ANPDB

Select a section from the left sidebar

1-O-caffeoylquinic acid

Family: Plantae - Rutaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Caffeoylquinic Acid

Canonical Smiles	O=C(O[C@@]1(C[C@H](O)[C@@H]([C@H](C1)O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O
InChI	InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(21)25-16(15(23)24)6-11(19)14(22)12(20)7-16/h1-5,11-12,14,17-20,22H,6-7H2,(H,23,24)/b4-2+/t11-,12-,14-,16+/m0/s1
InChIKey	GWTUHAXUUFROTF-KJOPMHRFSA-N
Formula	C₁₆H₁₈O₉
HBA	8
HBD	6
MW	354.31
Rotatable Bonds	4
TPSA	164.75
LogP	-0.65
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.38
Exact Mass	354.1
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Citrus nobilis x Citrus deliciosa	Rutaceae	Plantae	558547

Showing of synonyms

El-Hawary S.S, Issa M.Y, et al. (2022). Potential of (Citrus nobilis Lour x Citrus deliciosa Tenora) metabolites on COVID-19 virus main protease supported by in silico analysis. Natural product research, 2022, 36(11), 2843-2847. [View] [PubMed]

Pubchem: 53393476

Cas: 1241-87-8

Gnps: CCMSLIB00005757055

Zinc: ZINC000033985715

CPRiL: 416950

SMILES: C1CCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 354.31 g/mol

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 354.31 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 354.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.42
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.13
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.27

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.69
Plasma Protein Binding: 68.44
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 9.44
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -1.8
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.45
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 5.02
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -0.47
Rat (Acute): 1.85
Rat (Chronic Oral): 2.99
Fathead Minnow: 4.03
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 478.93
Hydration Free Energy: -13.17
Log(D) at pH=7.4: -1.46
Log(P): -1.14
Log S: -1.59
Log(Vapor Pressure): -12.94
Melting Point: 182.15
pKa Acid: 4.08
pKa Basic: 6.22

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9255
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9148
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9116
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9022
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.9016
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8657
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8573
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	3	0.8443
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.8391
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8366
2-dehydro-3-deoxyphosphooctonate aldolase	P0A715	KDSA_ECOLI	Escherichia coli	3	0.8250
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8210
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8170
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.8086
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8052
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7978
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7970
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7922
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7883
Nucleoside diphosphate kinase	O58429	NDK_PYRHO	Pyrococcus horikoshii	3	0.7816
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7805
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7784
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7763
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7743
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7711
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7683
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7553
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7530
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	4	0.7519
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	3	0.7508
Plasma membrane ATPase	Q42932	Q42932_NICPL	Nicotiana plumbaginifolia	3	0.7489
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.7462
Lysosomal acid glucosylceramidase	P04062	GLCM_HUMAN	Homo sapiens	3	0.7445
Acetylglutamate kinase	Q9HTN2	ARGB_PSEAE	Pseudomonas aeruginosa	4	0.7443
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7424
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7374
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7366
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7366
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7365
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7314
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7311
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7301
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7280
Riboflavin biosynthesis protein	Q9WZW1	Q9WZW1_THEMA	Thermotoga maritima	4	0.7277
Putative choline kinase	Q5CUP2	Q5CUP2_CRYPI	Cryptosporidium parvum	3	0.7277
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7262
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7261
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7246
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7228
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7206
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7204
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7201
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7195
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7168
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7166
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7156
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7149
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7142
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7125
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	3	0.7123
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7091
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7088
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7061
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.7046
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7046
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7035
5-formaminoimidazole-4-carboxamide-1-(beta)-D-ribofuranosyl 5'-monophosphate synthetase	Q8U0R7	PURP_PYRFU	Pyrococcus furiosus	3	0.7032
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7029
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7012
Chorismate mutase AroH	P19080	AROH_BACSU	Bacillus subtilis	3	0.7009
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7006

Download SDF