NP-MRD: Showing NP-Card for 13-hydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-17-yl acetate (NP0301621)

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Record Information

Version

2.0

Created at

2022-09-10 14:42:10 UTC

Updated at

2022-09-10 14:42:11 UTC

NP-MRD ID

NP0301621

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13-hydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-17-yl acetate

Description

13-Hydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]Nonadeca-3(7),5-dien-17-yl acetate belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. 13-hydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-17-yl acetate is found in Caesalpinia minax. 13-Hydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]Nonadeca-3(7),5-dien-17-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161518192D          

 28 32  0  0  0  0            999 V2000
    3.8028   -3.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3368   -3.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5142   -3.3498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6933   -2.5426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2272   -1.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4046   -1.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9386   -1.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2951   -0.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5005   -0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3756    0.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1176   -0.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6516    0.2436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4741    0.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2967    0.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8001    1.0238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5773    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2580    1.2131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -0.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7628   -0.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4063   -1.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662   -1.6814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9576   -1.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6603   -1.8808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2886   -1.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9742   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1516   -0.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5837   -1.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0498   -1.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 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  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 18 26  1  0  0  0  0
 22 26  2  0  0  0  0
 20 27  1  0  0  0  0
  5 27  1  0  0  0  0
 11 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

     RDKit          3D

 56 60  0  0  0  0  0  0  0  0999 V2000
   -2.8447    4.3033   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0511    3.1788   -0.6689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3734    3.3583   -1.7184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0210    1.9360   -0.0903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2730    0.8407   -0.5997 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3097   -0.0615   -1.2186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0023   -0.8805   -0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9266   -1.8297    0.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4783   -2.6186   -0.9290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5543   -2.8287    1.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7841   -1.1052    0.9783 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3400   -0.9733    2.2925 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2560   -2.1643    1.1569 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6566   -1.7756    1.1728 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1132   -0.8616    2.1196 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2228   -0.2480    1.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868    0.5422    2.1444 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3450   -0.6817    0.1267 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7450    0.3539   -0.8040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9888    0.7752   -1.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7832    1.8106   -2.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4889    2.0002   -2.2359 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8365    1.1423   -1.4407 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3495    1.0631   -1.2782 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0890    0.3269    0.0183 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8454   -0.9549   -0.1190 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3615    0.1900    0.3986 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4679    1.1681    1.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8440    3.9349    0.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0573    5.0183   -0.9345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3018    4.7751    0.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7645    1.2484   -1.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0884    0.5658   -1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8670   -0.6702   -2.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3366   -0.1956    0.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8232   -1.4197   -0.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6019   -2.1916   -1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766   -3.7234   -0.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3283   -2.6183   -1.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4123   -3.8767    0.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0904   -2.7443    2.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6440   -2.6630    1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1278   -0.3993    2.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0605   -2.8121    2.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1832   -2.9305    0.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3045   -2.6432    1.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9173   -1.6283    0.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9282    0.3562   -0.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5446    2.3685   -2.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0147    2.1207   -1.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0032    0.5160   -2.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6935    0.9325    0.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6676   -1.5323   -1.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1362    2.0709    1.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5243    1.4828    1.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1838    0.6523    2.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 26  1  0
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 25 27  1  0
 27 28  1  1
 27  5  1  0
 27 11  1  0
 26 14  1  0
 22 23  1  0
 19 18  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  5 32  1  6
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 10 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  6
 18 47  1  1
 26 53  1  6
 25 52  1  1
 24 50  1  0
 24 51  1  0
 20 48  1  0
 21 49  1  0
 28 54  1  0
 28 55  1  0
 28 56  1  0
M  END


  Mrv1533004161518192D          

 28 32  0  0  0  0            999 V2000
    3.8028   -3.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3368   -3.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5142   -3.3498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6933   -2.5426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2272   -1.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4046   -1.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9386   -1.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2951   -0.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5005   -0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3756    0.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1176   -0.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6516    0.2436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4741    0.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2967    0.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8001    1.0238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5773    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2580    1.2131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -0.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7628   -0.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4063   -1.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662   -1.6814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9576   -1.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6603   -1.8808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2886   -1.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9742   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1516   -0.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5837   -1.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0498   -1.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 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  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 18 26  1  0  0  0  0
 22 26  2  0  0  0  0
 20 27  1  0  0  0  0
  5 27  1  0  0  0  0
 11 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0301621

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CCC(C)(C)C2(O)CC3OC(=O)C4C3C(CC3=C4C=CO3)C12C

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O6/c1-11(23)27-16-5-7-20(2,3)22(25)10-15-18-13(21(16,22)4)9-14-12(6-8-26-14)17(18)19(24)28-15/h6,8,13,15-18,25H,5,7,9-10H2,1-4H3

> <INCHI_KEY>
GXBMHMVGIRRPBD-UHFFFAOYSA-N

> <FORMULA>
C22H28O6

> <MOLECULAR_WEIGHT>
388.46

> <EXACT_MASS>
388.188588622

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
41.106253650264996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-hydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-17-yl acetate

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
1.928430655666666

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.280962163978298

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.883885877149904

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8238216582777005

> <JCHEM_POLAR_SURFACE_AREA>
85.97000000000001

> <JCHEM_REFRACTIVITY>
98.9156

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-hydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-17-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       7.099  -7.406   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.229  -6.135   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.693  -6.253   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.894  -4.746   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.024  -3.475   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.489  -3.593   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.619  -2.323   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.284  -0.934   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.801  -0.520   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.434   0.599   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.820  -0.816   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.950   0.455   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.485   0.573   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.021   0.691   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.960   1.911   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.411   1.394   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.682   2.264   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.368  -0.145   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.891  -0.580   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.225  -1.969   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.644  -3.139   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.121  -2.704   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.433  -3.511   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      13.605  -2.513   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.019  -1.089   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.483  -1.207   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.690  -2.087   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.560  -3.357   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   13   27                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   26                                                  
CONECT   19   18   14   20                                                  
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   18   22                                                  
CONECT   27   20    5   11   28                                             
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Value	Source
13-Hydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0,.0,.0,]nonadeca-3(7),5-dien-17-yl acetic acid	Generator
13-Hydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-17-yl acetic acid	Generator

Chemical Formula

C₂₂H₂₈O₆

Average Mass

388.4600 Da

Monoisotopic Mass

388.18859 Da

IUPAC Name

13-hydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-17-yl acetate

Traditional Name

13-hydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-17-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CCC(C)(C)C2(O)CC3OC(=O)C4C3C(CC3=C4C=CO3)C12C

InChI Identifier

InChI=1S/C22H28O6/c1-11(23)27-16-5-7-20(2,3)22(25)10-15-18-13(21(16,22)4)9-14-12(6-8-26-14)17(18)19(24)28-15/h6,8,13,15-18,25H,5,7,9-10H2,1-4H3

InChI Key

GXBMHMVGIRRPBD-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
Caesalpinia minax	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Benzofuran
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Heteroaromatic compound
Furan
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	2.99	ALOGPS
logP	1.93	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	13.88	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.97 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	98.92 m³·mol⁻¹	ChemAxon
Polarizability	41.11 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

78384629

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 13-hydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-17-yl acetate (NP0301621)

MOL for NP0301621 (13-hydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-17-yl acetate)

3D MOL for NP0301621 (13-hydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-17-yl acetate)

3D SDF for NP0301621 (13-hydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-17-yl acetate)

3D-SDF for NP0301621 (13-hydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-17-yl acetate)

PDB for NP0301621 (13-hydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-17-yl acetate)

3D PDB for NP0301621 (13-hydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-17-yl acetate)

SMILES for NP0301621 (13-hydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-17-yl acetate)

INCHI for NP0301621 (13-hydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-17-yl acetate)

Structure for NP0301621 (13-hydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-17-yl acetate)

3D Structure for NP0301621 (13-hydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0³,⁷.0⁸,¹⁹.0¹³,¹⁸]nonadeca-3(7),5-dien-17-yl acetate)