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Isoorientin 3'-methyl ether

Family: Plantae - Cucurbitaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone

Canonical Smiles	OCC1OC(C(C(C1O)O)O)c1c(O)cc2c(c1O)c(=O)cc(o2)c1ccc(cc1)OC(=O)C
InChI	InChI=1S/C23H22O11/c1-9(25)32-11-4-2-10(3-5-11)14-6-12(26)17-15(33-14)7-13(27)18(20(17)29)23-22(31)21(30)19(28)16(8-24)34-23/h2-7,16,19,21-24,27-31H,8H2,1H3
InChIKey	VICHKAGWBBRUFV-UHFFFAOYSA-N
Formula	C₂₃H₂₂O₁₁
HBA	11
HBD	6
MW	474.42
Rotatable Bonds	4
TPSA	187.12
LogP	0.31
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	34
Formal Charge	0
Fraction CSP3	0.3
Exact Mass	474.12
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Citrullus colocynthis	Cucurbitaceae	Plantae	252529

Showing of synonyms

Yoshikawa M, Morikawa T, et al. (2007). Bioactive Saponins and Glycosides. XXVII. 1) Structures of New Cucurbitane-Type Triterpene Glycosides and Antiallergic Constituents from Citrullus colocynthis. Chemical & pharmaceutical bulletin, 2007, 55(3), 428-34. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4CCCCO4

Level: 2

Mol. Weight: 474.42 g/mol

SMILES: O=c1ccoc(c12)ccc(c2)C3CCCCO3

Level: 1

Mol. Weight: 474.42 g/mol

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

Level: 1

Mol. Weight: 474.42 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 474.42 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 474.42 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 474.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.48
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.47
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1.09

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.92
Plasma Protein Binding: 28.61
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: 6.67
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -1.78
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.87
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.15
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: -174.11
Rat (Acute): 2.35
Rat (Chronic Oral): 4.07
Fathead Minnow: 4.58
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 590.88
Hydration Free Energy: -3.54
Log(D) at pH=7.4: 0.61
Log(P): 1.2
Log S: -4.41
Log(Vapor Pressure): -11.45
Melting Point: 199.97
pKa Acid: 5.95
pKa Basic: 7.23

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9753
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9454
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.9445
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9369
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9153
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9123
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8648
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8630
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8619
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.8612
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8453
Matrix metalloproteinase-9	P14780	MMP9_HUMAN	Homo sapiens	3	0.8434
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8287
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8249
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8184
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8113
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8044
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8027
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7998
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7985
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7894
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7866
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7795
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7765
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.7725
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7697
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7647
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7641
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7633
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7619
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7605
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7562
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7559
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7535
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7502
DNA polymerase theta	O75417	DPOLQ_HUMAN	Homo sapiens	4	0.7491
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7463
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7420
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7403
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7396
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7329
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.7312
Metallo-beta-lactamase type 2	P26918	BLAB_AERHY	Aeromonas hydrophila	2	0.7285
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7283
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7278
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7273
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7269
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7262
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7257
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7240
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7226
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7220
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7210
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7206
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7196
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	2	0.7185
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7179
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7174
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7168
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7156
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7155
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7144
Chorismate mutase AroH	P19080	AROH_BACSU	Bacillus subtilis	2	0.7131
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7120
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7112
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.7085
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7080
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7065
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7061
Rifampin ADP-ribosyl transferase	A0QRS5	A0QRS5_MYCS2	Mycolicibacterium smegmatis155)	4	0.7053
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	2	0.7052
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7051
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7048
Tyrosine-protein kinase HCK	P08631	HCK_HUMAN	Homo sapiens	4	0.7034
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7025
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase	P47229	BPHD_PARXL	Paraburkholderia xenovorans	2	0.7013
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7011
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7009
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7007

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