NP-MRD: Showing NP-Card for 2,6,8-trihydroxy-4-isopropyl-3,7,11-trimethyl-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-12-yl acetate (NP0291040)

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Record Information

Version

2.0

Created at

2022-09-09 21:58:57 UTC

Updated at

2022-09-09 21:58:58 UTC

NP-MRD ID

NP0291040

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,6,8-trihydroxy-4-isopropyl-3,7,11-trimethyl-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-12-yl acetate

Description

Anhydrocinnzeylanine belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Anhydrocinnzeylanine is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, anhydrocinnzeylanine has been detected, but not quantified in, chinese cinnamons and herbs and spices. 2,6,8-trihydroxy-4-isopropyl-3,7,11-trimethyl-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-12-yl acetate is found in Cinnamomum aromaticum and Persea indica. This could make anhydrocinnzeylanine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 09111222022D          

 29 32  0  0  0  0            999 V2000
   -0.6229    1.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6134    0.4855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0303   -0.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3051    0.6269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5485   -0.7200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7793   -0.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4070    0.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3491    1.1133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7985    0.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0711    0.5421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3504    0.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2413   -0.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4331   -0.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0796   -1.4111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1168    1.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7985    0.7267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2328    0.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4295   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8501   -1.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8897   -1.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9261   -1.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4047   -2.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1138   -1.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6404   -2.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3491   -1.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0508   -2.3257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0494    1.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0494    2.3257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500    1.1133    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
  2 11  2  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  3 13  1  0  0  0  0
  5  6  1  0  0  0  0
  5 25  1  0  0  0  0
  6  7  1  0  0  0  0
  6 20  1  0  0  0  0
  7  8  1  0  0  0  0
  7 17  1  0  0  0  0
  8 27  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 23  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  1  0  0  0  0
 20 21  1  0  0  0  0
 20 23  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
M  END

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
   -3.2496    3.8995    1.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0525    2.4436    1.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4247    1.7903    2.2736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4949    1.7276    0.2227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3306    0.3549    0.2523 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2905   -0.2486   -0.7729 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2280    0.6657   -1.9992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9703   -1.6207   -1.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0563   -2.4210   -0.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0639   -1.6341    0.4171 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3417   -1.5946    1.7876 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3772   -2.0316    0.2458 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6792   -3.3808    0.8581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7832   -2.0621   -1.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2468   -0.9633   -1.9917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6333   -0.7713   -3.1563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7059   -0.1262   -1.4410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9850   -0.1808   -0.0461 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1710    0.3292    0.7255 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2377    0.9204    1.9271 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1255    1.1447   -0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8406    2.4329   -0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3416    0.6540    0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792    1.2201   -0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6617    1.4489    0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1348    0.2184   -1.6420 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3958   -0.5968    0.7927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9854   -0.9055    1.0491 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8412   -1.2194    2.4055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0562    4.3729    0.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3207    4.1176    1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6393    4.4124    2.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7287   -0.0140    1.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3091   -0.1299   -0.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5743    1.5254   -1.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2278    1.0504   -2.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8650    0.1045   -2.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9441   -2.1870   -1.2998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5582   -1.6451   -2.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6957   -2.9767    0.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6067   -3.2342   -0.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4868   -2.4804    2.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3037   -3.8319    1.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1587   -4.0758    0.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3316   -3.2237    1.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3143   -3.0015   -1.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8614   -2.2355   -1.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2913    1.7154    2.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2040    2.5353   -1.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2651    3.2688   -0.1856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4096    2.4259   -1.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3395    2.1531   -1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3383    2.2607    0.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2015    1.7265    1.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2218    0.5008    0.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3786    0.0532   -2.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0398    0.6998   -2.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4657   -0.7105   -1.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9291   -1.3329    0.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0066   -0.4640    1.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6027   -0.8732    2.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 26  1  0
 24 23  1  0
 23 21  2  0
 21 22  1  0
 21 19  1  0
 19 20  1  1
 19 28  1  0
 28 29  1  1
 28 27  1  0
 28 12  1  0
 12 13  1  1
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 18 17  1  6
 18  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
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 27 23  1  0
 10 12  1  0
 18 19  1  0
 10 18  1  0
 25 53  1  0
 25 54  1  0
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 26 56  1  0
 26 57  1  0
 26 58  1  0
 22 49  1  0
 22 50  1  0
 22 51  1  0
 20 48  1  0
 29 61  1  0
 27 59  1  0
 27 60  1  0
 13 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
  5 33  1  1
  1 30  1  0
  1 31  1  0
  1 32  1  0
  6 34  1  1
  7 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 11 42  1  0
M  END


  Mrv0541 09111222022D          

 29 32  0  0  0  0            999 V2000
   -0.6229    1.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6134    0.4855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0303   -0.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3051    0.6269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5485   -0.7200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7793   -0.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4070    0.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3491    1.1133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7985    0.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0711    0.5421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3504    0.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2413   -0.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4331   -0.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0796   -1.4111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1168    1.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7985    0.7267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2328    0.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4295   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8501   -1.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8897   -1.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9261   -1.8137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4047   -2.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1138   -1.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6404   -2.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3491   -1.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0508   -2.3257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0494    1.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0494    2.3257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500    1.1133    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
  2 11  2  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  3 13  1  0  0  0  0
  5  6  1  0  0  0  0
  5 25  1  0  0  0  0
  6  7  1  0  0  0  0
  6 20  1  0  0  0  0
  7  8  1  0  0  0  0
  7 17  1  0  0  0  0
  8 27  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 23  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  1  0  0  0  0
 20 21  1  0  0  0  0
 20 23  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0291040

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C(C)C2(O)C(O)(C1)C1(C)CC(=O)OC22C(OC(C)=O)C(C)CCC12O

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O7/c1-11(2)15-9-20(26)18(6)10-16(24)29-22(21(20,27)13(15)4)17(28-14(5)23)12(3)7-8-19(18,22)25/h11-12,17,25-27H,7-10H2,1-6H3

> <INCHI_KEY>
UEXGXCDLLOHGAS-UHFFFAOYSA-N

> <FORMULA>
C22H32O7

> <MOLECULAR_WEIGHT>
408.4853

> <EXACT_MASS>
408.214803378

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
42.66259160526847

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6,8-trihydroxy-3,7,11-trimethyl-14-oxo-4-(propan-2-yl)-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-12-yl acetate

> <ALOGPS_LOGP>
1.21

> <JCHEM_LOGP>
0.8829596586666685

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.083138203209916

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.896033854579633

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6570925344750185

> <JCHEM_POLAR_SURFACE_AREA>
113.28999999999999

> <JCHEM_REFRACTIVITY>
102.35309999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6,8-trihydroxy-4-isopropyl-3,7,11-trimethyl-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-12-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-12         0                                  
HETATM    1  C   UNK     0      -1.163   2.425   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.145   0.906   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.057  -0.270   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.570   1.170   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.891  -1.344   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.455  -0.557   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.626   0.527   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.518   2.078   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -5.224   0.152   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.866   1.012   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.521   0.263   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.317  -1.168   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.809  -1.613   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.015  -2.634   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.951   2.506   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.224   1.356   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.168   0.172   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.535  -1.263   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.454  -2.224   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.661  -1.990   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.729  -3.386   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.755  -4.185   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.212  -2.820   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.195  -4.271   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.518  -3.499   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.828  -4.341   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.826   2.833   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.826   4.341   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.133   2.078   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    6   13                                             
CONECT    4    3                                                            
CONECT    5    6   25                                                       
CONECT    6    3    5    7   20                                             
CONECT    7    6    8   17                                                  
CONECT    8    7   27                                                       
CONECT    9   10                                                            
CONECT   10    9   11   15                                                  
CONECT   11    2   10   12                                                  
CONECT   12   11   13                                                       
CONECT   13    3   12   14   23                                             
CONECT   14   13                                                            
CONECT   15   10                                                            
CONECT   16   17                                                            
CONECT   17    7   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20    6   19   21   23                                             
CONECT   21   20                                                            
CONECT   22   23                                                            
CONECT   23   13   20   22   24                                             
CONECT   24   23   25                                                       
CONECT   25    5   24   26                                                  
CONECT   26   25                                                            
CONECT   27    8   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
2,6,8-Trihydroxy-3,7,11-trimethyl-14-oxo-4-(propan-2-yl)-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-12-yl acetic acid	Generator

Chemical Formula

C₂₂H₃₂O₇

Average Mass

408.4853 Da

Monoisotopic Mass

408.21480 Da

IUPAC Name

2,6,8-trihydroxy-3,7,11-trimethyl-14-oxo-4-(propan-2-yl)-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-12-yl acetate

Traditional Name

2,6,8-trihydroxy-4-isopropyl-3,7,11-trimethyl-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-12-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)C1=C(C)C2(O)C(O)(C1)C1(C)CC(=O)OC22C(OC(C)=O)C(C)CCC12O

InChI Identifier

InChI=1S/C22H32O7/c1-11(2)15-9-20(26)18(6)10-16(24)29-22(21(20,27)13(15)4)17(28-14(5)23)12(3)7-8-19(18,22)25/h11-12,17,25-27H,7-10H2,1-6H3

InChI Key

UEXGXCDLLOHGAS-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
Cinnamomum aromaticum	LOTUS Database	35616633
Persea indica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Not Available

Substituents

Not Available

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	1.21	ALOGPS
logP	0.88	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	11.9	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	102.35 m³·mol⁻¹	ChemAxon
Polarizability	42.66 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

HMDB0036864

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015818

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

131752069

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,6,8-trihydroxy-4-isopropyl-3,7,11-trimethyl-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-12-yl acetate (NP0291040)

MOL for NP0291040 (2,6,8-trihydroxy-4-isopropyl-3,7,11-trimethyl-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-12-yl acetate)

3D MOL for NP0291040 (2,6,8-trihydroxy-4-isopropyl-3,7,11-trimethyl-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-12-yl acetate)

3D SDF for NP0291040 (2,6,8-trihydroxy-4-isopropyl-3,7,11-trimethyl-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-12-yl acetate)

3D-SDF for NP0291040 (2,6,8-trihydroxy-4-isopropyl-3,7,11-trimethyl-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-12-yl acetate)

PDB for NP0291040 (2,6,8-trihydroxy-4-isopropyl-3,7,11-trimethyl-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-12-yl acetate)

3D PDB for NP0291040 (2,6,8-trihydroxy-4-isopropyl-3,7,11-trimethyl-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-12-yl acetate)

SMILES for NP0291040 (2,6,8-trihydroxy-4-isopropyl-3,7,11-trimethyl-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-12-yl acetate)

INCHI for NP0291040 (2,6,8-trihydroxy-4-isopropyl-3,7,11-trimethyl-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-12-yl acetate)

Structure for NP0291040 (2,6,8-trihydroxy-4-isopropyl-3,7,11-trimethyl-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-12-yl acetate)

3D Structure for NP0291040 (2,6,8-trihydroxy-4-isopropyl-3,7,11-trimethyl-14-oxo-13-oxatetracyclo[5.5.3.0¹,⁸.0²,⁶]pentadec-3-en-12-yl acetate)