NP-MRD: Showing NP-Card for (1s,2r,5s,6s,7r,8r,9r,12r)-5-(acetyloxy)-8,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl furan-3-carboxylate (NP0220262)

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Record Information

Version

1.0

Created at

2022-09-05 21:31:29 UTC

Updated at

2022-09-05 21:31:29 UTC

NP-MRD ID

NP0220262

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,5s,6s,7r,8r,9r,12r)-5-(acetyloxy)-8,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl furan-3-carboxylate

Description

(3R,9aS,10R)-2,2,5abeta,9beta-Tetramethyl-3,4,5,5a,6,7,8,9-octahydro-2H-3,9a-methano-1-benzoxepin-4beta,5alpha,6beta,10-tetrol 5-(furan-3-carboxylate)6-acetate belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene). (1s,2r,5s,6s,7r,8r,9r,12r)-5-(acetyloxy)-8,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl furan-3-carboxylate is found in Maytenus boaria. It was first documented in 2022 (PMID: 36075691). Based on a literature review a significant number of articles have been published on (3R,9aS,10R)-2,2,5abeta,9beta-Tetramethyl-3,4,5,5a,6,7,8,9-octahydro-2H-3,9a-methano-1-benzoxepin-4beta,5alpha,6beta,10-tetrol 5-(furan-3-carboxylate)6-acetate (PMID: 36075690) (PMID: 36075689) (PMID: 36075688) (PMID: 36075687).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052223312D          

 30 33  0  0  1  0            999 V2000
    5.1773   -2.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7927   -1.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2326   -1.0007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9683   -1.6668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5838   -0.9369    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0331   -0.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6599    0.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8351    0.5561    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4857    1.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349   -0.1234    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6531    0.4578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8934    0.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1047   -0.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5700    0.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0588   -0.8122    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4269   -1.5948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9576   -2.2733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2845   -1.6626    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6599   -2.3973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2114   -3.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3874   -3.0475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5868   -3.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2131   -4.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7971   -5.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5318   -4.7671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4017   -3.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7420   -0.9114    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1352   -1.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7368   -0.5133    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1297   -1.2387    0.0000 O   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  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 15 12  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 26  2  0  0  0  0
 18 27  1  0  0  0  0
  5 27  1  0  0  0  0
 10 27  1  0  0  0  0
 27 28  1  6  0  0  0
 15 29  1  0  0  0  0
 10 29  1  0  0  0  0
 29 30  1  6  0  0  0
M  END

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
    1.1652    4.7382   -0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4063    3.5256    0.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3149    3.2371    1.6084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2090    2.7025   -0.5522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9240    1.5573   -0.1037 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4354    1.8959   -0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2426    0.7429    0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4205   -0.4190    0.6907 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4382   -1.4185    1.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3162   -0.8604   -0.1568 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3386   -1.4569    0.6776 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0691   -2.6401    0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7184   -3.8702    0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5044   -3.0361    0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1169   -2.4139   -1.3210 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8526   -1.4077   -1.7783 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9295   -1.4278   -3.1701 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.0122   -1.2461 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5540    0.2941   -0.1989 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6265    1.1755   -0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8136    1.7304   -1.3807 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    1.4520    0.8785 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4373    0.9545    2.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4706    1.5240    2.8738 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0953    2.3226    2.0483 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5529    2.3173    0.8579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7057    0.3406   -0.9103 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3751    0.5429   -2.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5582   -1.8726   -1.2174 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3945   -2.9149   -0.8989 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2363    4.4930    0.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8685    5.0566   -1.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514    5.5542    0.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8213    1.4643    0.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6624    2.2351   -1.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545    2.8068    0.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0461    0.4140   -0.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8369    1.0890    1.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9647   -0.0266    1.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2318   -0.7901    1.6835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0133   -1.9115    0.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0943   -2.0838    1.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1168   -4.5448    1.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6328   -3.6906    1.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8272   -4.5243   -0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1281   -2.1656    0.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9725   -3.4921   -0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6127   -3.8239    1.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0600   -3.3251   -1.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8793   -1.7324   -1.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4716   -0.7022   -3.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0361    0.6497   -2.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6897    0.2368    2.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6849    1.3183    3.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8949    2.9003    0.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4352    0.3951   -2.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8796    0.0094   -3.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1754    1.6312   -2.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8121   -1.5260   -2.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9446   -3.2181   -1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5 27  1  0
 27 28  1  6
 27 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 26  2  0
 26 25  1  0
 25 24  1  0
 24 23  2  0
 18 16  1  0
 16 17  1  0
 16 15  1  0
 15 29  1  0
 29 30  1  0
 29 10  1  0
 10 11  1  1
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 12 13  1  0
 12 14  1  0
 10  8  1  0
 10 27  1  0
 23 22  1  0
 12 15  1  0
  9 40  1  0
  9 41  1  0
  9 42  1  0
  8 39  1  1
  7 37  1  0
  7 38  1  0
  6 35  1  0
  6 36  1  0
  5 34  1  1
  1 31  1  0
  1 32  1  0
  1 33  1  0
 28 56  1  0
 28 57  1  0
 28 58  1  0
 18 52  1  6
 26 55  1  0
 24 54  1  0
 23 53  1  0
 16 50  1  1
 17 51  1  0
 15 49  1  6
 29 59  1  6
 30 60  1  0
 13 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 14 48  1  0
M  END


  Mrv1652309052223312D          

 30 33  0  0  1  0            999 V2000
    5.1773   -2.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7927   -1.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2326   -1.0007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9683   -1.6668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5838   -0.9369    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0331   -0.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6599    0.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8351    0.5561    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4857    1.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349   -0.1234    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6531    0.4578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8934    0.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1047   -0.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5700    0.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0588   -0.8122    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4269   -1.5948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9576   -2.2733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2845   -1.6626    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6599   -2.3973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2114   -3.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3874   -3.0475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5868   -3.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2131   -4.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7971   -5.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5318   -4.7671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4017   -3.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7420   -0.9114    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1352   -1.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7368   -0.5133    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1297   -1.2387    0.0000 O   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  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 15 12  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 26  2  0  0  0  0
 18 27  1  0  0  0  0
  5 27  1  0  0  0  0
 10 27  1  0  0  0  0
 27 28  1  6  0  0  0
 15 29  1  0  0  0  0
 10 29  1  0  0  0  0
 29 30  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0220262

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@H](OC(C)=O)[C@@]2(C)[C@@H](OC(=O)C3=COC=C3)[C@H](O)[C@@H]3[C@@H](O)[C@]12OC3(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O8/c1-11-6-7-14(28-12(2)23)21(5)18(29-19(26)13-8-9-27-10-13)16(24)15-17(25)22(11,21)30-20(15,3)4/h8-11,14-18,24-25H,6-7H2,1-5H3/t11-,14+,15-,16-,17-,18+,21+,22-/m1/s1

> <INCHI_KEY>
LNDWEPPMGLXUIC-BPQRXJEKSA-N

> <FORMULA>
C22H30O8

> <MOLECULAR_WEIGHT>
422.474

> <EXACT_MASS>
422.194067926

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
42.86776849130167

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,5S,6S,7R,8R,9R,12R)-5-(acetyloxy)-8,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl furan-3-carboxylate

> <JCHEM_LOGP>
1.7276085756666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.056750893387914

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.343409640434302

> <JCHEM_PKA_STRONGEST_BASIC>
-3.051431779698285

> <JCHEM_POLAR_SURFACE_AREA>
115.43

> <JCHEM_REFRACTIVITY>
103.30629999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,6S,7R,8R,9R,12R)-5-(acetyloxy)-8,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl furan-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       9.664  -4.533   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.946  -3.171   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       9.767  -1.868   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.408  -3.111   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.690  -1.749   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.528  -0.443   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.832   0.943   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.292   1.038   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.640   2.433   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.358  -0.230   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.086   0.855   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.668   0.065   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.195  -0.387   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.064   1.482   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.976  -1.516   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.664  -2.977   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.788  -4.244   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.264  -3.104   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.965  -4.475   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.128  -5.767   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.590  -5.689   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.829  -7.139   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.131  -8.512   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.221  -9.599   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.593  -8.899   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.350  -7.378   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.118  -1.701   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.852  -3.055   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.242  -0.958   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.976  -2.312   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   27   29                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16   29                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   22                                                       
CONECT   27   18    5   10   28                                             
CONECT   28   27                                                            
CONECT   29   15   10   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
(3R,9AS,10R)-2,2,5abeta,9b-tetramethyl-3,4,5,5a,6,7,8,9-octahydro-2H-3,9a-methano-1-benzoxepin-4b,5a,6b,10-tetrol 5-(furan-3-carboxylate)6-acetate	Generator
(3R,9AS,10R)-2,2,5abeta,9b-tetramethyl-3,4,5,5a,6,7,8,9-octahydro-2H-3,9a-methano-1-benzoxepin-4b,5a,6b,10-tetrol 5-(furan-3-carboxylic acid)6-acetic acid	Generator
(3R,9AS,10R)-2,2,5abeta,9beta-tetramethyl-3,4,5,5a,6,7,8,9-octahydro-2H-3,9a-methano-1-benzoxepin-4beta,5alpha,6beta,10-tetrol 5-(furan-3-carboxylic acid)6-acetic acid	Generator
(3R,9AS,10R)-2,2,5abeta,9β-tetramethyl-3,4,5,5a,6,7,8,9-octahydro-2H-3,9a-methano-1-benzoxepin-4β,5α,6β,10-tetrol 5-(furan-3-carboxylate)6-acetate	Generator
(3R,9AS,10R)-2,2,5abeta,9β-tetramethyl-3,4,5,5a,6,7,8,9-octahydro-2H-3,9a-methano-1-benzoxepin-4β,5α,6β,10-tetrol 5-(furan-3-carboxylic acid)6-acetic acid	Generator

Chemical Formula

C₂₂H₃₀O₈

Average Mass

422.4740 Da

Monoisotopic Mass

422.19407 Da

IUPAC Name

(1S,2R,5S,6S,7R,8R,9R,12R)-5-(acetyloxy)-8,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl furan-3-carboxylate

Traditional Name

(1S,2R,5S,6S,7R,8R,9R,12R)-5-(acetyloxy)-8,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl furan-3-carboxylate

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@H](OC(C)=O)[C@@]2(C)[C@@H](OC(=O)C3=COC=C3)[C@H](O)[C@@H]3[C@@H](O)[C@]12OC3(C)C

InChI Identifier

InChI=1S/C22H30O8/c1-11-6-7-14(28-12(2)23)21(5)18(29-19(26)13-8-9-27-10-13)16(24)15-17(25)22(11,21)30-20(15,3)4/h8-11,14-18,24-25H,6-7H2,1-5H3/t11-,14+,15-,16-,17-,18+,21+,22-/m1/s1

InChI Key

LNDWEPPMGLXUIC-BPQRXJEKSA-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
Maytenus boaria	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Agarofurans

Alternative Parents

Substituents

Agarofuran
Furoic acid ester
Furoic acid or derivatives
Furan-3-carboxylic acid ester
Furan-3-carboxylic acid or derivatives
Oxepane
Dicarboxylic acid or derivatives
Cyclic alcohol
Furan
Tetrahydrofuran
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
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	1.73	ChemAxon
pKa (Strongest Acidic)	13.34	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	115.43 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	103.31 m³·mol⁻¹	ChemAxon
Polarizability	42.87 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

101682234

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Abioye AI, Sudfeld CR, Hughes MD, Aboud S, Muhihi A, Ulenga N, Nagu TJ, Wang M, Mugusi F, Fawzi WW: Iron status among HIV-infected adults during the first year of antiretroviral therapy in Tanzania. HIV Med. 2022 Sep 8. doi: 10.1111/hiv.13396. [PubMed:36075691 ]
Authors unspecified: Resources Round-up. Altern Lab Anim. 2022 Sep 8:2611929221121256. doi: 10.1177/02611929221121256. [PubMed:36075690 ]
Kim JU, Khan W, Arowoshola L, Ahmad M: Correspondence. Eur Heart J Qual Care Clin Outcomes. 2022 Aug 26. pii: 6677390. doi: 10.1093/ehjqcco/qcac051. [PubMed:36075689 ]
DaVault L: Field Amputations Facilitated by a Surgical Extraction Team. Am Surg. 2022 Sep 8:31348221114521. doi: 10.1177/00031348221114521. [PubMed:36075688 ]
Szanyi J, Walles JK, Tesfaye F, Gudeta AN, Bjorkman P: Intrauterine HIV exposure is associated with linear growth restriction among Ethiopian children in the first 18 months of life. Trop Med Int Health. 2022 Sep;27(9):823-830. doi: 10.1111/tmi.13805. Epub 2022 Aug 17. [PubMed:36075687 ]
LOTUS database [Link]

Showing NP-Card for (1s,2r,5s,6s,7r,8r,9r,12r)-5-(acetyloxy)-8,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl furan-3-carboxylate (NP0220262)

MOL for NP0220262 ((1s,2r,5s,6s,7r,8r,9r,12r)-5-(acetyloxy)-8,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl furan-3-carboxylate)

3D MOL for NP0220262 ((1s,2r,5s,6s,7r,8r,9r,12r)-5-(acetyloxy)-8,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl furan-3-carboxylate)

3D SDF for NP0220262 ((1s,2r,5s,6s,7r,8r,9r,12r)-5-(acetyloxy)-8,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl furan-3-carboxylate)

3D-SDF for NP0220262 ((1s,2r,5s,6s,7r,8r,9r,12r)-5-(acetyloxy)-8,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl furan-3-carboxylate)

PDB for NP0220262 ((1s,2r,5s,6s,7r,8r,9r,12r)-5-(acetyloxy)-8,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl furan-3-carboxylate)

3D PDB for NP0220262 ((1s,2r,5s,6s,7r,8r,9r,12r)-5-(acetyloxy)-8,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl furan-3-carboxylate)

SMILES for NP0220262 ((1s,2r,5s,6s,7r,8r,9r,12r)-5-(acetyloxy)-8,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl furan-3-carboxylate)

INCHI for NP0220262 ((1s,2r,5s,6s,7r,8r,9r,12r)-5-(acetyloxy)-8,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl furan-3-carboxylate)

Structure for NP0220262 ((1s,2r,5s,6s,7r,8r,9r,12r)-5-(acetyloxy)-8,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl furan-3-carboxylate)

3D Structure for NP0220262 ((1s,2r,5s,6s,7r,8r,9r,12r)-5-(acetyloxy)-8,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-7-yl furan-3-carboxylate)