NP-MRD: Showing NP-Card for (2s)-1-{3,10-dihydroxy-12-[(2s)-2-[(4-hydroxyphenoxycarbonyl)oxy]propyl]-2,6,7,11-tetramethoxy-4,9-dioxoperylen-1-yl}propan-2-yl benzoate (NP0251438)

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Record Information

Version

2.0

Created at

2022-09-07 14:38:07 UTC

Updated at

2022-09-07 14:38:07 UTC

NP-MRD ID

NP0251438

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-1-{3,10-dihydroxy-12-[(2s)-2-[(4-hydroxyphenoxycarbonyl)oxy]propyl]-2,6,7,11-tetramethoxy-4,9-dioxoperylen-1-yl}propan-2-yl benzoate

Description

Calphostin C, also known as ucn 1028C, belongs to the class of organic compounds known as perylenequinones. These are heterocyclic compounds characterized by two 8-hydroxy-1,4-dihydronaphthalen-1-one moieties joined together one or two CC-bonds. (2s)-1-{3,10-dihydroxy-12-[(2s)-2-[(4-hydroxyphenoxycarbonyl)oxy]propyl]-2,6,7,11-tetramethoxy-4,9-dioxoperylen-1-yl}propan-2-yl benzoate is found in Cladosporium cladosporioides. (2s)-1-{3,10-dihydroxy-12-[(2s)-2-[(4-hydroxyphenoxycarbonyl)oxy]propyl]-2,6,7,11-tetramethoxy-4,9-dioxoperylen-1-yl}propan-2-yl benzoate was first documented in 2021 (PMID: 34500007). Based on a literature review a significant number of articles have been published on calphostin C (PMID: 34358110) (PMID: 35782063) (PMID: 35599854) (PMID: 34998939) (PMID: 34709697) (PMID: 34634367).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072216382D          

 58 64  0  0  1  0            999 V2000
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   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  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 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  1  0  0  0  0
 15 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
 27 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
  3 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  1  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 47 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
 55 56  2  0  0  0  0
 50 56  1  0  0  0  0
 41 57  2  0  0  0  0
  6 57  1  0  0  0  0
 13 57  1  0  0  0  0
 40 58  2  0  0  0  0
 21 58  1  0  0  0  0
 14 58  1  0  0  0  0
M  END


  Mrv1652309072216382D          

 58 64  0  0  1  0            999 V2000
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   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  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 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  1  0  0  0  0
 15 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
 27 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
  3 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  1  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 47 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
 55 56  2  0  0  0  0
 50 56  1  0  0  0  0
 41 57  2  0  0  0  0
  6 57  1  0  0  0  0
 13 57  1  0  0  0  0
 40 58  2  0  0  0  0
 21 58  1  0  0  0  0
 14 58  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0251438

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)C2=C(O)C(OC)=C(C[C@H](C)OC(=O)OC3=CC=C(O)C=C3)C3=C2C1=C1C(OC)=CC(=O)C2=C(O)C(OC)=C(C[C@H](C)OC(=O)C4=CC=CC=C4)C3=C12

> <INCHI_IDENTIFIER>
InChI=1S/C44H38O14/c1-20(56-43(50)22-10-8-7-9-11-22)16-25-31-32-26(17-21(2)57-44(51)58-24-14-12-23(45)13-15-24)42(55-6)40(49)34-28(47)19-30(53-4)36(38(32)34)35-29(52-3)18-27(46)33(37(31)35)39(48)41(25)54-5/h7-15,18-21,45,48-49H,16-17H2,1-6H3/t20-,21-/m0/s1

> <INCHI_KEY>
LSUTUUOITDQYNO-SFTDATJTSA-N

> <FORMULA>
C44H38O14

> <MOLECULAR_WEIGHT>
790.774

> <EXACT_MASS>
790.226155904

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
80.25555435693147

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-{3,10-dihydroxy-12-[(2S)-2-{[(4-hydroxyphenoxy)carbonyl]oxy}propyl]-2,6,7,11-tetramethoxy-4,9-dioxo-4,9-dihydroperylen-1-yl}propan-2-yl benzoate

> <JCHEM_LOGP>
7.721836935999998

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.821845710363893

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.216325488384638

> <JCHEM_PKA_STRONGEST_BASIC>
3.6629969962836113

> <JCHEM_POLAR_SURFACE_AREA>
193.57999999999998

> <JCHEM_REFRACTIVITY>
212.99059999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-{3,10-dihydroxy-12-[(2S)-2-[(4-hydroxyphenoxycarbonyl)oxy]propyl]-2,6,7,11-tetramethoxy-4,9-dioxoperylen-1-yl}propan-2-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

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  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.668   6.930   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.667  10.780   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -0.000   9.240   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -0.000  10.780   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       1.334  11.550   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      -1.334  11.550   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -1.334  13.090   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -2.667  13.860   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -2.667  15.400   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -1.334  16.170   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      -1.334  17.710   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      -0.000  15.400   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      -0.000  13.860   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   42                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   57                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   57                                                  
CONECT   14   13   15   58                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   58                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   40                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   34                                                       
CONECT   40   27   41   58                                                  
CONECT   41   40   42   57                                                  
CONECT   42   41    3   43                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50                                                       
CONECT   50   49   51   56                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56                                                       
CONECT   56   55   50                                                       
CONECT   57   41    6   13                                                  
CONECT   58   40   21   14                                                  
MASTER        0    0    0    0    0    0    0    0   58    0  128    0
END

View in JSmol

Synonyms

Value	Source
UCN 1028C	MeSH
UCN 1028 C	MeSH
UCN-1028C	MeSH

Chemical Formula

C₄₄H₃₈O₁₄

Average Mass

790.7740 Da

Monoisotopic Mass

790.22616 Da

IUPAC Name

(2S)-1-{3,10-dihydroxy-12-[(2S)-2-{[(4-hydroxyphenoxy)carbonyl]oxy}propyl]-2,6,7,11-tetramethoxy-4,9-dioxo-4,9-dihydroperylen-1-yl}propan-2-yl benzoate

Traditional Name

(2S)-1-{3,10-dihydroxy-12-[(2S)-2-[(4-hydroxyphenoxycarbonyl)oxy]propyl]-2,6,7,11-tetramethoxy-4,9-dioxoperylen-1-yl}propan-2-yl benzoate

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)C2=C(O)C(OC)=C(C[C@H](C)OC(=O)OC3=CC=C(O)C=C3)C3=C2C1=C1C(OC)=CC(=O)C2=C(O)C(OC)=C(C[C@H](C)OC(=O)C4=CC=CC=C4)C3=C12

InChI Identifier

InChI=1S/C44H38O14/c1-20(56-43(50)22-10-8-7-9-11-22)16-25-31-32-26(17-21(2)57-44(51)58-24-14-12-23(45)13-15-24)42(55-6)40(49)34-28(47)19-30(53-4)36(38(32)34)35-29(52-3)18-27(46)33(37(31)35)39(48)41(25)54-5/h7-15,18-21,45,48-49H,16-17H2,1-6H3/t20-,21-/m0/s1

InChI Key

LSUTUUOITDQYNO-SFTDATJTSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cladosporium cladosporioides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as perylenequinones. These are heterocyclic compounds characterized by two 8-hydroxy-1,4-dihydronaphthalen-1-one moieties joined together one or two CC-bonds.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Perylenequinones

Sub Class

Not Available

Direct Parent

Perylenequinones

Alternative Parents

Substituents

Perylenequinone
Phenanthrol
Anthracene
Phenanthrene
2-naphthol
1-naphthol
Benzoate ester
Benzoic acid or derivatives
Anisole
Phenoxy compound
Benzoyl
Phenol ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Carbonic acid diester
Vinylogous ester
Vinylogous acid
Carboxylic acid ester
Carbonic acid derivative
Carboxylic acid derivative
Ether
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
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	7.72	ChemAxon
pKa (Strongest Acidic)	7.22	ChemAxon
pKa (Strongest Basic)	3.66	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	193.58 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	212.99 m³·mol⁻¹	ChemAxon
Polarizability	80.26 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Calphostin C

METLIN ID

Not Available

PubChem Compound

97041723

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Alves SAS, Florentino LS, Teixeira DE, Silva-Aguiar RP, Peruchetti DB, Oliveira AC, Scharfstein J, Marzolo MP, Pinheiro AAS, Caruso-Neves C: Surface megalin expression is a target to the inhibitory effect of bradykinin on the renal albumin endocytosis. Peptides. 2021 Sep 6;146:170646. doi: 10.1016/j.peptides.2021.170646. [PubMed:34500007 ]
Singina GN, Shedova EN, Lopukhov AV, Mityashova OS, Lebedeva IY: Delaying Effects of Prolactin and Growth Hormone on Aging Processes in Bovine Oocytes Matured In Vitro. Pharmaceuticals (Basel). 2021 Jul 16;14(7). pii: ph14070684. doi: 10.3390/ph14070684. [PubMed:34358110 ]
Lu N, Tan G, Tan H, Zhang X, Lv Y, Song X, You D, Gao Z: Maackiain Prevents Amyloid-Beta-Induced Cellular Injury via Priming PKC-Nrf2 Pathway. Biomed Res Int. 2022 Jun 22;2022:4243210. doi: 10.1155/2022/4243210. eCollection 2022. [PubMed:35782063 ]
Villar-Delfino PH, Gomes NAO, Christo PP, Nogueira-Machado JA, Volpe CMO: Edaravone Inhibits the Production of Reactive Oxygen Species in Phagocytosis- and PKC-Stimulated Granulocytes from Multiple Sclerosis Patients Edaravone Modulate Oxidative Stress in Multiple Sclerosis. J Cent Nerv Syst Dis. 2022 May 16;14:11795735221092524. doi: 10.1177/11795735221092524. eCollection 2022. [PubMed:35599854 ]
Janach GMS, Bohm M, Dohne N, Kim HR, Rosario M, Strauss U: Interferon-gamma enhances neocortical synaptic inhibition by promoting membrane association and phosphorylation of GABA(A) receptors in a protein kinase C-dependent manner. Brain Behav Immun. 2022 Mar;101:153-164. doi: 10.1016/j.bbi.2022.01.001. Epub 2022 Jan 6. [PubMed:34998939 ]
Gu SH, Chen CH, Lin PL: Protein kinase C signalling involved in prothoracicotropic hormone-stimulated prothoracic glands in the silkworm, Bombyx mori. Insect Mol Biol. 2022 Feb;31(1):115-126. doi: 10.1111/imb.12744. Epub 2021 Nov 16. [PubMed:34709697 ]
Lin HJ, Mahendran R, Huang HY, Chiu PL, Chang YM, Day CH, Chen RJ, Padma VV, Liang-Yo Y, Kuo WW, Huang CY: Aqueous extract of Solanum nigrum attenuates Angiotensin-II induced cardiac hypertrophy and improves cardiac function by repressing protein kinase C-zeta to restore HSF2 deSUMOlyation and Mel-18-IGF-IIR signaling suppression. J Ethnopharmacol. 2022 Feb 10;284:114728. doi: 10.1016/j.jep.2021.114728. Epub 2021 Oct 8. [PubMed:34634367 ]
Smejkalova T, Korinek M, Krusek J, Hrcka Krausova B, Candelas Serra M, Hajdukovic D, Kudova E, Chodounska H, Vyklicky L: Endogenous neurosteroids pregnanolone and pregnanolone sulfate potentiate presynaptic glutamate release through distinct mechanisms. Br J Pharmacol. 2021 Oct;178(19):3888-3904. doi: 10.1111/bph.15529. Epub 2021 Jun 22. [PubMed:33988248 ]
LOTUS database [Link]

Showing NP-Card for (2s)-1-{3,10-dihydroxy-12-[(2s)-2-[(4-hydroxyphenoxycarbonyl)oxy]propyl]-2,6,7,11-tetramethoxy-4,9-dioxoperylen-1-yl}propan-2-yl benzoate (NP0251438)

MOL for NP0251438 ((2s)-1-{3,10-dihydroxy-12-[(2s)-2-[(4-hydroxyphenoxycarbonyl)oxy]propyl]-2,6,7,11-tetramethoxy-4,9-dioxoperylen-1-yl}propan-2-yl benzoate)

3D MOL for NP0251438 ((2s)-1-{3,10-dihydroxy-12-[(2s)-2-[(4-hydroxyphenoxycarbonyl)oxy]propyl]-2,6,7,11-tetramethoxy-4,9-dioxoperylen-1-yl}propan-2-yl benzoate)

3D SDF for NP0251438 ((2s)-1-{3,10-dihydroxy-12-[(2s)-2-[(4-hydroxyphenoxycarbonyl)oxy]propyl]-2,6,7,11-tetramethoxy-4,9-dioxoperylen-1-yl}propan-2-yl benzoate)

3D-SDF for NP0251438 ((2s)-1-{3,10-dihydroxy-12-[(2s)-2-[(4-hydroxyphenoxycarbonyl)oxy]propyl]-2,6,7,11-tetramethoxy-4,9-dioxoperylen-1-yl}propan-2-yl benzoate)

PDB for NP0251438 ((2s)-1-{3,10-dihydroxy-12-[(2s)-2-[(4-hydroxyphenoxycarbonyl)oxy]propyl]-2,6,7,11-tetramethoxy-4,9-dioxoperylen-1-yl}propan-2-yl benzoate)

3D PDB for NP0251438 ((2s)-1-{3,10-dihydroxy-12-[(2s)-2-[(4-hydroxyphenoxycarbonyl)oxy]propyl]-2,6,7,11-tetramethoxy-4,9-dioxoperylen-1-yl}propan-2-yl benzoate)

SMILES for NP0251438 ((2s)-1-{3,10-dihydroxy-12-[(2s)-2-[(4-hydroxyphenoxycarbonyl)oxy]propyl]-2,6,7,11-tetramethoxy-4,9-dioxoperylen-1-yl}propan-2-yl benzoate)

INCHI for NP0251438 ((2s)-1-{3,10-dihydroxy-12-[(2s)-2-[(4-hydroxyphenoxycarbonyl)oxy]propyl]-2,6,7,11-tetramethoxy-4,9-dioxoperylen-1-yl}propan-2-yl benzoate)

Structure for NP0251438 ((2s)-1-{3,10-dihydroxy-12-[(2s)-2-[(4-hydroxyphenoxycarbonyl)oxy]propyl]-2,6,7,11-tetramethoxy-4,9-dioxoperylen-1-yl}propan-2-yl benzoate)

3D Structure for NP0251438 ((2s)-1-{3,10-dihydroxy-12-[(2s)-2-[(4-hydroxyphenoxycarbonyl)oxy]propyl]-2,6,7,11-tetramethoxy-4,9-dioxoperylen-1-yl}propan-2-yl benzoate)