NP-MRD: Showing NP-Card for (1s,3's,5ar,7ar,8r,9s,11ar,11br)-1-(acetyloxy)-9-[(s)-furan-3-yl({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-hexahydro-1h-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid (NP0198729)

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Record Information

Version

1.0

Created at

2022-09-04 17:13:20 UTC

Updated at

2022-09-04 17:13:20 UTC

NP-MRD ID

NP0198729

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3's,5ar,7ar,8r,9s,11ar,11br)-1-(acetyloxy)-9-[(s)-furan-3-yl({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-hexahydro-1h-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid

Description

(1S,3'S,5aR,7aR,8R,9S,11aR,11bR)-1-(acetyloxy)-9-[(R)-(furan-3-yl)({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-dodecahydro-1H-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid 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. (1s,3's,5ar,7ar,8r,9s,11ar,11br)-1-(acetyloxy)-9-[(s)-furan-3-yl({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-hexahydro-1h-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid is found in Citrus aurantium. Based on a literature review very few articles have been published on (1S,3'S,5aR,7aR,8R,9S,11aR,11bR)-1-(acetyloxy)-9-[(R)-(furan-3-yl)({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-dodecahydro-1H-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042219132D          

 49 54  0  0  1  0            999 V2000
    0.2203   -1.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0385   -1.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3557   -2.6438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5394   -1.2267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2221   -0.4651    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3984   -0.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0804    0.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8935    0.1115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1464    1.0446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9080    1.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4565    1.9781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292    2.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6308    0.9642    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2651    1.4918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0391    1.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6733    1.7340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1789    0.3933    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8131    0.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5447   -0.1343    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6845   -0.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4586   -1.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0928   -0.7052    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8692   -0.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5023   -1.4214    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3273   -1.4249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7367   -2.1411    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3212   -2.8538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7307   -3.5700    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3152   -4.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7246   -4.9990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5557   -3.5735    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9652   -4.2897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9712   -2.8608    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7962   -2.8643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5617   -2.1446    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.0867   -2.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4191   -2.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037   -3.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2659   -2.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9530    0.1079    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2384    0.8819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7660    0.2477    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5401   -0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6799   -0.8508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1743    0.4899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7706    0.1511    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9708   -0.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  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  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
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 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  6  0  0  0
 24 25  1  1  0  0  0
 26 25  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 26 35  1  0  0  0  0
 35 36  1  6  0  0  0
 24 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 37 41  2  0  0  0  0
 22 42  1  0  0  0  0
 17 42  1  0  0  0  0
 42 43  1  6  0  0  0
 43 44  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  6  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
 19 48  1  0  0  0  0
  5 48  1  0  0  0  0
 13 48  1  0  0  0  0
 48 49  1  6  0  0  0
M  END

     RDKit          3D

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   -4.3122   -2.0608   -1.5171 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4588    0.9994    1.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5178    0.2682   -0.8894 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6120    0.1551   -2.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7426   -1.3590   -0.4720 C   0  0  1  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
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 35 26  1  0
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  1 50  1  0
  1 51  1  0
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 35 86  1  1
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 41 90  1  0
 39 89  1  0
 38 88  1  0
 44 91  1  1
 47 92  1  0
 49 93  1  0
 49 94  1  0
 49 95  1  0
M  END


  Mrv1652309042219132D          

 49 54  0  0  1  0            999 V2000
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    1.0385   -1.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3557   -2.6438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5394   -1.2267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2221   -0.4651    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3984   -0.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0804    0.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8935    0.1115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1464    1.0446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9080    1.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4565    1.9781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292    2.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6308    0.9642    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2651    1.4918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0391    1.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6733    1.7340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1789    0.3933    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8131    0.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5447   -0.1343    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6845   -0.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4586   -1.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0928   -0.7052    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8692   -0.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5023   -1.4214    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3273   -1.4249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7367   -2.1411    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3212   -2.8538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7307   -3.5700    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3152   -4.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7246   -4.9990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5557   -3.5735    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9652   -4.2897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9712   -2.8608    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7962   -2.8643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5617   -2.1446    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9772   -1.4319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0867   -2.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4191   -2.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037   -3.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0910   -3.0231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2659   -2.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9530    0.1079    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2384    0.8819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7660    0.2477    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5401   -0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6799   -0.8508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1743    0.4899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7706    0.1511    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9708   -0.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  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  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 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  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  6  0  0  0
 24 25  1  1  0  0  0
 26 25  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 26 35  1  0  0  0  0
 35 36  1  6  0  0  0
 24 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 37 41  2  0  0  0  0
 22 42  1  0  0  0  0
 17 42  1  0  0  0  0
 42 43  1  6  0  0  0
 43 44  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  6  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
 19 48  1  0  0  0  0
  5 48  1  0  0  0  0
 13 48  1  0  0  0  0
 48 49  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0198729

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1CC(=O)OC(C)(C)[C@@H]2CC(=O)[C@]3(C)[C@H](CC[C@@](C)([C@@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C4=COC=C4)[C@@]33O[C@@H]3C(O)=O)[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C34H46O15/c1-15(36)45-21-12-22(38)48-30(2,3)19-11-20(37)33(6)18(32(19,21)5)7-9-31(4,34(33)27(49-34)28(42)43)26(16-8-10-44-14-16)47-29-25(41)24(40)23(39)17(13-35)46-29/h8,10,14,17-19,21,23-27,29,35,39-41H,7,9,11-13H2,1-6H3,(H,42,43)/t17-,18-,19+,21+,23-,24+,25-,26+,27-,29+,31+,32-,33+,34-/m1/s1

> <INCHI_KEY>
GIVMXHQLQAIYEX-ANSWNMHUSA-N

> <FORMULA>
C34H46O15

> <MOLECULAR_WEIGHT>
694.727

> <EXACT_MASS>
694.283670781

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
95

> <JCHEM_AVERAGE_POLARIZABILITY>
68.80557490127202

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3'S,5aR,7aR,8R,9S,11aR,11bR)-1-(acetyloxy)-9-[(R)-(furan-3-yl)({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-dodecahydro-1H-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid

> <JCHEM_LOGP>
0.5820773653333312

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.210049101105058

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.941123429831346

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8886742628528506

> <JCHEM_POLAR_SURFACE_AREA>
232.01999999999998

> <JCHEM_REFRACTIVITY>
161.51160000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3'S,5aR,7aR,8R,9S,11aR,11bR)-1-(acetyloxy)-9-[(R)-furan-3-yl({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-hexahydro-1H-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid

> <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       0.411  -3.315   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.938  -3.513   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.531  -4.935   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.874  -2.290   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.281  -0.868   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.744  -0.785   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.150   0.469   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.668   0.208   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.273   1.950   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.695   2.542   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.719   3.692   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.801   3.796   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.044   1.800   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.228   2.785   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.673   2.252   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.857   3.237   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.934   0.734   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.118   1.719   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.750  -0.251   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.011  -1.768   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.456  -2.301   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.640  -1.316   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.089  -0.796   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.404  -2.653   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.944  -2.660   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.709  -3.997   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.933  -5.327   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      10.697  -6.664   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.922  -7.994   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.686  -9.331   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.237  -6.671   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      13.002  -8.007   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      13.013  -5.340   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      14.553  -5.347   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      12.249  -4.003   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      13.024  -2.673   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.629  -3.984   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.249  -5.393   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.100  -6.419   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       5.770  -5.643   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       6.096  -4.138   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       7.379   0.201   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       7.912   1.646   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       8.897   0.462   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      10.341  -0.070   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      10.602  -1.588   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      11.525   0.914   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       3.305   0.282   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       3.679  -1.212   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   48                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14   48                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   42                                             
CONECT   18   17                                                            
CONECT   19   17   20   48                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   42                                             
CONECT   23   22                                                            
CONECT   24   22   25   37                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   35                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   26   36                                                  
CONECT   36   35                                                            
CONECT   37   24   38   41                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   37                                                       
CONECT   42   22   17   43   44                                             
CONECT   43   42   44                                                       
CONECT   44   43   42   45                                                  
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45                                                            
CONECT   48   19    5   13   49                                             
CONECT   49   48                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  108    0
END

View in JSmol

Synonyms

Value	Source
(1S,3's,5AR,7ar,8R,9S,11ar,11BR)-1-(acetyloxy)-9-[(R)-(furan-3-yl)({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-dodecahydro-1H-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylate	Generator

Chemical Formula

C₃₄H₄₆O₁₅

Average Mass

694.7270 Da

Monoisotopic Mass

694.28367 Da

IUPAC Name

Traditional Name

(1S,3'S,5aR,7aR,8R,9S,11aR,11bR)-1-(acetyloxy)-9-[(R)-furan-3-yl({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-hexahydro-1H-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1CC(=O)OC(C)(C)[C@@H]2CC(=O)[C@]3(C)[C@H](CC[C@@](C)([C@@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C4=COC=C4)[C@@]33O[C@@H]3C(O)=O)[C@@]12C

InChI Identifier

InChI=1S/C34H46O15/c1-15(36)45-21-12-22(38)48-30(2,3)19-11-20(37)33(6)18(32(19,21)5)7-9-31(4,34(33)27(49-34)28(42)43)26(16-8-10-44-14-16)47-29-25(41)24(40)23(39)17(13-35)46-29/h8,10,14,17-19,21,23-27,29,35,39-41H,7,9,11-13H2,1-6H3,(H,42,43)/t17-,18-,19+,21+,23-,24+,25-,26+,27-,29+,31+,32-,33+,34-/m1/s1

InChI Key

GIVMXHQLQAIYEX-ANSWNMHUSA-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
Citrus aurantium	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
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Tricarboxylic acid or derivatives
Caprolactone
Oxepane
Oxirane carboxylic acid or derivatives
Oxirane carboxylic acid
Monosaccharide
Oxane
Furan
Heteroaromatic compound
Secondary alcohol
Ketone
Lactone
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Polyol
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organic oxygen compound
Organooxygen 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	0.58	ChemAxon
pKa (Strongest Acidic)	3.94	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	232.02 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	161.51 m³·mol⁻¹	ChemAxon
Polarizability	68.81 Å³	ChemAxon
Number of Rings	6	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

Not Available

METLIN ID

Not Available

PubChem Compound

162872861

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3's,5ar,7ar,8r,9s,11ar,11br)-1-(acetyloxy)-9-[(s)-furan-3-yl({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-hexahydro-1h-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid (NP0198729)

MOL for NP0198729 ((1s,3's,5ar,7ar,8r,9s,11ar,11br)-1-(acetyloxy)-9-[(s)-furan-3-yl({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-hexahydro-1h-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid)

3D MOL for NP0198729 ((1s,3's,5ar,7ar,8r,9s,11ar,11br)-1-(acetyloxy)-9-[(s)-furan-3-yl({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-hexahydro-1h-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid)

3D SDF for NP0198729 ((1s,3's,5ar,7ar,8r,9s,11ar,11br)-1-(acetyloxy)-9-[(s)-furan-3-yl({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-hexahydro-1h-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid)

3D-SDF for NP0198729 ((1s,3's,5ar,7ar,8r,9s,11ar,11br)-1-(acetyloxy)-9-[(s)-furan-3-yl({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-hexahydro-1h-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid)

PDB for NP0198729 ((1s,3's,5ar,7ar,8r,9s,11ar,11br)-1-(acetyloxy)-9-[(s)-furan-3-yl({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-hexahydro-1h-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid)

3D PDB for NP0198729 ((1s,3's,5ar,7ar,8r,9s,11ar,11br)-1-(acetyloxy)-9-[(s)-furan-3-yl({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-hexahydro-1h-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid)

SMILES for NP0198729 ((1s,3's,5ar,7ar,8r,9s,11ar,11br)-1-(acetyloxy)-9-[(s)-furan-3-yl({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-hexahydro-1h-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid)

INCHI for NP0198729 ((1s,3's,5ar,7ar,8r,9s,11ar,11br)-1-(acetyloxy)-9-[(s)-furan-3-yl({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-hexahydro-1h-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid)

Structure for NP0198729 ((1s,3's,5ar,7ar,8r,9s,11ar,11br)-1-(acetyloxy)-9-[(s)-furan-3-yl({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-hexahydro-1h-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid)

3D Structure for NP0198729 ((1s,3's,5ar,7ar,8r,9s,11ar,11br)-1-(acetyloxy)-9-[(s)-furan-3-yl({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-hexahydro-1h-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid)