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Rosmarinic acid–O–hexoside

Family: Plantae - Lamiaceae
Kingdom: Plantae
Class: Phenolic

Canonical Smiles	OC[C@H]1O[C@@H](OC(=O)[C@@H](Cc2ccc(c(c2)O)O)OC(=O)/C=C/c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C24H26O13/c25-10-18-20(31)21(32)22(33)24(36-18)37-23(34)17(9-12-2-5-14(27)16(29)8-12)35-19(30)6-3-11-1-4-13(26)15(28)7-11/h1-8,17-18,20-22,24-29,31-33H,9-10H2/b6-3+/t17-,18-,20-,21+,22-,24+/m1/s1
InChIKey	YBDQDVRROCQHQM-BHTLWRRDSA-N
Formula	C₂₄H₂₆O₁₃
HBA	13
HBD	8
MW	522.46
Rotatable Bonds	8
TPSA	223.67
LogP	-0.98
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	37
Formal Charge	0
Fraction CSP3	0.33
Exact Mass	522.14
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Rosmarinuseriocalyx	Lamiaceae	Plantae	—

Showing of synonyms

Boudiar T, Lozano-Sánchez J, et al. (2019). Phytochemical characterization of bioactive compounds composition of Rosmarinus eriocalyx by RP–HPLC–ESI–QTOF–MS. Natural product research, 2019, 33(15), 2208-2214. [View] [PubMed]

Pubchem: 132604855

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OC(C(=O)OC2CCCCO2)Cc3ccccc3

Level: 2

Mol. Weight: 522.46 g/mol

SMILES: c1ccccc1C=CC(=O)OCC(=O)OC2CCCCO2

Level: 1

Mol. Weight: 522.46 g/mol

SMILES: c1ccccc1C=CC(=O)OCCc2ccccc2

Level: 1

Mol. Weight: 522.46 g/mol

SMILES: O1CCCCC1OC(=O)CCc2ccccc2

Level: 1

Mol. Weight: 522.46 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 522.46 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 522.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -7.06
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.12
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.67

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.76
Plasma Protein Binding: 72.14
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: 13.66
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -3.36
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.78
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 5.19
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: -553.03
Rat (Acute): 2.16
Rat (Chronic Oral): 4.21
Fathead Minnow: 4.17
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: 632.94
Hydration Free Energy: -3.2
Log(D) at pH=7.4: 0.11
Log(P): -0.35
Log S: -2.73
Log(Vapor Pressure): -13.97
Melting Point: 199.52
pKa Acid: 5.12
pKa Basic: 5.89

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	0.9353
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9214
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9091
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8755
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8734
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8684
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8596
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.8550
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.8513
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8481
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8452
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.8413
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.8372
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8347
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8320
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.8218
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8177
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8177
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8176
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8146
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8096
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8093
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8067
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8061
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8035
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7996
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7994
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7953
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7939
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7934
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7928
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7920
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.7898
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7835
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7828
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7805
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7794
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7726
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7690
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7672
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7614
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7603
Tubulin--tyrosine ligase	F6Z895	A9ULH4_XENTR	Xenopus tropicalis	4	0.7601
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7576
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7529
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7504
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7497
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7445
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7437
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7436
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7435
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7427
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7376
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7373
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7367
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7353
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7333
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7333
Ribosomal RNA small subunit methyltransferase NEP1	Q06287	NEP1_YEAST	Saccharomyces cerevisiae	4	0.7290
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7287
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7283
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7270
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7253
Bifunctional protein GAL10	P04397	GAL10_YEAST	Saccharomyces cerevisiae	5	0.7251
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7248
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7240
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.7226
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7218
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7209
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7206
Uncharacterized protein MJ0489	Q57913	Y489_METJA	Methanocaldococcus jannaschii	4	0.7198
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7193
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7184
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7184
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7181
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7175
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7166
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7161
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.7159
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7155
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	4	0.7152
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7148
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7142
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	2	0.7136
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7127
Tryptophan--tRNA ligase	Q9PIB4	SYW_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	4	0.7126
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7125
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7124
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7114
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7110
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7098
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7093
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7092
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7076
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7073
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7070
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7065
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7054
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7043
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7039
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7033
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7031
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7027
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.7026
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7024
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7022
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7015
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7014
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7013
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7011
Neopullulanase 2	Q08751	NEPU2_THEVU	Thermoactinomyces vulgaris	3	0.7007
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7005

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