NP-MRD: Showing NP-Card for (1r,2r,5s,8r,14s,18s)-15-formyl-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-15-ene-5-carboxylic acid (NP0169846)

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Record Information

Version

2.0

Created at

2022-09-03 05:53:01 UTC

Updated at

2022-09-03 05:53:01 UTC

NP-MRD ID

NP0169846

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,5s,8r,14s,18s)-15-formyl-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-15-ene-5-carboxylic acid

Description

(1R,2R,5S,8R,14S,18S)-15-formyl-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]Icos-15-ene-5-carboxylic acid belongs to the class of organic compounds known as triterpenoids. (1r,2r,5s,8r,14s,18s)-15-formyl-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-15-ene-5-carboxylic acid is found in Paliurus hemsleyanus and Ziziphus mauritiana. These are terpene molecules containing six isoprene units (1R,2R,5S,8R,14S,18S)-15-formyl-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]Icos-15-ene-5-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

Zizyberenalic acid
  Mrv1652304022019552D          
  Mrv0541 01231312052D          
 33 37  0  0  1  0            999 V2000
    2.0232    0.2550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7040   -0.9455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7457    0.2156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8373   -0.5690    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5273   -0.9674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8373    0.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2174   -0.5690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    0.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9424   -0.9728    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4032    0.2442    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9488   -1.8027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1251   -0.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5145   -1.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5273    0.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2174    0.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4032   -0.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2300   -2.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9577    1.4616    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7360   -2.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5649   -1.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0151   -1.5778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7958    0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1378    1.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7257   -0.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9363   -0.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2153   -1.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7100   -0.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4943    2.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3850   -2.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4969   -2.8097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9674    0.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2526    2.8097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2727    1.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 27  1  0  0  0  0
  2 27  2  0  0  0  0
  3 31  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4 12  1  0  0  0  0
  4 20  1  1  0  0  0
  5  7  1  0  0  0  0
  5 13  1  0  0  0  0
  5 21  1  6  0  0  0
  6  8  1  0  0  0  0
  6 14  1  0  0  0  0
  7  9  1  0  0  0  0
  7 15  1  0  0  0  0
  8 10  1  0  0  0  0
  8 18  1  0  0  0  0
  9 11  1  0  0  0  0
  9 24  1  0  0  0  0
  9 25  1  6  0  0  0
 10 16  1  0  0  0  0
 10 22  1  0  0  0  0
 10 27  1  6  0  0  0
 11 17  1  6  0  0  0
 11 19  1  0  0  0  0
 12 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 18 23  1  0  0  0  0
 18 28  1  1  0  0  0
 19 26  1  0  0  0  0
 19 29  1  0  0  0  0
 19 30  1  0  0  0  0
 22 23  1  0  0  0  0
 24 26  2  0  0  0  0
 24 31  1  0  0  0  0
 28 32  1  0  0  0  0
 28 33  2  0  0  0  0
M  END

     RDKit          3D

 77 81  0  0  0  0  0  0  0  0999 V2000
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   -3.1765   -1.1293    1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7305   -1.2261    1.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8822   -0.1741    0.8892 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2223    1.0921    1.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2610   -0.2895   -0.5281 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4345    0.7333   -1.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8867   -0.0237   -1.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2616   -0.8450   -0.3147 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7795   -0.7428   -0.2939 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4542   -1.9207    0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3857   -0.6314   -1.6326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0746   -1.3921   -2.8430 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7158   -1.1589   -3.8996 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3226    0.2866   -1.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4365    0.8817   -0.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5723    0.3023    0.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6279    2.3726   -0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0899    0.5852    0.2920 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7905    0.5678    1.7202 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2655    0.5357    1.8245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6113   -0.5220    0.9837 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7163   -1.7966    1.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7168    3.3479    0.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1323    3.1091    0.7891 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.4579    1.1508   -1.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9685   -0.2035   -2.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4543   -0.2544    0.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4860   -1.5093   -0.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0215   -4.4878    0.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7311   -0.3176    1.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6354   -2.0644    1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7288   -0.9660    2.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3876   -2.2424    1.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9755    2.0214    1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2834    1.0747    1.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6896    1.0967    2.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8596   -1.3455   -0.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1705    1.6115   -0.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9094    0.9848   -2.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6050   -0.7080   -2.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0805   -1.9217   -0.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3270   -2.1520   -2.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3500    0.1971    1.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5473   -1.0163   -1.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  1  0
  5  6  1  0
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 27 68  1  0
 24 62  1  0
 22 61  1  0
 33 77  1  6
 10 44  1  0
M  END

Zizyberenalic acid
  Mrv1652304022019552D          
  Mrv0541 01231312052D          
 33 37  0  0  1  0            999 V2000
    2.0232    0.2550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7040   -0.9455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7457    0.2156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8373   -0.5690    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5273   -0.9674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8373    0.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2174   -0.5690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    0.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9424   -0.9728    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4032    0.2442    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9488   -1.8027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1251   -0.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5145   -1.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5273    0.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2174    0.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4032   -0.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2300   -2.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3850   -2.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9674    0.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2526    2.8097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2727    1.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 27  1  0  0  0  0
  2 27  2  0  0  0  0
  3 31  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4 12  1  0  0  0  0
  4 20  1  1  0  0  0
  5  7  1  0  0  0  0
  5 13  1  0  0  0  0
  5 21  1  6  0  0  0
  6  8  1  0  0  0  0
  6 14  1  0  0  0  0
  7  9  1  0  0  0  0
  7 15  1  0  0  0  0
  8 10  1  0  0  0  0
  8 18  1  0  0  0  0
  9 11  1  0  0  0  0
  9 24  1  0  0  0  0
  9 25  1  6  0  0  0
 10 16  1  0  0  0  0
 10 22  1  0  0  0  0
 10 27  1  6  0  0  0
 11 17  1  6  0  0  0
 11 19  1  0  0  0  0
 12 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 18 23  1  0  0  0  0
 18 28  1  1  0  0  0
 19 26  1  0  0  0  0
 19 29  1  0  0  0  0
 19 30  1  0  0  0  0
 22 23  1  0  0  0  0
 24 26  2  0  0  0  0
 24 31  1  0  0  0  0
 28 32  1  0  0  0  0
 28 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0169846

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@@H]1CC[C@@]2(CC[C@]3(C)C(CCC4[C@]5(C)[C@@H](CC[C@@]34C)C(C)(C)C=C5C=O)C12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O3/c1-18(2)20-10-13-30(25(32)33)15-14-27(5)21(24(20)30)8-9-23-28(27,6)12-11-22-26(3,4)16-19(17-31)29(22,23)7/h16-17,20-24H,1,8-15H2,2-7H3,(H,32,33)/t20-,21?,22-,23?,24?,27+,28+,29-,30-/m0/s1

> <INCHI_KEY>
GUPQNHIGLNUBOG-HYYJCJJOSA-N

> <FORMULA>
C30H44O3

> <MOLECULAR_WEIGHT>
452.679

> <EXACT_MASS>
452.329045277

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
53.31736136654423

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,8R,14S,18S)-15-formyl-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0^{2,10}.0^{5,9}.0^{14,18}]icos-15-ene-5-carboxylic acid

> <ALOGPS_LOGP>
6.21

> <JCHEM_LOGP>
6.340497443666667

> <ALOGPS_LOGS>
-6.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.69638139322645

> <JCHEM_PKA_STRONGEST_BASIC>
-4.758072629298545

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
132.6994

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.56e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,8R,14S,18S)-15-formyl-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0^{2,10}.0^{5,9}.0^{14,18}]icos-15-ene-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Zizyberenalic acid                                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-APR-20         0                                  
HETATM    1  O   UNK     0       3.777   0.476   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.047  -1.765   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      16.325   0.402   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       9.030  -1.062   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.318  -1.806   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.030   0.425   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.606  -1.062   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.700   1.220   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.959  -1.816   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.353   0.456   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.971  -3.365   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.700  -1.857   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.294  -3.355   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.318   1.169   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.606   0.425   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.353  -1.093   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.629  -4.140   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.388   2.728   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.441  -3.826   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.521  -2.460   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.362  -2.945   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.219   1.498   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.857   2.900   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.421  -1.333   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.948  -0.329   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.335  -2.572   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.059  -0.278   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.389   3.827   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.652  -4.689   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.994  -5.245   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.872   0.085   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.938   5.245   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.842   3.510   0.000  0.00  0.00           C+0
CONECT    1   27                                                            
CONECT    2   27                                                            
CONECT    3   31                                                            
CONECT    4    5    6   12   20                                             
CONECT    5    4    7   13   21                                             
CONECT    6    4    8   14                                                  
CONECT    7    5    9   15                                                  
CONECT    8    6   10   18                                                  
CONECT    9    7   11   24   25                                             
CONECT   10    8   16   22   27                                             
CONECT   11    9   17   19                                                  
CONECT   12    4   16                                                       
CONECT   13    5   17                                                       
CONECT   14    6   15                                                       
CONECT   15    7   14                                                       
CONECT   16   10   12                                                       
CONECT   17   11   13                                                       
CONECT   18    8   23   28                                                  
CONECT   19   11   26   29   30                                             
CONECT   20    4                                                            
CONECT   21    5                                                            
CONECT   22   10   23                                                       
CONECT   23   18   22                                                       
CONECT   24    9   26   31                                                  
CONECT   25    9                                                            
CONECT   26   19   24                                                       
CONECT   27    1    2   10                                                  
CONECT   28   18   32   33                                                  
CONECT   29   19                                                            
CONECT   30   19                                                            
CONECT   31    3   24                                                       
CONECT   32   28                                                            
CONECT   33   28                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,5S,8R,14S,18S)-15-Formyl-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0,.0,.0,]icos-15-ene-5-carboxylate	Generator
(1R,2R,5S,8R,14S,18S)-15-Formyl-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-15-ene-5-carboxylate	Generator

Chemical Formula

C₃₀H₄₄O₃

Average Mass

452.6790 Da

Monoisotopic Mass

452.32905 Da

IUPAC Name

(1R,2R,5S,8R,14S,18S)-15-formyl-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0^{2,10}.0^{5,9}.0^{14,18}]icos-15-ene-5-carboxylic acid

Traditional Name

(1R,2R,5S,8R,14S,18S)-15-formyl-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0^{2,10}.0^{5,9}.0^{14,18}]icos-15-ene-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(=C)[C@@H]1CC[C@@]2(CC[C@]3(C)C(CCC4[C@]5(C)[C@@H](CC[C@@]34C)C(C)(C)C=C5C=O)C12)C(O)=O

InChI Identifier

InChI=1S/C30H44O3/c1-18(2)20-10-13-30(25(32)33)15-14-27(5)21(24(20)30)8-9-23-28(27,6)12-11-22-26(3,4)16-19(17-31)29(22,23)7/h16-17,20-24H,1,8-15H2,2-7H3,(H,32,33)/t20-,21?,22-,23?,24?,27+,28+,29-,30-/m0/s1

InChI Key

GUPQNHIGLNUBOG-HYYJCJJOSA-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
Paliurus hemsleyanus	LOTUS Database	35616633
Ziziphus mauritiana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Steroid acid
3-carboxy steroid
18-oxosteroid
18-hydroxysteroid
Hydroxysteroid
Oxosteroid
Steroid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Aldehyde
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	6.21	ALOGPS
logP	6.34	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	4.7	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	132.7 m³·mol⁻¹	ChemAxon
Polarizability	53.32 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

15958448

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,5s,8r,14s,18s)-15-formyl-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-15-ene-5-carboxylic acid (NP0169846)

MOL for NP0169846 ((1r,2r,5s,8r,14s,18s)-15-formyl-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-15-ene-5-carboxylic acid)

3D MOL for NP0169846 ((1r,2r,5s,8r,14s,18s)-15-formyl-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-15-ene-5-carboxylic acid)

3D SDF for NP0169846 ((1r,2r,5s,8r,14s,18s)-15-formyl-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-15-ene-5-carboxylic acid)

3D-SDF for NP0169846 ((1r,2r,5s,8r,14s,18s)-15-formyl-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-15-ene-5-carboxylic acid)

PDB for NP0169846 ((1r,2r,5s,8r,14s,18s)-15-formyl-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-15-ene-5-carboxylic acid)

3D PDB for NP0169846 ((1r,2r,5s,8r,14s,18s)-15-formyl-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-15-ene-5-carboxylic acid)

SMILES for NP0169846 ((1r,2r,5s,8r,14s,18s)-15-formyl-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-15-ene-5-carboxylic acid)

INCHI for NP0169846 ((1r,2r,5s,8r,14s,18s)-15-formyl-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-15-ene-5-carboxylic acid)

Structure for NP0169846 ((1r,2r,5s,8r,14s,18s)-15-formyl-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-15-ene-5-carboxylic acid)

3D Structure for NP0169846 ((1r,2r,5s,8r,14s,18s)-15-formyl-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icos-15-ene-5-carboxylic acid)