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Isorhamnetin-6-deoxyhexopyranoside

Family: Lamiaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonol Glycoside

Canonical Smiles	COc1cc(ccc1O)c1oc2cc(O)cc(c2c(=O)c1OC1OC(C)C(C(C1O)O)O)O
InChI	InChI=1S/C22H22O11/c1-8-16(26)18(28)19(29)22(31-8)33-21-17(27)15-12(25)6-10(23)7-14(15)32-20(21)9-3-4-11(24)13(5-9)30-2/h3-8,16,18-19,22-26,28-29H,1-2H3
InChIKey	UXXAEVMOIUAYQT-UHFFFAOYSA-N
Formula	C₂₂H₂₂O₁₁
HBA	11
HBD	6
MW	462.41
Rotatable Bonds	4
TPSA	179.28
LogP	0.79
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	33
Formal Charge	0
Fraction CSP3	0.32
Exact Mass	462.12
Number of Lipinski Rule Violations	2

#	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: 13988312

Nmrshiftdb2: 70017252

No compound-protein relationship available.

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 322.36 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 246.26 g/mol

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 222.24 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 146.14 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 86.13 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.79
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.310
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 0.48

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.940
Plasma Protein Binding: 32.61
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: 14.850
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.400
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.150
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.670
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: -104.760
Rat (Acute): 2.340
Rat (Chronic Oral): 3.910
Fathead Minnow: 4.080
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 592.700
Hydration Free Energy: -4.070
Log(D) at pH=7.4: 1.180
Log(P): 1.13
Log S: -4.66
Log(Vapor Pressure): -9.8
Melting Point: 197.58
pKa Acid: 5.65
pKa Basic: 5.33

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9289
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9193
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9126
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9108
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8961
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8914
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8876
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8858
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8726
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8656
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8600
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8595
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8559
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8482
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8335
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8278
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8253
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8201
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.8053
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8027
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7983
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7977
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7853
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7837
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7831
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7769
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7756
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7750
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7744
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7730
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7671
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7662
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7659
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7616
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7563
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7552
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7548
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7521
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7472
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7467
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7465
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7408
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7359
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7349
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7318
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7309
Botulinum neurotoxin type A	P0DPI0	BXA1_CLOBO	Clostridium botulinum	3	0.7298
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7287
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7275
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	3	0.7243
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7240
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7232
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7226
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7221
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7219
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7186
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7167
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7160
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.7155
Kinesin heavy chain	Q41460	Q41460_SOLTU	Solanum tuberosum	3	0.7127
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7126
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7120
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7103
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	7	0.7079
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7079
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7077
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7026

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