Cryptochlorogenic acid

Details

• Internal ID: 000c5f2a-3f86-43b7-b303-2c0a5f293f1f
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
• IUPAC Name: (3R,5R)-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,3,5-trihydroxycyclohexane-1-carboxylic acid
• SMILES (Canonical): C1C(C(C(CC1(C(=O)O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O
• SMILES (Isomeric): C1[C@H](C([C@@H](CC1(C(=O)O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O
• InChI: InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(21)25-14-11(19)6-16(24,15(22)23)7-12(14)20/h1-5,11-12,14,17-20,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14?,16?/m1/s1
• InChI Key: GYFFKZTYYAFCTR-AVXJPILUSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₈O₉
• Molecular Weight: 354.31 g/mol
• Exact Mass: 354.09508215 g/mol
• Topological Polar Surface Area (TPSA): 165.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -0.65
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• 905-99-7
• 4-Caffeoylquinic acid
• 4-O-Caffeoylquinic acid
• 4-Cqa
• 4-o-Caffeoyl quinic acid
• Quinic acid 4-O-caffeate
• 4-O-trans-caffeoylquinic acid
• 4-O-(3,4-Dihydroxycinnamoyl)-D-quinic acid
• F23DJ84IZ9
• (3R,5R)-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,3,5-trihydroxycyclohexane-1-carboxylic acid
• CHEMBL4203706
• 4-(3,4-Dihydroxycinnamoyl)quinic acid
• (1alpha,3alpha,4alpha,5beta)-4-(3-(3,4-(Dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,3,5-trihydroxycyclohexanecarboxylic acid
• 82638-23-1
• 87099-73-8
• rel-(1S,3R,4S,5R)-4-(((E)-3-(3,4-Dihydroxyphenyl)acryloyl)oxy)-1,3,5-trihydroxycyclohexanecarboxylic acid
• MFCD10566638
• Cryptochlorogenic-acid
• 4-Caffeoylquinic acid;4-O-Caffeoylquinic acid
• Quinic acid, 4-caffeoyl-
• UNII-F23DJ84IZ9
• 4-O-(E)-caffeoylquinic acid
• CHEMBL3092676
• Cinnamic acid, 3,4-dihydroxy-, 4-carboxy-2,4,6-trihydroxycyclohexyl ester
• Quinic acid, 4-caffeoyl-, E-
• SCHEMBL18180782
• SCHEMBL20883249
• ACon1_000120
• CHEBI:75491
• HY-N0787
• BDBM50455380
• s9319
• 4-O-Caffeoylquinic acid, >=98.0%
• AKOS037514601
• CCG-268076
• CS-3767
• NCGC00180861-01
• (3R,5R)-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,3,5-trihydroxy-cyclohexanecarboxylic acid
• BS-17821
• PD118874
• Cryptochlorogenic acid, analytical standard
• 4-Caffeoylquinic acid/ Cryptochlorogenic acid
• Q-100886
• B0B55D52-5101-4E6D-AA67-72D1CECBAA5A
• Q27145347
• 49B68A4C-6EC9-4441-B7D7-E3B740A8CDEC
• (1alpha,3R,4alpha,5R)-4-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,3,5-trihydroxycyclohexanecarboxylic acid
• (1S,3R,4S,5R)-4-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,3,5-trihydroxycyclohexanecarboxylic acid
• 1,3beta,5alpha-Trihydroxy-4alpha-(3,4-dihydroxycinnamoyloxy)cyclohexane-1beta-carboxylic acid
• CYCLOHEXANECARBOXYLIC ACID, 4-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,3,5-TRIHYDROXY-, (1.ALPHA.,3R,4.ALPHA.,5R)-
• Cyclohexanecarboxylic acid, 4-(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-1,3,5-trihydroxy-, (1alpha,3R,4alpha,5R)-
• Cyclohexanecarboxylic acid, 4-((3-(3,4-dihydroxyphenyl)-1-oxo-2-1R-propenyl)oxy)-1,3,5-trihydroxy-, (1R-(1alpha,3alpha,4alpha,5beta))-
• CYCLOHEXANECARBOXYLIC ACID, 4-((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,3,5-TRIHYDROXY-, (1.ALPHA.,3R,4.ALPHA.,5R)-
• Cyclohexanecarboxylic acid, 4-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-1,3,5-trihydroxy-, (1alpha,3R,4alpha,5R)-
• Cyclohexanecarboxylic acid, 4-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,3,5-trihydroxy-, (1alpha,3R,4alpha,5R)-
• Cyclohexanecarboxylic acid, 4-(3-(3,4-(dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,3,5-trihydroxy-, (1alpha,3alpha,4alpha,5beta)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8565	85.65%
Caco-2	-	0.9431	94.31%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6770	67.70%
OATP2B1 inhibitior	-	0.7188	71.88%
OATP1B1 inhibitior	+	0.9602	96.02%
OATP1B3 inhibitior	+	0.9473	94.73%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8588	85.88%
BSEP inhibitior	-	0.5525	55.25%
P-glycoprotein inhibitior	-	0.9335	93.35%
P-glycoprotein substrate	-	0.8793	87.93%
CYP3A4 substrate	+	0.5187	51.87%
CYP2C9 substrate	-	0.5941	59.41%
CYP2D6 substrate	-	0.8566	85.66%
CYP3A4 inhibition	-	0.8744	87.44%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9069	90.69%
CYP2D6 inhibition	-	0.9388	93.88%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.6814	68.14%
CYP inhibitory promiscuity	-	0.9686	96.86%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	0.9064	90.64%
Carcinogenicity (trinary)	Non-required	0.6128	61.28%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9194	91.94%
Skin irritation	-	0.6297	62.97%
Skin corrosion	-	0.8862	88.62%
Ames mutagenesis	-	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5137	51.37%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.5785	57.85%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8929	89.29%
Acute Oral Toxicity (c)	III	0.7775	77.75%
Estrogen receptor binding	+	0.7669	76.69%
Androgen receptor binding	+	0.6667	66.67%
Thyroid receptor binding	+	0.5172	51.72%
Glucocorticoid receptor binding	+	0.6051	60.51%
Aromatase binding	-	0.6253	62.53%
PPAR gamma	+	0.5328	53.28%
Honey bee toxicity	-	0.8427	84.27%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5955	59.55%
Fish aquatic toxicity	+	0.9844	98.44%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.65%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.24%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.62%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.21%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.75%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.95%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.94%	94.45%
CHEMBL3194	P02766	Transthyretin	90.66%	90.71%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.55%	94.62%
CHEMBL4208	P20618	Proteasome component C5	88.73%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.41%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.16%	96.00%
CHEMBL2179	P04062	Beta-glucocerebrosidase	86.61%	85.31%
CHEMBL221	P23219	Cyclooxygenase-1	86.39%	90.17%
CHEMBL340	P08684	Cytochrome P450 3A4	85.61%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.50%	97.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.74%	94.08%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.63%	95.50%

Plants that contains it

• Apocynum venetum
• Arctium lappa
• Artemisia absinthium
• Artemisia annua
• Artemisia argyi
• Artemisia capillaris
• Artemisia carvifolia
• Artemisia montana
• Artemisia princeps
• Aster tataricus
• Centaurea horrida
• Chrysanthemum indicum
• Cichorium intybus
• Cichorium pumilum
• Coffea arabica
• Coffea canephora
• Cynara cardunculus
• Erigeron breviscapus
• Erycibe obtusifolia
• Erycibe schmidtii
• Eucommia ulmoides
• Euphorbia watanabei
• Foeniculum vulgare
• Gardenia jasminoides
• Helichrysum italicum
• Helichrysum stoechas
• Houttuynia cordata
• Humulus lupulus
• Hydrangea macrophylla
• Hypericum perforatum
• Juglans regia
• Lonicera confusa
• Lonicera hypoglauca
• Lonicera japonica
• Lonicera macrantha
• Morus alba
• Nicotiana tabacum
• Phlomoides tuberosa
• Prunus domestica
• Prunus dulcis
• Pyrrosia hastata
• Pyrrosia lingua
• Pyrrosia petiolosa
• Pyrus calleryana
• Rubus ulmifolius
• Sarcandra glabra
• Saussurea involucrata
• Solidago altissima
• Taraxacum coreanum
• Taraxacum mongolicum
• Taraxacum officinale
• Taraxacum platycarpum
• Taraxacum sinicum
• Thymus quinquecostatus
• Thymus vulgaris
• Uncaria macrophylla
• Uncaria rhynchophylla
• Uncaria sinensis
• Vaccinium arctostaphylos
• Viburnum dilatatum
• Withania somnifera
• Xanthium strumarium
• Xanthium strumarium subsp. strumarium

Cross-Links

• PubChem: 9798666
• NPASS: NPC92774
• LOTUS: LTS0165819
• wikiData: Q104254155