NP-MRD: Showing NP-Card for 1-(3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid (NP0286273)

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Record Information

Version

2.0

Created at

2022-09-09 14:46:40 UTC

Updated at

2022-09-09 14:46:40 UTC

NP-MRD ID

NP0286273

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

Description

1-(5-Benzyl-3-methylhex-3-en-1-yl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]Octane-3,4,5-tricarboxylic acid belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Based on a literature review very few articles have been published on 1-(5-benzyl-3-methylhex-3-en-1-yl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]Octane-3,4,5-tricarboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092216462D          

 32 34  0  0  0  0            999 V2000
   -0.6681    2.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1202    2.6882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7250    3.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5414    4.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2470    4.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1462    4.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    5.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1742    5.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0093    6.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5954    7.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3838    6.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5673    5.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3038    1.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0921    1.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2757    0.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6307    0.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6307   -0.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2757   -1.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0921   -1.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3038   -2.0648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6969   -2.3828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0440   -0.0905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0800   -0.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0800   -1.6588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8843   -1.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1275   -1.8057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4455   -0.4126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4380   -0.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2630   -0.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6755    0.6240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0167   -0.4260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0800    0.6528    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
  3  4  1  4  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 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
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
 15 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 28 32  1  0  0  0  0
 15 32  1  0  0  0  0
M  END

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
    1.4461    1.9103    1.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4516    0.6976    0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5767    0.3642   -0.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8289   -0.7575   -0.9190 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3837   -0.1626   -2.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8650   -1.7004   -0.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1181   -0.9851   -0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1455   -0.8808   -0.9302 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2927   -0.2168   -0.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4908    0.3790    0.6014 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4763    0.2808    1.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3247   -0.3877    1.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1893   -0.0160    0.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7776    0.9910   -0.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1309    0.3931   -0.5189 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1160   -0.7586   -1.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9032   -1.8080   -0.6994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6393   -0.9096    0.3039 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1500   -1.6885    1.4417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0857   -2.5223    1.3182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5964   -1.5118    2.6933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6215   -0.0752    0.7096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7348   -0.2040   -0.4586 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2292   -1.1169   -1.3885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8360    0.1521    0.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9664   -0.3524    0.3073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6094    1.0484    1.4791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2475    0.9923   -1.2309 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1959    2.0962   -0.9877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4184    1.9512   -1.1978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7225    3.3039   -0.5216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9835    1.3924   -0.9302 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4252    1.9792    1.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2620    2.8310    0.8537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6767    1.8325    2.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4549    1.0088    0.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9147   -1.2958   -1.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2772    0.4395   -1.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5775   -0.9677   -2.9420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6015    0.4868   -2.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4786   -2.1773    0.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1095   -2.4552   -1.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9810   -1.3504   -1.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1119   -0.1254   -1.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4304    0.9062    0.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6274    0.7490    2.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5444   -0.4392    1.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2895   -0.8685   -0.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1836   -0.3132    1.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3028    1.3855   -1.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8392    1.8279    0.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7333   -0.5208   -2.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1288   -1.1056   -1.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2317   -2.5149   -0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6179   -2.3543   -1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0400   -0.9580    3.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7088   -1.8647   -0.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3438    1.4405    2.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2742    0.8152   -2.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9836    3.7107    0.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 13  1  0
 13 14  1  0
 15 14  1  1
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 22  1  0
 18 19  1  1
 19 21  1  0
 19 20  2  0
 18 23  1  0
 23 24  1  6
 23 28  1  0
 28 32  1  0
 28 29  1  0
 29 31  1  0
 29 30  2  0
 23 25  1  0
 25 27  1  0
 25 26  2  0
 12  7  1  0
 22 15  1  0
 32 15  1  0
  5 38  1  0
  5 39  1  0
  5 40  1  0
  4 37  1  6
  6 41  1  0
  6 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 12 47  1  0
  3 36  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 16 52  1  0
 16 53  1  0
 17 54  1  0
 17 55  1  0
 21 56  1  0
 24 57  1  0
 28 59  1  6
 31 60  1  0
 27 58  1  0
M  END


  Mrv1652309092216462D          

 32 34  0  0  0  0            999 V2000
   -0.6681    2.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1202    2.6882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7250    3.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5414    4.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2470    4.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1462    4.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    5.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1742    5.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0093    6.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5954    7.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3838    6.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5673    5.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3038    1.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0921    1.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2757    0.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6307    0.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6307   -0.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2757   -1.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0921   -1.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3038   -2.0648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6969   -2.3828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0440   -0.0905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0800   -0.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0800   -1.6588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8843   -1.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1275   -1.8057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4455   -0.4126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4380   -0.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2630   -0.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6755    0.6240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0167   -0.4260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0800    0.6528    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
  3  4  1  4  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 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
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
 15 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 28 32  1  0  0  0  0
 15 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0286273

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC1=CC=CC=C1)C=C(C)CCC12CCC(O1)(C(O)=O)C(O)(C(O2)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O9/c1-14(12-15(2)13-16-6-4-3-5-7-16)8-9-21-10-11-22(32-21,19(26)27)23(30,20(28)29)17(31-21)18(24)25/h3-7,12,15,17,30H,8-11,13H2,1-2H3,(H,24,25)(H,26,27)(H,28,29)

> <INCHI_KEY>
OGZGHCQBWIVONK-UHFFFAOYSA-N

> <FORMULA>
C23H28O9

> <MOLECULAR_WEIGHT>
448.468

> <EXACT_MASS>
448.173332482

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
44.952317502914845

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(5-benzyl-3-methylhex-3-en-1-yl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

> <JCHEM_LOGP>
3.3506975556666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.44296334597533

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5903600960751305

> <JCHEM_PKA_STRONGEST_BASIC>
-4.163398599321608

> <JCHEM_POLAR_SURFACE_AREA>
150.59

> <JCHEM_REFRACTIVITY>
110.72519999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-(5-benzyl-3-methylhex-3-en-1-yl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.247   5.472   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.224   5.018   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.353   6.065   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.011   7.567   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.461   8.021   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.140   8.614   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.797  10.116   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.325  10.570   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.017  12.071   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.111  13.118   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.583  12.665   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.926  11.163   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.567   3.517   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.039   3.063   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.381   1.561   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.177   0.601   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.177  -0.939   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.381  -1.899   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.039  -3.400   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.567  -3.854   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.168  -4.448   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.949  -0.169   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.883  -1.556   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.883  -3.096   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.384  -1.899   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.838  -3.371   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       6.432  -0.770   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.551  -0.169   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.091  -0.169   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.861   1.165   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       7.498  -0.795   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       3.883   1.219   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    2   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   22   32                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   22   23                                             
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   18   15                                                       
CONECT   23   18   24   25   28                                             
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   29   32                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   28   15                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
1-(5-Benzyl-3-methylhex-3-en-1-yl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate	Generator

Chemical Formula

C₂₃H₂₈O₉

Average Mass

448.4680 Da

Monoisotopic Mass

448.17333 Da

IUPAC Name

1-(5-benzyl-3-methylhex-3-en-1-yl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

Traditional Name

1-(5-benzyl-3-methylhex-3-en-1-yl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

CAS Registry Number

Not Available

SMILES

CC(CC1=CC=CC=C1)C=C(C)CCC12CCC(O1)(C(O)=O)C(O)(C(O2)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C23H28O9/c1-14(12-15(2)13-16-6-4-3-5-7-16)8-9-21-10-11-22(32-21,19(26)27)23(30,20(28)29)17(31-21)18(24)25/h3-7,12,15,17,30H,8-11,13H2,1-2H3,(H,24,25)(H,26,27)(H,28,29)

InChI Key

OGZGHCQBWIVONK-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Phenylpropane
Tricarboxylic acid or derivatives
Oxepane
Ketal
Meta-dioxane
Alpha-hydroxy acid
Monocyclic benzene moiety
Hydroxy acid
Benzenoid
Tertiary alcohol
Tetrahydrofuran
Acetal
Carboxylic acid
Organoheterocyclic compound
Oxacycle
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
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	3.35	ChemAxon
pKa (Strongest Acidic)	3.59	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	150.59 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	110.73 m³·mol⁻¹	ChemAxon
Polarizability	44.95 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73078296

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid (NP0286273)

MOL for NP0286273 (1-(3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid)

3D MOL for NP0286273 (1-(3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid)

3D SDF for NP0286273 (1-(3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid)

3D-SDF for NP0286273 (1-(3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid)

PDB for NP0286273 (1-(3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid)

3D PDB for NP0286273 (1-(3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid)

SMILES for NP0286273 (1-(3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid)

INCHI for NP0286273 (1-(3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid)

Structure for NP0286273 (1-(3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid)

3D Structure for NP0286273 (1-(3,5-dimethyl-6-phenylhex-3-en-1-yl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid)