NP-MRD: Showing NP-Card for 1-[(5s)-2,4-dihydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-5h-pyrrol-3-yl]ethanone (NP0306090)

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Record Information

Version

2.0

Created at

2022-09-10 22:21:02 UTC

Updated at

2022-09-10 22:21:02 UTC

NP-MRD ID

NP0306090

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[(5s)-2,4-dihydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-5h-pyrrol-3-yl]ethanone

Description

(5S)-3-acetyl-4-hydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-1,5-dihydro-2H-pyrrol-2-one, also known as beta-cyclopiazonic acid or b-cyclopiazonate, belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. 1-[(5s)-2,4-dihydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-5h-pyrrol-3-yl]ethanone is found in Penicillium cyclopium. Based on a literature review very few articles have been published on (5S)-3-acetyl-4-hydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-1,5-dihydro-2H-pyrrol-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112200212D          

 25 27  0  0  1  0            999 V2000
   -2.6719   -2.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0044   -1.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0907   -1.0260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2508   -2.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5363   -1.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500   -0.9490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2587   -3.0752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0792   -2.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6313   -3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 16 22  2  0  0  0  0
  9 22  1  0  0  0  0
 12 22  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  2  0  0  0  0
  4 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END

     RDKit          3D

 47 49  0  0  0  0  0  0  0  0999 V2000
    5.8191    1.2508    0.9552 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4291   -0.1739    1.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0916   -1.0205    1.7172 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2074   -0.5907    0.3235 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4219    0.1688   -0.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6381    1.5355   -0.6042 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3499   -0.6797   -0.9319 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9724   -0.1442   -0.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0122   -1.0160   -1.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167   -2.1097   -2.0479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7826   -2.7087   -2.4759 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8320   -2.0516   -2.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1962   -2.2986   -2.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0978   -1.4527   -1.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6331   -0.3941   -0.8387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2620   -0.1532   -0.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7653    0.9651    0.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9586    1.7733    0.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3145    1.9871    1.8030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5108    1.4095    2.9291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5222    2.8062    2.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3849   -1.0004   -1.2588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6021   -1.9722   -0.4279 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6564   -1.9469    0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2683   -3.0125    0.9816 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8949    1.5610   -0.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8201    1.3319    1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1030    1.8361    1.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9317    2.2310   -0.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5265   -0.7213   -2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8706    0.1339    0.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9387    0.8284   -1.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3169   -2.4856   -2.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8383   -3.5620   -3.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5358   -3.1284   -2.7832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1713   -1.6223   -1.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3296    0.2747   -0.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3295    0.6432    1.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1300    1.6841   -0.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5592    2.2035   -0.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4733    1.7736    2.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0013    1.6179    3.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4722    0.3011    2.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0935    2.9859    1.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2817    3.7442    2.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1738    2.1762    2.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4867   -2.9778    1.9526 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 21  1  0
 19 18  2  3
 18 17  1  0
 17 16  1  0
 16 22  2  0
 22  9  1  0
  9  8  1  0
  8  7  1  0
  7 23  1  0
 23 24  2  0
 24 25  1  0
 24  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  4  5  2  0
  5  6  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 12 22  1  0
  5  7  1  0
 20 41  1  0
 20 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
 21 46  1  0
 18 40  1  0
 17 38  1  0
 17 39  1  0
  8 31  1  0
  8 32  1  0
  7 30  1  6
 25 47  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
M  END


  Mrv1652309112200212D          

 25 27  0  0  1  0            999 V2000
   -2.6719   -2.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0044   -1.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0907   -1.0260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2508   -2.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5363   -1.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500   -0.9490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2587   -3.0752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0792   -2.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6313   -3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 16 22  2  0  0  0  0
  9 22  1  0  0  0  0
 12 22  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  2  0  0  0  0
  4 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0306090

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C2C(C[C@@H]3N=C(O)C(C(C)=O)=C3O)=CNC2=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H22N2O3/c1-11(2)7-8-13-5-4-6-15-18(13)14(10-21-15)9-16-19(24)17(12(3)23)20(25)22-16/h4-7,10,16,21,24H,8-9H2,1-3H3,(H,22,25)/t16-/m0/s1

> <INCHI_KEY>
MVUXMIXDFMUPLL-INIZCTEOSA-N

> <FORMULA>
C20H22N2O3

> <MOLECULAR_WEIGHT>
338.407

> <EXACT_MASS>
338.163042576

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
37.43325191770181

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(2S)-3,5-dihydroxy-2-{[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-2H-pyrrol-4-yl]ethan-1-one

> <JCHEM_LOGP>
3.539977875

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.668356081399052

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.2565441688998975

> <JCHEM_PKA_STRONGEST_BASIC>
1.7243837003195466

> <JCHEM_POLAR_SURFACE_AREA>
85.67999999999999

> <JCHEM_REFRACTIVITY>
99.6037

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-[(5S)-2,4-dihydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-5H-pyrrol-3-yl]ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.987  -4.352   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.742  -3.447   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.903  -1.915   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.335  -4.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.001  -3.303   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.840  -1.771   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.924  -7.463   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      -0.483  -5.740   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      -2.015  -5.579   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.045  -6.724   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   24                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   23                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   16    9   12                                                  
CONECT   23    7   24                                                       
CONECT   24   23    4   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
(S)-3-Acetyl-1,5-dihydro-4-hydroxy-5-((4-(3-methyl-2-butenyl)-1H-indol-3-yl)methyl)-2H-pyrrol-2-one	ChEBI
beta-Cyclopiazonate	ChEBI
beta-Cyclopiazonic acid	ChEBI
Dehydrodisecocyclopiazonic acid	ChEBI
b-Cyclopiazonate	Generator
b-Cyclopiazonic acid	Generator
Β-cyclopiazonate	Generator
Β-cyclopiazonic acid	Generator
Dehydrodisecocyclopiazonate	Generator

Chemical Formula

C₂₀H₂₂N₂O₃

Average Mass

338.4070 Da

Monoisotopic Mass

338.16304 Da

IUPAC Name

1-[(2S)-3,5-dihydroxy-2-{[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-2H-pyrrol-4-yl]ethan-1-one

Traditional Name

1-[(5S)-2,4-dihydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-5H-pyrrol-3-yl]ethanone

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C2C(C[C@@H]3N=C(O)C(C(C)=O)=C3O)=CNC2=CC=C1

InChI Identifier

InChI=1S/C20H22N2O3/c1-11(2)7-8-13-5-4-6-15-18(13)14(10-21-15)9-16-19(24)17(12(3)23)20(25)22-16/h4-7,10,16,21,24H,8-9H2,1-3H3,(H,22,25)/t16-/m0/s1

InChI Key

MVUXMIXDFMUPLL-INIZCTEOSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Penicillium cyclopium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Substituted pyrrole
Benzenoid
Pyrrole
Pyrroline
Heteroaromatic compound
Vinylogous acid
Carboxamide group
Ketone
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Enol
Azacycle
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-cyclopiazonic acid (CHEBI:10365 )

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	3.54	ChemAxon
pKa (Strongest Acidic)	4.26	ChemAxon
pKa (Strongest Basic)	1.72	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	85.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	99.6 m³·mol⁻¹	ChemAxon
Polarizability	37.43 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00051803

Chemspider ID

21864764

KEGG Compound ID

C02899

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54675760

PDB ID

Not Available

ChEBI ID

10365

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-[(5s)-2,4-dihydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-5h-pyrrol-3-yl]ethanone (NP0306090)

MOL for NP0306090 (1-[(5s)-2,4-dihydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-5h-pyrrol-3-yl]ethanone)

3D MOL for NP0306090 (1-[(5s)-2,4-dihydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-5h-pyrrol-3-yl]ethanone)

3D SDF for NP0306090 (1-[(5s)-2,4-dihydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-5h-pyrrol-3-yl]ethanone)

3D-SDF for NP0306090 (1-[(5s)-2,4-dihydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-5h-pyrrol-3-yl]ethanone)

PDB for NP0306090 (1-[(5s)-2,4-dihydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-5h-pyrrol-3-yl]ethanone)

3D PDB for NP0306090 (1-[(5s)-2,4-dihydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-5h-pyrrol-3-yl]ethanone)

SMILES for NP0306090 (1-[(5s)-2,4-dihydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-5h-pyrrol-3-yl]ethanone)

INCHI for NP0306090 (1-[(5s)-2,4-dihydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-5h-pyrrol-3-yl]ethanone)

Structure for NP0306090 (1-[(5s)-2,4-dihydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-5h-pyrrol-3-yl]ethanone)

3D Structure for NP0306090 (1-[(5s)-2,4-dihydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-5h-pyrrol-3-yl]ethanone)