NP-MRD: Showing NP-Card for 3-[(1r,7s,8s,9r)-7-(acetyloxy)-4-(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-3-en-9-yl]propanoic acid (NP0156246)

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Record Information

Version

1.0

Created at

2022-09-02 13:25:49 UTC

Updated at

2022-09-02 13:25:50 UTC

NP-MRD ID

NP0156246

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(1r,7s,8s,9r)-7-(acetyloxy)-4-(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-3-en-9-yl]propanoic acid

Description

Pseudolaric acid B3, also known as pseudolarate B3, belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 3-[(1r,7s,8s,9r)-7-(acetyloxy)-4-(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-3-en-9-yl]propanoic acid is found in Larix kaempferi. It was first documented in 2003 (PMID: 14527554). Based on a literature review very few articles have been published on pseudolaric acid B3.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022215252D          

 28 30  0  0  1  0            999 V2000
    5.5612    0.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7835    0.4951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1353    1.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4431    1.8448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2469    0.8437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0745    0.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3362   -0.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5880    0.0163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9202    0.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5368    1.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7267    1.6578    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3933    0.8180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5871    0.4901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0142   -0.2906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3002   -1.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8319   -0.1815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8987    1.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7236    1.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0998    1.1215    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8164    1.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3782    1.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2115    2.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3340    3.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1018    3.3666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6886    3.5787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1282    0.2970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7905   -0.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8019   -1.0842    0.0000 O   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
  8 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END

     RDKit          3D

 54 56  0  0  0  0  0  0  0  0999 V2000
   -5.7927    2.1156   -0.5567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7527    1.3809    0.0295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0562    0.4141   -0.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3532    0.1727   -1.8424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9855   -0.3335   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6529   -0.0938    1.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6126   -0.7208    2.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2875   -0.8229    1.4038 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6515    0.1155    2.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3835    0.8821    1.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2710   -0.0101   -0.0978 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2428   -0.2578   -0.0011 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8633    1.0091    0.0668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0413    1.8959   -0.9471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7176    3.2049   -0.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6315    1.6298   -2.1003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8310   -1.1211   -1.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3199   -1.3563   -0.8720 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0961   -1.2326   -0.1095 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4348   -1.5082   -1.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3168   -1.3291    0.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5054   -0.5000    0.5560 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3731   -0.5848   -0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3664   -1.4832   -1.4354 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3075    0.4525   -0.8058 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2791   -2.3569    0.3534 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3421   -2.1379    1.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0781   -3.0274    2.2120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5712    3.1997   -0.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8848    1.7656   -1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7392    1.8591   -0.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2305    0.6692    1.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9009   -1.7648    2.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5792   -0.1540    3.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2623   -0.4008    2.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0542    0.8678    2.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3259    1.2940    1.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7239    1.7792    0.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5099    0.6275   -0.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3656    3.3852   -1.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9664    4.0031   -0.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3418    3.1323    0.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4186   -2.1455   -1.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7054   -0.6670   -2.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7831   -1.3658   -1.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4731   -2.3595   -0.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9551   -2.4498   -1.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4860   -1.4653   -2.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0194   -0.6769   -2.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0652   -1.4797    1.8154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6951   -2.4149    0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3293    0.6009    0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2159   -0.8463    1.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0530    0.6102   -0.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 17  1  0
 17 18  1  0
 12 13  1  1
 13 14  1  0
 14 15  1  0
 14 16  2  0
 11 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 25  1  0
 23 24  2  0
 19 26  1  0
 26 27  1  0
 27 28  2  0
 18  5  1  0
 12  8  1  0
  8 27  1  6
  1 29  1  0
  1 30  1  0
  1 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  6
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 25 54  1  0
M  END


  Mrv1652309022215252D          

 28 30  0  0  1  0            999 V2000
    5.5612    0.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7835    0.4951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1353    1.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4431    1.8448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2469    0.8437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0745    0.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3362   -0.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5880    0.0163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9202    0.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5368    1.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7267    1.6578    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3933    0.8180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5871    0.4901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0142   -0.2906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3002   -1.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8319   -0.1815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8987    1.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7236    1.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0998    1.1215    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8164    1.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3782    1.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2115    2.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3340    3.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1018    3.3666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6886    3.5787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1282    0.2970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7905   -0.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8019   -1.0842    0.0000 O   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
  8 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0156246

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC[C@]23CC[C@H]([C@]2(CC1)OC(C)=O)[C@@](C)(CCC(O)=O)OC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O8/c1-12(21)27-20-11-5-13(16(24)26-3)4-9-19(20)10-6-14(20)18(2,28-17(19)25)8-7-15(22)23/h4,14H,5-11H2,1-3H3,(H,22,23)/t14-,18+,19+,20-/m0/s1

> <INCHI_KEY>
IQFROZIBHYYWNH-PSAKCFHXSA-N

> <FORMULA>
C20H26O8

> <MOLECULAR_WEIGHT>
394.42

> <EXACT_MASS>
394.162767797

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
40.05227446839518

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(1R,7S,8S,9R)-7-(acetyloxy)-4-(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0^{1,7}]tridec-3-en-9-yl]propanoic acid

> <ALOGPS_LOGP>
2.28

> <JCHEM_LOGP>
1.8711096269999996

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.253859843270347

> <JCHEM_PKA_STRONGEST_BASIC>
-6.51149519413493

> <JCHEM_POLAR_SURFACE_AREA>
116.20000000000002

> <JCHEM_REFRACTIVITY>
95.51649999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(1R,7S,8S,9R)-7-(acetyloxy)-4-(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0^{1,7}]tridec-3-en-9-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      10.381   1.438   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.929   0.924   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.719   1.957   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.294   3.444   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.061   1.575   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.739   0.069   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.361  -0.619   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.964   0.030   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.584   1.440   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.869   2.804   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.356   3.095   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.601   1.527   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.096   0.915   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.026  -0.542   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.560  -1.966   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.553  -0.339   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.544   2.744   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.084   2.765   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.186   2.093   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.524   2.274   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.706   3.586   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.261   4.198   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.490   5.721   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.923   6.284   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.285   6.680   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.239   0.554   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.476  -0.364   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.497  -2.024   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   12   27                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11    8   13   17                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12   18                                                       
CONECT   18   17    5                                                       
CONECT   19   11   20   21   26                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   19   27                                                       
CONECT   27   26    8   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
Pseudolarate b3	Generator

Chemical Formula

C₂₀H₂₆O₈

Average Mass

394.4200 Da

Monoisotopic Mass

394.16277 Da

IUPAC Name

3-[(1R,7S,8S,9R)-7-(acetyloxy)-4-(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0^{1,7}]tridec-3-en-9-yl]propanoic acid

Traditional Name

3-[(1R,7S,8S,9R)-7-(acetyloxy)-4-(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0^{1,7}]tridec-3-en-9-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC[C@]23CC[C@H]([C@]2(CC1)OC(C)=O)[C@@](C)(CCC(O)=O)OC3=O

InChI Identifier

InChI=1S/C20H26O8/c1-12(21)27-20-11-5-13(16(24)26-3)4-9-19(20)10-6-14(20)18(2,28-17(19)25)8-7-15(22)23/h4,14H,5-11H2,1-3H3,(H,22,23)/t14-,18+,19+,20-/m0/s1

InChI Key

IQFROZIBHYYWNH-PSAKCFHXSA-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
Larix kaempferi	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

Substituents

Terpene lactone
Sesquiterpenoid
Daucane sesquiterpenoid
Tetracarboxylic acid or derivatives
Caprolactone
Delta valerolactone
Delta_valerolactone
Oxepane
Oxane
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Organic oxygen compound
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	2.28	ALOGPS
logP	1.87	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.25	ChemAxon
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	116.2 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	95.52 m³·mol⁻¹	ChemAxon
Polarizability	40.05 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

23310301

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44444977

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang SP, Dong L, Wang Y, Wu Y, Yue JM: Antifungal diterpenoids of Pseudolarix kaempferi, and their structure-activity relationship study. Bioorg Med Chem. 2003 Oct 15;11(21):4577-84. doi: 10.1016/s0968-0896(03)00531-5. [PubMed:14527554 ]
LOTUS database [Link]

Showing NP-Card for 3-[(1r,7s,8s,9r)-7-(acetyloxy)-4-(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-3-en-9-yl]propanoic acid (NP0156246)

MOL for NP0156246 (3-[(1r,7s,8s,9r)-7-(acetyloxy)-4-(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-3-en-9-yl]propanoic acid)

3D MOL for NP0156246 (3-[(1r,7s,8s,9r)-7-(acetyloxy)-4-(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-3-en-9-yl]propanoic acid)

3D SDF for NP0156246 (3-[(1r,7s,8s,9r)-7-(acetyloxy)-4-(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-3-en-9-yl]propanoic acid)

3D-SDF for NP0156246 (3-[(1r,7s,8s,9r)-7-(acetyloxy)-4-(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-3-en-9-yl]propanoic acid)

PDB for NP0156246 (3-[(1r,7s,8s,9r)-7-(acetyloxy)-4-(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-3-en-9-yl]propanoic acid)

3D PDB for NP0156246 (3-[(1r,7s,8s,9r)-7-(acetyloxy)-4-(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-3-en-9-yl]propanoic acid)

SMILES for NP0156246 (3-[(1r,7s,8s,9r)-7-(acetyloxy)-4-(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-3-en-9-yl]propanoic acid)

INCHI for NP0156246 (3-[(1r,7s,8s,9r)-7-(acetyloxy)-4-(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-3-en-9-yl]propanoic acid)

Structure for NP0156246 (3-[(1r,7s,8s,9r)-7-(acetyloxy)-4-(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-3-en-9-yl]propanoic acid)

3D Structure for NP0156246 (3-[(1r,7s,8s,9r)-7-(acetyloxy)-4-(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-3-en-9-yl]propanoic acid)