NP-MRD: Showing NP-Card for (17s)-13-(acetyloxy)-5-methoxy-4,7,12-trimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.0³,⁸.0¹⁴,¹⁸]octadeca-1(11),3,5,7,12,14(18)-hexaen-17-yl acetate (NP0189142)

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Record Information

Version

2.0

Created at

2022-09-04 05:35:03 UTC

Updated at

2022-09-04 05:35:03 UTC

NP-MRD ID

NP0189142

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(17s)-13-(acetyloxy)-5-methoxy-4,7,12-trimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.0³,⁸.0¹⁴,¹⁸]octadeca-1(11),3,5,7,12,14(18)-hexaen-17-yl acetate

Description

(17S)-13-(acetyloxy)-5-methoxy-4,7,12-trimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.0³,⁸.0¹⁴,¹⁸]Octadeca-1(11),3(8),4,6,12,14(18)-hexaen-17-yl acetate belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. (17s)-13-(acetyloxy)-5-methoxy-4,7,12-trimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.0³,⁸.0¹⁴,¹⁸]octadeca-1(11),3,5,7,12,14(18)-hexaen-17-yl acetate is found in Nephroma australe. Based on a literature review very few articles have been published on (17S)-13-(acetyloxy)-5-methoxy-4,7,12-trimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.0³,⁸.0¹⁴,¹⁸]Octadeca-1(11),3(8),4,6,12,14(18)-hexaen-17-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042207352D          

 33 36  0  0  1  0            999 V2000
    4.2394    0.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6821    1.3533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3006    2.0848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7433    2.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3618    3.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8045    4.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5376    3.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0948    2.8516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4763    2.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0336    1.4240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2745    2.7637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6944    3.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7912    4.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1301    4.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2269    5.4824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3721    4.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2890    4.8308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1921    5.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8532    6.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5658    5.9759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2753    3.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9364    3.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6713    2.2432    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1476    1.5696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8023    0.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2785    0.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0192    0.7447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1536    2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    3.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1796    3.3068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4921    4.6047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2693    4.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8559    4.9081    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
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  2  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 21 29  1  0  0  0  0
 29 30  2  0  0  0  0
 13 31  1  0  0  0  0
 31 32  1  0  0  0  0
  7 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
   -6.2481   -1.5996    0.8967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8633   -1.8511    0.9745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9947   -0.9612    0.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4673    0.1414   -0.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6344    1.0802   -0.9085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1559    2.2686   -1.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2906    0.7917   -0.8058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7698   -0.3133   -0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6352   -1.1843    0.4365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1623   -2.3861    1.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4209   -0.6998    0.0107 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6627    0.1934    0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7550    1.4623   -0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9179    2.2042   -0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9802    3.5618   -0.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9537    1.6461    0.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1411    2.3695    0.6433 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1204    2.2075   -0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3905    2.9711   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9420    1.4650   -1.3222 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    0.3688    0.9876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7444   -0.3488    0.7984 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9411   -1.6691    1.4086 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1074   -2.6571    0.3816 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4080   -3.8229    0.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6023   -4.8310   -0.7843 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5515   -4.0886    1.1834 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1854   -1.5934    2.0573 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8237   -0.4186    1.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9804   -0.0196    2.1263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1947    2.1932   -1.1817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4977    1.8255   -1.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1127    2.3909   -2.4125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5814   -1.4145   -0.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8448   -2.4384    1.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4349   -0.6550    1.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5266    0.3257   -0.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8258    3.2488   -1.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3493    2.1769   -2.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2389    2.3218   -1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8988   -3.1382    0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9404   -2.7847    1.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2681   -2.1094    1.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9981    3.7528   -1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7226    4.2764   -0.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2947    3.6358   -1.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9193    3.0319   -1.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1230    3.9584    0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9833    2.3801    0.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1263   -1.9602    2.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4961   -4.3858   -1.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6572   -5.2197   -0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9297   -5.6995   -0.6545 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
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8 11  1  0
 11 12  1  0
 12 13  2  0
 13 31  1  0
 31 32  1  0
 32 33  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 16 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 23 28  1  0
 28 29  1  0
 29 30  2  0
  8  9  2  0
  9 10  1  0
  9  3  1  0
 32  7  1  0
 29 21  1  0
 22 12  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  6 38  1  0
  6 39  1  0
  6 40  1  0
 15 44  1  0
 15 45  1  0
 15 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 23 50  1  1
 26 51  1  0
 26 52  1  0
 26 53  1  0
 10 41  1  0
 10 42  1  0
 10 43  1  0
M  END


  Mrv1652309042207352D          

 33 36  0  0  1  0            999 V2000
    4.2394    0.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6821    1.3533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3006    2.0848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7433    2.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3618    3.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8045    4.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5376    3.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0948    2.8516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4763    2.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0336    1.4240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2745    2.7637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6944    3.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7912    4.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1301    4.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2269    5.4824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3721    4.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2890    4.8308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1921    5.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8532    6.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5658    5.9759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2753    3.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9364    3.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6713    2.2432    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1476    1.5696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8023    0.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2785    0.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0192    0.7447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1536    2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    3.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1796    3.3068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4921    4.6047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2693    4.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8559    4.9081    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
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  2  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 21 29  1  0  0  0  0
 29 30  2  0  0  0  0
 13 31  1  0  0  0  0
 31 32  1  0  0  0  0
  7 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0189142

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C)=C2C(OC3=C(OC2=O)C(C)=C(OC(C)=O)C2=C3[C@@H](OC(C)=O)OC2=O)=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C23H20O10/c1-8-7-13(28-6)9(2)17-14(8)21(26)32-19-10(3)18(29-11(4)24)15-16(20(19)31-17)23(30-12(5)25)33-22(15)27/h7,23H,1-6H3/t23-/m0/s1

> <INCHI_KEY>
LRDSRPNZXUTRCA-QHCPKHFHSA-N

> <FORMULA>
C23H20O10

> <MOLECULAR_WEIGHT>
456.403

> <EXACT_MASS>
456.105646844

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
44.80323643715967

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(17S)-13-(acetyloxy)-5-methoxy-4,7,12-trimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.0^{3,8}.0^{14,18}]octadeca-1(11),3,5,7,12,14(18)-hexaen-17-yl acetate

> <JCHEM_LOGP>
3.583182206333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.056271588201145

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7671942411612336

> <JCHEM_POLAR_SURFACE_AREA>
123.66000000000003

> <JCHEM_REFRACTIVITY>
111.52419999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(17S)-13-(acetyloxy)-5-methoxy-4,7,12-trimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.0^{3,8}.0^{14,18}]octadeca-1(11),3,5,7,12,14(18)-hexaen-17-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       7.913   1.227   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.740   2.526   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.028   3.892   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.854   5.191   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.142   6.557   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.968   7.856   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.603   6.623   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.777   5.323   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.489   3.958   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.663   2.658   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.246   5.159   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.163   6.254   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.344   7.783   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.110   8.704   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.290  10.234   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.695   8.096   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.539   9.018   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.359  10.547   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.593  11.468   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.056  11.155   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.514   6.567   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.748   5.646   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.253   4.187   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.142   2.930   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.498   1.531   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.387   0.274   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.036   1.390   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.287   4.207   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.744   5.678   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.202   6.173   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       4.652   8.595   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.103   8.079   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.198   9.162   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   32                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14   31                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   22   29                                                  
CONECT   22   21   12   23                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   29                                                       
CONECT   29   28   21   30                                                  
CONECT   30   29                                                            
CONECT   31   13   32                                                       
CONECT   32   31    7   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(17S)-13-(Acetyloxy)-5-methoxy-4,7,12-trimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.0,.0,]octadeca-1(11),3(8),4,6,12,14(18)-hexaen-17-yl acetic acid	Generator

Chemical Formula

C₂₃H₂₀O₁₀

Average Mass

456.4030 Da

Monoisotopic Mass

456.10565 Da

IUPAC Name

(17S)-13-(acetyloxy)-5-methoxy-4,7,12-trimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.0^{3,8}.0^{14,18}]octadeca-1(11),3,5,7,12,14(18)-hexaen-17-yl acetate

Traditional Name

(17S)-13-(acetyloxy)-5-methoxy-4,7,12-trimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.0^{3,8}.0^{14,18}]octadeca-1(11),3,5,7,12,14(18)-hexaen-17-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC(C)=C2C(OC3=C(OC2=O)C(C)=C(OC(C)=O)C2=C3[C@@H](OC(C)=O)OC2=O)=C1C

InChI Identifier

InChI=1S/C23H20O10/c1-8-7-13(28-6)9(2)17-14(8)21(26)32-19-10(3)18(29-11(4)24)15-16(20(19)31-17)23(30-12(5)25)33-22(15)27/h7,23H,1-6H3/t23-/m0/s1

InChI Key

LRDSRPNZXUTRCA-QHCPKHFHSA-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
Nephroma australe	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Diaryl ether
Isobenzofuranone
Benzofuranone
Phthalide
Isocoumaran
Anisole
1,4-dioxepine
Alkyl aryl ether
Dioxepine
Benzenoid
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Acetal
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	3.58	ChemAxon
pKa (Strongest Acidic)	11.06	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	123.66 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	111.52 m³·mol⁻¹	ChemAxon
Polarizability	44.8 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

162863473

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (17s)-13-(acetyloxy)-5-methoxy-4,7,12-trimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.0³,⁸.0¹⁴,¹⁸]octadeca-1(11),3,5,7,12,14(18)-hexaen-17-yl acetate (NP0189142)

MOL for NP0189142 ((17s)-13-(acetyloxy)-5-methoxy-4,7,12-trimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.0³,⁸.0¹⁴,¹⁸]octadeca-1(11),3,5,7,12,14(18)-hexaen-17-yl acetate)

3D MOL for NP0189142 ((17s)-13-(acetyloxy)-5-methoxy-4,7,12-trimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.0³,⁸.0¹⁴,¹⁸]octadeca-1(11),3,5,7,12,14(18)-hexaen-17-yl acetate)

3D SDF for NP0189142 ((17s)-13-(acetyloxy)-5-methoxy-4,7,12-trimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.0³,⁸.0¹⁴,¹⁸]octadeca-1(11),3,5,7,12,14(18)-hexaen-17-yl acetate)

3D-SDF for NP0189142 ((17s)-13-(acetyloxy)-5-methoxy-4,7,12-trimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.0³,⁸.0¹⁴,¹⁸]octadeca-1(11),3,5,7,12,14(18)-hexaen-17-yl acetate)

PDB for NP0189142 ((17s)-13-(acetyloxy)-5-methoxy-4,7,12-trimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.0³,⁸.0¹⁴,¹⁸]octadeca-1(11),3,5,7,12,14(18)-hexaen-17-yl acetate)

3D PDB for NP0189142 ((17s)-13-(acetyloxy)-5-methoxy-4,7,12-trimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.0³,⁸.0¹⁴,¹⁸]octadeca-1(11),3,5,7,12,14(18)-hexaen-17-yl acetate)

SMILES for NP0189142 ((17s)-13-(acetyloxy)-5-methoxy-4,7,12-trimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.0³,⁸.0¹⁴,¹⁸]octadeca-1(11),3,5,7,12,14(18)-hexaen-17-yl acetate)

INCHI for NP0189142 ((17s)-13-(acetyloxy)-5-methoxy-4,7,12-trimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.0³,⁸.0¹⁴,¹⁸]octadeca-1(11),3,5,7,12,14(18)-hexaen-17-yl acetate)

Structure for NP0189142 ((17s)-13-(acetyloxy)-5-methoxy-4,7,12-trimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.0³,⁸.0¹⁴,¹⁸]octadeca-1(11),3,5,7,12,14(18)-hexaen-17-yl acetate)

3D Structure for NP0189142 ((17s)-13-(acetyloxy)-5-methoxy-4,7,12-trimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.0³,⁸.0¹⁴,¹⁸]octadeca-1(11),3,5,7,12,14(18)-hexaen-17-yl acetate)