NP-MRD: Showing NP-Card for 9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-3,11-dioxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-10-yl acetate (NP0219054)

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Record Information

Version

2.0

Created at

2022-09-05 19:55:37 UTC

Updated at

2022-09-05 19:55:37 UTC

NP-MRD ID

NP0219054

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-3,11-dioxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-10-yl acetate

Description

9-[2-(Furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-3,11-dioxo-2-oxatricyclo[6.3.1.0⁴,¹²]Dodecan-10-yl acetate belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom). 9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-3,11-dioxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-10-yl acetate is found in Leonurus sibiricus. Based on a literature review very few articles have been published on 9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-3,11-dioxo-2-oxatricyclo[6.3.1.0⁴,¹²]Dodecan-10-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052221552D          

 29 32  0  0  0  0            999 V2000
   -1.3281   -0.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5351   -1.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3355   -1.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0584   -0.4493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4898   -1.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377    0.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2702    0.6287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913    0.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9463    1.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713    1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562    1.9314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262    0.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6393    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7799    0.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987   -1.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3019   -1.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -1.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8279   -1.9266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0575   -1.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4192   -2.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9579   -3.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2400   -4.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5899   -4.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0940   -4.0929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1334   -3.2999    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  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
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
  9 20  1  0  0  0  0
 13 20  1  0  0  0  0
 18 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 29  2  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
    2.1773   -3.5498    1.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4469   -3.1588    0.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1669   -4.0922   -0.2520 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1168   -1.8419    0.2944 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4226   -1.4591   -0.8965 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3030   -1.8589   -2.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8658   -2.1253   -0.8491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0093   -3.2162   -1.3986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9911   -1.5451   -0.1746 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5152   -2.1961    0.9631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3606   -1.2004    1.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3132   -1.4446    2.2879 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9063    0.1523    0.9987 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8800    1.1468    2.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8337    0.5399   -0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2812    0.8887   -1.4094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8816    0.5064   -1.7212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9274    0.6134   -0.5192 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9994    2.0682   -0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5336   -0.2541    0.5360 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3730    0.0831   -0.9132 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5549    0.4659   -2.2781 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6256    0.4853   -0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9761    1.9104   -0.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3382    2.0382    0.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4925    2.1073   -0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5428    2.2154    0.7431 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0386    2.2101    1.9275 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7112    2.1051    1.8999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4608   -4.1873    2.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9995   -4.2243    1.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5252   -2.6752    2.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9270   -0.9916   -2.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0166   -2.6538   -1.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6940   -2.1975   -2.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8312   -1.3873   -0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7558    0.8813    2.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1193    2.1535    1.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9707    1.1146    2.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3976    1.4492    0.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6783   -0.2093   -0.2085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4973    1.9670   -1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9070    0.3477   -2.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4824    1.3001   -2.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595   -0.4276   -2.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    2.7381   -0.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0642    2.4579   -0.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8597    2.2497    0.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8967   -0.5040    1.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1468   -0.1532   -2.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7239   -0.0816    0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5366    0.0374   -0.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3243    2.4790    0.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    2.4706   -0.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6348    2.0875   -1.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5828    2.2898    0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0229    2.0752    2.7341 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
  5  4  1  1
  5  6  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 18 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 29  2  0
 29 28  1  0
 28 27  1  0
 27 26  2  0
 21  5  1  0
 26 25  1  0
 20  9  1  0
 20 13  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  6 33  1  0
  6 34  1  0
  6 35  1  0
  9 36  1  6
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 17 45  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  1
 22 50  1  0
 23 51  1  0
 23 52  1  0
 24 53  1  0
 24 54  1  0
 29 57  1  0
 27 56  1  0
 26 55  1  0
M  END


  Mrv1652309052221552D          

 29 32  0  0  0  0            999 V2000
   -1.3281   -0.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5351   -1.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3355   -1.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0584   -0.4493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4898   -1.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377    0.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2702    0.6287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913    0.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9463    1.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713    1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562    1.9314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262    0.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6393    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7799    0.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987   -1.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3019   -1.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -1.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8279   -1.9266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0575   -1.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4192   -2.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9579   -3.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2400   -4.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5899   -4.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0940   -4.0929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1334   -3.2999    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  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
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
  9 20  1  0  0  0  0
 13 20  1  0  0  0  0
 18 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0219054

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1(C)C(=O)C2OC(=O)C3(C)CCCC(C)(C23)C1(O)CCC1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O7/c1-13(23)29-21(4)17(24)15-16-19(2,18(25)28-15)8-5-9-20(16,3)22(21,26)10-6-14-7-11-27-12-14/h7,11-12,15-16,26H,5-6,8-10H2,1-4H3

> <INCHI_KEY>
PHOWZNFLUQUNMX-UHFFFAOYSA-N

> <FORMULA>
C22H28O7

> <MOLECULAR_WEIGHT>
404.459

> <EXACT_MASS>
404.183503242

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.21683301737984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-3,11-dioxo-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-10-yl acetate

> <JCHEM_LOGP>
3.043355204000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.280406407900472

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.931578329950007

> <JCHEM_PKA_STRONGEST_BASIC>
-2.786084154094415

> <JCHEM_POLAR_SURFACE_AREA>
103.04000000000002

> <JCHEM_REFRACTIVITY>
100.8195

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-3,11-dioxo-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-10-yl acetate

> <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      -2.479  -1.484   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.999  -1.909   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.626  -3.403   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.109  -0.839   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.589  -1.263   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.914  -2.647   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.750   0.268   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.504   1.174   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.157   0.895   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.633   2.359   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.173   2.359   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.078   3.605   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.649   0.895   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.793   1.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.056   0.268   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.217  -1.263   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.971  -2.168   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.242  -1.542   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.297  -3.081   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.403  -0.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.835  -2.168   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.412  -3.596   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.974  -3.445   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.649  -4.829   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.788  -6.106   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.315  -7.553   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.101  -8.501   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.176  -7.640   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.249  -6.160   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    7   21                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   20                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18    9   13                                                  
CONECT   21   18    5   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   25                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
9-[2-(Furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-3,11-dioxo-2-oxatricyclo[6.3.1.0,]dodecan-10-yl acetic acid	Generator

Chemical Formula

C₂₂H₂₈O₇

Average Mass

404.4590 Da

Monoisotopic Mass

404.18350 Da

IUPAC Name

9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-3,11-dioxo-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-10-yl acetate

Traditional Name

9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-3,11-dioxo-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-10-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1(C)C(=O)C2OC(=O)C3(C)CCCC(C)(C23)C1(O)CCC1=COC=C1

InChI Identifier

InChI=1S/C22H28O7/c1-13(23)29-21(4)17(24)15-16-19(2,18(25)28-15)8-5-9-20(16,3)22(21,26)10-6-14-7-11-27-12-14/h7,11-12,15-16,26H,5-6,8-10H2,1-4H3

InChI Key

PHOWZNFLUQUNMX-UHFFFAOYSA-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
Leonurus sibiricus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-acyloxy ketones

Alternative Parents

Substituents

Alpha-acyloxy ketone
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Heteroaromatic compound
Furan
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Ketone
Lactone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
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	3.04	ChemAxon
pKa (Strongest Acidic)	12.93	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.04 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	100.82 m³·mol⁻¹	ChemAxon
Polarizability	41.22 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

85190352

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-3,11-dioxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-10-yl acetate (NP0219054)

MOL for NP0219054 (9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-3,11-dioxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-10-yl acetate)

3D MOL for NP0219054 (9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-3,11-dioxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-10-yl acetate)

3D SDF for NP0219054 (9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-3,11-dioxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-10-yl acetate)

3D-SDF for NP0219054 (9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-3,11-dioxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-10-yl acetate)

PDB for NP0219054 (9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-3,11-dioxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-10-yl acetate)

3D PDB for NP0219054 (9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-3,11-dioxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-10-yl acetate)

SMILES for NP0219054 (9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-3,11-dioxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-10-yl acetate)

INCHI for NP0219054 (9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-3,11-dioxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-10-yl acetate)

Structure for NP0219054 (9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-3,11-dioxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-10-yl acetate)

3D Structure for NP0219054 (9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-3,11-dioxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodecan-10-yl acetate)