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Caffeate

Family: Plantae - Cistaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Hydroxycinnamic Acid

Canonical Smiles	O=C(OC1C[C@]2(C([C@@H]1CC2)(C)C)C)/C=C/c1ccc(c(c1)O)O
InChI	InChI=1S/C19H24O4/c1-18(2)13-8-9-19(18,3)11-16(13)23-17(22)7-5-12-4-6-14(20)15(21)10-12/h4-7,10,13,16,20-21H,8-9,11H2,1-3H3/b7-5+/t13-,16?,19+/m1/s1
InChIKey	OJFYZRANZJDPQB-BJXYJGNWSA-N
Formula	C₁₉H₂₄O₄
HBA	4
HBD	2
MW	316.4
Rotatable Bonds	3
TPSA	66.76
LogP	3.87
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.53
Exact Mass	316.17
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Cistus libanotis	Cistaceae	Plantae	335171

Showing of synonyms

Venditti A, Bianco A, et al. (2015). Phytochemical study of Cistus libanotis L. Natural product research, 2015, 29(2), 189-92. [View] [PubMed]

Pubchem: 689043

Cas: 501-16-6

Gnps: CCMSLIB00005759142

Zinc: ZINC000000058172

Kegg Ligand: C01197

Chebi: 16433

Nmrshiftdb2: 20039649

Metabolights: MTBLC16433

Chembl: CHEMBL145

Drugbank: DB01880

Pdb Ligand: DHC

Bindingdb: 4375

Selleck: Caffeic-acid

CPRiL: 6346

SMILES: C1CC(C2)CC(C12)OC(=O)C=Cc3ccccc3

Level: 1

Mol. Weight: 316.4 g/mol

SMILES: C12CC(CC1)CC2

Level: 0

Mol. Weight: 316.4 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 316.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.67
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.55
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.94

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.9
Plasma Protein Binding: 75.4
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: 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: 14.72
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.53
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.38
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 5.26
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Toxic
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 2.5
Rat (Acute): 2.1
Rat (Chronic Oral): 2.34
Fathead Minnow: 4.1
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 384.16
Hydration Free Energy: -7.26
Log(D) at pH=7.4: 3.81
Log(P): 4.57
Log S: -4.97
Log(Vapor Pressure): -6.4
Melting Point: 183.71
pKa Acid: 8.42
pKa Basic: 6.27

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	0.9337
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9117
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9039
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8675
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8671
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8464
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8417
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8365
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8170
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.8047
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	4	0.8019
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7984
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7935
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.7870
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7830
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7781
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7778
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7754
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7720
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7693
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7669
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7662
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7643
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7601
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7596
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7487
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7475
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7464
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7461
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7435
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7429
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.7409
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7386
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7379
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7322
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7317
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7316
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7315
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7310
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7307
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7285
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7282
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7282
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7273
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7220
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7215
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7188
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7168
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7160
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7145
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7143
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7136
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7129
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7125
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7110
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7099
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7086
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7085
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7073
Lanosterol 14-alpha-demethylase	Q385E8	Q385E8_TRYB2	Trypanosoma brucei brucei	3	0.7071
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7057
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7048
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7038
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7025
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7010
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7007

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