NP-MRD: Showing NP-Card for methyl (2z)-3-[(1r,2r,4s,7s,8s,9r,11r,12r,13r,17s)-9-(acetyloxy)-7-(furan-3-yl)-13,17-dihydroxy-1,8,12,15,15-pentamethyl-5,14-dioxo-3,6,16-trioxapentacyclo[9.6.0.0²,⁴.0²,⁸.0¹³,¹⁷]heptadecan-12-yl]prop-2-enoate (NP0273892)

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Record Information

Version

2.0

Created at

2022-09-08 21:05:03 UTC

Updated at

2022-09-08 21:05:03 UTC

NP-MRD ID

NP0273892

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2z)-3-[(1r,2r,4s,7s,8s,9r,11r,12r,13r,17s)-9-(acetyloxy)-7-(furan-3-yl)-13,17-dihydroxy-1,8,12,15,15-pentamethyl-5,14-dioxo-3,6,16-trioxapentacyclo[9.6.0.0²,⁴.0²,⁸.0¹³,¹⁷]heptadecan-12-yl]prop-2-enoate

Description

12Beta-Acetoxyharrisonin belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. methyl (2z)-3-[(1r,2r,4s,7s,8s,9r,11r,12r,13r,17s)-9-(acetyloxy)-7-(furan-3-yl)-13,17-dihydroxy-1,8,12,15,15-pentamethyl-5,14-dioxo-3,6,16-trioxapentacyclo[9.6.0.0²,⁴.0²,⁸.0¹³,¹⁷]heptadecan-12-yl]prop-2-enoate is found in Harrisonia abyssinica. methyl (2z)-3-[(1r,2r,4s,7s,8s,9r,11r,12r,13r,17s)-9-(acetyloxy)-7-(furan-3-yl)-13,17-dihydroxy-1,8,12,15,15-pentamethyl-5,14-dioxo-3,6,16-trioxapentacyclo[9.6.0.0²,⁴.0²,⁸.0¹³,¹⁷]heptadecan-12-yl]prop-2-enoate was first documented in 2001 (PMID: 11720527). Based on a literature review very few articles have been published on 12beta-Acetoxyharrisonin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082223052D          

 41 46  0  0  1  0            999 V2000
    5.8531   -2.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0644   -2.7182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4604   -2.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6451   -1.3521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6718   -2.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0678   -1.8363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2525   -1.0322    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0328   -1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4335   -0.9326    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8115   -1.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0311   -1.2068    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4091   -1.7488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5674   -2.5584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3478   -2.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0546   -3.1004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8728   -0.3972    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2508   -0.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0924   -0.1294    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5296   -0.6714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4568   -1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2158   -1.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7578   -1.1943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3337   -0.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0659    0.6802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5562    1.2222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3978    2.0318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3365    0.9544    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1169    0.6867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4948    0.1448    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2752   -0.1229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.9963    0.2778    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5955    0.9989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3441    1.0259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1631    0.9263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1766    1.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9849    0.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3214    0.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0695   -0.2312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6003   -0.2842    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2043   -0.8461    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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  6  1  6  0  0  0
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  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
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 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
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 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 29 28  1  1  0  0  0
 27 29  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  1  0  0  0  0
  9 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
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 34 35  1  0  0  0  0
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 35 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 32 40  1  0  0  0  0
  7 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  END

     RDKit          3D

 75 80  0  0  0  0  0  0  0  0999 V2000
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    3.3819    1.8576    2.8719 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8825    1.3691    1.6574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2323    0.3707    1.8697 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1898    2.0548    0.4964 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8197    1.7457   -0.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0178    0.6451   -1.1135 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8632    0.9407   -2.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6096    0.5169   -0.6815 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4679    1.2397   -1.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7155    1.1740   -0.4881 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8055    1.4708   -1.3330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3397    2.7736   -1.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4774    3.1312   -2.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0020   -2.2453    3.4988 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4502   -2.4263    0.1412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8365   -1.0803    0.3202 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1759   -0.9181   -0.7599 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6129   -1.2485   -2.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4134   -1.6848   -0.7113 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2879   -2.7496   -1.6433 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8269   -2.2437    0.4583 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2142   -2.3718    0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8009   -2.4745    1.8194 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6814   -3.5570   -0.3563 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6405   -1.1357   -0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7232   -0.5988   -0.1510 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5455   -0.7386   -1.1179 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9293   -1.2056   -2.4153 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2244    2.4928   -1.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1046   -0.5534   -1.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0694   -2.6270    1.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6641   -2.3853   -2.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6806   -0.9585   -1.9355 H   0  0  0  0  0  0  0  0  0  0  0  0
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 41 75  1  0
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M  END


  Mrv1652309082223052D          

 41 46  0  0  1  0            999 V2000
    5.8531   -2.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0644   -2.7182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4604   -2.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6451   -1.3521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0678   -1.8363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2525   -1.0322    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0328   -1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4335   -0.9326    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8115   -1.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4091   -1.7488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2158   -1.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7578   -1.1943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3337   -0.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0659    0.6802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5562    1.2222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3978    2.0318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3365    0.9544    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1169    0.6867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4948    0.1448    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2752   -0.1229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4599    0.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9963    0.2778    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5955    0.9989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3441    1.0259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1631    0.9263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1766    1.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9849    0.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3214    0.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0695   -0.2312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6003   -0.2842    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2043   -0.8461    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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  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  1  0  0  0  0
 19 23  2  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 29 28  1  1  0  0  0
 27 29  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  1  0  0  0  0
  9 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 32 40  1  0  0  0  0
  7 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0273892

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)\C=C/[C@]1(C)[C@H]2C[C@@H](OC(C)=O)[C@@]3(C)[C@@H](OC(=O)[C@H]4O[C@@]34[C@]2(C)[C@]2(O)OC(C)(C)C(=O)[C@]12O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H34O12/c1-14(30)38-17-12-16-24(4,10-8-18(31)36-7)27(34)22(33)23(2,3)41-29(27,35)26(16,6)28-20(40-28)21(32)39-19(25(17,28)5)15-9-11-37-13-15/h8-11,13,16-17,19-20,34-35H,12H2,1-7H3/b10-8-/t16-,17-,19+,20-,24-,25+,26-,27+,28-,29+/m1/s1

> <INCHI_KEY>
HOHMQEBYHJKCEM-BSMXYMBBSA-N

> <FORMULA>
C29H34O12

> <MOLECULAR_WEIGHT>
574.579

> <EXACT_MASS>
574.205026535

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
56.443946392964904

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2Z)-3-[(1R,2R,4S,7R,8S,9R,11R,12R,13R,17S)-9-(acetyloxy)-7-(furan-3-yl)-13,17-dihydroxy-1,8,12,15,15-pentamethyl-5,14-dioxo-3,6,16-trioxapentacyclo[9.6.0.0^{2,4}.0^{2,8}.0^{13,17}]heptadecan-12-yl]prop-2-enoate

> <JCHEM_LOGP>
2.2135756026666673

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.745567910928163

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.244687004125542

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8614827765423976

> <JCHEM_POLAR_SURFACE_AREA>
171.33

> <JCHEM_REFRACTIVITY>
135.62830000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2Z)-3-[(1R,2R,4S,7R,8S,9R,11R,12R,13R,17S)-9-(acetyloxy)-7-(furan-3-yl)-13,17-dihydroxy-1,8,12,15,15-pentamethyl-5,14-dioxo-3,6,16-trioxapentacyclo[9.6.0.0^{2,4}.0^{2,8}.0^{13,17}]heptadecan-12-yl]prop-2-enoate

> <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      10.926  -4.622   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.454  -5.074   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.326  -4.025   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.671  -2.524   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.854  -4.477   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.727  -3.428   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.071  -1.927   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.528  -2.427   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.543  -1.741   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.381  -2.753   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.925  -2.253   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.764  -3.264   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.059  -4.776   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.516  -5.276   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.102  -5.787   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.629  -0.741   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.468  -1.753   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.173  -0.242   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.989  -1.253   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.853  -2.787   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.270  -3.391   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.281  -2.229   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.489  -0.909   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.123   1.270   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.038   2.281   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.743   3.793   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.495   1.782   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.951   1.282   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.790   0.270   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.247  -0.230   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.592   1.271   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.593   0.519   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.845   1.865   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       6.242   1.915   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.771   1.729   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.796   3.269   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.305   1.865   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.067   0.218   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       9.463  -0.432   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       6.721  -0.530   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       7.848  -1.579   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   40                                             
CONECT    8    7                                                            
CONECT    9    7   10   30                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11   17   18   29                                             
CONECT   17   16                                                            
CONECT   18   16   19   24                                                  
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   19                                                       
CONECT   24   18   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27   29                                                       
CONECT   29   28   27   16   30                                             
CONECT   30   29    9   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33   34   40                                             
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36   37   38                                             
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   35   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   32    7   41                                             
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

View in JSmol

Synonyms

Value	Source
12b-Acetoxyharrisonin	Generator
12Β-acetoxyharrisonin	Generator

Chemical Formula

C₂₉H₃₄O₁₂

Average Mass

574.5790 Da

Monoisotopic Mass

574.20503 Da

IUPAC Name

methyl (2Z)-3-[(1R,2R,4S,7R,8S,9R,11R,12R,13R,17S)-9-(acetyloxy)-7-(furan-3-yl)-13,17-dihydroxy-1,8,12,15,15-pentamethyl-5,14-dioxo-3,6,16-trioxapentacyclo[9.6.0.0^{2,4}.0^{2,8}.0^{13,17}]heptadecan-12-yl]prop-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)\C=C/[C@]1(C)[C@H]2C[C@@H](OC(C)=O)[C@@]3(C)[C@@H](OC(=O)[C@H]4O[C@@]34[C@]2(C)[C@]2(O)OC(C)(C)C(=O)[C@]12O)C1=COC=C1

InChI Identifier

InChI=1S/C29H34O12/c1-14(30)38-17-12-16-24(4,10-8-18(31)36-7)27(34)22(33)23(2,3)41-29(27,35)26(16,6)28-20(40-28)21(32)39-19(25(17,28)5)15-9-11-37-13-15/h8-11,13,16-17,19-20,34-35H,12H2,1-7H3/b10-8-/t16-,17-,19+,20-,24-,25+,26-,27+,28-,29+/m1/s1

InChI Key

HOHMQEBYHJKCEM-BSMXYMBBSA-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
Harrisonia abyssinica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Tricarboxylic acid or derivatives
1,4-dioxepane
Delta valerolactone
Dioxepane
Fatty acid ester
Delta_valerolactone
3-furanone
Fatty acyl
Oxane
Cyclic alcohol
Heteroaromatic compound
Furan
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Tetrahydrofuran
Methyl ester
Ketone
Hemiacetal
Carboxylic acid ester
Lactone
Oxacycle
Carboxylic acid derivative
Ether
Oxirane
Dialkyl ether
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Alcohol
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.21	ChemAxon
pKa (Strongest Acidic)	10.24	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	171.33 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	135.63 m³·mol⁻¹	ChemAxon
Polarizability	56.44 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

C00038136

Chemspider ID

4944931

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6440676

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rugutt JK, Rugutt KJ, Berner DK: Limonoids from Nigerian Harrisonia abyssinica and their stimulatory activity against Striga hermonthica seeds. J Nat Prod. 2001 Nov;64(11):1434-8. doi: 10.1021/np0100183. [PubMed:11720527 ]
LOTUS database [Link]

Showing NP-Card for methyl (2z)-3-[(1r,2r,4s,7s,8s,9r,11r,12r,13r,17s)-9-(acetyloxy)-7-(furan-3-yl)-13,17-dihydroxy-1,8,12,15,15-pentamethyl-5,14-dioxo-3,6,16-trioxapentacyclo[9.6.0.0²,⁴.0²,⁸.0¹³,¹⁷]heptadecan-12-yl]prop-2-enoate (NP0273892)

MOL for NP0273892 (methyl (2z)-3-[(1r,2r,4s,7s,8s,9r,11r,12r,13r,17s)-9-(acetyloxy)-7-(furan-3-yl)-13,17-dihydroxy-1,8,12,15,15-pentamethyl-5,14-dioxo-3,6,16-trioxapentacyclo[9.6.0.0²,⁴.0²,⁸.0¹³,¹⁷]heptadecan-12-yl]prop-2-enoate)

3D MOL for NP0273892 (methyl (2z)-3-[(1r,2r,4s,7s,8s,9r,11r,12r,13r,17s)-9-(acetyloxy)-7-(furan-3-yl)-13,17-dihydroxy-1,8,12,15,15-pentamethyl-5,14-dioxo-3,6,16-trioxapentacyclo[9.6.0.0²,⁴.0²,⁸.0¹³,¹⁷]heptadecan-12-yl]prop-2-enoate)

3D SDF for NP0273892 (methyl (2z)-3-[(1r,2r,4s,7s,8s,9r,11r,12r,13r,17s)-9-(acetyloxy)-7-(furan-3-yl)-13,17-dihydroxy-1,8,12,15,15-pentamethyl-5,14-dioxo-3,6,16-trioxapentacyclo[9.6.0.0²,⁴.0²,⁸.0¹³,¹⁷]heptadecan-12-yl]prop-2-enoate)

3D-SDF for NP0273892 (methyl (2z)-3-[(1r,2r,4s,7s,8s,9r,11r,12r,13r,17s)-9-(acetyloxy)-7-(furan-3-yl)-13,17-dihydroxy-1,8,12,15,15-pentamethyl-5,14-dioxo-3,6,16-trioxapentacyclo[9.6.0.0²,⁴.0²,⁸.0¹³,¹⁷]heptadecan-12-yl]prop-2-enoate)

PDB for NP0273892 (methyl (2z)-3-[(1r,2r,4s,7s,8s,9r,11r,12r,13r,17s)-9-(acetyloxy)-7-(furan-3-yl)-13,17-dihydroxy-1,8,12,15,15-pentamethyl-5,14-dioxo-3,6,16-trioxapentacyclo[9.6.0.0²,⁴.0²,⁸.0¹³,¹⁷]heptadecan-12-yl]prop-2-enoate)

3D PDB for NP0273892 (methyl (2z)-3-[(1r,2r,4s,7s,8s,9r,11r,12r,13r,17s)-9-(acetyloxy)-7-(furan-3-yl)-13,17-dihydroxy-1,8,12,15,15-pentamethyl-5,14-dioxo-3,6,16-trioxapentacyclo[9.6.0.0²,⁴.0²,⁸.0¹³,¹⁷]heptadecan-12-yl]prop-2-enoate)

SMILES for NP0273892 (methyl (2z)-3-[(1r,2r,4s,7s,8s,9r,11r,12r,13r,17s)-9-(acetyloxy)-7-(furan-3-yl)-13,17-dihydroxy-1,8,12,15,15-pentamethyl-5,14-dioxo-3,6,16-trioxapentacyclo[9.6.0.0²,⁴.0²,⁸.0¹³,¹⁷]heptadecan-12-yl]prop-2-enoate)

INCHI for NP0273892 (methyl (2z)-3-[(1r,2r,4s,7s,8s,9r,11r,12r,13r,17s)-9-(acetyloxy)-7-(furan-3-yl)-13,17-dihydroxy-1,8,12,15,15-pentamethyl-5,14-dioxo-3,6,16-trioxapentacyclo[9.6.0.0²,⁴.0²,⁸.0¹³,¹⁷]heptadecan-12-yl]prop-2-enoate)

Structure for NP0273892 (methyl (2z)-3-[(1r,2r,4s,7s,8s,9r,11r,12r,13r,17s)-9-(acetyloxy)-7-(furan-3-yl)-13,17-dihydroxy-1,8,12,15,15-pentamethyl-5,14-dioxo-3,6,16-trioxapentacyclo[9.6.0.0²,⁴.0²,⁸.0¹³,¹⁷]heptadecan-12-yl]prop-2-enoate)

3D Structure for NP0273892 (methyl (2z)-3-[(1r,2r,4s,7s,8s,9r,11r,12r,13r,17s)-9-(acetyloxy)-7-(furan-3-yl)-13,17-dihydroxy-1,8,12,15,15-pentamethyl-5,14-dioxo-3,6,16-trioxapentacyclo[9.6.0.0²,⁴.0²,⁸.0¹³,¹⁷]heptadecan-12-yl]prop-2-enoate)