NP-MRD: Showing NP-Card for [5aR-(5aalpha,6alpha,8alpha,9beta,9abeta,9balpha)]-8-(Acetyloxy)-3-[(acetyloxy)methyl]-5,5a,6,7,8,9,9a,9b-octahydro-6,9-dihydroxy-5a,9-dimethylnaphtho[1,2-b]furan-2(4H)-one (NP0059538)

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Record Information

Version

1.0

Created at

2022-04-28 04:45:34 UTC

Updated at

2022-04-28 04:45:34 UTC

NP-MRD ID

NP0059538

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[5aR-(5aalpha,6alpha,8alpha,9beta,9abeta,9balpha)]-8-(Acetyloxy)-3-[(acetyloxy)methyl]-5,5a,6,7,8,9,9a,9b-octahydro-6,9-dihydroxy-5a,9-dimethylnaphtho[1,2-b]furan-2(4H)-one

Description

(5AR)-4,5,5a,6,7,8,9,9abeta-Octahydro-8alpha-acetoxy-3-(acetoxymethyl)-6alpha,9beta-dihydroxy-5aalpha,9-dimethylnaphtho[1,2-b]furan-2(9balphaH)-one belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. [5aR-(5aalpha,6alpha,8alpha,9beta,9abeta,9balpha)]-8-(Acetyloxy)-3-[(acetyloxy)methyl]-5,5a,6,7,8,9,9a,9b-octahydro-6,9-dihydroxy-5a,9-dimethylnaphtho[1,2-b]furan-2(4H)-one is found in Achillea fragrantissima and Artemisia ludoviciana. It was first documented in 2022 (PMID: 35483916). Based on a literature review a significant number of articles have been published on (5aR)-4,5,5a,6,7,8,9,9abeta-Octahydro-8alpha-acetoxy-3-(acetoxymethyl)-6alpha,9beta-dihydroxy-5aalpha,9-dimethylnaphtho[1,2-b]furan-2(9balphaH)-one (PMID: 35483915) (PMID: 35483914) (PMID: 35483913) (PMID: 35483912).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282206452D          

 27 29  0  0  1  0            999 V2000
    5.1704    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804    1.1137    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9558    1.1395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5212    0.4383    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9112   -0.2887    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7358   -0.3145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1258   -1.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620   -0.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4608   -0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6989    1.2168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640    1.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966    0.4640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8307   -0.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0544   -0.2939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5756   -0.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3519   -0.5472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4293   -1.6384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3012   -1.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9528    1.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2702    1.5983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2150    1.8150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0396    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4742    2.4905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4296    1.0622    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 14  1  6  0  0  0
  4 15  1  1  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  5 21  1  1  0  0  0
  3 22  1  1  0  0  0
  3 23  1  6  0  0  0
  2 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
M  END

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
    6.0260   -1.0949    0.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0276   -0.1556    1.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475   -0.5408    2.0553 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9005    1.1551    0.6990 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0140    2.0938    1.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5744    1.8764    0.8283 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    0.9530    0.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3563   -0.2749   -0.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946   -0.7135   -1.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1140   -0.6395   -1.0522 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8748    0.1134   -2.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2182    0.0610    0.2714 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4891    1.3520    0.1171 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3363    2.3479    1.0287 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5699    2.8155    1.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8372    3.8529    2.1086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5817    0.0990    0.8633 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1934    1.5073    0.8290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4562   -0.1302    2.2663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6014   -0.8323    0.3485 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8074   -0.1515   -0.0245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0053   -0.3880    0.6080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2706    0.3302    0.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0247   -1.2358    1.5456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2262   -1.7723   -0.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7883   -2.0018   -0.9978 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6530   -2.5552   -2.2749 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9493   -2.0552    1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0248   -0.6384    0.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8323   -1.1368   -0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2841    3.1318    0.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1511    2.1686    2.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5305   -1.1569    0.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2713   -0.1165   -1.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4942   -1.7975   -1.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4575   -0.1910   -2.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2407    0.8985   -2.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9955   -0.6503   -2.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8716    0.4191   -1.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4069   -0.5684    0.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3693    1.8013   -0.9045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8655    2.1132    1.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2823    1.3643    0.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0630    2.0125   -0.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4531   -1.1075    2.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9370   -1.5099    1.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8943    0.3809    1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0699    1.3109   -0.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8012   -0.3366   -0.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6953   -2.7967   -0.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7052   -1.4162   -1.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2944   -2.6864   -0.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4213   -3.5082   -2.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  6
 10 26  1  0
 26 27  1  0
 26 25  1  0
 25 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 20 17  1  0
 17 18  1  0
 17 19  1  1
 17 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15  6  1  0
 13  7  1  0
 12 10  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  5 31  1  0
  5 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 11 37  1  0
 11 38  1  0
 11 39  1  0
 26 52  1  1
 27 53  1  0
 25 50  1  0
 25 51  1  0
 20 46  1  1
 23 47  1  0
 23 48  1  0
 23 49  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 12 40  1  1
 13 41  1  6
M  END


  Mrv1652304282206452D          

 27 29  0  0  1  0            999 V2000
    5.1704    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804    1.1137    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9558    1.1395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5212    0.4383    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9112   -0.2887    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7358   -0.3145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1258   -1.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620   -0.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4608   -0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6989    1.2168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640    1.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966    0.4640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8307   -0.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0544   -0.2939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5756   -0.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3519   -0.5472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4293   -1.6384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3012   -1.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9528    1.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2702    1.5983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2150    1.8150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0396    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4742    2.4905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4296    1.0622    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 14  1  6  0  0  0
  4 15  1  1  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  5 21  1  1  0  0  0
  3 22  1  1  0  0  0
  3 23  1  6  0  0  0
  2 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0059538

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1=C2CC[C@@]3(C)[C@H](O)C[C@H](OC(C)=O)[C@@](C)(O)[C@@H]3[C@H]2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O8/c1-9(20)25-8-12-11-5-6-18(3)13(22)7-14(26-10(2)21)19(4,24)16(18)15(11)27-17(12)23/h13-16,22,24H,5-8H2,1-4H3/t13-,14+,15+,16-,18+,19-/m1/s1

> <INCHI_KEY>
DZOYBWIJERJQJX-ROSLGNJOSA-N

> <FORMULA>
C19H26O8

> <MOLECULAR_WEIGHT>
382.409

> <EXACT_MASS>
382.162767797

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
39.1081306625052

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(5aR,6R,8S,9S,9aS,9bR)-8-(acetyloxy)-6,9-dihydroxy-5a,9-dimethyl-2-oxo-2H,4H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-b]furan-3-yl]methyl acetate

> <ALOGPS_LOGP>
0.39

> <JCHEM_LOGP>
-0.36869614600000106

> <ALOGPS_LOGS>
-2.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.917691588840594

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.079245858264134

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9729076852506138

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
91.64320000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(5aR,6R,8S,9S,9aS,9bR)-8-(acetyloxy)-6,9-dihydroxy-5a,9-dimethyl-2-oxo-4H,5H,6H,7H,8H,9aH,9bH-naphtho[1,2-b]furan-3-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       9.651   0.722   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.923   2.079   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.384   2.127   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.573   0.818   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.301  -0.539   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.840  -0.587   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.568  -1.944   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.490  -1.848   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.950  -1.800   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.222  -0.443   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.727  -0.076   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.614   1.460   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.305   2.271   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.039   2.042   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.034   0.866   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.551  -1.070   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.102  -0.549   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.074  -1.543   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.523  -1.021   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.801  -3.058   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.029  -1.896   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.379   3.667   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.104   2.984   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       9.735   3.388   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      11.274   3.340   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.085   4.649   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      12.002   1.983   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   24                                                  
CONECT    3    2    4   22   23                                             
CONECT    4    3    5   15                                                  
CONECT    5    4    6    8   21                                             
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    4   10                                                  
CONECT   16   11   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    5                                                            
CONECT   22    3                                                            
CONECT   23    3                                                            
CONECT   24    2   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
(5AR)-4,5,5a,6,7,8,9,9abeta-octahydro-8a-acetoxy-3-(acetoxymethyl)-6a,9b-dihydroxy-5aalpha,9-dimethylnaphtho[1,2-b]furan-2(9balphah)-one	Generator
(5AR)-4,5,5a,6,7,8,9,9abeta-octahydro-8α-acetoxy-3-(acetoxymethyl)-6α,9β-dihydroxy-5aalpha,9-dimethylnaphtho[1,2-b]furan-2(9balphah)-one	Generator

Chemical Formula

C₁₉H₂₆O₈

Average Mass

382.4090 Da

Monoisotopic Mass

382.16277 Da

IUPAC Name

[(5aR,6R,8S,9S,9aS,9bR)-8-(acetyloxy)-6,9-dihydroxy-5a,9-dimethyl-2-oxo-2H,4H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-b]furan-3-yl]methyl acetate

Traditional Name

[(5aR,6R,8S,9S,9aS,9bR)-8-(acetyloxy)-6,9-dihydroxy-5a,9-dimethyl-2-oxo-4H,5H,6H,7H,8H,9aH,9bH-naphtho[1,2-b]furan-3-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1=C2CC[C@@]3(C)[C@H](O)C[C@H](OC(C)=O)[C@@](C)(O)[C@@H]3[C@H]2OC1=O

InChI Identifier

InChI=1S/C19H26O8/c1-9(20)25-8-12-11-5-6-18(3)13(22)7-14(26-10(2)21)19(4,24)16(18)15(11)27-17(12)23/h13-16,22,24H,5-8H2,1-4H3/t13-,14+,15+,16-,18+,19-/m1/s1

InChI Key

DZOYBWIJERJQJX-ROSLGNJOSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Achillea fragrantissima	Plant	KNApSAcK
Artemisia ludoviciana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Tricarboxylic acid or derivatives
Cyclitol or derivatives
2-furanone
Cyclic alcohol
Dihydrofuran
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic oxide
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.39	ALOGPS
logP	-0.37	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	12.08	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	91.64 m³·mol⁻¹	ChemAxon
Polarizability	39.11 Å³	ChemAxon
Number of Rings	3	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

15627980

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Uchida Y, Kan H, Sakurai K, Horimoto Y, Hayashi E, Iida A, Okamura N, Oishi K, Matsukawa N: APOE varepsilon4 dose associates with increased brain iron and beta-amyloid via blood-brain barrier dysfunction. J Neurol Neurosurg Psychiatry. 2022 Apr 28. pii: jnnp-2021-328519. doi: 10.1136/jnnp-2021-328519. [PubMed:35483916 ]
Cacciaguerra L, Pagani E, Radaelli M, Mesaros S, Martinelli V, Ivanovic J, Drulovic J, Filippi M, Rocca MA: MR T2-relaxation time as an indirect measure of brain water content and disease activity in NMOSD. J Neurol Neurosurg Psychiatry. 2022 Apr 28. pii: jnnp-2022-328956. doi: 10.1136/jnnp-2022-328956. [PubMed:35483915 ]
Broomfield NM, West R, Barber M, Quinn TJ, Gillespie D, Walters M, House A: TEARS: a longitudinal investigation of the prevalence, psychological associations and trajectory of poststroke emotionalism. J Neurol Neurosurg Psychiatry. 2022 Apr 28. pii: jnnp-2022-329042. doi: 10.1136/jnnp-2022-329042. [PubMed:35483914 ]
Khankari J, Yu Y, Ouyang J, Hussein R, Do HM, Heit JJ, Zaharchuk G: Automated detection of arterial landmarks and vascular occlusions in patients with acute stroke receiving digital subtraction angiography using deep learning. J Neurointerv Surg. 2022 Apr 28. pii: neurintsurg-2021-018638. doi: 10.1136/neurintsurg-2021-018638. [PubMed:35483913 ]
Adeeb N, Dibas M, Diestro JDB, Phan K, Cuellar-Saenz HH, Sweid A, Lay SV, Guenego A, Aslan A, Renieri L, Sundararajan SH, Saliou G, Mohlenbruch M, Regenhardt RW, Vranic JE, Lylyk I, Foreman PM, Vachhani JA, Zupancic V, Hafeez MU, Rutledge C, Waqas M, Tutino VM, Rabinov JD, Ren Y, Schirmer CM, Piano M, Kuhn AL, Michelozzi C, Elens S, Starke RM, Hassan A, Salehani A, Brehm A, MohammedAli M, Jones J, Psychogios M, Spears J, Lubicz B, Panni P, Puri AS, Pero G, Griessenauer CJ, Asadi H, Siddiqui A, Ducruet A, Albuquerque FC, Du R, Kan P, Kalousek V, Lylyk P, Stapleton CJ, Boddu S, Knopman J, Aziz-Sultan MA, Limbucci N, Jabbour P, Cognard C, Patel AB, Dmytriw AA: Comparing treatment outcomes of various intracranial bifurcation aneurysms locations using the Woven EndoBridge (WEB) device. J Neurointerv Surg. 2022 Apr 28. pii: neurintsurg-2022-018694. doi: 10.1136/neurintsurg-2022-018694. [PubMed:35483912 ]

Showing NP-Card for [5aR-(5aalpha,6alpha,8alpha,9beta,9abeta,9balpha)]-8-(Acetyloxy)-3-[(acetyloxy)methyl]-5,5a,6,7,8,9,9a,9b-octahydro-6,9-dihydroxy-5a,9-dimethylnaphtho[1,2-b]furan-2(4H)-one (NP0059538)

MOL for NP0059538 ([5aR-(5aalpha,6alpha,8alpha,9beta,9abeta,9balpha)]-8-(Acetyloxy)-3-[(acetyloxy)methyl]-5,5a,6,7,8,9,9a,9b-octahydro-6,9-dihydroxy-5a,9-dimethylnaphtho[1,2-b]furan-2(4H)-one)

3D MOL for NP0059538 ([5aR-(5aalpha,6alpha,8alpha,9beta,9abeta,9balpha)]-8-(Acetyloxy)-3-[(acetyloxy)methyl]-5,5a,6,7,8,9,9a,9b-octahydro-6,9-dihydroxy-5a,9-dimethylnaphtho[1,2-b]furan-2(4H)-one)

3D SDF for NP0059538 ([5aR-(5aalpha,6alpha,8alpha,9beta,9abeta,9balpha)]-8-(Acetyloxy)-3-[(acetyloxy)methyl]-5,5a,6,7,8,9,9a,9b-octahydro-6,9-dihydroxy-5a,9-dimethylnaphtho[1,2-b]furan-2(4H)-one)

3D-SDF for NP0059538 ([5aR-(5aalpha,6alpha,8alpha,9beta,9abeta,9balpha)]-8-(Acetyloxy)-3-[(acetyloxy)methyl]-5,5a,6,7,8,9,9a,9b-octahydro-6,9-dihydroxy-5a,9-dimethylnaphtho[1,2-b]furan-2(4H)-one)

PDB for NP0059538 ([5aR-(5aalpha,6alpha,8alpha,9beta,9abeta,9balpha)]-8-(Acetyloxy)-3-[(acetyloxy)methyl]-5,5a,6,7,8,9,9a,9b-octahydro-6,9-dihydroxy-5a,9-dimethylnaphtho[1,2-b]furan-2(4H)-one)

3D PDB for NP0059538 ([5aR-(5aalpha,6alpha,8alpha,9beta,9abeta,9balpha)]-8-(Acetyloxy)-3-[(acetyloxy)methyl]-5,5a,6,7,8,9,9a,9b-octahydro-6,9-dihydroxy-5a,9-dimethylnaphtho[1,2-b]furan-2(4H)-one)

SMILES for NP0059538 ([5aR-(5aalpha,6alpha,8alpha,9beta,9abeta,9balpha)]-8-(Acetyloxy)-3-[(acetyloxy)methyl]-5,5a,6,7,8,9,9a,9b-octahydro-6,9-dihydroxy-5a,9-dimethylnaphtho[1,2-b]furan-2(4H)-one)

INCHI for NP0059538 ([5aR-(5aalpha,6alpha,8alpha,9beta,9abeta,9balpha)]-8-(Acetyloxy)-3-[(acetyloxy)methyl]-5,5a,6,7,8,9,9a,9b-octahydro-6,9-dihydroxy-5a,9-dimethylnaphtho[1,2-b]furan-2(4H)-one)

Structure for NP0059538 ([5aR-(5aalpha,6alpha,8alpha,9beta,9abeta,9balpha)]-8-(Acetyloxy)-3-[(acetyloxy)methyl]-5,5a,6,7,8,9,9a,9b-octahydro-6,9-dihydroxy-5a,9-dimethylnaphtho[1,2-b]furan-2(4H)-one)

3D Structure for NP0059538 ([5aR-(5aalpha,6alpha,8alpha,9beta,9abeta,9balpha)]-8-(Acetyloxy)-3-[(acetyloxy)methyl]-5,5a,6,7,8,9,9a,9b-octahydro-6,9-dihydroxy-5a,9-dimethylnaphtho[1,2-b]furan-2(4H)-one)