NP-MRD: Showing NP-Card for bufotenine (NP0036326)

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Record Information

Version

2.0

Created at

2021-06-20 19:31:43 UTC

Updated at

2021-06-30 00:07:55 UTC

NP-MRD ID

NP0036326

Secondary Accession Numbers

None

Natural Product Identification

Common Name

bufotenine

Provided By

JEOL Database JEOL Logo

Description

Bufotenin, also known as DM5-HT or mappin, belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5. Bufotenin has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make bufotenin a potential biomarker for the consumption of these foods. Bufotenin 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. bufotenine is found in Amanita citrina, Anadenanthera colubrina, Anadenanthera peregrina, Bufo bufo, Citrus reticulata, Mimosa somnians, Ohwia caudata, Paramuricea clavata, Phalaris aquatica, Phyllodium pulchellum and Umbellularia californica. bufotenine was first documented in 1975 (PMID: 1058643). Based on a literature review a small amount of articles have been published on Bufotenin (PMID: 8747157) (PMID: 9468359) (PMID: 10350367).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121313D          

 31 32  0  0  0  0            999 V2000
   -0.1141    0.8826   -1.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7409    1.3380   -0.2393 N   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1995    1.2710   -0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3068    0.5354    0.9233 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1750    0.7309    1.2915 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5373    0.0234    2.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1163   -1.2263    2.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2847   -1.5104    3.9989 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8239   -0.4700    4.7709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7928   -0.3256    6.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2600    0.8592    6.6785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7836    1.8487    5.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2769    2.9811    6.4009 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8175    1.6992    4.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3506    0.5105    3.8978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4799    1.4681   -2.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3153   -0.1758   -1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9695    1.0335   -1.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6867    1.6621    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5403    1.8956   -1.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5530    0.2471   -0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5127   -0.5309    0.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9076    0.8329    1.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939    1.8007    1.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8214    0.3580    0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4241   -1.9355    1.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6892   -2.3600    4.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665   -1.0996    6.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2184    1.0091    7.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0054    3.5811    5.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    2.4728    3.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
 15  9  2  0  0  0  0
 11 12  1  0  0  0  0
  9  8  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
  8  7  1  0  0  0  0
  6  5  1  0  0  0  0
  6 15  1  0  0  0  0
  5  4  1  0  0  0  0
  7  6  2  0  0  0  0
  4  2  1  0  0  0  0
  9 10  1  0  0  0  0
 12 13  1  0  0  0  0
  2  1  1  0  0  0  0
 10 11  2  0  0  0  0
  2  3  1  0  0  0  0
  7 26  1  0  0  0  0
  8 27  1  0  0  0  0
 10 28  1  0  0  0  0
 11 29  1  0  0  0  0
 14 31  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  4 22  1  0  0  0  0
  4 23  1  0  0  0  0
 13 30  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  3 19  1  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
M  END

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
   -0.1141    0.8826   -1.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7409    1.3380   -0.2393 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1995    1.2710   -0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3068    0.5354    0.9233 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1750    0.7309    1.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5373    0.0234    2.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1163   -1.2263    2.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2847   -1.5104    3.9989 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8239   -0.4700    4.7709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7928   -0.3256    6.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2600    0.8592    6.6785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7836    1.8487    5.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2769    2.9811    6.4009 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8175    1.6992    4.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3506    0.5105    3.8978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4799    1.4681   -2.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3153   -0.1758   -1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9695    1.0335   -1.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6867    1.6621    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5403    1.8956   -1.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5530    0.2471   -0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5127   -0.5309    0.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9076    0.8329    1.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939    1.8007    1.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8214    0.3580    0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4241   -1.9355    1.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6892   -2.3600    4.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665   -1.0996    6.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2184    1.0091    7.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0054    3.5811    5.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    2.4728    3.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
 15  9  2  0
 11 12  1  0
  9  8  1  0
 12 14  2  0
 14 15  1  0
  8  7  1  0
  6  5  1  0
  6 15  1  0
  5  4  1  0
  7  6  2  0
  4  2  1  0
  9 10  1  0
 12 13  1  0
  2  1  1  0
 10 11  2  0
  2  3  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 14 31  1  0
  5 24  1  0
  5 25  1  0
  4 22  1  0
  4 23  1  0
 13 30  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
M  END


  Mrv1652306202121313D          

 31 32  0  0  0  0            999 V2000
   -0.1141    0.8826   -1.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7409    1.3380   -0.2393 N   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1995    1.2710   -0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3068    0.5354    0.9233 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1750    0.7309    1.2915 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5373    0.0234    2.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1163   -1.2263    2.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2847   -1.5104    3.9989 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8239   -0.4700    4.7709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7928   -0.3256    6.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2600    0.8592    6.6785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7836    1.8487    5.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2769    2.9811    6.4009 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8175    1.6992    4.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3506    0.5105    3.8978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4799    1.4681   -2.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3153   -0.1758   -1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9695    1.0335   -1.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6867    1.6621    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5403    1.8956   -1.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5530    0.2471   -0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5127   -0.5309    0.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9076    0.8329    1.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939    1.8007    1.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8214    0.3580    0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4241   -1.9355    1.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6892   -2.3600    4.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665   -1.0996    6.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2184    1.0091    7.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0054    3.5811    5.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    2.4728    3.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
 15  9  2  0  0  0  0
 11 12  1  0  0  0  0
  9  8  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
  8  7  1  0  0  0  0
  6  5  1  0  0  0  0
  6 15  1  0  0  0  0
  5  4  1  0  0  0  0
  7  6  2  0  0  0  0
  4  2  1  0  0  0  0
  9 10  1  0  0  0  0
 12 13  1  0  0  0  0
  2  1  1  0  0  0  0
 10 11  2  0  0  0  0
  2  3  1  0  0  0  0
  7 26  1  0  0  0  0
  8 27  1  0  0  0  0
 10 28  1  0  0  0  0
 11 29  1  0  0  0  0
 14 31  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  4 22  1  0  0  0  0
  4 23  1  0  0  0  0
 13 30  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  3 19  1  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036326

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(N([H])C([H])=C2C([H])([H])C([H])([H])N(C([H])([H])[H])C([H])([H])[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3

> <INCHI_KEY>
VTTONGPRPXSUTJ-UHFFFAOYSA-N

> <FORMULA>
C12H16N2O

> <MOLECULAR_WEIGHT>
204.2682

> <EXACT_MASS>
204.126263144

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.290220670308504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[2-(dimethylamino)ethyl]-1H-indol-5-ol

> <ALOGPS_LOGP>
2.04

> <JCHEM_LOGP>
1.2922694904624674

> <ALOGPS_LOGS>
-1.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.218197203699578

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.232412171709068

> <JCHEM_PKA_STRONGEST_BASIC>
9.910793391467232

> <JCHEM_POLAR_SURFACE_AREA>
39.26

> <JCHEM_REFRACTIVITY>
62.423100000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bufotenine

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
   -0.1141    0.8826   -1.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7409    1.3380   -0.2393 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1995    1.2710   -0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3068    0.5354    0.9233 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1750    0.7309    1.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5373    0.0234    2.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1163   -1.2263    2.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2847   -1.5104    3.9989 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8239   -0.4700    4.7709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7928   -0.3256    6.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2600    0.8592    6.6785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7836    1.8487    5.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2769    2.9811    6.4009 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8175    1.6992    4.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3506    0.5105    3.8978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4799    1.4681   -2.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3153   -0.1758   -1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9695    1.0335   -1.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6867    1.6621    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5403    1.8956   -1.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5530    0.2471   -0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5127   -0.5309    0.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9076    0.8329    1.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939    1.8007    1.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8214    0.3580    0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4241   -1.9355    1.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6892   -2.3600    4.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665   -1.0996    6.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2184    1.0091    7.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0054    3.5811    5.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    2.4728    3.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
 15  9  2  0
 11 12  1  0
  9  8  1  0
 12 14  2  0
 14 15  1  0
  8  7  1  0
  6  5  1  0
  6 15  1  0
  5  4  1  0
  7  6  2  0
  4  2  1  0
  9 10  1  0
 12 13  1  0
  2  1  1  0
 10 11  2  0
  2  3  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 14 31  1  0
  5 24  1  0
  5 25  1  0
  4 22  1  0
  4 23  1  0
 13 30  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.114   0.883  -1.482  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.741   1.338  -0.239  0.00  0.00           N+0
HETATM    3  C   UNK     0      -2.200   1.271  -0.371  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.307   0.535   0.923  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.175   0.731   1.292  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.537   0.023   2.563  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.116  -1.226   2.671  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.285  -1.510   3.999  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.824  -0.470   4.771  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.793  -0.326   6.163  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.260   0.859   6.678  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.784   1.849   5.829  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.277   2.981   6.401  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.818   1.699   4.441  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.351   0.510   3.898  0.00  0.00           C+0
HETATM   16  H   UNK     0      -0.480   1.468  -2.334  0.00  0.00           H+0
HETATM   17  H   UNK     0      -0.315  -0.176  -1.683  0.00  0.00           H+0
HETATM   18  H   UNK     0       0.970   1.034  -1.458  0.00  0.00           H+0
HETATM   19  H   UNK     0      -2.687   1.662   0.529  0.00  0.00           H+0
HETATM   20  H   UNK     0      -2.540   1.896  -1.204  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.553   0.247  -0.539  0.00  0.00           H+0
HETATM   22  H   UNK     0      -0.513  -0.531   0.757  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.908   0.833   1.794  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.394   1.801   1.400  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.821   0.358   0.488  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.424  -1.936   1.914  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.689  -2.360   4.367  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.167  -1.100   6.825  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.218   1.009   7.754  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.005   3.581   5.691  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.444   2.473   3.779  0.00  0.00           H+0
CONECT    1    2   16   17   18                                             
CONECT    2    4    1    3                                                  
CONECT    3    2   19   20   21                                             
CONECT    4    5    2   22   23                                             
CONECT    5    6    4   24   25                                             
CONECT    6    5   15    7                                                  
CONECT    7    8    6   26                                                  
CONECT    8    9    7   27                                                  
CONECT    9   15    8   10                                                  
CONECT   10    9   11   28                                                  
CONECT   11   12   10   29                                                  
CONECT   12   11   14   13                                                  
CONECT   13   12   30                                                       
CONECT   14   12   15   31                                                  
CONECT   15    9   14    6                                                  
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    3                                                            
CONECT   20    3                                                            
CONECT   21    3                                                            
CONECT   22    4                                                            
CONECT   23    4                                                            
CONECT   24    5                                                            
CONECT   25    5                                                            
CONECT   26    7                                                            
CONECT   27    8                                                            
CONECT   28   10                                                            
CONECT   29   11                                                            
CONECT   30   13                                                            
CONECT   31   14                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

RDKit          3D

31 32  0  0  0  0  0  0  0  0999 V2000
   -0.1141    0.8826   -1.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7409    1.3380   -0.2393 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1995    1.2710   -0.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3068    0.5354    0.9233 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1750    0.7309    1.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5373    0.0234    2.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1163   -1.2263    2.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2847   -1.5104    3.9989 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8239   -0.4700    4.7709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7928   -0.3256    6.1635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2600    0.8592    6.6785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7836    1.8487    5.8289 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2769    2.9811    6.4009 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8175    1.6992    4.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3506    0.5105    3.8978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4799    1.4681   -2.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3153   -0.1758   -1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9695    1.0335   -1.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6867    1.6621    0.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5403    1.8956   -1.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5530    0.2471   -0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5127   -0.5309    0.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9076    0.8329    1.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939    1.8007    1.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8214    0.3580    0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4241   -1.9355    1.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6892   -2.3600    4.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665   -1.0996    6.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2184    1.0091    7.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0054    3.5811    5.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    2.4728    3.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
 15  9  2  0
 11 12  1  0
  9  8  1  0
 12 14  2  0
 14 15  1  0
  8  7  1  0
  6  5  1  0
  6 15  1  0
  5  4  1  0
  7  6  2  0
  4  2  1  0
  9 10  1  0
 12 13  1  0
  2  1  1  0
 10 11  2  0
  2  3  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 14 31  1  0
  5 24  1  0
  5 25  1  0
  4 22  1  0
  4 23  1  0
 13 30  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
M  END

View in JSmol

Synonyms

Value	Source
3-[2-(Dimethylamino)ethyl]-5-indolol	ChEBI
3-[2-(Dimethylamino)ethyl]indol-5-ol	ChEBI
3-[beta-(Dimethylamino)ethyl]-5-hydroxyindole	ChEBI
5-Hydroxy-N,N-dimethyltryptamine	ChEBI
Bufotenine	ChEBI
DM5-HT	ChEBI
N,N-Dimethylserotonin	ChEBI
3-[b-(Dimethylamino)ethyl]-5-hydroxyindole	Generator
3-[Β-(dimethylamino)ethyl]-5-hydroxyindole	Generator
1H-indol-5-Ol, {3-[2-(dimethylamino)ethyl]-}	HMDB
3-(2-(Dimethylamino)ethyl)-1H-indol-5-ol (acd/name 4.0)	HMDB
3-(2-Dimethylaminoethyl)-5-indolol	HMDB
3-(2-Dimethylaminoethyl)indol-5-ol	HMDB
3-(beta-Dimethylaminoethyl)-5-hydroxyindole	HMDB
3-[2-(Dimethylamino)ethyl]-1H-indol-5-ol	HMDB
3-[2-(Dimethylamino)ethyl]-indol-5-ol	HMDB
5-Hydroxy-N, N-dimethyltryptamine	HMDB
Cinobufotenine	HMDB
Cohoba	HMDB
Dimethylserotonin	HMDB
indol-5-Ol, {3-[2-(dimethylamino)ethyl]-}	HMDB
Mapine	HMDB
Mappin	HMDB
Mappine	HMDB
N, N-Dimethylserotonin	HMDB
N,N-Dimethyl-5-hydroxytryptamine	HMDB
{3-[(2-dimethylamino)ethyl]-5-indolol}	HMDB
{3-[(beta-dimethylamino)ethyl]-5-hydroxyindole}	HMDB
N,N Dimethyl 5 hydroxytryptamine	HMDB
5 Hydroxy N,N dimethyltryptamine	HMDB
Bufotenin	KEGG

Chemical Formula

C₁₂H₁₆N₂O

Average Mass

204.2682 Da

Monoisotopic Mass

204.12626 Da

IUPAC Name

3-[2-(dimethylamino)ethyl]-1H-indol-5-ol

Traditional Name

bufotenine

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C(N([H])C([H])=C2C([H])([H])C([H])([H])N(C([H])([H])[H])C([H])([H])[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3

InChI Key

VTTONGPRPXSUTJ-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Amanita citrina	LOTUS Database	35616633
Anadenanthera colubrina	LOTUS Database	35616633
Anadenanthera peregrina	LOTUS Database	35616633
Arundo donax	KNApSAcK Database	22123792
Bufo bufo	LOTUS Database	35616633
Citrus reticulata	LOTUS Database	35616633
Citrus unshiu	KNApSAcK Database	22123792
Codariocalyx motorius	KNApSAcK Database	22123792
Desmodium caudatum	KNApSAcK Database	22123792
Lespedeza bicolor	KNApSAcK Database	22123792
Mimosa somnians	LOTUS Database	35616633
Mucuna pruriens	KNApSAcK Database	22123792
Ohwia caudata	LOTUS Database	35616633
Paramuricea clavata	JEOL database	Penez, N., et al, J. Nat. Prod. 74, 2304 (2011)
Parapiptadenia excelsa	KNApSAcK Database	22123792
Phalaris aquatica	LOTUS Database	35616633
Phyllodium pulchellum	LOTUS Database	35616633
Piptadenia macrocarpa	KNApSAcK Database	22123792
Piptadenia moniliformis	KNApSAcK Database	22123792
Piptadenia peregrina	KNApSAcK Database	22123792
Pseudopiptadenia contorta	KNApSAcK Database	22123792
Umbellularia californica	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Amanita mappa	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Serotonins

Alternative Parents

Substituents

Serotonin
Hydroxyindole
3-alkylindole
Indole
Alkaloid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amine (CHEBI:3210 )
tryptamine alkaloid (CHEBI:3210 )
Indole alkaloids (C08299 )

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	2.04	ALOGPS
logP	1.29	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.23	ChemAxon
pKa (Strongest Basic)	9.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	39.26 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	62.42 m³·mol⁻¹	ChemAxon
Polarizability	23.29 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0041842

DrugBank ID

DB01445

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bufotenin

METLIN ID

Not Available

PubChem Compound

10257

PDB ID

Not Available

ChEBI ID

3210

Good Scents ID

Not Available

References

General References

Takeda N, Ikeda R, Ohba K, Kondo M: Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders. Neuroreport. 1995 Nov 27;6(17):2378-80. doi: 10.1097/00001756-199511270-00024. [PubMed:8747157 ]
Carpenter WT Jr, Fink EB, Narasimhachari N, Himwich HE: A test of the transmethylation hypothesis in acute schizophrenic patients. Am J Psychiatry. 1975 Oct;132(10):1067-71. doi: 10.1176/ajp.132.10.1067. [PubMed:1058643 ]
Ciprian-Ollivier J, Cetkovich-Bakmas MG: Altered consciousness states and endogenous psychoses: a common molecular pathway? Schizophr Res. 1997 Dec 19;28(2-3):257-65. doi: 10.1016/s0920-9964(97)00116-3. [PubMed:9468359 ]
Pomilio AB, Vitale AA, Ciprian-Ollivier J, Cetkovich-Bakmas M, Gomez R, Vazquez G: Ayahoasca: an experimental psychosis that mirrors the transmethylation hypothesis of schizophrenia. J Ethnopharmacol. 1999 Apr;65(1):29-51. doi: 10.1016/s0378-8741(98)00163-9. [PubMed:10350367 ]
Penez, N., et al. (2011). Penez, N., et al, J. Nat. Prod. 74, 2304 (2011). J. Nat. Prod..

Showing NP-Card for bufotenine (NP0036326)

MOL for NP0036326 (bufotenine)

3D MOL for NP0036326 (bufotenine)

3D SDF for NP0036326 (bufotenine)

3D-SDF for NP0036326 (bufotenine)

PDB for NP0036326 (bufotenine)

3D PDB for NP0036326 (bufotenine)

SMILES for NP0036326 (bufotenine)

INCHI for NP0036326 (bufotenine)

Structure for NP0036326 (bufotenine)

3D Structure for NP0036326 (bufotenine)