NP-MRD: Showing NP-Card for cypridina luciferin (NP0286955)

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Record Information

Version

2.0

Created at

2022-09-09 15:46:48 UTC

Updated at

2022-09-09 15:46:48 UTC

NP-MRD ID

NP0286955

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cypridina luciferin

Description

Cypridina luciferin belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. cypridina luciferin is found in Siphamia versicolor. cypridina luciferin was first documented in 2020 (PMID: 32736692). Based on a literature review a small amount of articles have been published on Cypridina luciferin (PMID: 35955625) (PMID: 35198542) (PMID: 33053850) (PMID: 32929428).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092217462D          

 30 33  0  0  1  0            999 V2000
    4.7356    3.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3231    2.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7356    1.8225    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5606    1.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3231    1.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6587    0.3544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0456   -0.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0456   -1.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7600   -1.4352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4745   -1.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1890   -1.4352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9035   -1.0227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6179   -1.4352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3324   -1.0227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6179   -2.2602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3311   -1.4352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6166   -1.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9022   -1.4352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8159   -2.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0090   -2.4272    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5965   -1.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2105   -1.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4655   -0.7566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0866   -0.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8935   -0.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1485   -1.0996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6166   -0.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3311    0.2148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5026    1.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9506    1.6349    0.0000 O   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  6  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  8 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
 20 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
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 18 26  1  0  0  0  0
 21 26  1  0  0  0  0
 17 27  2  0  0  0  0
 27 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
    5.7788   -2.2360   -0.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3796   -1.4022   -0.2788 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9722   -0.2089   -0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9328    0.8290    0.0414 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6022    0.0961    0.0336 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7294   -0.8124    0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2882   -0.5284    0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257   -0.4654   -0.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1431   -0.3153   -0.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6259   -1.4481   -0.4515 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9104   -1.4793   -0.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7755   -2.6376   -0.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1854   -2.5646   -0.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7159   -3.7822    0.0534 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7152   -4.6744    0.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7153   -6.0425    0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5348   -6.7575    0.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3375   -6.0956    0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022   -4.6958   -0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4848   -3.9752   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4465   -0.2219    0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7820    0.9185    0.2223 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0661    2.2002    0.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1932    2.6170    0.8290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9268    2.9867    0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9680    4.4341    0.5818 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4399    4.9115    0.9798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3150    5.2291   -0.6903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3314    6.6945   -0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0679    2.1665   -0.0943 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3805    0.8987   -0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2751    1.1069    1.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2388    0.9867   -0.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9530   -1.8831    0.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0133   -0.8958    1.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7787   -1.3991    1.2035 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0655    0.3337    1.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9889    0.4749   -1.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8438   -1.3224   -1.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1337   -2.2931   -0.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7181   -1.6423   -0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7241   -4.0647    0.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6592   -6.5414    0.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6102   -7.8173    0.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4182   -6.6368    0.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3778   -4.1945   -0.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4911   -0.1971    0.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6813    4.6573    1.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8949    4.1093    1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3591    5.8592    1.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9695    5.0599   -0.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3814    4.9489   -0.9454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6579    4.9512   -1.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8957    7.2800   -1.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8144    7.0325    0.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3817    7.1043   -0.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 28 26  1  0
 26 27  1  0
 26 25  1  0
 25 30  2  0
 30 31  1  0
 31  9  2  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  9 10  1  0
 10 11  1  0
 11 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 23 25  1  0
 20 12  1  0
 22 31  1  0
 20 15  1  0
 29 55  1  0
 29 56  1  0
 29 57  1  0
 28 53  1  0
 28 54  1  0
 26 49  1  1
 27 50  1  0
 27 51  1  0
 27 52  1  0
  8 39  1  0
  8 40  1  0
  7 37  1  0
  7 38  1  0
  6 35  1  0
  6 36  1  0
  5 34  1  0
  4 32  1  0
  4 33  1  0
  2  1  1  0
 10 41  1  0
 21 48  1  0
 13 42  1  0
 14 43  1  0
 16 44  1  0
 17 45  1  0
 18 46  1  0
 19 47  1  0
M  END


  Mrv1652309092217462D          

 30 33  0  0  1  0            999 V2000
    4.7356    3.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3231    2.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7356    1.8225    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5606    1.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3231    1.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6587    0.3544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0456   -0.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0456   -1.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7600   -1.4352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4745   -1.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1890   -1.4352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9035   -1.0227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6179   -1.4352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3324   -1.0227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6179   -2.2602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3311   -1.4352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6166   -1.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9022   -1.4352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8159   -2.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0090   -2.4272    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5965   -1.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2105   -1.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4655   -0.7566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0866   -0.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8935   -0.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1485   -1.0996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6166   -0.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3311    0.2148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5026    1.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9506    1.6349    0.0000 O   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  6  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  8 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
 20 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
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 18 26  1  0  0  0  0
 21 26  1  0  0  0  0
 17 27  2  0  0  0  0
 27 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0286955

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)C1=NC2=C(CCCNC(N)=N)NC(=CN2C1=O)C1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C22H27N7O/c1-3-13(2)19-21(30)29-12-18(15-11-26-16-8-5-4-7-14(15)16)27-17(20(29)28-19)9-6-10-25-22(23)24/h4-5,7-8,11-13,26-27H,3,6,9-10H2,1-2H3,(H4,23,24,25)/t13-/m0/s1

> <INCHI_KEY>
ZWPWSXGBDMGKKS-ZDUSSCGKSA-N

> <FORMULA>
C22H27N7O

> <MOLECULAR_WEIGHT>
405.506

> <EXACT_MASS>
405.227708517

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
45.82300794205696

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(3-{2-[(2S)-butan-2-yl]-6-(1H-indol-3-yl)-3-oxo-3H,7H-imidazo[1,2-a]pyrazin-8-yl}propyl)guanidine

> <JCHEM_LOGP>
1.6385398356812686

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.069555765927237

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.030359502484417

> <JCHEM_PKA_STRONGEST_BASIC>
12.001333646690371

> <JCHEM_POLAR_SURFACE_AREA>
122.39000000000001

> <JCHEM_REFRACTIVITY>
138.90380000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
cypridina luciferin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       8.840   6.069   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.070   4.736   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.840   3.402   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.380   3.402   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.070   2.068   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       8.696   0.661   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.552  -0.369   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.552  -1.909   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.885  -2.679   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.219  -1.909   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.553  -2.679   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      12.886  -1.909   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      14.220  -2.679   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      15.554  -1.909   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      14.220  -4.219   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       6.218  -2.679   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       4.884  -1.909   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.551  -2.679   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.390  -4.211   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       1.883  -4.531   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       1.113  -3.197   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.393  -2.877   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.869  -1.412   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.162  -0.268   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.668  -0.588   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.144  -2.053   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.884  -0.369   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       6.218   0.401   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       6.538   1.907   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.508   3.052   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   29                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   28                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    8   17                                                       
CONECT   17   16   18   27                                                  
CONECT   18   17   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   18   21                                                  
CONECT   27   17   28                                                       
CONECT   28   27    7   29                                                  
CONECT   29   28    5   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
[3-[3,7-Dihydro-6-(1H-indol-3-yl)-2-[(S)-1-methyl-6-propyl]-3-oxoimidazo[1,2-a]pyrazin-8-yl]propyl]guanidine	ChEBI
Cypridinluciferin	ChEBI

Chemical Formula

C₂₂H₂₇N₇O

Average Mass

405.5060 Da

Monoisotopic Mass

405.22771 Da

IUPAC Name

N-(3-{2-[(2S)-butan-2-yl]-6-(1H-indol-3-yl)-3-oxo-3H,7H-imidazo[1,2-a]pyrazin-8-yl}propyl)guanidine

Traditional Name

cypridina luciferin

CAS Registry Number

Not Available

SMILES

CC[C@H](C)C1=NC2=C(CCCNC(N)=N)NC(=CN2C1=O)C1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C22H27N7O/c1-3-13(2)19-21(30)29-12-18(15-11-26-16-8-5-4-7-14(15)16)27-17(20(29)28-19)9-6-10-25-22(23)24/h4-5,7-8,11-13,26-27H,3,6,9-10H2,1-2H3,(H4,23,24,25)/t13-/m0/s1

InChI Key

ZWPWSXGBDMGKKS-ZDUSSCGKSA-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
Siphamia versicolor	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

Indoles

Alternative Parents

Substituents

Indole
Imidazopyrazine
N-substituted imidazole
Pyrazine
Substituted pyrrole
Benzenoid
Azole
Imidazole
Pyrrole
Heteroaromatic compound
Guanidine
Lactam
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

guanidines (CHEBI:17073 )
indoles (CHEBI:17073 )
imidazopyrazine (CHEBI:17073 )

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	1.64	ChemAxon
pKa (Strongest Acidic)	11.03	ChemAxon
pKa (Strongest Basic)	12	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	122.39 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	138.9 m³·mol⁻¹	ChemAxon
Polarizability	45.82 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

388868

KEGG Compound ID

C02825

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Vargulin

METLIN ID

Not Available

PubChem Compound

439820

PDB ID

Not Available

ChEBI ID

17073

Good Scents ID

Not Available

References

General References

Nakamura M, Matsuda K, Morikawa T, Ishizuka K, Inouye S: Efficient conversion to Cypridina luciferin from Cypridina luciferyl sulfate, coupled with enzymatic sulfation of acetic acid. Biochem Biophys Res Commun. 2020 Aug 27;529(3):678-684. doi: 10.1016/j.bbrc.2020.05.167. Epub 2020 Jul 18. [PubMed:32736692 ]
Sousa J, Magalhaes CM, Gonzalez-Berdullas P, Esteves da Silva JCG, Pinto da Silva L: Comparative Investigation of the Chemiluminescent Properties of a Dibrominated Coelenterazine Analog. Int J Mol Sci. 2022 Jul 30;23(15):8490. doi: 10.3390/ijms23158490. [PubMed:35955625 ]
Mitani Y, Yasuno R, Kihira K, Chung K, Mitsuda N, Kanie S, Tomioka A, Kaji H, Ohmiya Y: Host-Dependent Producibility of Recombinant Cypridina noctiluca Luciferase With Glycosylation Defects. Front Bioeng Biotechnol. 2022 Feb 7;10:774786. doi: 10.3389/fbioe.2022.774786. eCollection 2022. [PubMed:35198542 ]
Kanie S, Komatsu M, Mitani Y: Luminescence of Cypridina Luciferin in the Presence of Human Plasma Alpha 1-Acid Glycoprotein. Int J Mol Sci. 2020 Oct 12;21(20):7516. doi: 10.3390/ijms21207516. [PubMed:33053850 ]
Yang M, Huang J, Fan J, Du J, Pu K, Peng X: Chemiluminescence for bioimaging and therapeutics: recent advances and challenges. Chem Soc Rev. 2020 Oct 7;49(19):6800-6815. doi: 10.1039/d0cs00348d. Epub 2020 Sep 15. [PubMed:32929428 ]
LOTUS database [Link]

Showing NP-Card for cypridina luciferin (NP0286955)

MOL for NP0286955 (cypridina luciferin)

3D MOL for NP0286955 (cypridina luciferin)

3D SDF for NP0286955 (cypridina luciferin)

3D-SDF for NP0286955 (cypridina luciferin)

PDB for NP0286955 (cypridina luciferin)

3D PDB for NP0286955 (cypridina luciferin)

SMILES for NP0286955 (cypridina luciferin)

INCHI for NP0286955 (cypridina luciferin)

Structure for NP0286955 (cypridina luciferin)

3D Structure for NP0286955 (cypridina luciferin)