NP-MRD: Showing NP-Card for 2,5-dihydroxy-3-(1h-indol-3-yl)-6-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]cyclohexa-2,5-diene-1,4-dione (NP0177473)

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Record Information

Version

1.0

Created at

2022-09-03 15:19:24 UTC

Updated at

2022-09-03 15:19:24 UTC

NP-MRD ID

NP0177473

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,5-dihydroxy-3-(1h-indol-3-yl)-6-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]cyclohexa-2,5-diene-1,4-dione

Description

Asterriquinone C1, also known as truncaquinone b, belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain. 2,5-dihydroxy-3-(1h-indol-3-yl)-6-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]cyclohexa-2,5-diene-1,4-dione is found in Annulohypoxylon truncatum. It was first documented in 1991 (PMID: 1703412). Based on a literature review a small amount of articles have been published on asterriquinone C1 (PMID: 14695798) (PMID: 16562864) (PMID: 17704773) (PMID: 18029206).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032217192D          

 33 37  0  0  0  0            999 V2000
    0.7144   -6.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -5.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -5.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -5.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -5.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1190   -5.8387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6657   -5.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3801   -5.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0946   -5.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0946   -4.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3801   -4.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6657   -4.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1190   -4.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 O   0  0  0  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
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -2.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428   -2.5916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -3.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -4.1608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
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  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
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  8 13  1  0  0  0  0
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  6 14  2  0  0  0  0
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 15 16  2  0  0  0  0
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 15 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
   -5.2844   -0.7481    2.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3870    0.1988    2.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9895    0.0075    1.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6023   -1.3637    2.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1210    1.0578    2.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0023    0.1478    0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1516    0.4261   -0.4499 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8617    0.5287   -1.7538 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0942    0.8635   -4.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7262    0.6516   -4.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9540    0.3793   -3.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5288    0.3250   -1.9610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9989    0.0833   -0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5759   -0.1784   -0.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2398    0.8506   -0.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3333    2.0519   -1.1763 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6853    0.6944   -0.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3885    1.7114   -0.9332 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3037   -0.5536   -0.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7540   -0.7440   -0.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3770   -1.8784   -0.6765 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6789   -1.7645   -0.3973 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9050   -0.6205    0.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0413   -0.0569    0.7932 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9837    1.1428    1.4648 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7830    1.7882    1.6341 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6112    1.2388    1.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6886    0.0308    0.4541 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4756   -1.5683    0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0539   -2.7679    0.3910 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0110   -1.4362   -0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6631   -2.4624    0.1473 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6262    1.1550    2.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9483   -2.1553    1.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1237   -1.5738    3.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5339   -1.4270    2.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5084    1.2447    3.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2606    2.0066    1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0678    0.7368    2.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0889    0.5376   -0.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6812    0.9635   -2.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6700    1.0761   -5.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3120    0.7031   -5.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9035    0.2138   -3.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6548    2.6663   -0.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9045   -2.6750   -1.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4153   -2.4424   -0.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9699   -0.5993    0.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8636    1.5887    1.8636 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6930    2.7333    2.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6802    1.7542    1.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1650   -3.0269    1.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3  5  1  0
  3  2  1  0
  2  1  2  3
  3  6  1  0
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 14 13  1  0
 13 12  2  0
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 10  9  1  0
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 29 21  1  0
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  2 36  1  0
  1 34  1  0
  1 35  1  0
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 10 45  1  0
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  7 43  1  0
 17 48  1  0
 22 49  1  0
 23 50  1  0
 25 51  1  0
 26 52  1  0
 27 53  1  0
 28 54  1  0
 31 55  1  0
M  END


  Mrv1652309032217192D          

 33 37  0  0  0  0            999 V2000
    0.7144   -6.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -5.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -5.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -5.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -5.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1190   -5.8387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6657   -5.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3801   -5.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0946   -5.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0946   -4.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3801   -4.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6657   -4.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1190   -4.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    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
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    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2428   -2.5916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -3.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -4.1608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  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
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  8 13  1  0  0  0  0
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 30 32  1  0  0  0  0
 15 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0177473

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(C=C)C1=C(C2=CC=CC=C2N1)C1=C(O)C(=O)C(C2=CNC3=CC=CC=C23)=C(O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H22N2O4/c1-4-27(2,3)26-19(15-10-6-8-12-18(15)29-26)21-24(32)22(30)20(23(31)25(21)33)16-13-28-17-11-7-5-9-14(16)17/h4-13,28-30,33H,1H2,2-3H3

> <INCHI_KEY>
BKRWGHXVQLNRMR-UHFFFAOYSA-N

> <FORMULA>
C27H22N2O4

> <MOLECULAR_WEIGHT>
438.483

> <EXACT_MASS>
438.157957196

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
46.89608278723696

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5-dihydroxy-3-(1H-indol-3-yl)-6-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione

> <JCHEM_LOGP>
5.126136098333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.485910643014986

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.452117368674398

> <JCHEM_PKA_STRONGEST_BASIC>
-5.204241136382476

> <JCHEM_POLAR_SURFACE_AREA>
106.17999999999999

> <JCHEM_REFRACTIVITY>
129.2293

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2,5-dihydroxy-3-(1H-indol-3-yl)-6-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione

> <JCHEM_VEBER_RULE>
0

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HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334 -11.963   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667 -11.193   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -9.653   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.207  -9.653   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -8.113   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.127  -9.653   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.222 -10.899   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.243 -10.423   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.576 -11.193   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.910 -10.423   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.910  -8.883   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.576  -8.113   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.243  -8.883   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.222  -8.407   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.698  -6.943   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.839  -6.118   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.887  -3.189   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.680  -5.158   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.187  -4.838   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.204  -6.622   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.235  -7.767   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13    6   15                                                  
CONECT   15   14   16   32                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   30                                                  
CONECT   21   20   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   21   24                                                  
CONECT   30   20   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   15   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
Asterriquinone C-1	ChEBI
Truncaquinone b	ChEBI

Chemical Formula

C₂₇H₂₂N₂O₄

Average Mass

438.4830 Da

Monoisotopic Mass

438.15796 Da

IUPAC Name

2,5-dihydroxy-3-(1H-indol-3-yl)-6-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione

Traditional Name

2,5-dihydroxy-3-(1H-indol-3-yl)-6-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione

CAS Registry Number

Not Available

SMILES

CC(C)(C=C)C1=C(C2=CC=CC=C2N1)C1=C(O)C(=O)C(C2=CNC3=CC=CC=C23)=C(O)C1=O

InChI Identifier

InChI=1S/C27H22N2O4/c1-4-27(2,3)26-19(15-10-6-8-12-18(15)29-26)21-24(32)22(30)20(23(31)25(21)33)16-13-28-17-11-7-5-9-14(16)17/h4-13,28-30,33H,1H2,2-3H3

InChI Key

BKRWGHXVQLNRMR-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, 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
Annulohypoxylon truncatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Prenylquinones

Alternative Parents

Substituents

Prenylbenzoquinone
Indole
Indole or derivatives
P-benzoquinone
Quinone
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Vinylogous acid
Cyclic ketone
Ketone
Azacycle
Enol
Organoheterocyclic compound
Carbonyl group
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

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	5.13	ChemAxon
pKa (Strongest Acidic)	5.45	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.18 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	129.23 m³·mol⁻¹	ChemAxon
Polarizability	46.9 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00044554

Chemspider ID

398756

KEGG Compound ID

Not Available

BioCyc ID

CPD-16845

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

452719

PDB ID

Not Available

ChEBI ID

192555

Good Scents ID

Not Available

References

General References

Wijeratne EM, Turbyville TJ, Zhang Z, Bigelow D, Pierson LS 3rd, VanEtten HD, Whitesell L, Canfield LM, Gunatilaka AA: Cytotoxic constituents of Aspergillus terreus from the rhizosphere of Opuntia versicolor of the Sonoran Desert. J Nat Prod. 2003 Dec;66(12):1567-73. doi: 10.1021/np030266u. [PubMed:14695798 ]
Ono K, Nakane H, Shimizu S, Koshimura S: Inhibition of HIV-reverse transcriptase activity by asterriquinone and its analogues. Biochem Biophys Res Commun. 1991 Jan 15;174(1):56-62. doi: 10.1016/0006-291x(91)90484-o. [PubMed:1703412 ]
Gunatilaka AA: Natural products from plant-associated microorganisms: distribution, structural diversity, bioactivity, and implications of their occurrence. J Nat Prod. 2006 Mar;69(3):509-26. doi: 10.1021/np058128n. [PubMed:16562864 ]
Balibar CJ, Howard-Jones AR, Walsh CT: Terrequinone A biosynthesis through L-tryptophan oxidation, dimerization and bisprenylation. Nat Chem Biol. 2007 Sep;3(9):584-92. doi: 10.1038/nchembio.2007.20. Epub 2007 Aug 12. [PubMed:17704773 ]
Schneider P, Weber M, Hoffmeister D: The Aspergillus nidulans enzyme TdiB catalyzes prenyltransfer to the precursor of bioactive asterriquinones. Fungal Genet Biol. 2008 Mar;45(3):302-9. doi: 10.1016/j.fgb.2007.09.004. Epub 2007 Sep 25. [PubMed:18029206 ]
LOTUS database [Link]

Showing NP-Card for 2,5-dihydroxy-3-(1h-indol-3-yl)-6-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]cyclohexa-2,5-diene-1,4-dione (NP0177473)

MOL for NP0177473 (2,5-dihydroxy-3-(1h-indol-3-yl)-6-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]cyclohexa-2,5-diene-1,4-dione)

3D MOL for NP0177473 (2,5-dihydroxy-3-(1h-indol-3-yl)-6-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]cyclohexa-2,5-diene-1,4-dione)

3D SDF for NP0177473 (2,5-dihydroxy-3-(1h-indol-3-yl)-6-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]cyclohexa-2,5-diene-1,4-dione)

3D-SDF for NP0177473 (2,5-dihydroxy-3-(1h-indol-3-yl)-6-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]cyclohexa-2,5-diene-1,4-dione)

PDB for NP0177473 (2,5-dihydroxy-3-(1h-indol-3-yl)-6-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]cyclohexa-2,5-diene-1,4-dione)

3D PDB for NP0177473 (2,5-dihydroxy-3-(1h-indol-3-yl)-6-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]cyclohexa-2,5-diene-1,4-dione)

SMILES for NP0177473 (2,5-dihydroxy-3-(1h-indol-3-yl)-6-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]cyclohexa-2,5-diene-1,4-dione)

INCHI for NP0177473 (2,5-dihydroxy-3-(1h-indol-3-yl)-6-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]cyclohexa-2,5-diene-1,4-dione)

Structure for NP0177473 (2,5-dihydroxy-3-(1h-indol-3-yl)-6-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]cyclohexa-2,5-diene-1,4-dione)

3D Structure for NP0177473 (2,5-dihydroxy-3-(1h-indol-3-yl)-6-[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]cyclohexa-2,5-diene-1,4-dione)