ANPDB

Select a section from the left sidebar

1-O-caffeoyl-beta-xylose

Family: Plantae - Rosaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Caffeoyl Ester

Canonical Smiles	O=C(O[C@@H]1OC[C@H](C([C@@H]1O)O)O)/C=C/c1ccc(c(c1)O)O
InChI	InChI=1S/C14H16O8/c15-8-3-1-7(5-9(8)16)2-4-11(18)22-14-13(20)12(19)10(17)6-21-14/h1-5,10,12-17,19-20H,6H2/b4-2+/t10-,12?,13+,14+/m1/s1
InChIKey	PSYRONNZYLYIOG-IKFJILKUSA-N
Formula	C₁₄H₁₆O₈
HBA	8
HBD	5
MW	312.27
Rotatable Bonds	3
TPSA	136.68
LogP	-0.91
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.36
Exact Mass	312.08
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Rubus sanctus	Rosaceae	Plantae	75089

Showing of synonyms

Hussein S.A, Ayoub N.A, et al. (2003). Caffeoyl sugar esters and an ellagitannin from Rubus sanctus. Phytochemistry, 2003, 63(8), 905-11. [View] [PubMed]

No compound-protein relationship available.

SMILES: O1CCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 312.27 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 312.27 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 312.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.56
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.71
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.99

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.63
Plasma Protein Binding: 44.13
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: 12.38
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -1.7
Biodegradation: Toxic
Carcinogenesis: Toxic
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.7
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.63
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 0.95
Rat (Acute): 1.82
Rat (Chronic Oral): 3.23
Fathead Minnow: 4.05
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 461.6
Hydration Free Energy: -17.59
Log(D) at pH=7.4: -0.11
Log(P): -0.38
Log S: -1.51
Log(Vapor Pressure): -11.08
Melting Point: 173.59
pKa Acid: 5.8
pKa Basic: 5.6

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	0.9262
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9142
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9124
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9116
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8943
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8891
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8560
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8441
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.8437
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8366
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.8348
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8210
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8099
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8083
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8035
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.8020
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8014
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.8001
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7980
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7968
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7964
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7931
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7915
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7905
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7902
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7897
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7831
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7784
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7719
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7686
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7683
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7670
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	4	0.7666
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7660
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7651
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7636
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7584
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7561
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7544
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	5	0.7521
NAD-dependent protein deacetylase sirtuin-3, mitochondrial	Q9NTG7	SIR3_HUMAN	Homo sapiens	4	0.7486
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7421
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7412
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7385
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7366
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7356
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7345
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7344
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7305
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7255
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7254
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7228
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7201
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7201
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7189
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7176
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7155
Ribosomal RNA small subunit methyltransferase Nep1	Q57977	NEP1_METJA	Methanocaldococcus jannaschii	3	0.7150
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7147
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7133
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7107
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7083
Tubulin--tyrosine ligase	F6Z895	A9ULH4_XENTR	Xenopus tropicalis	4	0.7073
Purine nucleoside phosphorylase DeoD-type	B1JL34	DEOD_YERPY	Yersinia pseudotuberculosis serotype O:3	2	0.7066
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7032
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7031
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7008
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7006

Download SDF