NP-MRD: Showing NP-Card for (-)-Spirotryprostatin A (NP0068648)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 13:54:11 UTC

Updated at

2022-04-28 13:54:12 UTC

NP-MRD ID

NP0068648

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Spirotryprostatin A

Description

Spirotryprostatin A belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. (-)-Spirotryprostatin A is found in Aspergillus fumigatus, Aspergillus sydowi PFW1-13, Cordyceps tenuipes, Isaria tenuipes BCC12625 and Talaromyces sp. LGT-2. (-)-Spirotryprostatin A was first documented in 2013 (PMID: 24121553). Based on a literature review a small amount of articles have been published on spirotryprostatin A (PMID: 33332106) (PMID: 26721713) (PMID: 30609181) (PMID: 28906026).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282215542D          

 29 33  0  0  1  0            999 V2000
    4.8101   -0.1376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5881    0.6570    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7890    0.8620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5669    1.6566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2119    0.2724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4339   -0.5221    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2330   -0.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4550   -1.5217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7468   -0.9788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1002   -0.4665    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3876    0.3068    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9309    0.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2976    1.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1209    1.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8409    2.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4535    0.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7664   -0.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9885   -1.2054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8127   -1.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2694   -1.9269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0274   -0.0442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0246    0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6625    1.2359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4015    0.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7636    1.1459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8156    1.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2752    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9218    0.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6344   -0.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  2  0  0  0  0
 17 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 16 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  1 29  1  0  0  0  0
M  END

     RDKit          3D

 54 58  0  0  0  0  0  0  0  0999 V2000
    6.2434   -1.8312    0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9430   -2.1775    0.7454 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8164   -1.5806    0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5535   -1.9326    0.6080 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4341   -1.3304    0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5730   -0.3839   -0.9538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8134   -0.0131   -1.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9217   -0.6324   -0.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7261    0.9745   -2.4225 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561    1.2436   -2.6351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8367    2.0483   -3.4462 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5899    0.3893   -1.7094 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4363   -0.4558   -2.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7455   -0.1810   -1.7195 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5674   -1.3776   -1.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4179   -2.3332   -2.3455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4856   -1.4391   -0.4769 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6396   -2.2575   -0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4162   -2.6420    1.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5640   -1.5257    1.8024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3481   -0.5483    0.6451 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0495    0.1253    0.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5530    0.4175    1.8015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3341    0.4584   -0.4817 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2351    1.3116   -0.8398 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5000    1.8690    0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1704    3.0358    0.7863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9454    3.7984    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9176    3.5903    1.9298 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2864   -1.7884   -0.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4899   -0.8243    0.6857 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0049   -2.5483    0.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4580   -2.6796    1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4492   -1.6321    0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9071   -0.3329   -1.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5627    1.4109   -2.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1235   -1.5077   -2.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4652   -0.1030   -3.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2715    0.6005   -2.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5840   -1.6923   -0.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6453   -3.1556   -0.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3558   -2.7735    1.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8154   -3.5962    1.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5992   -1.9282    2.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0929   -1.0044    2.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2078    0.1672    0.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6510    2.0933   -1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3175    1.2933    0.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1136    4.7619    0.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6783    4.0216   -0.8659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9017    3.2378    0.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3844    2.8167    2.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7097    4.2647    1.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2777    4.2784    2.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  6 12  1  0
 12 13  1  6
 13 14  1  0
 14 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  3
 27 28  1  0
 27 29  1  0
 24 22  1  0
 22 23  2  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
  4  3  1  0
 25 12  1  0
 17 21  1  0
  9  7  1  0
 15 14  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  8 35  1  0
  5 34  1  0
  4 33  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  6
 25 47  1  6
 26 48  1  0
 28 49  1  0
 28 50  1  0
 28 51  1  0
 29 52  1  0
 29 53  1  0
 29 54  1  0
 21 46  1  6
 20 44  1  0
 20 45  1  0
 19 42  1  0
 19 43  1  0
 18 40  1  0
 18 41  1  0
  9 36  1  0
M  END


  Mrv1652304282215542D          

 29 33  0  0  1  0            999 V2000
    4.8101   -0.1376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5881    0.6570    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7890    0.8620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5669    1.6566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2119    0.2724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4339   -0.5221    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2330   -0.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4550   -1.5217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7468   -0.9788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1002   -0.4665    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3876    0.3068    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9309    0.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2976    1.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1209    1.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8409    2.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4535    0.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7664   -0.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9885   -1.2054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8127   -1.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2694   -1.9269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0274   -0.0442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0246    0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6625    1.2359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4015    0.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7636    1.1459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8156    1.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2752    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9218    0.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6344   -0.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  2  0  0  0  0
 17 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 16 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  1 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068648

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1)[C@]1(C[C@@H]3N([C@H]1C=C(C)C)C(=O)[C@@H]1CCCN1C3=O)C(=O)N2

> <INCHI_IDENTIFIER>
InChI=1S/C22H25N3O4/c1-12(2)9-18-22(14-7-6-13(29-3)10-15(14)23-21(22)28)11-17-19(26)24-8-4-5-16(24)20(27)25(17)18/h6-7,9-10,16-18H,4-5,8,11H2,1-3H3,(H,23,28)/t16-,17-,18-,22-/m0/s1

> <INCHI_KEY>
MQJKGSIAJNXSCM-ORGXJRBJSA-N

> <FORMULA>
C22H25N3O4

> <MOLECULAR_WEIGHT>
395.459

> <EXACT_MASS>
395.184506297

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
41.12930738393804

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,3'S,6'S,9'S)-6-methoxy-6'-(2-methylprop-1-en-1-yl)-1,2-dihydro-1',7'-diazaspiro[indole-3,5'-tricyclo[7.3.0.0^{3,7}]dodecane]-2,2',8'-trione

> <ALOGPS_LOGP>
1.22

> <JCHEM_LOGP>
1.2651613843333338

> <ALOGPS_LOGS>
-2.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.26452326416537

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.842409659157127

> <JCHEM_PKA_STRONGEST_BASIC>
-3.376546581538778

> <JCHEM_POLAR_SURFACE_AREA>
78.95

> <JCHEM_REFRACTIVITY>
108.1258

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.37e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3'S,6'S,9'S)-6-methoxy-6'-(2-methylprop-1-en-1-yl)-1H-1',7'-diazaspiro[indole-3,5'-tricyclo[7.3.0.0^{3,7}]dodecane]-2,2',8'-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  N   UNK     0       8.979  -0.257   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       8.564   1.226   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.073   1.609   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.658   3.092   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       5.995   0.509   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.410  -0.975   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.902  -1.357   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.316  -2.840   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.127  -1.827   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.920  -0.871   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.457   0.573   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.604   1.855   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.289   3.235   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.826   3.332   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.436   4.517   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.713   0.086   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.431  -0.767   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.845  -2.250   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       3.384  -2.314   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.236  -3.597   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.051  -0.082   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.046   1.454   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.237   2.307   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.616   1.622   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.425   2.139   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.522   3.676   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.847   2.079   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.054   1.123   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.518  -0.321   0.000  0.00  0.00           C+0
CONECT    1    2    7   29                                                  
CONECT    2    1    3   27                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11   16   19                                             
CONECT   11   10    5   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10   17   24                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   10   20                                                  
CONECT   20   19                                                            
CONECT   21   17   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23   16                                                       
CONECT   25   22   26                                                       
CONECT   26   25                                                            
CONECT   27    2   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    1                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₅N₃O₄

Average Mass

395.4590 Da

Monoisotopic Mass

395.18451 Da

IUPAC Name

(3S,3'S,6'S,9'S)-6-methoxy-6'-(2-methylprop-1-en-1-yl)-1,2-dihydro-1',7'-diazaspiro[indole-3,5'-tricyclo[7.3.0.0^{3,7}]dodecane]-2,2',8'-trione

Traditional Name

(3S,3'S,6'S,9'S)-6-methoxy-6'-(2-methylprop-1-en-1-yl)-1H-1',7'-diazaspiro[indole-3,5'-tricyclo[7.3.0.0^{3,7}]dodecane]-2,2',8'-trione

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1)[C@]1(C[C@@H]3N([C@H]1C=C(C)C)C(=O)[C@@H]1CCCN1C3=O)C(=O)N2

InChI Identifier

InChI=1S/C22H25N3O4/c1-12(2)9-18-22(14-7-6-13(29-3)10-15(14)23-21(22)28)11-17-19(26)24-8-4-5-16(24)20(27)25(17)18/h6-7,9-10,16-18H,4-5,8,11H2,1-3H3,(H,23,28)/t16-,17-,18-,22-/m0/s1

InChI Key

MQJKGSIAJNXSCM-ORGXJRBJSA-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
Aspergillus fumigatus	Fungi	KNApSAcK
Aspergillus sydowi PFW1-13	Fungi	KNApSAcK
Cordyceps tenuipes	LOTUS Database	35616633
Isaria tenuipes BCC12625	-	KNApSAcK
Talaromyces sp. LGT-2	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Indole or derivatives
Dihydroindole
Anisole
Dioxopiperazine
Phenol ether
2,5-dioxopiperazine
N-alkylpiperazine
Alkyl aryl ether
Benzenoid
1,4-diazinane
Piperazine
Tertiary carboxylic acid amide
Pyrrolidine
Carboxamide group
Secondary carboxylic acid amide
Lactam
Ether
Azacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organonitrogen compound
Organooxygen 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	1.22	ALOGPS
logP	1.27	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	12.84	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	78.95 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	108.13 m³·mol⁻¹	ChemAxon
Polarizability	41.13 Å³	ChemAxon
Number of Rings	5	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

C00026639

Chemspider ID

8583811

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Spirotryprostatin A

METLIN ID

Not Available

PubChem Compound

10408374

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Matsushita T, Kishimoto S, Hara K, Hashimoto H, Watanabe K: Structural and Functional Analyses of a Spiro-Carbon-Forming, Highly Promiscuous Epoxidase from Fungal Natural Product Biosynthesis. Biochemistry. 2020 Dec 29;59(51):4787-4792. doi: 10.1021/acs.biochem.0c00896. Epub 2020 Dec 17. [PubMed:33332106 ]
Shen L, Zhu L, Luo Q, Li XW, Xi JQ, Kong GM, Song YC: Fumigaclavine I, a new alkaloid isolated from endophyte Aspergillus terreus. Chin J Nat Med. 2015 Dec;13(12):937-41. doi: 10.1016/S1875-5364(15)30101-1. [PubMed:26721713 ]
Xi YK, Zhang H, Li RX, Kang SY, Li J, Li Y: Total Synthesis of Spirotryprostatins through Organomediated Intramolecular Umpolung Cyclization. Chemistry. 2019 Feb 26;25(12):3005-3009. doi: 10.1002/chem.201806411. Epub 2019 Jan 29. [PubMed:30609181 ]
Ma Y, Fan C, Jia B, Cheng P, Liu J, Ma Y, Qiao K: Total synthesis and biological evaluation of spirotryprostatin A analogs. Chirality. 2017 Nov;29(11):737-746. doi: 10.1002/chir.22746. Epub 2017 Sep 14. [PubMed:28906026 ]
Tsunematsu Y, Ishikawa N, Wakana D, Goda Y, Noguchi H, Moriya H, Hotta K, Watanabe K: Distinct mechanisms for spiro-carbon formation reveal biosynthetic pathway crosstalk. Nat Chem Biol. 2013 Dec;9(12):818-25. doi: 10.1038/nchembio.1366. Epub 2013 Oct 13. [PubMed:24121553 ]

Showing NP-Card for (-)-Spirotryprostatin A (NP0068648)

MOL for NP0068648 ((-)-Spirotryprostatin A)

3D MOL for NP0068648 ((-)-Spirotryprostatin A)

3D SDF for NP0068648 ((-)-Spirotryprostatin A)

3D-SDF for NP0068648 ((-)-Spirotryprostatin A)

PDB for NP0068648 ((-)-Spirotryprostatin A)

3D PDB for NP0068648 ((-)-Spirotryprostatin A)

SMILES for NP0068648 ((-)-Spirotryprostatin A)

INCHI for NP0068648 ((-)-Spirotryprostatin A)

Structure for NP0068648 ((-)-Spirotryprostatin A)

3D Structure for NP0068648 ((-)-Spirotryprostatin A)