NP-MRD: Showing NP-Card for (5s,8ar,10as)-2-hydroxy-4-isopropyl-3-methoxy-6,10a-dimethyl-5-(3-methylbut-2-en-1-yl)-9,10-dioxo-8,8a-dihydro-5h-anthracene-1-carbaldehyde (NP0267240)

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Record Information

Version

2.0

Created at

2022-09-08 11:57:28 UTC

Updated at

2022-09-08 11:57:28 UTC

NP-MRD ID

NP0267240

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5s,8ar,10as)-2-hydroxy-4-isopropyl-3-methoxy-6,10a-dimethyl-5-(3-methylbut-2-en-1-yl)-9,10-dioxo-8,8a-dihydro-5h-anthracene-1-carbaldehyde

Description

(5S,8aR,10aS)-2-hydroxy-3-methoxy-6,10a-dimethyl-5-(3-methylbut-2-en-1-yl)-9,10-dioxo-4-(propan-2-yl)-5,8,8a,9,10,10a-hexahydroanthracene-1-carbaldehyde belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. (5s,8ar,10as)-2-hydroxy-4-isopropyl-3-methoxy-6,10a-dimethyl-5-(3-methylbut-2-en-1-yl)-9,10-dioxo-8,8a-dihydro-5h-anthracene-1-carbaldehyde is found in Gossypium barbadense. Based on a literature review very few articles have been published on (5S,8aR,10aS)-2-hydroxy-3-methoxy-6,10a-dimethyl-5-(3-methylbut-2-en-1-yl)-9,10-dioxo-4-(propan-2-yl)-5,8,8a,9,10,10a-hexahydroanthracene-1-carbaldehyde.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082213572D          

 31 33  0  0  1  0            999 V2000
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   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 C   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  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
    0.7145   -0.4125    0.0000 C   0  0  1  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   -1.6500    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
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    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 C   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 C   0  0  1  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
    2.1434    2.0625    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  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 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
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  1  0  0  0
 17 29  1  0  0  0  0
 29 30  1  0  0  0  0
  9 30  1  0  0  0  0
 30 31  2  0  0  0  0
M  END

     RDKit          3D

 63 65  0  0  0  0  0  0  0  0999 V2000
   -5.7701    1.4333   -1.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1018    1.1000   -0.3725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0466    0.2728   -0.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3275   -1.1146   -0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6352   -1.4747   -0.1448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3441   -2.0483    0.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6701   -3.4552    0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8914   -4.4028    0.5616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0725   -1.6147    0.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7679   -0.2660    0.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7389    0.7085   -0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2845    2.0746   -0.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8942    2.6688    1.1476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1673    3.0437   -0.9112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3131    0.0213    0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0867    1.0690    0.6887 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6778   -0.9180   -0.3544 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4775   -0.6916   -1.8967 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0784   -0.5568   -0.1250 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5516   -0.0728    1.1952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9872    0.3610    0.9974 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4091    1.5809    1.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8951    1.8506    0.8426 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5972    2.7820    1.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9605   -1.6822   -0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1480   -1.4165   -1.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6772   -2.9104   -0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4446   -3.0860    0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296   -2.3598   -0.0553 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9367   -2.5073    0.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1296   -3.3738    1.5150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9232    2.5544   -1.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8323    1.0552   -1.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2858    1.1220   -2.4835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0340   -2.3725   -0.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7234   -3.7654    0.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2553    2.0751   -0.7352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9935    3.2624    1.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9144    1.9303    1.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7086    3.4667    1.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4670    2.7371   -1.9333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0591    3.3326   -0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6137    4.0617   -1.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514   -1.3589   -2.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5924   -0.7752   -2.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7729    0.3845   -2.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3433    0.2934   -0.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5231   -0.8037    2.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0202    0.8150    1.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7064   -0.4506    0.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1729    2.7529    1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0355    2.0420   -0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5028    0.9680    1.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9118    3.5619    0.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5200    2.6755    1.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8938    3.1993    2.3415 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0530   -2.0157   -2.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1399   -0.3379   -1.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1066   -1.7292   -1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2766   -3.7540   -0.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2049   -4.1753    0.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6175   -2.8812    1.6692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2210   -2.8851   -1.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
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  6  7  1  0
  7  8  2  0
  6  9  2  0
  9 30  1  0
 30 31  2  0
 30 29  1  0
 29 28  1  0
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 21 22  2  3
 22 23  1  0
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 19 17  1  0
 17 18  1  6
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 10 11  2  0
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 12 13  1  0
 12 14  1  0
 11  3  1  0
 10  9  1  0
 17 29  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  5 35  1  0
  7 36  1  0
 29 63  1  6
 28 61  1  0
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 23 52  1  0
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 12 37  1  0
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 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
M  END


  Mrv1652309082213572D          

 31 33  0  0  1  0            999 V2000
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   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 C   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  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
    0.7145   -0.4125    0.0000 C   0  0  1  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   -1.6500    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
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    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 C   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 C   0  0  1  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
    2.1434    2.0625    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  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
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 17 19  1  0  0  0  0
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 22 23  1  0  0  0  0
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 19 25  1  0  0  0  0
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 29 28  1  1  0  0  0
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 29 30  1  0  0  0  0
  9 30  1  0  0  0  0
 30 31  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0267240

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C(C=O)=C2C(=O)[C@@H]3CC=C(C)[C@H](CC=C(C)C)[C@]3(C)C(=O)C2=C1C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O5/c1-13(2)8-10-17-15(5)9-11-18-23(29)20-16(12-27)22(28)24(31-7)19(14(3)4)21(20)25(30)26(17,18)6/h8-9,12,14,17-18,28H,10-11H2,1-7H3/t17-,18-,26-/m0/s1

> <INCHI_KEY>
LTDXHSVIDXPYBK-XWXLMPLOSA-N

> <FORMULA>
C26H32O5

> <MOLECULAR_WEIGHT>
424.537

> <EXACT_MASS>
424.22497413

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
46.8744034017636

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S,8aR,10aS)-2-hydroxy-3-methoxy-6,10a-dimethyl-5-(3-methylbut-2-en-1-yl)-9,10-dioxo-4-(propan-2-yl)-5,8,8a,9,10,10a-hexahydroanthracene-1-carbaldehyde

> <JCHEM_LOGP>
5.734026830000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.839925557423111

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.976456312087676

> <JCHEM_PKA_STRONGEST_BASIC>
-4.913923010562485

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
124.53069999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5S,8aR,10aS)-2-hydroxy-4-isopropyl-3-methoxy-6,10a-dimethyl-5-(3-methylbut-2-en-1-yl)-9,10-dioxo-8,8a-dihydro-5H-anthracene-1-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.668   2.310   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       5.335   4.620   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10   30                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10    3   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   29                                             
CONECT   18   17                                                            
CONECT   19   17   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   19   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   17   30                                                  
CONECT   30   29    9   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₅

Average Mass

424.5370 Da

Monoisotopic Mass

424.22497 Da

IUPAC Name

(5S,8aR,10aS)-2-hydroxy-3-methoxy-6,10a-dimethyl-5-(3-methylbut-2-en-1-yl)-9,10-dioxo-4-(propan-2-yl)-5,8,8a,9,10,10a-hexahydroanthracene-1-carbaldehyde

Traditional Name

(5S,8aR,10aS)-2-hydroxy-4-isopropyl-3-methoxy-6,10a-dimethyl-5-(3-methylbut-2-en-1-yl)-9,10-dioxo-8,8a-dihydro-5H-anthracene-1-carbaldehyde

CAS Registry Number

Not Available

SMILES

COC1=C(O)C(C=O)=C2C(=O)[C@@H]3CC=C(C)[C@H](CC=C(C)C)[C@]3(C)C(=O)C2=C1C(C)C

InChI Identifier

InChI=1S/C26H32O5/c1-13(2)8-10-17-15(5)9-11-18-23(29)20-16(12-27)22(28)24(31-7)19(14(3)4)21(20)25(30)26(17,18)6/h8-9,12,14,17-18,28H,10-11H2,1-7H3/t17-,18-,26-/m0/s1

InChI Key

LTDXHSVIDXPYBK-XWXLMPLOSA-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
Gossypium barbadense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
Cadinane sesquiterpenoid
Sesquiterpenoid
Tetralin
Anisole
Quinone
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
Aryl-aldehyde
Vinylogous acid
Ketone
Ether
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aldehyde
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	5.73	ChemAxon
pKa (Strongest Acidic)	6.98	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	124.53 m³·mol⁻¹	ChemAxon
Polarizability	46.87 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162859193

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5s,8ar,10as)-2-hydroxy-4-isopropyl-3-methoxy-6,10a-dimethyl-5-(3-methylbut-2-en-1-yl)-9,10-dioxo-8,8a-dihydro-5h-anthracene-1-carbaldehyde (NP0267240)

MOL for NP0267240 ((5s,8ar,10as)-2-hydroxy-4-isopropyl-3-methoxy-6,10a-dimethyl-5-(3-methylbut-2-en-1-yl)-9,10-dioxo-8,8a-dihydro-5h-anthracene-1-carbaldehyde)

3D MOL for NP0267240 ((5s,8ar,10as)-2-hydroxy-4-isopropyl-3-methoxy-6,10a-dimethyl-5-(3-methylbut-2-en-1-yl)-9,10-dioxo-8,8a-dihydro-5h-anthracene-1-carbaldehyde)

3D SDF for NP0267240 ((5s,8ar,10as)-2-hydroxy-4-isopropyl-3-methoxy-6,10a-dimethyl-5-(3-methylbut-2-en-1-yl)-9,10-dioxo-8,8a-dihydro-5h-anthracene-1-carbaldehyde)

3D-SDF for NP0267240 ((5s,8ar,10as)-2-hydroxy-4-isopropyl-3-methoxy-6,10a-dimethyl-5-(3-methylbut-2-en-1-yl)-9,10-dioxo-8,8a-dihydro-5h-anthracene-1-carbaldehyde)

PDB for NP0267240 ((5s,8ar,10as)-2-hydroxy-4-isopropyl-3-methoxy-6,10a-dimethyl-5-(3-methylbut-2-en-1-yl)-9,10-dioxo-8,8a-dihydro-5h-anthracene-1-carbaldehyde)

3D PDB for NP0267240 ((5s,8ar,10as)-2-hydroxy-4-isopropyl-3-methoxy-6,10a-dimethyl-5-(3-methylbut-2-en-1-yl)-9,10-dioxo-8,8a-dihydro-5h-anthracene-1-carbaldehyde)

SMILES for NP0267240 ((5s,8ar,10as)-2-hydroxy-4-isopropyl-3-methoxy-6,10a-dimethyl-5-(3-methylbut-2-en-1-yl)-9,10-dioxo-8,8a-dihydro-5h-anthracene-1-carbaldehyde)

INCHI for NP0267240 ((5s,8ar,10as)-2-hydroxy-4-isopropyl-3-methoxy-6,10a-dimethyl-5-(3-methylbut-2-en-1-yl)-9,10-dioxo-8,8a-dihydro-5h-anthracene-1-carbaldehyde)

Structure for NP0267240 ((5s,8ar,10as)-2-hydroxy-4-isopropyl-3-methoxy-6,10a-dimethyl-5-(3-methylbut-2-en-1-yl)-9,10-dioxo-8,8a-dihydro-5h-anthracene-1-carbaldehyde)

3D Structure for NP0267240 ((5s,8ar,10as)-2-hydroxy-4-isopropyl-3-methoxy-6,10a-dimethyl-5-(3-methylbut-2-en-1-yl)-9,10-dioxo-8,8a-dihydro-5h-anthracene-1-carbaldehyde)