NP-MRD: Showing NP-Card for Baeocystin (NP0021720)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-01-06 06:59:50 UTC

Updated at

2021-07-15 17:37:05 UTC

NP-MRD ID

NP0021720

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Baeocystin

Provided By

NPAtlas

Description

Baeocystin 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. Baeocystin is found in Gymnopilus purpuratus, Inocybe aeruginascens, Psilocybe baeocystis, Psilocybe cubensis, Psilocybe liniformans, Psilocybe samuiensis and Psilocybe semilanceata. Baeocystin was first documented in 1968 (PMID: 5684732). Based on a literature review a small amount of articles have been published on Baeocystin (PMID: 17269025) (PMID: 17269094) (PMID: 17342589) (PMID: 2614674).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105183D          

 33 34  0  0  0  0            999 V2000
   -4.7367    0.5414   -0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3105    0.4307   -0.6636 N   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6779    1.0420    0.4884 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1832    0.8746    0.3750 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7833   -0.5459    0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5268   -1.6935    0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6905   -2.7488    0.2858 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5873   -2.3369    0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8004   -2.9842    0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9648   -2.2680    0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9414   -0.8898    0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7347   -0.2554    0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7085    1.1344    0.1642 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1247    2.0527    0.0725 P   0  0  1  0  0  5  0  0  0  0  0  0
    4.0092    1.8785    1.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9777    1.6036   -1.3286 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896    3.6802   -0.0910 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5332   -0.9537    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2823   -0.3879   -0.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0407    0.9449    0.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0568    1.3077   -1.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8550    0.6644   -1.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0475    0.6225    1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9173    2.1230    0.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7393    1.3179    1.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7743    1.4750   -0.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6061   -1.6939    0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9571   -3.7603    0.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8448   -4.0704    0.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9312   -2.7740   -0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8940   -0.3717   -0.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9343    1.8504   -1.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5092    4.1905   -0.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 12 18  2  0  0  0  0
 18  5  1  0  0  0  0
 18  8  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  2 22  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  4 25  1  0  0  0  0
  4 26  1  0  0  0  0
  6 27  1  0  0  0  0
  7 28  1  0  0  0  0
  9 29  1  0  0  0  0
 10 30  1  0  0  0  0
 11 31  1  0  0  0  0
 16 32  1  0  0  0  0
 17 33  1  0  0  0  0
M  END

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -4.7367    0.5414   -0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3105    0.4307   -0.6636 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6779    1.0420    0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1832    0.8746    0.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833   -0.5459    0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5268   -1.6935    0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6905   -2.7488    0.2858 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5873   -2.3369    0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8004   -2.9842    0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9648   -2.2680    0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9414   -0.8898    0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7347   -0.2554    0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7085    1.1344    0.1642 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1247    2.0527    0.0725 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.0092    1.8785    1.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9777    1.6036   -1.3286 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896    3.6802   -0.0910 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5332   -0.9537    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2823   -0.3879   -0.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0407    0.9449    0.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0568    1.3077   -1.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8550    0.6644   -1.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0475    0.6225    1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9173    2.1230    0.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7393    1.3179    1.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7743    1.4750   -0.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6061   -1.6939    0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9571   -3.7603    0.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8448   -4.0704    0.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9312   -2.7740   -0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8940   -0.3717   -0.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9343    1.8504   -1.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5092    4.1905   -0.1892 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 12 18  2  0
 18  5  1  0
 18  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 16 32  1  0
 17 33  1  0
M  END


  Mrv1652306242105183D          

 33 34  0  0  0  0            999 V2000
   -4.7367    0.5414   -0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3105    0.4307   -0.6636 N   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6779    1.0420    0.4884 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1832    0.8746    0.3750 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7833   -0.5459    0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5268   -1.6935    0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6905   -2.7488    0.2858 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5873   -2.3369    0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8004   -2.9842    0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9648   -2.2680    0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9414   -0.8898    0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7347   -0.2554    0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7085    1.1344    0.1642 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1247    2.0527    0.0725 P   0  0  1  0  0  5  0  0  0  0  0  0
    4.0092    1.8785    1.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9777    1.6036   -1.3286 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896    3.6802   -0.0910 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5332   -0.9537    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2823   -0.3879   -0.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0407    0.9449    0.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0568    1.3077   -1.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8550    0.6644   -1.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0475    0.6225    1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9173    2.1230    0.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7393    1.3179    1.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7743    1.4750   -0.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6061   -1.6939    0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9571   -3.7603    0.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8448   -4.0704    0.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9312   -2.7740   -0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8940   -0.3717   -0.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9343    1.8504   -1.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5092    4.1905   -0.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 12 18  2  0  0  0  0
 18  5  1  0  0  0  0
 18  8  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  2 22  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  4 25  1  0  0  0  0
  4 26  1  0  0  0  0
  6 27  1  0  0  0  0
  7 28  1  0  0  0  0
  9 29  1  0  0  0  0
 10 30  1  0  0  0  0
 11 31  1  0  0  0  0
 16 32  1  0  0  0  0
 17 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021720

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H15N2O4P/c1-12-6-5-8-7-13-9-3-2-4-10(11(8)9)17-18(14,15)16/h2-4,7,12-13H,5-6H2,1H3,(H2,14,15,16)

> <INCHI_KEY>
WTPBXXCVZZZXKR-UHFFFAOYSA-N

> <FORMULA>
C11H15N2O4P

> <MOLECULAR_WEIGHT>
270.225

> <EXACT_MASS>
270.076943969

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.70935847975727

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
({3-[2-(methylamino)ethyl]-1H-indol-4-yl}oxy)phosphonic acid

> <ALOGPS_LOGP>
0.49

> <JCHEM_LOGP>
-0.260071639100017

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.718820445385029

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.751017529405419

> <JCHEM_PKA_STRONGEST_BASIC>
10.302997055501413

> <JCHEM_POLAR_SURFACE_AREA>
94.58

> <JCHEM_REFRACTIVITY>
68.00130000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
baeocystin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -4.7367    0.5414   -0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3105    0.4307   -0.6636 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6779    1.0420    0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1832    0.8746    0.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833   -0.5459    0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5268   -1.6935    0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6905   -2.7488    0.2858 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5873   -2.3369    0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8004   -2.9842    0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9648   -2.2680    0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9414   -0.8898    0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7347   -0.2554    0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7085    1.1344    0.1642 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1247    2.0527    0.0725 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.0092    1.8785    1.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9777    1.6036   -1.3286 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896    3.6802   -0.0910 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5332   -0.9537    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2823   -0.3879   -0.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0407    0.9449    0.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0568    1.3077   -1.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8550    0.6644   -1.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0475    0.6225    1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9173    2.1230    0.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7393    1.3179    1.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7743    1.4750   -0.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6061   -1.6939    0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9571   -3.7603    0.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8448   -4.0704    0.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9312   -2.7740   -0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8940   -0.3717   -0.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9343    1.8504   -1.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5092    4.1905   -0.1892 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 12 18  2  0
 18  5  1  0
 18  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 16 32  1  0
 17 33  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.737   0.541  -0.643  0.00  0.00           C+0
HETATM    2  N   UNK     0      -3.311   0.431  -0.664  0.00  0.00           N+0
HETATM    3  C   UNK     0      -2.678   1.042   0.488  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.183   0.875   0.375  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.783  -0.546   0.325  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.527  -1.694   0.363  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.691  -2.749   0.286  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.587  -2.337   0.197  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.800  -2.984   0.098  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.965  -2.268   0.022  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.941  -0.890   0.043  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.735  -0.255   0.142  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.708   1.134   0.164  0.00  0.00           O+0
HETATM   14  P   UNK     0       3.125   2.053   0.073  0.00  0.00           P+0
HETATM   15  O   UNK     0       4.009   1.879   1.301  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.978   1.604  -1.329  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.690   3.680  -0.091  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.533  -0.954   0.221  0.00  0.00           C+0
HETATM   19  H   UNK     0      -5.282  -0.388  -0.810  0.00  0.00           H+0
HETATM   20  H   UNK     0      -5.041   0.945   0.362  0.00  0.00           H+0
HETATM   21  H   UNK     0      -5.057   1.308  -1.397  0.00  0.00           H+0
HETATM   22  H   UNK     0      -2.855   0.664  -1.551  0.00  0.00           H+0
HETATM   23  H   UNK     0      -3.047   0.623   1.424  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.917   2.123   0.461  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.739   1.318   1.303  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.774   1.475  -0.466  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.606  -1.694   0.443  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.957  -3.760   0.291  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.845  -4.070   0.079  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.931  -2.774  -0.058  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.894  -0.372  -0.020  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.934   1.850  -1.273  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.509   4.191  -0.189  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2    1    3   22                                                  
CONECT    3    2    4   23   24                                             
CONECT    4    3    5   25   26                                             
CONECT    5    4    6   18                                                  
CONECT    6    5    7   27                                                  
CONECT    7    6    8   28                                                  
CONECT    8    7    9   18                                                  
CONECT    9    8   10   29                                                  
CONECT   10    9   11   30                                                  
CONECT   11   10   12   31                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14   32                                                       
CONECT   17   14   33                                                       
CONECT   18   12    5    8                                                  
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    2                                                            
CONECT   23    3                                                            
CONECT   24    3                                                            
CONECT   25    4                                                            
CONECT   26    4                                                            
CONECT   27    6                                                            
CONECT   28    7                                                            
CONECT   29    9                                                            
CONECT   30   10                                                            
CONECT   31   11                                                            
CONECT   32   16                                                            
CONECT   33   17                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

RDKit          3D

33 34  0  0  0  0  0  0  0  0999 V2000
   -4.7367    0.5414   -0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3105    0.4307   -0.6636 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6779    1.0420    0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1832    0.8746    0.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833   -0.5459    0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5268   -1.6935    0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6905   -2.7488    0.2858 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5873   -2.3369    0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8004   -2.9842    0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9648   -2.2680    0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9414   -0.8898    0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7347   -0.2554    0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7085    1.1344    0.1642 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1247    2.0527    0.0725 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.0092    1.8785    1.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9777    1.6036   -1.3286 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896    3.6802   -0.0910 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5332   -0.9537    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2823   -0.3879   -0.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0407    0.9449    0.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0568    1.3077   -1.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8550    0.6644   -1.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0475    0.6225    1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9173    2.1230    0.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7393    1.3179    1.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7743    1.4750   -0.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6061   -1.6939    0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9571   -3.7603    0.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8448   -4.0704    0.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9312   -2.7740   -0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8940   -0.3717   -0.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9343    1.8504   -1.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5092    4.1905   -0.1892 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 12 18  2  0
 18  5  1  0
 18  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 16 32  1  0
 17 33  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
4-Hydroxy-N-methyltryptamine 4-phosphate	ChEBI
4-Hydroxy-N-methyltryptamine phosphate	ChEBI
N-Desmethylpsilocybin	ChEBI
4-Hydroxy-N-methyltryptamine 4-phosphoric acid	Generator
4-Hydroxy-N-methyltryptamine phosphoric acid	Generator

Chemical Formula

C₁₁H₁₅N₂O₄P

Average Mass

270.2250 Da

Monoisotopic Mass

270.07694 Da

IUPAC Name

({3-[2-(methylamino)ethyl]-1H-indol-4-yl}oxy)phosphonic acid

Traditional Name

baeocystin

CAS Registry Number

Not Available

SMILES

CNCCC1=CNC2=C1C(OP(O)(O)=O)=CC=C2

InChI Identifier

InChI=1S/C11H15N2O4P/c1-12-6-5-8-7-13-9-3-2-4-10(11(8)9)17-18(14,15)16/h2-4,7,12-13H,5-6H2,1H3,(H2,14,15,16)

InChI Key

WTPBXXCVZZZXKR-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Gymnopilus purpuratus	LOTUS Database	35616633
Inocybe aeruginascens	LOTUS Database	35616633
Psilocybe baeocystis	NPAtlas	5684732
Psilocybe cubensis	LOTUS Database	35616633
Psilocybe liniformans	LOTUS Database	35616633
Psilocybe samuiensis	LOTUS Database	35616633
Psilocybe semilanceata	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Conocybe cyanopus	KNApSAcK Database	22123792
Conocybe kuehneriana	KNApSAcK Database	22123792
Conocybe siligineoides	KNApSAcK Database	22123792
Conocybe smithii	KNApSAcK Database	22123792
Psilocybe azurescens	KNApSAcK Database	22123792
Psilocybe bohemica	KNApSAcK Database	22123792
Psilocybe caerulescens	KNApSAcK Database	22123792
Psilocybe cyanescens	KNApSAcK Database	22123792
Psilocybe semilaceata	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as tryptamines and derivatives. These are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Tryptamines and derivatives

Alternative Parents

Substituents

Tryptamine
Aryl phosphate
Aryl phosphomonoester
3-alkylindole
Indole
Aralkylamine
Organic phosphoric acid derivative
Phosphoric acid ester
Benzenoid
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Secondary aliphatic amine
Azacycle
Secondary amine
Amine
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.49	ALOGPS
logP	-0.26	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	1.75	ChemAxon
pKa (Strongest Basic)	10.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	94.58 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	68 m³·mol⁻¹	ChemAxon
Polarizability	26.71 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA003384

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00055727

Chemspider ID

141741

KEGG Compound ID

Not Available

BioCyc ID

CPD-20579

BiGG ID

Not Available

Wikipedia Link

Baeocystin

METLIN ID

Not Available

PubChem Compound

161359

PDB ID

Not Available

ChEBI ID

139505

Good Scents ID

Not Available

References

General References

Leung AY, Paul AG: Baeocystin and norbaeocystin: new analogs of psilocybin from Psilocybe baeocystis. J Pharm Sci. 1968 Oct;57(10):1667-71. doi: 10.1002/jps.2600571007. [PubMed:5684732 ]
Gartz J: Occurrence of Psilocybin and Baeocystin in Fruit Bodies of Pluteus salicinus. Planta Med. 1987 Jun;53(3):290-1. doi: 10.1055/s-2006-962710. [PubMed:17269025 ]
Gartz J: Variation of the Amount of Alkaloids in Fruit Bodies of Inocybe aeruginascens. Planta Med. 1987 Dec;53(6):539-41. doi: 10.1055/s-2006-962805. [PubMed:17269094 ]
Stijve T, Kuyper TW: Occurrence of psilocybin in various higher fungi from several European countries. Planta Med. 1985 Oct;51(5):385-7. doi: 10.1055/s-2007-969526. [PubMed:17342589 ]
Gartz J: Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe. J Basic Microbiol. 1989;29(6):347-52. doi: 10.1002/jobm.3620290608. [PubMed:2614674 ]

Showing NP-Card for Baeocystin (NP0021720)

MOL for NP0021720 (Baeocystin)

3D MOL for NP0021720 (Baeocystin)

3D SDF for NP0021720 (Baeocystin)

3D-SDF for NP0021720 (Baeocystin)

PDB for NP0021720 (Baeocystin)

3D PDB for NP0021720 (Baeocystin)

SMILES for NP0021720 (Baeocystin)

INCHI for NP0021720 (Baeocystin)

Structure for NP0021720 (Baeocystin)

3D Structure for NP0021720 (Baeocystin)