precursor

Showing entry for Carnosic Acid

Identification

PhytoHub ID
PHUB002020
Name
Carnosic Acid
Systematic Name
Not Available
Synonyms
  • (4AR)-5,6-dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carbox
  • 4a(2H)-Phenanthrenecarboxylic acid
  • RoseOx
  • Salvin
CAS Number
3650-09-7
Average Mass
332.44
Monoisotopic Mass
332.198759382
Chemical Formula
C20H28O4
IUPAC Name
(4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylic acid
InChI Key
QRYRORQUOLYVBU-VBKZILBWSA-N
InChI Identifier
InChI=1S/C20H28O4/c1-11(2)13-10-12-6-7-14-19(3,4)8-5-9-20(14,18(23)24)15(12)17(22)16(13)21/h10-11,14,21-22H,5-9H2,1-4H3,(H,23,24)/t14-,20+/m0/s1
SMILES
CC(C)C1=C(O)C(O)=C2C(CC[C@H]3C(C)(C)CCC[C@]23C(O)=O)=C1
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
7.79e-02 g/l
LogS (ALOGPS)
-3.63
LogP (ALOGPS)
4.16
Hydrogen Acceptors
4
Hydrogen Donors
3
Rotatable Bond Count
2
Polar Surface Area
77.76
Refractivity
93.40579999999999
Polarizability
37.29537052089125
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-6.009160585229941
pKa (strongest acidic)
4.292945414120731
Number of Rings
3
Rule of Five
No
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Food Phytochemical

Family
Terpenoids
Class
Diterpenoids
Sub-class
Not Available

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Prenol lipids
Super-class
Lipids and lipid-like molecules
Sub-class
Diterpenoids
Direct Parent Name
Diterpenoids
Alternative Parent Names
["1-hydroxy-4-unsubstituted benzenoids", "Carbonyl compounds", "Carboxylic acids", "Hydrocarbon derivatives", "Hydrophenanthrenes", "Monocarboxylic acids and derivatives", "Naphthalenecarboxylic acids", "Organic oxides", "Tetralins"]
External Descriptor Annotations
["abietane diterpenoid", "carbotricyclic compound", "catechols", "monocarboxylic acid"]
Substituent Names
["1-hydroxy-4-unsubstituted benzenoid", "1-naphthalenecarboxylic acid", "1-naphthalenecarboxylic acid or derivatives", "Abietane diterpenoid", "Aromatic homopolycyclic compound", "Benzenoid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Diterpenoid", "Hydrocarbon derivative", "Hydrophenanthrene", "Monocarboxylic acid or derivatives", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Phenanthrene", "Tetralin"]

Spectra from Phytohub

Spectrum TypeInstrument TypeIon ModeCollision Energy LevelViewPeaks
Predicted LC-MS/MSNot AvailablePositivelowView Spectrum(57.07042529,0.7549725176);(69.07042529,0.5244849767);(71.08607535,1.091988153);(149.0602545,0.2775178862);(153.0915547,0.2785991624);(163.0759046,0.3616031834);(165.0915547,0.4209913883);(169.1228548,0.2771451682);(177.0915547,0.3368757465);(243.1385048,1.308232103);(245.1541549,0.4160205924);(247.169805,0.386171419);(261.112684,0.3585902075);(263.1283341,0.8296982401);(269.1905404,0.3065325553);(271.1334195,0.3097618225);(273.1490695,0.7389038836);(275.1283341,0.3463614878);(275.1647196,0.3618756235);(277.1439842,0.5704331979);(285.185455,2.019975091);(287.2011051,15.2304703);(289.1439842,1.322448312);(289.2167552,2.534770105);(291.1596342,3.896379023);(293.1752843,0.389447334);(297.185455,0.8756678303);(305.1752843,0.5884219952);(315.1960197,15.49936581);(317.1752843,0.6985147015);(333.2065844,46.68778018)
Predicted LC-MS/MSNot AvailablePositivemedView Spectrum(43.05477522,3.131765603);(57.07042529,1.590453229);(69.07042529,1.511644131);(71.08607535,1.916680061);(83.08607535,1.803548335);(109.1017254,1.432924441);(137.1330255,1.361315254);(149.0602545,1.586984595);(151.0759046,5.049096932);(155.1072047,2.504939486);(165.0915547,4.040369742);(169.1228548,1.581707708);(177.0915547,1.74458802);(179.1072047,5.475968939);(183.1385048,1.928741894);(243.1385048,4.94635585);(245.1541549,1.781857943);(247.169805,3.656146625);(257.1905404,2.154588174);(271.1334195,1.317200716);(273.1490695,2.54532885);(275.1647196,1.450803078);(283.169805,1.231328716);(285.185455,2.505556239);(287.2011051,12.24829071);(289.1439842,2.083744243);(289.2167552,2.97379636);(291.1596342,5.562454401);(303.1960197,2.116422505);(315.1960197,8.039127293);(333.2065844,8.726269926)
Predicted LC-MS/MSNot AvailablePositivehighView Spectrum(41.03912516,4.420265816);(57.07042529,7.269350219);(65.03912516,1.544969603);(67.05477522,3.983489718);(69.07042529,3.102270318);(71.08607535,3.082452319);(81.07042529,4.767945166);(83.08607535,6.214102766);(109.1017254,1.683105592);(121.1017254,2.769331786);(123.1173755,1.886338607);(137.1330255,1.854907338);(173.1330255,2.063609289);(177.0915547,1.533862998);(203.1072047,2.25437866);(205.1228548,1.969194876);(217.1228548,4.327724376);(225.1643257,2.842877209);(229.1956258,4.505220767);(231.1385048,4.584456564);(245.1541549,2.744816797);(257.1905404,6.367007393);(259.169805,2.894999586);(259.2061905,4.208957128);(269.1905404,4.052867839);(271.1334195,1.722532886);(271.169805,3.664105908);(287.1647196,2.056533601);(305.1752843,1.58159372);(317.1752843,2.530925214);(317.1752843,1.515805943)
Predicted LC-MS/MSNot AvailableNegativelowView Spectrum(44.99765427,0.1314800556);(55.05477522,0.161456139);(69.07042529,0.0696189422);(83.04968984,0.1068225178);(149.0602545,0.204970663);(153.0915547,0.1411975121);(155.1072047,0.059998215);(163.0759046,0.1612160946);(167.1072047,0.1022044265);(177.0915547,0.2107029777);(181.1228548,0.1408814264);(229.1956258,0.125285551);(243.1385048,0.1081833303);(245.1541549,0.1330747573);(261.112684,0.0621627338);(269.1905404,0.6465496552);(271.169805,0.518519279);(273.185455,0.2793564197);(275.1283341,0.1338779814);(283.169805,0.1992483503);(285.185455,0.6105815983);(287.1283341,0.1024731726);(287.2011051,25.9956225);(289.1439842,0.741458516);(301.1803697,0.0629049045);(303.1596342,0.14305887);(303.1596342,0.2328992508);(313.1803697,2.044654245);(315.1596342,0.0937861786);(315.1596342,0.6227288238);(331.1909343,65.65302491)
Predicted LC-MS/MSNot AvailableNegativemedView Spectrum(44.99765427,0.3653520002);(55.05477522,0.2565175337);(83.04968984,0.1467419695);(149.0602545,0.4024525696);(151.0759046,0.1613573682);(153.0915547,0.3435124469);(175.0759046,0.1480956429);(177.0915547,0.4273597968);(179.1072047,0.1459287087);(181.1228548,0.3361840224);(227.1799757,0.1648997587);(229.1956258,0.5869197411);(241.1228548,0.267159596);(243.1385048,2.827860623);(245.1541549,4.599604327);(247.169805,0.2070541096);(257.1905404,0.2500540385);(269.1905404,2.002778224);(271.1334195,0.2469741074);(271.169805,1.491040848);(273.185455,0.5740620163);(275.2011051,0.2111231504);(283.169805,0.714994462);(285.185455,2.298365277);(287.1283341,0.5500505554);(287.2011051,43.21481433);(289.1439842,3.183590135);(303.1596342,0.1948162201);(313.1803697,2.345809751);(315.1596342,0.8000869847);(331.1909343,30.53443968)
Predicted LC-MS/MSNot AvailableNegativehighView Spectrum(44.99765427,4.598232097);(55.05477522,1.519046863);(69.07042529,1.290414516);(123.1173755,1.088430421);(149.0602545,2.644436465);(151.0759046,1.956757965);(163.0759046,1.835365614);(165.0915547,1.907398559);(175.0759046,0.9935322716);(177.0915547,1.484728268);(179.1072047,1.186163495);(227.1799757,1.216964891);(229.1956258,3.548044683);(243.1385048,6.736444192);(245.1541549,7.786819732);(255.1748904,1.412833341);(257.1905404,2.786023623);(267.1748904,1.070166575);(269.1541549,2.64014519);(269.1905404,6.873757137);(271.1334195,1.512336051);(271.169805,12.71815429);(273.185455,1.365819587);(283.169805,2.985729492);(285.185455,1.869354694);(287.1283341,2.283139784);(287.2011051,10.20267921);(289.1439842,3.456120527);(313.1803697,3.436178852);(315.1596342,3.533112523);(331.1909343,2.061669096)

Food Sources

NameGroup
BasilHerbs and Spices PublicationsShow
Common oreganoHerbs and Spices PublicationsShow
Common sageHerbs and Spices PublicationsShow
RosemaryHerbs and Spices PublicationsShow
Rosemary teaTeas and herbal teas PublicationsShow
Thyme (Thymus capitatus )Herbs and Spices PublicationsShow

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Carnosic Acid Carnosic Acidratplasmaunchanged1h-3h>20µmol/LNo dataC20H28O4332.198759382 Detailed Intervention Studies Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
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