NP-MRD: Showing NP-Card for octacyclo[15.13.1.1²²,²⁶.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0²¹,³¹.0³⁰,³²]dotriaconta-1,3,5(14),6(11),9,12,15,17(31),18,20,22(32),23,25,27,29-pentadecaene-7,8-dione (NP0242680)

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Record Information

Version

2.0

Created at

2022-09-07 03:03:11 UTC

Updated at

2022-09-07 03:03:11 UTC

NP-MRD ID

NP0242680

Secondary Accession Numbers

None

Natural Product Identification

Common Name

octacyclo[15.13.1.1²²,²⁶.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0²¹,³¹.0³⁰,³²]dotriaconta-1,3,5(14),6(11),9,12,15,17(31),18,20,22(32),23,25,27,29-pentadecaene-7,8-dione

Description

Phenanthroperylenequinone belongs to the class of organic compounds known as chrysenes. Chrysenes are compounds containing the polyaromatic chrysene moiety, which consists of a benzene ring fused to a phenanthrene ring system to form Benzo[a]phenanthrene. octacyclo[15.13.1.1²²,²⁶.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0²¹,³¹.0³⁰,³²]dotriaconta-1,3,5(14),6(11),9,12,15,17(31),18,20,22(32),23,25,27,29-pentadecaene-7,8-dione is found in Himerometra robustipinna. octacyclo[15.13.1.1²²,²⁶.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0²¹,³¹.0³⁰,³²]dotriaconta-1,3,5(14),6(11),9,12,15,17(31),18,20,22(32),23,25,27,29-pentadecaene-7,8-dione was first documented in 2004 (PMID: 15295634). Based on a literature review a small amount of articles have been published on phenanthroperylenequinone (PMID: 20158243) (PMID: 20003155).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072205032D          

 34 41  0  0  0  0            999 V2000
    6.1698    1.9266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8420    1.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3337    0.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0059   -0.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1863   -0.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8585   -1.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0389   -1.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5472   -0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7277   -0.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3998   -1.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5803   -1.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2525   -2.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4329   -2.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0588   -1.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2690   -0.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2227   -0.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0423   -0.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5340    0.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062    1.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3866    1.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0588    1.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7607    2.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2525    1.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9246    0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1051    0.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4164   -0.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2359    0.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5637    0.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3833    0.8857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8750    0.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6946    0.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0224    1.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5307    1.7374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0885   -0.8177    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  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  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  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  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 16 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
  9 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
  8 30  1  0  0  0  0
 30 31  2  0  0  0  0
  5 31  1  0  0  0  0
 31 32  1  0  0  0  0
  2 32  1  0  0  0  0
 32 33  2  0  0  0  0
 26 34  1  0  0  0  0
 11 34  1  0  0  0  0
 15 34  2  0  0  0  0
M  END

     RDKit          3D

 50 57  0  0  0  0  0  0  0  0999 V2000
    6.8487    2.2864   -1.9231 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2897    1.4931   -1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0766    0.7230   -0.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4873   -0.1625    0.5532 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0989   -0.2621    0.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4973   -1.1356    1.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1250   -1.2800    1.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3367   -0.5147    0.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9395   -0.5966    0.7202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4215   -1.5962    1.4781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9546   -1.8357    1.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4384   -2.9001    2.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7712   -3.1795    2.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6110   -2.4064    1.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1184   -1.3358    0.5558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9704   -0.5380   -0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3190   -0.7808   -0.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2150    0.0978   -0.7493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7170    1.1813   -1.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3380    1.4002   -1.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8710    2.5443   -2.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5317    2.8142   -2.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6237    1.9462   -1.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0501    0.8123   -0.8383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4331    0.5531   -0.8162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2106   -0.0119   -0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1494    0.2057   -0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7444    1.0553   -0.9657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1496    1.1430   -1.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9434    0.3934   -0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3261    0.5179   -0.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8921    1.4072   -1.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3232    2.1605   -1.9280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7689   -1.0616    0.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1603    0.7770   -0.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0739   -0.7850    1.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0912   -1.7485    2.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6849   -1.9635    2.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0063   -2.2215    2.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7488   -3.4865    2.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1981   -3.9862    2.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6565   -2.6348    1.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8080   -1.6090    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2818   -0.0667   -0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3700    1.8927   -1.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6028    3.1978   -2.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2228    3.7298   -2.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6550    2.3816   -1.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2559    1.5507   -1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5641    1.8351   -1.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 34  2  0
 34 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 26 24  1  0
 24 25  2  0
 25 20  1  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 16  2  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 32  2  1  0
 23 24  1  0
 31  5  1  0
 16 25  1  0
 30  8  1  0
 27  9  1  0
 34 11  1  0
 16 15  1  0
  3 35  1  0
  4 36  1  0
  6 37  1  0
  7 38  1  0
 10 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 28 49  1  0
 29 50  1  0
 19 45  1  0
 18 44  1  0
 17 43  1  0
 21 46  1  0
 22 47  1  0
 23 48  1  0
M  END


  Mrv1652309072205032D          

 34 41  0  0  0  0            999 V2000
    6.1698    1.9266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8420    1.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3337    0.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0059   -0.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1863   -0.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8585   -1.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0389   -1.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5472   -0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7277   -0.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3998   -1.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5803   -1.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2525   -2.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4329   -2.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0588   -1.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2690   -0.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2227   -0.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0423   -0.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5340    0.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062    1.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3866    1.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0588    1.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7607    2.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2525    1.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9246    0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1051    0.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4164   -0.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2359    0.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5637    0.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3833    0.8857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8750    0.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6946    0.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0224    1.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5307    1.7374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0885   -0.8177    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  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  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  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  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 16 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
  9 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
  8 30  1  0  0  0  0
 30 31  2  0  0  0  0
  5 31  1  0  0  0  0
 31 32  1  0  0  0  0
  2 32  1  0  0  0  0
 32 33  2  0  0  0  0
 26 34  1  0  0  0  0
 11 34  1  0  0  0  0
 15 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0242680

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1C=CC2=CC=C3C4=CC5=CC=CC6=C5C(=C4C=CC3=C2C1=O)C1=C2C(C=CC=C62)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H16O2/c33-27-15-11-18-10-12-20-23(30(18)32(27)34)13-14-24-26(20)16-19-6-3-8-22-21-7-1-4-17-5-2-9-25(28(17)21)31(24)29(19)22/h1-16H

> <INCHI_KEY>
PLZNOIQFBGLPHO-UHFFFAOYSA-N

> <FORMULA>
C32H16O2

> <MOLECULAR_WEIGHT>
432.478

> <EXACT_MASS>
432.115029755

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
48.71094210451103

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
octacyclo[15.13.1.1^{22,26}.0^{2,15}.0^{5,14}.0^{6,11}.0^{21,31}.0^{30,32}]dotriaconta-1,3,5,9,11,13,15,17,19,21(31),22,24,26,28,30(32)-pentadecaene-7,8-dione

> <JCHEM_LOGP>
7.485411095333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-8.732817194437592

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
136.1802

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
octacyclo[15.13.1.1^{22,26}.0^{2,15}.0^{5,14}.0^{6,11}.0^{21,31}.0^{30,32}]dotriaconta-1,3,5,9,11,13,15,17,19,21(31),22,24,26,28,30(32)-pentadecaene-7,8-dione

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0      11.517   3.596   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.905   2.183   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.823   0.947   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.211  -0.467   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.681  -0.643   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.069  -2.056   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.539  -2.233   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.621  -0.997   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.092  -1.173   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.480  -2.586   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.950  -2.763   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.338  -4.176   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.808  -4.353   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.110  -3.116   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.502  -1.703   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.416  -0.467   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.946  -0.643   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.864   0.593   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.252   2.007   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.722   2.183   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.110   3.596   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.420   3.773   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.338   2.537   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.726   1.123   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.196   0.947   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.644  -0.113   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.174   0.063   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.786   1.477   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.315   1.653   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.233   0.417   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.763   0.593   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.375   2.007   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.457   3.243   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.032  -1.526   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   31                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   30                                                  
CONECT    9    8   10   27                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   34                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   34                                                  
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24   20   16                                                  
CONECT   26   24   27   34                                                  
CONECT   27   26    9   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    8   31                                                  
CONECT   31   30    5   32                                                  
CONECT   32   31    2   33                                                  
CONECT   33   32                                                            
CONECT   34   26   11   15                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₁₆O₂

Average Mass

432.4780 Da

Monoisotopic Mass

432.11503 Da

IUPAC Name

octacyclo[15.13.1.1^{22,26}.0^{2,15}.0^{5,14}.0^{6,11}.0^{21,31}.0^{30,32}]dotriaconta-1,3,5,9,11,13,15,17,19,21(31),22,24,26,28,30(32)-pentadecaene-7,8-dione

Traditional Name

octacyclo[15.13.1.1^{22,26}.0^{2,15}.0^{5,14}.0^{6,11}.0^{21,31}.0^{30,32}]dotriaconta-1,3,5,9,11,13,15,17,19,21(31),22,24,26,28,30(32)-pentadecaene-7,8-dione

CAS Registry Number

Not Available

SMILES

O=C1C=CC2=CC=C3C4=CC5=CC=CC6=C5C(=C4C=CC3=C2C1=O)C1=C2C(C=CC=C62)=CC=C1

InChI Identifier

InChI=1S/C32H16O2/c33-27-15-11-18-10-12-20-23(30(18)32(27)34)13-14-24-26(20)16-19-6-3-8-22-21-7-1-4-17-5-2-9-25(28(17)21)31(24)29(19)22/h1-16H

InChI Key

PLZNOIQFBGLPHO-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
Himerometra robustipinna	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chrysenes. Chrysenes are compounds containing the polyaromatic chrysene moiety, which consists of a benzene ring fused to a phenanthrene ring system to form Benzo[a]phenanthrene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Chrysenes

Direct Parent

Chrysenes

Alternative Parents

Substituents

Chrysene
Anthracene
Cyclic ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	7.49	ChemAxon
pKa (Strongest Basic)	-8.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	136.18 m³·mol⁻¹	ChemAxon
Polarizability	48.71 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

Not Available

Chemspider ID

24785833

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

87170386

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kemami Wangun HV, Wood A, Fiorilla C, Reed JK, McCarthy PJ, Wright AE: Gymnochromes E and F, cytotoxic phenanthroperylenequinones from a deep-water crinoid, Holopus rangii. J Nat Prod. 2010 Apr 23;73(4):712-5. doi: 10.1021/np900526y. [PubMed:20158243 ]
Theodossiou TA, Tsiourvas D, Hothersall JS: Hypericin hydroquinone: potential as a red-far red photosensitizer? Photochem Photobiol. 2010 Jan-Feb;86(1):18-22. doi: 10.1111/j.1751-1097.2009.00668.x. Epub 2009 Dec 7. [PubMed:20003155 ]
Kamuhabwa A, Agostinis P, Ahmed B, Landuyt W, van Cleynenbreugel B, van Poppel H, de Witte P: Hypericin as a potential phototherapeutic agent in superficial transitional cell carcinoma of the bladder. Photochem Photobiol Sci. 2004 Aug;3(8):772-80. doi: 10.1039/b315586b. Epub 2004 Apr 2. [PubMed:15295634 ]
LOTUS database [Link]

Showing NP-Card for octacyclo[15.13.1.1²²,²⁶.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0²¹,³¹.0³⁰,³²]dotriaconta-1,3,5(14),6(11),9,12,15,17(31),18,20,22(32),23,25,27,29-pentadecaene-7,8-dione (NP0242680)

MOL for NP0242680 (octacyclo[15.13.1.1²²,²⁶.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0²¹,³¹.0³⁰,³²]dotriaconta-1,3,5(14),6(11),9,12,15,17(31),18,20,22(32),23,25,27,29-pentadecaene-7,8-dione)

3D MOL for NP0242680 (octacyclo[15.13.1.1²²,²⁶.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0²¹,³¹.0³⁰,³²]dotriaconta-1,3,5(14),6(11),9,12,15,17(31),18,20,22(32),23,25,27,29-pentadecaene-7,8-dione)

3D SDF for NP0242680 (octacyclo[15.13.1.1²²,²⁶.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0²¹,³¹.0³⁰,³²]dotriaconta-1,3,5(14),6(11),9,12,15,17(31),18,20,22(32),23,25,27,29-pentadecaene-7,8-dione)

3D-SDF for NP0242680 (octacyclo[15.13.1.1²²,²⁶.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0²¹,³¹.0³⁰,³²]dotriaconta-1,3,5(14),6(11),9,12,15,17(31),18,20,22(32),23,25,27,29-pentadecaene-7,8-dione)

PDB for NP0242680 (octacyclo[15.13.1.1²²,²⁶.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0²¹,³¹.0³⁰,³²]dotriaconta-1,3,5(14),6(11),9,12,15,17(31),18,20,22(32),23,25,27,29-pentadecaene-7,8-dione)

3D PDB for NP0242680 (octacyclo[15.13.1.1²²,²⁶.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0²¹,³¹.0³⁰,³²]dotriaconta-1,3,5(14),6(11),9,12,15,17(31),18,20,22(32),23,25,27,29-pentadecaene-7,8-dione)

SMILES for NP0242680 (octacyclo[15.13.1.1²²,²⁶.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0²¹,³¹.0³⁰,³²]dotriaconta-1,3,5(14),6(11),9,12,15,17(31),18,20,22(32),23,25,27,29-pentadecaene-7,8-dione)

INCHI for NP0242680 (octacyclo[15.13.1.1²²,²⁶.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0²¹,³¹.0³⁰,³²]dotriaconta-1,3,5(14),6(11),9,12,15,17(31),18,20,22(32),23,25,27,29-pentadecaene-7,8-dione)

Structure for NP0242680 (octacyclo[15.13.1.1²²,²⁶.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0²¹,³¹.0³⁰,³²]dotriaconta-1,3,5(14),6(11),9,12,15,17(31),18,20,22(32),23,25,27,29-pentadecaene-7,8-dione)

3D Structure for NP0242680 (octacyclo[15.13.1.1²²,²⁶.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0²¹,³¹.0³⁰,³²]dotriaconta-1,3,5(14),6(11),9,12,15,17(31),18,20,22(32),23,25,27,29-pentadecaene-7,8-dione)