Ursolic acid (cis-3-O-hydroxycinnamoyl-)
precursor
Showing entry for Ursolic acid (cis-3-O-hydroxycinnamoyl-)
Identification
- PhytoHub ID
- PHUB000192
- Name
- Ursolic acid (cis-3-O-hydroxycinnamoyl-)
- Systematic Name
- Not Available
- Synonyms
- Not Available
- CAS Number
- Not Available
- Average Mass
- 602.856
- Monoisotopic Mass
- 602.397124839
- Chemical Formula
- C39H54O5
- IUPAC Name
- (1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-{[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid
- InChI Key
- ZOXDAGKKDOEJBW-HNPRZPGGSA-N
- InChI Identifier
InChI=1S/C39H54O5/c1-24-16-21-39(34(42)43)23-22-37(6)28(33(39)25(24)2)13-14-30-36(5)19-18-31(35(3,4)29(36)17-20-38(30,37)7)44-32(41)15-10-26-8-11-27(40)12-9-26/h8-13,15,24-25,29-31,33,40H,14,16-23H2,1-7H3,(H,42,43)/b15-10-/t24-,25+,29+,30-,31+,33+,36+,37-,38-,39+/m1/s1
- SMILES
C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](OC(=O)\C=C/C6=CC=C(O)C=C6)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2[C@H]1C)C(O)=O
- Structure
Structure for Ursolic acid (cis-3-O-hydroxycinnamoyl-)
Calculated Properties
- Solubility (ALOGPS)
- 1.47e-04 g/l
- LogS (ALOGPS)
- -6.61
- LogP (ALOGPS)
- 7.92
- Hydrogen Acceptors
- 4
- Hydrogen Donors
- 2
- Rotatable Bond Count
- 5
- Polar Surface Area
- 83.83
- Refractivity
- 175.24659999999997
- Polarizability
- 70.00187109223063
- Formal Charge
- 0
- Physiological Charge
- -1
- pKa (strongest basic)
- -5.954731874958879
- pKa (strongest acidic)
- 4.744115799385438
- Number of Rings
- 6
- Rule of Five
- No
- Bioavailability
- No
- Ghose Filter
- No
- Veber's Rule
- No
- MDDR-like Rule
- No
External Links
- PubChem
- 24203732
- Chemistry Dashboard
- DTXSID80639812
- PeakForestCompound
- 000176
Taxonomy as Food Phytochemical
- Family
- Terpenoids
- Class
- Triterpenoids
- Sub-class
- Ursanes
Classyfire Taxonomy
- Kingdom Name
- Organic compounds
- Class
- Prenol lipids
- Super-class
- Lipids and lipid-like molecules
- Sub-class
- Triterpenoids
- Direct Parent Name
- Triterpenoids
- Alternative Parent Names
- ["1-hydroxy-2-unsubstituted benzenoids", "Carbonyl compounds", "Carboxylic acids", "Cinnamic acid esters", "Coumaric acid esters", "Coumaric acids and derivatives", "Dicarboxylic acids and derivatives", "Enoate esters", "Fatty acid esters", "Hydrocarbon derivatives", "Organic oxides", "Styrenes"]
- External Descriptor Annotations
- Not Available
- Substituent Names
- ["1-hydroxy-2-unsubstituted benzenoid", "Alpha,beta-unsaturated carboxylic ester", "Aromatic homopolycyclic compound", "Benzenoid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Carboxylic acid ester", "Cinnamic acid ester", "Cinnamic acid or derivatives", "Coumaric acid ester", "Coumaric acid or derivatives", "Dicarboxylic acid or derivatives", "Enoate ester", "Fatty acid ester", "Fatty acyl", "Hydrocarbon derivative", "Hydroxycinnamic acid or derivatives", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Phenol", "Styrene", "Triterpenoid"]
Spectra from Phytohub
| Spectrum Type | Instrument Type | Ion Mode | Collision Energy Level | View | Peaks | |
|---|---|---|---|---|---|---|
| Predicted LC-MS/MS | Not Available | Positive | low | View Spectrum | (107.0496898,2.164476943);(109.0653399,1.985534782);(119.0496898,0.89049178);(145.0289544,1.926600582);(147.0446045,15.53020086);(169.1228548,0.6356577884);(235.169805,0.6356577884);(301.1803697,0.6356577884);(303.2324052,0.6356577884);(393.3521264,2.183083148);(409.3470411,1.522962105);(411.3626911,0.9652094111);(421.3470411,1.55649346);(435.2899201,0.6356577884);(437.3419557,1.176270211);(439.3576057,8.89786055);(441.3732558,1.034852918);(457.3681704,5.918023589);(497.363085,1.303125867);(509.363085,1.017407974);(533.3266995,0.6356577884);(555.3838205,1.375804159);(557.3994706,8.154261665);(559.4151206,1.690624016);(567.3838205,1.326245231);(573.3579997,0.9019389612);(575.3736497,1.086235661);(585.3943852,9.680600376);(585.3943852,0.874000432);(587.3736497,1.045070589);(603.4049499,21.978678) | |
| Predicted LC-MS/MS | Not Available | Positive | med | View Spectrum | (83.08607535,1.027745994);(107.0496898,4.395492901);(119.0496898,4.578539023);(145.0289544,1.399479184);(147.0446045,19.87608342);(383.2950055,1.130660531);(391.3364764,1.903988133);(393.3521264,4.978723607);(395.2950055,0.988994528);(395.3677765,2.414169489);(397.3106556,1.031659259);(409.3470411,4.262643874);(411.3626911,3.10807448);(413.3783412,2.156716658);(421.3470411,3.317511975);(423.3626911,1.256060272);(427.3576057,1.931471711);(439.3576057,13.01564899);(441.3732558,1.280143186);(457.3681704,6.474662655);(493.3317849,1.13634805);(495.347435,1.088334946);(509.363085,1.643850993);(547.3423496,0.9485101231);(555.3838205,1.173114581);(557.3994706,3.925647517);(559.4151206,2.261496691);(573.3579997,1.086094319);(585.3943852,3.167172559);(587.3736497,0.901173204);(603.4049499,2.13978714) | |
| Predicted LC-MS/MS | Not Available | Positive | high | View Spectrum | (53.03912516,1.838198066);(55.05477522,3.868164639);(77.03912516,3.35991667);(83.08607535,3.208262049);(107.0496898,3.399978376);(115.0183897,1.890415002);(117.0340398,2.059477409);(119.0496898,2.172800443);(147.0446045,7.360964255);(303.2687907,1.605768195);(353.2480553,2.223453399);(353.3208263,3.72097153);(379.3000909,2.010384883);(381.3521264,7.971869866);(393.3157409,1.523781673);(393.3521264,6.89966191);(395.2950055,1.861949752);(395.331391,2.23333115);(409.3106556,1.948079163);(409.3470411,10.63476266);(411.3626911,3.186874044);(423.3263056,2.045824041);(427.3576057,2.128964701);(439.3576057,3.646186451);(445.27427,1.685987039);(451.3212202,2.321217825);(545.3266995,1.7463112);(555.3838205,1.720729408);(573.3579997,3.801116362);(575.3736497,2.977838885);(587.3736497,2.946758956) | |
| Predicted LC-MS/MS | Not Available | Negative | low | View Spectrum | (105.0340398,0.4233266498);(107.0496898,0.5736314386);(117.0340398,0.2683917138);(119.0496898,1.527385097);(143.0133043,0.3106782852);(145.0289544,6.718046952);(153.0915547,0.1918995051);(163.0395191,2.814336007);(393.3521264,1.00735181);(395.3677765,0.2849878649);(407.331391,0.5622118039);(409.3470411,1.525449249);(411.3626911,1.996384142);(435.3263056,0.445677878);(437.3419557,3.825713384);(439.3212202,0.339696086);(439.3212202,0.218139168);(439.3576057,0.3780999888);(453.3368703,0.2231679907);(455.3525204,14.99744371);(493.3317849,0.3163601515);(495.347435,0.6259785418);(539.3889059,0.5309281169);(541.3681704,0.5121344401);(555.3838205,0.413682054);(557.3994706,15.89971374);(573.3579997,0.2302548121);(583.3787351,1.404621778);(583.3787351,0.4241212131);(585.3579997,0.2364132804);(601.3892998,40.77377315) | |
| Predicted LC-MS/MS | Not Available | Negative | med | View Spectrum | (105.0340398,7.497592724);(107.0496898,2.943395206);(117.0340398,0.8119918403);(119.0496898,3.458865048);(121.0653399,0.7274370352);(145.0289544,8.695521404);(149.0602545,0.4184059185);(163.0395191,6.260021715);(393.3521264,3.545806264);(395.3677765,1.343168258);(407.331391,1.63544133);(409.3470411,5.668844791);(411.3626911,8.109167241);(437.3419557,0.6383505912);(437.3419557,2.315927366);(439.3212202,0.7437513921);(439.3576057,0.9441521346);(451.3576057,1.601692082);(453.3368703,0.4144645015);(455.3525204,13.03400295);(481.3317849,0.5660210122);(483.347435,0.4423706213);(493.3317849,1.496137425);(495.347435,2.580025764);(539.3889059,1.671288192);(541.3681704,0.753006683);(555.3838205,0.8124594127);(557.3994706,10.4358227);(583.3787351,1.611045866);(585.3579997,0.4120031609);(601.3892998,8.411819364) | |
| Predicted LC-MS/MS | Not Available | Negative | high | View Spectrum | (41.00273965,3.133955749);(43.01838972,1.054864215);(44.99765427,1.780418278);(71.04968984,1.603050146);(105.0340398,1.241943091);(117.0340398,1.720828271);(119.0496898,2.479934974);(143.0133043,1.084586791);(145.0289544,15.25528715);(163.0395191,2.502406859);(381.3521264,1.092301034);(393.3521264,2.31524537);(395.3677765,1.141425462);(407.331391,1.943096091);(409.3470411,10.40490041);(411.3626911,14.03281499);(423.3263056,1.849607439);(425.3419557,1.770461823);(437.3419557,0.9728664671);(437.3419557,2.75268815);(439.3212202,7.380212793);(439.3212202,6.83557788);(439.3576057,1.158486413);(451.3212202,1.009022025);(451.3576057,1.195607055);(453.3368703,1.705876419);(455.3525204,5.168237292);(493.3317849,0.9322035285);(573.3579997,0.8072404095);(583.3787351,1.827303894);(585.3579997,1.847549524) | |
| Predicted LC-MS/MS | Not Available | Positive | low | View Spectrum | (147.04406,11.09);(147.04406,11.09);(147.04406,11.09);(147.04406,11.09);(147.04406,11.09);(219.10157,3.19);(245.15361,4.27);(247.16926,11.89);(247.16926,11.89);(301.21621,4.39);(315.23186,3.9);(315.23186,3.9);(315.23186,3.9);(315.23186,3.9);(315.23186,3.9);(351.19547,3.67);(353.24751,4.73);(355.26316,6.07);(355.26316,6.07);(383.29446,3.19);(383.29446,3.19);(393.35158,15.71);(395.36723,4.28);(421.34649,4.13);(425.34141,13.32);(425.34141,13.32);(425.34141,13.32);(433.31011,11.96);(437.34141,3.23);(437.34141,3.23);(437.34141,3.23);(437.34141,3.23);(437.34141,3.23);(437.34141,3.23);(437.34141,3.23);(439.35706,100.0);(439.35706,100.0);(439.35706,100.0);(439.35706,100.0);(439.35706,100.0);(439.35706,100.0);(439.35706,100.0);(439.35706,100.0);(439.35706,100.0);(439.35706,100.0);(439.35706,100.0);(439.35706,100.0);(439.35706,100.0);(439.35706,100.0);(439.35706,100.0);(439.35706,100.0);(439.35706,100.0);(439.35706,100.0);(439.35706,100.0);(439.35706,100.0);(439.35706,100.0);(439.35706,100.0);(441.37271,12.36);(441.37271,12.36);(441.37271,12.36);(441.37271,12.36);(441.37271,12.36);(441.37271,12.36);(495.34689,5.12);(495.34689,5.12);(557.39892,6.51);(557.39892,6.51);(557.39892,6.51);(557.39892,6.51);(557.39892,6.51);(575.3731,2.85);(575.3731,2.85);(575.3731,2.85);(575.3731,2.85);(575.3731,2.85);(585.39384,26.64);(585.39384,26.64);(585.39384,26.64);(585.39384,26.64);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87);(603.4044,95.87) | |
| Predicted LC-MS/MS | Not Available | Positive | medium | View Spectrum | (105.03349,16.07);(105.03349,16.07);(119.04914,100.0);(119.04914,100.0);(123.11683,19.23);(123.11683,19.23);(129.03349,11.54);(129.03349,11.54);(133.10118,14.44);(133.10118,14.44);(133.10118,14.44);(135.04406,17.23);(147.04406,87.73);(147.04406,87.73);(147.04406,87.73);(147.04406,87.73);(147.04406,87.73);(163.03897,11.68);(165.05462,49.66);(165.05462,49.66);(165.05462,49.66);(165.05462,49.66);(283.13287,30.75);(283.13287,30.75);(283.13287,30.75);(283.13287,30.75);(285.14852,26.18);(285.14852,26.18);(285.14852,26.18);(285.14852,26.18);(285.14852,26.18);(285.18491,41.37);(285.18491,41.37);(285.18491,41.37);(285.18491,41.37);(285.18491,41.37);(285.18491,41.37);(287.20056,20.83);(287.20056,20.83);(287.20056,20.83);(287.20056,20.83);(289.21621,11.61);(291.23186,22.8);(291.23186,22.8);(291.23186,22.8);(297.14852,12.28);(299.16417,28.01);(299.20056,22.37);(299.20056,22.37);(301.17982,33.89);(301.21621,17.23);(315.23186,14.7);(315.23186,14.7);(315.23186,14.7);(315.23186,14.7);(315.23186,14.7);(317.24751,12.52);(317.24751,12.52);(317.24751,12.52);(393.35158,34.37);(417.24242,12.85);(423.28937,15.84);(431.25807,12.35);(439.35706,13.78);(439.35706,13.78);(439.35706,13.78);(439.35706,13.78);(439.35706,13.78);(439.35706,13.78);(439.35706,13.78);(439.35706,13.78);(439.35706,13.78);(439.35706,13.78);(439.35706,13.78);(439.35706,13.78);(439.35706,13.78);(439.35706,13.78);(439.35706,13.78);(439.35706,13.78);(439.35706,13.78);(439.35706,13.78);(439.35706,13.78);(439.35706,13.78);(439.35706,13.78);(439.35706,13.78);(557.39892,20.04);(557.39892,20.04);(557.39892,20.04);(557.39892,20.04);(557.39892,20.04);(585.39384,14.51);(585.39384,14.51);(585.39384,14.51);(585.39384,14.51);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59);(603.4044,42.59) | |
| Predicted LC-MS/MS | Not Available | Positive | high | View Spectrum | (55.05423,18.85);(77.03858,25.59);(79.05423,45.09);(85.10118,11.76);(85.10118,11.76);(91.05423,31.93);(107.04914,20.85);(107.04914,20.85);(107.04914,20.85);(119.04914,100.0);(119.04914,100.0);(119.08553,11.52);(119.08553,11.52);(121.10118,16.61);(121.10118,16.61);(121.10118,16.61);(123.11683,62.6);(123.11683,62.6);(125.13248,31.89);(129.03349,11.91);(129.03349,11.91);(131.04914,15.24);(131.04914,15.24);(133.10118,20.64);(133.10118,20.64);(133.10118,20.64);(135.11683,32.19);(135.11683,32.19);(135.11683,32.19);(137.13248,19.99);(137.13248,19.99);(147.04406,23.39);(147.04406,23.39);(147.04406,23.39);(147.04406,23.39);(147.04406,23.39);(235.16926,26.56);(235.16926,26.56);(235.16926,26.56);(235.16926,26.56);(235.16926,26.56);(285.18491,20.45);(285.18491,20.45);(285.18491,20.45);(285.18491,20.45);(285.18491,20.45);(285.18491,20.45);(289.21621,38.35);(299.16417,11.35);(301.17982,16.4);(389.32028,23.13);(417.24242,10.21);(419.25807,9.67);(421.27372,16.67);(421.27372,16.67);(433.31011,77.71);(435.32576,12.96);(435.32576,12.96);(435.32576,12.96);(435.32576,12.96);(435.32576,12.96);(435.32576,12.96);(457.36762,9.95);(457.36762,9.95);(457.36762,9.95);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98);(603.4044,21.98) | |
| Predicted LC-MS/MS | Not Available | Negative | low | View Spectrum | (455.35307,24.85);(455.35307,24.85);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0) | |
| Predicted LC-MS/MS | Not Available | Negative | medium | View Spectrum | (107.05024,13.35);(107.05024,13.35);(107.05024,13.35);(109.06589,9.98);(109.06589,9.98);(109.06589,9.98);(109.06589,9.98);(119.05024,47.22);(119.05024,47.22);(119.05024,47.22);(119.05024,47.22);(145.0295,32.19);(145.0295,32.19);(145.0295,32.19);(145.0295,32.19);(147.04515,10.81);(163.04007,6.8);(393.35268,4.73);(437.3425,10.74);(437.3425,10.74);(437.3425,10.74);(439.35815,9.63);(439.35815,9.63);(455.35307,4.69);(455.35307,4.69);(495.34798,4.81);(557.40002,6.9);(557.40002,6.9);(557.40002,6.9);(557.40002,6.9);(599.3742,14.07);(599.3742,14.07);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0);(601.38985,100.0) | |
| Predicted LC-MS/MS | Not Available | Negative | high | View Spectrum | (51.02402,3.42);(65.03967,6.25);(65.03967,6.25);(91.05532,3.91);(91.05532,3.91);(93.03459,12.63);(93.03459,12.63);(101.03967,14.1);(117.03459,31.23);(117.03459,31.23);(119.05024,100.0);(119.05024,100.0);(119.05024,100.0);(119.05024,100.0);(137.02442,4.78);(437.3425,5.83);(437.3425,5.83);(437.3425,5.83);(451.35815,10.02);(493.33233,6.89);(493.33233,6.89);(493.33233,6.89);(569.36363,4.06);(571.3429,2.8);(571.37928,3.54);(583.37928,3.88);(583.37928,3.88);(583.37928,3.88);(585.35855,3.32);(585.35855,3.32);(585.35855,3.32);(599.3742,8.51);(599.3742,8.51);(601.38985,12.65);(601.38985,12.65);(601.38985,12.65);(601.38985,12.65);(601.38985,12.65);(601.38985,12.65);(601.38985,12.65);(601.38985,12.65);(601.38985,12.65);(601.38985,12.65);(601.38985,12.65);(601.38985,12.65);(601.38985,12.65);(601.38985,12.65);(601.38985,12.65);(601.38985,12.65);(601.38985,12.65) |
Food Sources
| Name | Group | |||
|---|---|---|---|---|
| American cranberry | Fruit, Berries | Publications | Show |
Role as Biomarker of intake
No roles as Biomarker of intake found
Metabolism
No metabolism information available
Inter-Individual Variations in Metabolism
No data on inter-individual variations available