NP-MRD: Showing NP-Card for methyl (1ar,3as,4r,5r,5's,7s,7as,7bs)-7-(acetyloxy)-5'-(furan-3-yl)-5,7a-dimethyl-2'-oxo-hexahydro-1ah-spiro[naphtho[1,2-b]oxirene-4,3'-oxolane]-7b-carboxylate (NP0158587)

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Record Information

Version

2.0

Created at

2022-09-02 16:12:21 UTC

Updated at

2022-09-02 16:12:21 UTC

NP-MRD ID

NP0158587

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1ar,3as,4r,5r,5's,7s,7as,7bs)-7-(acetyloxy)-5'-(furan-3-yl)-5,7a-dimethyl-2'-oxo-hexahydro-1ah-spiro[naphtho[1,2-b]oxirene-4,3'-oxolane]-7b-carboxylate

Description

Methyl (1aS,1bS,2S,4R,5R,5'S,5aS,7aR)-2-(acetyloxy)-5'-(furan-3-yl)-1b,4-dimethyl-2'-oxo-octahydro-1aH-spiro[naphtho[1,2-b]oxirene-5,3'-oxolane]-1a-carboxylate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. methyl (1ar,3as,4r,5r,5's,7s,7as,7bs)-7-(acetyloxy)-5'-(furan-3-yl)-5,7a-dimethyl-2'-oxo-hexahydro-1ah-spiro[naphtho[1,2-b]oxirene-4,3'-oxolane]-7b-carboxylate is found in Croton lechleri. Based on a literature review very few articles have been published on methyl (1aS,1bS,2S,4R,5R,5'S,5aS,7aR)-2-(acetyloxy)-5'-(furan-3-yl)-1b,4-dimethyl-2'-oxo-octahydro-1aH-spiro[naphtho[1,2-b]oxirene-5,3'-oxolane]-1a-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022218122D          

 31 35  0  0  1  0            999 V2000
    6.1694   -2.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8739   -1.6205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0591   -1.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0157   -2.3151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7636   -0.7210    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5338   -0.4255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8928    0.0938    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2518    0.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4815    0.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.4972    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9933   -1.0165    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6343   -1.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8641   -1.8313    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5051   -2.3506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3759   -3.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0169   -3.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6056   -3.4609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0938   -2.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4528   -1.6075    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6825   -1.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5820   -0.7927    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7851   -1.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3359   -0.3140    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5120   -0.2707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0073   -0.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7774   -0.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7341    0.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0628    0.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8552    0.3270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6254    0.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1447    0.6722    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
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  1  6  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  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  2  0  0  0  0
M  END

     RDKit          3D

 59 63  0  0  0  0  0  0  0  0999 V2000
   -4.9491    1.2983    2.5806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2989    1.4551    1.3236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9494    1.1735    1.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3350    0.7783    2.1863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2290    1.3201   -0.1091 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9389    1.9305   -1.1503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9083    2.6568   -0.5110 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6654    2.8733   -1.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141    2.0316   -0.8692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1325    0.8049   -0.0663 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1905    0.2759   -0.5355 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2415    0.2330   -2.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819   -1.0334    0.0117 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4027   -1.7243   -0.9556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6786   -2.1184   -0.6108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5752   -2.8367   -1.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1188   -1.8684    0.5581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4574   -1.9878    0.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7675   -1.3457    0.8884 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8337   -2.3991    1.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2300   -0.1839    0.0339 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4186    0.4428    0.7368 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4350    0.7183   -0.3478 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8206    0.4428    0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917   -0.7673    0.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7840   -0.5131    0.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9108    0.7805    0.6956 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7846    1.3892    0.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0036   -0.0007   -1.4854 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8122   -0.6589   -1.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3333   -1.5350   -1.9668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7162    2.1644    3.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0299    1.2703    2.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5348    0.3841    3.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3583    3.5129    0.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8111    2.8577   -2.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3762    3.9638   -1.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1832    2.6430   -0.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1359    1.7662   -1.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0476    1.1894    0.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3139    0.5655   -2.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5057   -0.8210   -2.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0731    0.8403   -2.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2002   -0.9583    0.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5499   -2.3870   -2.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6156   -2.8087   -1.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2794   -3.9041   -1.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8361   -2.7199    1.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2343   -2.5933   -0.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5054   -0.9248    1.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5164   -3.3500    0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8104   -2.0905    0.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9467   -2.6397    2.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1718    1.3841    1.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8733   -0.2300    1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3845    1.8040   -0.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0640   -1.7384   -0.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5767   -1.2585    0.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5627    2.4465    0.4358 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
  5  3  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 21  1  0
 21 22  1  0
 22 23  1  0
 23 29  1  0
 29 30  1  0
 30 31  2  0
 23 24  1  0
 24 28  2  0
 28 27  1  0
 27 26  1  0
 26 25  2  0
 21 19  1  0
 19 20  1  0
 19 18  1  0
 18 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 13 11  1  0
 11 12  1  6
  7  5  1  0
 11 10  1  0
 11  5  1  0
 21 30  1  6
 25 24  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  7 35  1  1
  8 36  1  0
  8 37  1  0
  9 38  1  0
  9 39  1  0
 10 40  1  1
 22 54  1  0
 22 55  1  0
 23 56  1  6
 28 59  1  0
 26 58  1  0
 25 57  1  0
 19 50  1  1
 20 51  1  0
 20 52  1  0
 20 53  1  0
 18 48  1  0
 18 49  1  0
 13 44  1  1
 16 45  1  0
 16 46  1  0
 16 47  1  0
 12 41  1  0
 12 42  1  0
 12 43  1  0
M  END


  Mrv1652309022218122D          

 31 35  0  0  1  0            999 V2000
    6.1694   -2.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8739   -1.6205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0591   -1.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0157   -2.3151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7636   -0.7210    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5338   -0.4255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8928    0.0938    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2518    0.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4815    0.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.4972    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9933   -1.0165    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6343   -1.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8641   -1.8313    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5051   -2.3506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3759   -3.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0169   -3.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6056   -3.4609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0938   -2.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4528   -1.6075    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6825   -1.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5820   -0.7927    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7851   -1.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3359   -0.3140    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5120   -0.2707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0073   -0.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7774   -0.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7341    0.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0628    0.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8552    0.3270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6254    0.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1447    0.6722    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
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  1  6  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  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0158587

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]12O[C@@H]1CC[C@@H]1[C@@]3(C[C@H](OC3=O)C3=COC=C3)[C@H](C)C[C@H](OC(C)=O)[C@@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O8/c1-12-9-18(29-13(2)24)21(3)16(5-6-17-23(21,31-17)20(26)27-4)22(12)10-15(30-19(22)25)14-7-8-28-11-14/h7-8,11-12,15-18H,5-6,9-10H2,1-4H3/t12-,15+,16+,17-,18+,21+,22-,23+/m1/s1

> <INCHI_KEY>
WOQMXORMRSBKNO-LFENPUTESA-N

> <FORMULA>
C23H28O8

> <MOLECULAR_WEIGHT>
432.469

> <EXACT_MASS>
432.178417862

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
43.93376704294613

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1aR,3aS,4R,5R,5'S,7S,7aS,7bS)-7-(acetyloxy)-5'-(furan-3-yl)-5,7a-dimethyl-2'-oxo-octahydro-1aH-spiro[naphtho[1,2-b]oxirene-4,3'-oxolane]-7b-carboxylate

> <ALOGPS_LOGP>
2.86

> <JCHEM_LOGP>
2.547861277333332

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.87227966871932

> <JCHEM_POLAR_SURFACE_AREA>
104.57

> <JCHEM_REFRACTIVITY>
104.62869999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.09e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1aR,3aS,4R,5R,5'S,7S,7aS,7bS)-7-(acetyloxy)-5'-(furan-3-yl)-5,7a-dimethyl-2'-oxo-hexahydro-1aH-spiro[naphtho[1,2-b]oxirene-4,3'-oxolane]-7b-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      11.516  -4.463   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.965  -3.025   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.444  -2.784   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.363  -4.322   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.892  -1.346   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.330  -0.794   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.133   0.175   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.937   1.145   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.499   0.593   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -0.928   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.454  -1.897   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.651  -2.867   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.213  -3.418   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.410  -4.388   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.168  -5.909   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.365  -6.878   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.730  -6.460   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.775  -3.970   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.579  -3.001   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.141  -3.552   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.820  -1.480   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.332  -1.878   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.494  -0.586   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.956  -0.505   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.014  -1.702   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.451  -1.150   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.370   0.388   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.117   0.786   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.463   0.610   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.901   0.058   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.870   1.255   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    7   11                                             
CONECT    6    5    7                                                       
CONECT    7    6    5    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   21                                                  
CONECT   11   10    5   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   10   22   30                                             
CONECT   22   21   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24                                                       
CONECT   29   23   30                                                       
CONECT   30   29   21   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1as,1BS,2S,4R,5R,5's,5as,7ar)-2-(acetyloxy)-5'-(furan-3-yl)-1b,4-dimethyl-2'-oxo-octahydro-1ah-spiro[naphtho[1,2-b]oxirene-5,3'-oxolane]-1a-carboxylic acid	Generator

Chemical Formula

C₂₃H₂₈O₈

Average Mass

432.4690 Da

Monoisotopic Mass

432.17842 Da

IUPAC Name

methyl (1aR,3aS,4R,5R,5'S,7S,7aS,7bS)-7-(acetyloxy)-5'-(furan-3-yl)-5,7a-dimethyl-2'-oxo-octahydro-1aH-spiro[naphtho[1,2-b]oxirene-4,3'-oxolane]-7b-carboxylate

Traditional Name

methyl (1aR,3aS,4R,5R,5'S,7S,7aS,7bS)-7-(acetyloxy)-5'-(furan-3-yl)-5,7a-dimethyl-2'-oxo-hexahydro-1aH-spiro[naphtho[1,2-b]oxirene-4,3'-oxolane]-7b-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]12O[C@@H]1CC[C@@H]1[C@@]3(C[C@H](OC3=O)C3=COC=C3)[C@H](C)C[C@H](OC(C)=O)[C@@]21C

InChI Identifier

InChI=1S/C23H28O8/c1-12-9-18(29-13(2)24)21(3)16(5-6-17-23(21,31-17)20(26)27-4)22(12)10-15(30-19(22)25)14-7-8-28-11-14/h7-8,11-12,15-18H,5-6,9-10H2,1-4H3/t12-,15+,16+,17-,18+,21+,22-,23+/m1/s1

InChI Key

WOQMXORMRSBKNO-LFENPUTESA-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
Croton lechleri	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Clerodane diterpenoid
Tricarboxylic acid or derivatives
Oxepane
Gamma butyrolactone
Oxirane carboxylic acid or derivatives
Oxirane carboxylic acid
Heteroaromatic compound
Furan
Methyl ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
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	2.86	ALOGPS
logP	2.55	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	104.57 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	104.63 m³·mol⁻¹	ChemAxon
Polarizability	43.93 Å³	ChemAxon
Number of Rings	5	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

8201367

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10025796

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1ar,3as,4r,5r,5's,7s,7as,7bs)-7-(acetyloxy)-5'-(furan-3-yl)-5,7a-dimethyl-2'-oxo-hexahydro-1ah-spiro[naphtho[1,2-b]oxirene-4,3'-oxolane]-7b-carboxylate (NP0158587)

MOL for NP0158587 (methyl (1ar,3as,4r,5r,5's,7s,7as,7bs)-7-(acetyloxy)-5'-(furan-3-yl)-5,7a-dimethyl-2'-oxo-hexahydro-1ah-spiro[naphtho[1,2-b]oxirene-4,3'-oxolane]-7b-carboxylate)

3D MOL for NP0158587 (methyl (1ar,3as,4r,5r,5's,7s,7as,7bs)-7-(acetyloxy)-5'-(furan-3-yl)-5,7a-dimethyl-2'-oxo-hexahydro-1ah-spiro[naphtho[1,2-b]oxirene-4,3'-oxolane]-7b-carboxylate)

3D SDF for NP0158587 (methyl (1ar,3as,4r,5r,5's,7s,7as,7bs)-7-(acetyloxy)-5'-(furan-3-yl)-5,7a-dimethyl-2'-oxo-hexahydro-1ah-spiro[naphtho[1,2-b]oxirene-4,3'-oxolane]-7b-carboxylate)

3D-SDF for NP0158587 (methyl (1ar,3as,4r,5r,5's,7s,7as,7bs)-7-(acetyloxy)-5'-(furan-3-yl)-5,7a-dimethyl-2'-oxo-hexahydro-1ah-spiro[naphtho[1,2-b]oxirene-4,3'-oxolane]-7b-carboxylate)

PDB for NP0158587 (methyl (1ar,3as,4r,5r,5's,7s,7as,7bs)-7-(acetyloxy)-5'-(furan-3-yl)-5,7a-dimethyl-2'-oxo-hexahydro-1ah-spiro[naphtho[1,2-b]oxirene-4,3'-oxolane]-7b-carboxylate)

3D PDB for NP0158587 (methyl (1ar,3as,4r,5r,5's,7s,7as,7bs)-7-(acetyloxy)-5'-(furan-3-yl)-5,7a-dimethyl-2'-oxo-hexahydro-1ah-spiro[naphtho[1,2-b]oxirene-4,3'-oxolane]-7b-carboxylate)

SMILES for NP0158587 (methyl (1ar,3as,4r,5r,5's,7s,7as,7bs)-7-(acetyloxy)-5'-(furan-3-yl)-5,7a-dimethyl-2'-oxo-hexahydro-1ah-spiro[naphtho[1,2-b]oxirene-4,3'-oxolane]-7b-carboxylate)

INCHI for NP0158587 (methyl (1ar,3as,4r,5r,5's,7s,7as,7bs)-7-(acetyloxy)-5'-(furan-3-yl)-5,7a-dimethyl-2'-oxo-hexahydro-1ah-spiro[naphtho[1,2-b]oxirene-4,3'-oxolane]-7b-carboxylate)

Structure for NP0158587 (methyl (1ar,3as,4r,5r,5's,7s,7as,7bs)-7-(acetyloxy)-5'-(furan-3-yl)-5,7a-dimethyl-2'-oxo-hexahydro-1ah-spiro[naphtho[1,2-b]oxirene-4,3'-oxolane]-7b-carboxylate)

3D Structure for NP0158587 (methyl (1ar,3as,4r,5r,5's,7s,7as,7bs)-7-(acetyloxy)-5'-(furan-3-yl)-5,7a-dimethyl-2'-oxo-hexahydro-1ah-spiro[naphtho[1,2-b]oxirene-4,3'-oxolane]-7b-carboxylate)