(Q27134233)

CHEMBL249447 (English)

(1R,3R,4R,5R)-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid

7 October 2016

stereoisomer of

2 references

(-)-3,5-Dicaffeoyl quinic acid

inferred from InChI

2 references

(1R,3S,4R,5S)-3,5-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,4-dihydroxycyclohexane-1-carboxylic acid

inferred from InChI

1 reference

inferred from InChI

chemical formula

C₂₅H₂₄O₁₂

0 references

canonical SMILES

C1=C(C=C(C(=C1)O)O)C=CC(=O)OC2C(C(CC(C2)(O)C(=O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)O

1 reference

3,5-dicaffeoylquinic acid (English)

20 November 2016

isomeric SMILES

C1=C(C=C(C(=C1)O)O)/C=C/C(=O)O[C@H]2[C@@H]([C@@H](C[C@@](C2)(O)C(=O)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)O

1 reference

Altitudinal variation of secondary metabolite profiles in flowering heads of Arnica montana cv. ARBO.

3,5-dicaffeoylquinic acid (English)

20 November 2016

1 reference

Baccharis gaudichaudiana

2 references

A new ent-clerodane diterpene from the aerial parts of Baccharis gaudichaudiana

A new ent-clerodane diterpene from the aerial parts of Baccharis gaudichaudiana

Chaerophyllum hirsutum

2 references

Cytotoxic constituents of roots of Chaerophyllum hirsutum

Cytotoxic constituents of roots of Chaerophyllum hirsutum

Scorzoneroides autumnalis

1 reference

Comparative molecular and phytochemical investigation of Leontodon autumnalis (Asteraceae, Lactuceae) populations from Central Europe

Ostericum grosseserratum

1 reference

A new chromone, 11-hydroxy-sec-O-glucosylhamaudol from Ostericum koreanum.

Scorzonera pseudodivaricata

1 reference

Biologically active natural products from Mongolian medicinal plants Scorzonera divaricata and Scorzonera pseudodivaricata

Strychnos axillaris

2 references

Phenolic and iridoid glycosides from Strychnos axillaris

Phenolic and iridoid glycosides from Strychnos axillaris

Echinops galalensis

1 reference

Protective effect of Echinops galalensis against CCl4-induced injury on the human hepatoma cell line (Huh7)

Aster koraiensis

2 references

Chemical constituents from the aerial parts of Aster koraiensis with protein glycation and aldose reductase inhibitory activities

Chemical constituents from the aerial parts of Aster koraiensis with protein glycation and aldose reductase inhibitory activities

Dichrocephala bicolor

2 references

Immunomodulatory principles of Dichrocephala bicolor

Immunomodulatory principles of Dichrocephala bicolor

Gardenia jasminoides

1 reference

Vanillic acid glycoside and quinic acid derivatives from Gardeniae Fructus.

Ipomoea pes-caprae

1 reference

Collagenase inhibitory quinic acid esters from Ipomoea pes-caprae

Phagnalon rupestre

3 references

Phenolic substances from Phagnalon rupestre protect against 2,4,6-trinitrochlorobenzene-induced contact hypersensitivity

Phenolic substances from Phagnalon rupestre protect against 2,4,6-trinitrochlorobenzene-induced contact hypersensitivity

Phagnalon rupestre as a source of compounds active on contact hypersensitivity

Coffea arabica

1 reference

Contribution of chlorogenic acids to the iron-reducing activity of coffee beverages

Coffea canephora

1 reference

Contribution of chlorogenic acids to the iron-reducing activity of coffee beverages

Cydonia

2 references

First report on Cydonia oblonga Miller anticancer potential: differential antiproliferative effect against human kidney and colon cancer cells

Influence of jam processing upon the contents of phenolics, organic acids and free amino acids in quince fruit ( Cydonia oblonga Miller)

Alternaria alternata

1 reference

3,5-Di-O-caffeoylquinic acid, an infection-inhibiting factor from Pyrus pyrifolia induced by infection with Alternaria alternata

Antonia ovata

1 reference

Cytotoxic triterpenoid saponins from the stem bark of Antonia ovata

Artemisia caruifolia

1 reference

Inhibitory effects on HIV-1 protease of tri-p-coumaroylspermidine from Artemisia caruifolia and related amides

Aster indicus

1 reference

Phenolic derivatives from Aster indicus

Baccharis dracunculifolia

1 reference

Studies on the constituents from the aerial part of Baccharis dracunculifolia DC.

Bidens pilosa

1 reference

Polyacetylenic compounds and butanol fraction from Bidens pilosa can modulate the differentiation of helper T cells and prevent autoimmune diabetes in non-obese diabetic mice

Bridelia ferruginea

1 reference

Complement-Inhibiting Constituents of Bridelia ferruginea Stem Bark

Psydrax schimperiana

1 reference

A cyanogenic glycoside from Canthium schimperianum

Centella asiatica

2 references

Irbic acid, a dicaffeoylquinic acid derivative from Centella asiatica cell cultures

The anti-thrombotic active constituents from Centella asiatica

Glebionis coronaria

1 reference

Structural Identification of Two Antioxidant Quinic Acid Derivatives from Garland (Chrysanthemum coronariumL.)

Glebionis coronarium

1 reference

Structural Identification of Two Antioxidant Quinic Acid Derivatives from Garland (Chrysanthemum coronariumL.)

Chrysanthemum morifolium

1 reference

Xanthine oxidase inhibitors from the flowers of Chrysanthemum sinense

Corchorus olitorius

1 reference

Phenolic antioxidants from the leaves of Corchorus olitorius L

Crassocephalum crepidioides

1 reference

Free radical scavenging and hepatoprotective actions of the medicinal herb, Crassocephalum crepidioides from the Okinawa Islands

Cressa cretica

1 reference

Isolation and NMR spectra of syringaresinol-beta-D-glucoside from Cressa cretica

Eupatorium perfoliatum

1 reference

Caffeic acid derivatives from Eupatorium perfoliatum L.

Helichrysum stoechas

1 reference

Constituents of Helichrysum stoechas variety olonnense

Hieracium gymnocephalum

1 reference

A taraxasterol derivative and phenolic compounds from Hieracium gymnocephalum

Ilex argentina

1 reference

Phenolic compounds in seven South American Ilex species

Ilex brevicuspis

1 reference

Phenolic compounds in seven South American Ilex species

Ilex dumosa

1 reference

Phenolic compounds in seven South American Ilex species

Ilex microdonta

1 reference

Phenolic compounds in seven South American Ilex species

yerba mate

1 reference

Phenolic compounds in seven South American Ilex species

Ilex pseudobuxus

1 reference

Phenolic compounds in seven South American Ilex species

Ilex taubertiana

1 reference

Phenolic compounds in seven South American Ilex species

Ilex theezans

1 reference

Phenolic compounds in seven South American Ilex species

sweet potato

4 references

New polyphenol derivative in Ipomoea batatas tubers and its antioxidant activity

Identification and characterization of foliar polyphenolic composition in sweetpotato (Ipomoea batatas L.) genotypes

Changes in caffeic acid derivatives in sweet potato (Ipomoea batatas L.) during cooking and processing

Antimutagenicity of mono-, di-, and tricaffeoylquinic acid derivatives isolated from sweetpotato (Ipomoea batatas L.) leaf

Ipomoea cairica

1 reference

Constituents of Ipomoea cairica Ethanolic Extract

Lactuca indica

1 reference

Isolation of quinic acid derivatives and flavonoids from the aerial parts of Lactuca indica L. and their hepatoprotective activity in vitro

Ophryosporus heptanthus

1 reference

Antioxidant activity of diterpenes and polyphenols from Ophryosporus heptanthus

Petasites japonicus

1 reference

Medicinal Foodstuffs. XXXII. Novel Sesquiterpene Glycoside Sulfate, Fukinoside A, with Antiallergic Activity from Japanese Butterbur (Petasites japonicus)

Neurolaena lobata

1 reference

Caffeoylquinic acids and some biological activities of Pluchea symphytifolia

Baccharis salicifolia

1 reference

Cyclohexanecarboxylic-Acid Derivatives fromPsiadia trinervia

Scorzonera latifolia

1 reference

Phenolic compounds from Scorzonera latifolia (Fisch. & Mey.) DC.

Smallanthus sonchifolius

1 reference

Caffeic acid derivatives in the roots of yacon (Smallanthus sonchifolius).

Solidago canadensis

1 reference

ChemInform Abstract: A New Labdane Diterpene from the Flowers of Solidago canadensis.

Werneria nubigena

1 reference

Benzopyran derivatives from Werneria nubigena

Xanthium strumarium

1 reference

1,3,5-Tri-O-caffeoylquinic acid from Xanthium strumarium

Youngia japonica

1 reference

Studies on the constituents of whole plants of Youngia japonica.

Pulicaria wightiana

1 reference

Phenolic derivatives from Aster indicus

Takhtajaniantha austriaca

1 reference

Phenolic compounds from Scorzonera latifolia (Fisch. & Mey.) DC.

Hubertia

1 reference

Targeted Natural Product Isolation Guided by HPLC–SPE–NMR: Constituents ofHubertiaSpecies

Senecio

1 reference

Targeted Natural Product Isolation Guided by HPLC–SPE–NMR: Constituents ofHubertiaSpecies

Dracocephalum ruyschiana

1 reference

Flavone tetraglycosides and benzyl alcohol glycosides from the Mongolian medicinal plant Dracocephalum ruyschiana.

Tripolium pannonicum

1 reference

Synthesis and bioactivity of tripolinolate A from Tripolium vulgare and its analogs

Tripolium vulgare

1 reference

Synthesis and bioactivity of tripolinolate A from Tripolium vulgare and its analogs

Artemisia carvifolia

1 reference

Inhibitory effects on HIV-1 protease of tri-p-coumaroylspermidine from Artemisia caruifolia and related amides

Coffea

1 reference

Quantitation of volatiles and nonvolatile acids in an extract from coffee beverages: correlation with antioxidant activity

Artemisia annua

2 references

Characterization of phenolic compounds in the Chinese herbal drug Artemisia annua by liquid chromatography coupled to electrospray ionization mass spectrometry

Phytochemical analysis of a herbal tea from Artemisia annua L.

Morus alba

1 reference

HPLC-DAD-ESI-MS/MS analysis and antioxidant activities of nonanthocyanin phenolics in mulberry (Morus alba L.).

radish

1 reference

HPLC–DAD–ESI/MSn characterization of environmentally friendly polyphenolic extract from Raphanus sativus L. var. “Cherry Belle” skin and stability of its red components

Chamaemelum nobile

1 reference

Nutrients, phytochemicals and bioactivity of wild Roman chamomile: a comparison between the herb and its preparations

common sunflower

1 reference

Identification and quantification of phenolic compounds from sunflower (Helianthus annuus L.) kernels and shells by HPLC-DAD/ESI-MSn

Helichrysum italicum

1 reference

Spectroscopic identification and anti-biofilm properties of polar metabolites from the medicinal plant Helichrysum italicum against Pseudomonas aeruginosa

Suaeda glauca

1 reference

In vitro hepatoprotective compounds from Suaeda glauca

subject has role

HIV integrase inhibitors

1 reference

Medical Subject Headings

MeSH descriptor ID

C100434

InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1

15 March 2018

Identifiers

InChI

1 reference

3,5-dicaffeoylquinic acid (English)

20 November 2016

2 references

3,5-dicaffeoylquinic acid (English)

20 November 2016

ChEBI release 2020-09-01

CAS Registry Number

900249-68-5

1 reference

3,5-dicaffeoylquinic acid (English)

20 November 2016

1 reference

3,5-O-dicaffeoylquinic acid (English)

20 November 2016

Reaxys registry number

4895191

1 reference

3,5-di-O-caffeoyl quinic acid (English)

7 October 2016

ChEBI ID

65751

mapping relation type

2 references

CHEMBL249447 (English)

20 November 2016

International Chemical Identifier

InChI

InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1

1 reference

CHEMBL249447 (English)

20 November 2016

2 references

SCHEMBL18318642

2 references

splash10-0udi-0209000000-546289f492330e8d136a

SPLASH

0 references

splash10-001l-1900000000-ef69390d51c1bba72d5a

0 references

splash10-03di-0900000000-b71d919a41ae4f4c562b

0 references

splash10-03di-0900300000-199a4631ff3cb6335be8

0 references

MeSH descriptor ID

C100434

1 reference

Medical Subject Headings

MeSH descriptor ID

C100434

Human Metabolome Database ID

14 March 2018

HMDB0030706

0 references

HMDB0029280

2 references

2 references

3,5-dicaffeoylquinic acid (English)

20 November 2016

inferred by common MeSH mappings on source and on Wikidata

0 references

1 reference

UMLS 2023