248    0.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1339    0.5474    0.9131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8995    0.1848   -0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3024    0.0841   -0.1467 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0203    1.2730    0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9520   -0.8375   -1.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1508   -0.4985    0.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4527   -1.7065    0.8096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2777   -2.8647    0.7739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6247   -2.7633    0.5331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3227   -3.9613    0.5475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6775   -3.9252    0.3524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3431   -2.7426    0.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6478   -1.5265    0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2961   -1.5643    0.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5383   -0.4020    0.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1028    0.8112    0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4255    1.0302   -0.1043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6836    1.2177   -1.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6314    4.5044    0.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1449    5.1785    0.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7949    4.6906   -0.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6345    2.7382    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3895   -0.0988    1.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4809    1.5786    1.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4935   -0.7048   -0.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7275    1.0232   -1.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3081    1.4174    1.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4774    2.1422   -0.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9977    1.2349   -0.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0364   -1.8520   -0.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3856   -0.7784   -2.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9757   -0.4448   -1.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5333   -1.7653    1.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2278   -3.8045    0.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8131   -4.9089    0.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2407   -4.8611    0.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4062   -2.7656    0.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2402   -0.6633    0.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2012    2.1668   -1.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1978    0.3621   -2.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7897    1.2407   -1.6650 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  5 11  2  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  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 21  3  1  0
 20 11  1  0
 19 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 12 38  1  0
 13 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 23 44  1  0
 23 45  1  0
 23 46  1  0
M  END


  Mrv0541 05061305082D          

 23 25  0  0  0  0            999 V2000
   -2.1730   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -1.7309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  2  0  0  0  0
 12 11  1  0  0  0  0
 14  7  2  0  0  0  0
 14  9  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  2  0  0  0  0
 16  8  2  0  0  0  0
 16 14  1  0  0  0  0
 17 10  1  0  0  0  0
 17 15  1  0  0  0  0
 18 13  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  2  0  0  0  0
 20 18  2  0  0  0  0
 20 19  1  0  0  0  0
 21  1  1  0  0  0  0
 21  2  1  0  0  0  0
 21 12  1  0  0  0  0
 22  3  1  0  0  0  0
 22 18  1  0  0  0  0
 23  4  1  0  0  0  0
 23 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030304

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C2=C(C=CC3=CC=CC=C23)C(CCN(C)C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H23NO2/c1-21(2)12-11-15-13-18(22-3)20(23-4)19-16-8-6-5-7-14(16)9-10-17(15)19/h5-10,13H,11-12H2,1-4H3

> <INCHI_KEY>
UZZFAUDNCIFFPM-UHFFFAOYSA-N

> <FORMULA>
C20H23NO2

> <MOLECULAR_WEIGHT>
309.4021

> <EXACT_MASS>
309.172878985

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.80593810181413

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[2-(3,4-dimethoxyphenanthren-1-yl)ethyl]dimethylamine

> <ALOGPS_LOGP>
3.97

> <JCHEM_LOGP>
3.8669147699999993

> <ALOGPS_LOGS>
-5.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.316512989936545

> <JCHEM_POLAR_SURFACE_AREA>
21.700000000000003

> <JCHEM_REFRACTIVITY>
95.18249999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[2-(3,4-dimethoxyphenanthren-1-yl)ethyl]dimethylamine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0030304
     RDKit          3D
Atherosperminine
 46 48  0  0  0  0  0  0  0  0999 V2000
   -1.3281    4.4203    0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9357    3.1683    0.0366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3030    1.9600    0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0356    1.8403    0.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6534    0.6248    0.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1339    0.5474    0.9131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8995    0.1848   -0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3024    0.0841   -0.1467 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0203    1.2730    0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9520   -0.8375   -1.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1508   -0.4985    0.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4527   -1.7065    0.8096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2777   -2.8647    0.7739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6247   -2.7633    0.5331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3227   -3.9613    0.5475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6775   -3.9252    0.3524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3431   -2.7426    0.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6478   -1.5265    0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2961   -1.5643    0.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5383   -0.4020    0.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1028    0.8112    0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4255    1.0302   -0.1043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6836    1.2177   -1.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6314    4.5044    0.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1449    5.1785    0.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7949    4.6906   -0.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6345    2.7382    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3895   -0.0988    1.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4809    1.5786    1.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4935   -0.7048   -0.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7275    1.0232   -1.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3081    1.4174    1.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4774    2.1422   -0.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9977    1.2349   -0.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0364   -1.8520   -0.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3856   -0.7784   -2.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9757   -0.4448   -1.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5333   -1.7653    1.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2278   -3.8045    0.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8131   -4.9089    0.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2407   -4.8611    0.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4062   -2.7656    0.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2402   -0.6633    0.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2012    2.1668   -1.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1978    0.3621   -2.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7897    1.2407   -1.6650 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  5 11  2  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  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 21  3  1  0
 20 11  1  0
 19 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 12 38  1  0
 13 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 23 44  1  0
 23 45  1  0
 23 46  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      -4.056  -3.231   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.746  -4.565   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.564   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.206  -1.897   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.746  -1.897   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      -2.516  -3.231   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.874   3.437   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   21                                                            
CONECT    3   22                                                            
CONECT    4   23                                                            
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5   14                                                       
CONECT    8    6   16                                                       
CONECT    9   10   14                                                       
CONECT   10    9   17                                                       
CONECT   11   12   15                                                       
CONECT   12   11   21                                                       
CONECT   13   15   18                                                       
CONECT   14    7    9   16                                                  
CONECT   15   11   13   17                                                  
CONECT   16    8   14   19                                                  
CONECT   17   10   15   19                                                  
CONECT   18   13   20   22                                                  
CONECT   19   16   17   20                                                  
CONECT   20   18   19   23                                                  
CONECT   21    1    2   12                                                  
CONECT   22    3   18                                                       
CONECT   23    4   20                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0030304
HETATM    1  C1  UNL     1      -1.328   4.420   0.062  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.936   3.168   0.037  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.303   1.960   0.231  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.036   1.840   0.481  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.653   0.625   0.673  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.134   0.547   0.913  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.900   0.185  -0.308  1.00  0.00           C  
HETATM    8  N1  UNL     1       4.302   0.084  -0.147  1.00  0.00           N  
HETATM    9  C7  UNL     1       5.020   1.273   0.115  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.952  -0.838  -1.041  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.151  -0.498   0.607  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.453  -1.707   0.810  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.278  -2.865   0.774  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.625  -2.763   0.533  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.323  -3.961   0.548  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.677  -3.925   0.352  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.343  -2.743   0.147  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.648  -1.527   0.130  1.00  0.00           C  
HETATM   19  C17 UNL     1      -2.296  -1.564   0.320  1.00  0.00           C  
HETATM   20  C18 UNL     1      -1.538  -0.402   0.353  1.00  0.00           C  
HETATM   21  C19 UNL     1      -2.103   0.811   0.164  1.00  0.00           C  
HETATM   22  O2  UNL     1      -3.425   1.030  -0.104  1.00  0.00           O  
HETATM   23  C20 UNL     1      -3.684   1.218  -1.541  1.00  0.00           C  
HETATM   24  H1  UNL     1      -0.631   4.504   0.914  1.00  0.00           H  
HETATM   25  H2  UNL     1      -2.145   5.178   0.201  1.00  0.00           H  
HETATM   26  H3  UNL     1      -0.795   4.691  -0.869  1.00  0.00           H  
HETATM   27  H4  UNL     1       0.634   2.738   0.529  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.389  -0.099   1.750  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.481   1.579   1.229  1.00  0.00           H  
HETATM   30  H7  UNL     1       2.494  -0.705  -0.821  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.727   1.023  -1.056  1.00  0.00           H  
HETATM   32  H9  UNL     1       5.308   1.417   1.178  1.00  0.00           H  
HETATM   33  H10 UNL     1       4.477   2.142  -0.303  1.00  0.00           H  
HETATM   34  H11 UNL     1       5.998   1.235  -0.443  1.00  0.00           H  
HETATM   35  H12 UNL     1       5.036  -1.852  -0.656  1.00  0.00           H  
HETATM   36  H13 UNL     1       4.386  -0.778  -2.015  1.00  0.00           H  
HETATM   37  H14 UNL     1       5.976  -0.445  -1.265  1.00  0.00           H  
HETATM   38  H15 UNL     1       1.533  -1.765   1.013  1.00  0.00           H  
HETATM   39  H16 UNL     1       0.228  -3.805   0.934  1.00  0.00           H  
HETATM   40  H17 UNL     1      -1.813  -4.909   0.709  1.00  0.00           H  
HETATM   41  H18 UNL     1      -4.241  -4.861   0.360  1.00  0.00           H  
HETATM   42  H19 UNL     1      -5.406  -2.766   0.001  1.00  0.00           H  
HETATM   43  H20 UNL     1      -4.240  -0.663   0.016  1.00  0.00           H  
HETATM   44  H21 UNL     1      -3.201   2.167  -1.829  1.00  0.00           H  
HETATM   45  H22 UNL     1      -3.198   0.362  -2.025  1.00  0.00           H  
HETATM   46  H23 UNL     1      -4.790   1.241  -1.665  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   27
CONECT    5    6   11   11
CONECT    6    7   28   29
CONECT    7    8   30   31
CONECT    8    9   10
CONECT    9   32   33   34
CONECT   10   35   36   37
CONECT   11   12   20
CONECT   12   13   13   38
CONECT   13   14   39
CONECT   14   15   15   19
CONECT   15   16   40
CONECT   16   17   17   41
CONECT   17   18   42
CONECT   18   19   19   43
CONECT   19   20
CONECT   20   21   21
CONECT   21   22
CONECT   22   23
CONECT   23   44   45   46
END

HMDB0030304
     RDKit          3D
Atherosperminine
 46 48  0  0  0  0  0  0  0  0999 V2000
   -1.3281    4.4203    0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9357    3.1683    0.0366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3030    1.9600    0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0356    1.8403    0.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6534    0.6248    0.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1339    0.5474    0.9131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8995    0.1848   -0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3024    0.0841   -0.1467 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0203    1.2730    0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9520   -0.8375   -1.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1508   -0.4985    0.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4527   -1.7065    0.8096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2777   -2.8647    0.7739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6247   -2.7633    0.5331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3227   -3.9613    0.5475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6775   -3.9252    0.3524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3431   -2.7426    0.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6478   -1.5265    0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2961   -1.5643    0.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5383   -0.4020    0.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1028    0.8112    0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4255    1.0302   -0.1043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6836    1.2177   -1.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6314    4.5044    0.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1449    5.1785    0.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7949    4.6906   -0.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6345    2.7382    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3895   -0.0988    1.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4809    1.5786    1.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4935   -0.7048   -0.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7275    1.0232   -1.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3081    1.4174    1.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4774    2.1422   -0.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9977    1.2349   -0.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0364   -1.8520   -0.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3856   -0.7784   -2.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9757   -0.4448   -1.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5333   -1.7653    1.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2278   -3.8045    0.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8131   -4.9089    0.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2407   -4.8611    0.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4062   -2.7656    0.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2402   -0.6633    0.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2012    2.1668   -1.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1978    0.3621   -2.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7897    1.2407   -1.6650 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  5 11  2  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  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 21  3  1  0
 20 11  1  0
 19 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 12 38  1  0
 13 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 23 44  1  0
 23 45  1  0
 23 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Dimethylaminoethyl-3,4-dimethoxyphenanthrene	HMDB
3,4-Dimethoxy-N,N-dimethyl-1-phenanthreneethanamine	HMDB
3,4-Dimethoxy-N,N-dimethyl-1-phenanthreneethanamine, 9ci	HMDB
Atherospermine	HMDB
Atherospermine hydrochloride	HMDB
Atherosperminine	MeSH

Chemical Formula

C₂₀H₂₃NO₂

Average Molecular Weight

309.4021

Monoisotopic Molecular Weight

309.172878985

IUPAC Name

[2-(3,4-dimethoxyphenanthren-1-yl)ethyl]dimethylamine

Traditional Name

[2-(3,4-dimethoxyphenanthren-1-yl)ethyl]dimethylamine

CAS Registry Number

5531-98-6

SMILES

COC1=C(OC)C2=C(C=CC3=CC=CC=C23)C(CCN(C)C)=C1

InChI Identifier

InChI=1S/C20H23NO2/c1-21(2)12-11-15-13-18(22-3)20(23-4)19-16-8-6-5-7-14(16)9-10-17(15)19/h5-10,13H,11-12H2,1-4H3

InChI Key

UZZFAUDNCIFFPM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6,6a-secoaporphines. These are alkaloids with a structure that contains an aminoethylphenanthrene moiety.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

6,6a-secoaporphines

Sub Class

Not Available

Direct Parent

6,6a-secoaporphines

Alternative Parents

Substituents

6,6a-secoaporphine
Phenanthrene
Naphthalene
Phenethylamine
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Ether
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0030304)

Cellular substructure

Membrane (HMDB: HMDB0030304)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030304)

Source

Endogenous

Endogenous (HMDB: HMDB0030304)

Plant

Plant (HMDB: HMDB0030304)

Exogenous

Food

Food (HMDB: HMDB0030304)

Fruit

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	199 - 200 °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	0.0016 g/L	ALOGPS
logP	3.97	ALOGPS
logP	3.87	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	9.32	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	21.7 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	95.18 m³·mol⁻¹	ChemAxon
Polarizability	35.81 Å³	ChemAxon
Number of Rings	3	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]+	173.236	31661259
DarkChem	[M-H]-	175.082	31661259
DeepCCS	[M-2H]-	213.042	30932474
DeepCCS	[M+Na]+	188.269	30932474
AllCCS	[M+H]+	173.7	32859911
AllCCS	[M+H-H2O]+	170.3	32859911
AllCCS	[M+NH4]+	176.9	32859911
AllCCS	[M+Na]+	177.8	32859911
AllCCS	[M-H]-	183.1	32859911
AllCCS	[M+Na-2H]-	182.8	32859911
AllCCS	[M+HCOO]-	182.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Atherosperminine	COC1=C(OC)C2=C(C=CC3=CC=CC=C23)C(CCN(C)C)=C1	3397.8	Standard polar	33892256
Atherosperminine	COC1=C(OC)C2=C(C=CC3=CC=CC=C23)C(CCN(C)C)=C1	2401.7	Standard non polar	33892256
Atherosperminine	COC1=C(OC)C2=C(C=CC3=CC=CC=C23)C(CCN(C)C)=C1	2653.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Atherosperminine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9060000000-689399e43230d398f5fb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Atherosperminine 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 - Atherosperminine 10V, Positive-QTOF	splash10-03di-0039000000-272dab278a8704b10df1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atherosperminine 20V, Positive-QTOF	splash10-03xr-0095000000-5d79c723ceb9e9cdd068	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atherosperminine 40V, Positive-QTOF	splash10-014s-1190000000-447148453dca5377763b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atherosperminine 10V, Negative-QTOF	splash10-0a4i-0009000000-ff9215dc900cd8700b67	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atherosperminine 20V, Negative-QTOF	splash10-0a4i-1079000000-5127f47113a089ba8d7b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atherosperminine 40V, Negative-QTOF	splash10-01oy-1090000000-6f73e26491ad07f6e039	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atherosperminine 10V, Positive-QTOF	splash10-03di-0009000000-2f49d18a71572e53f33c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atherosperminine 20V, Positive-QTOF	splash10-02t9-1094000000-23994942e697832e97b7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atherosperminine 40V, Positive-QTOF	splash10-0a4i-9060000000-ba721133f54c9826395f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atherosperminine 10V, Negative-QTOF	splash10-0a4i-0009000000-ef9ecbcc77a6beed41c8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atherosperminine 20V, Negative-QTOF	splash10-0zfr-0093000000-ee0ec5d2df4594e313e7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Atherosperminine 40V, Negative-QTOF	splash10-052r-0090000000-906d198016db13014482	2021-09-24	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

FDB002142

KNApSAcK ID

C00052850

Chemspider ID

87510

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

96918

PDB ID

Not Available

ChEBI ID

760438

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

Lin CH, Ko FN, Wu YC, Lu ST, Teng CM: The relaxant actions on guinea-pig trachealis of atherosperminine isolated from Fissistigma glaucescens. Eur J Pharmacol. 1993 Jun 11;237(1):109-16. [PubMed:8395388 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Atherosperminine (HMDB0030304)

MOL for HMDB0030304 (Atherosperminine)

3D MOL for HMDB0030304 (Atherosperminine)

3D SDF for HMDB0030304 (Atherosperminine)

3D-SDF for HMDB0030304 (Atherosperminine)

PDB for HMDB0030304 (Atherosperminine)

3D PDB for HMDB0030304 (Atherosperminine)

SMILES for HMDB0030304 (Atherosperminine)

INCHI for HMDB0030304 (Atherosperminine)

Structure for HMDB0030304 (Atherosperminine)

3D Structure for HMDB0030304 (Atherosperminine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra