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Isoorientin

Family: Plantae - Arecaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Isoflavone

Canonical Smiles	OCC1O[C@H]([C@H](C([C@@H]1O)O)O)c1c(O)cc2c(c1O)c(=O)cc(o2)c1ccc(c(c1)O)O
InChI	InChI=1S/C21H20O11/c22-6-14-17(27)19(29)20(30)21(32-14)16-11(26)5-13-15(18(16)28)10(25)4-12(31-13)7-1-2-8(23)9(24)3-7/h1-5,14,17,19-24,26-30H,6H2/t14?,17-,19?,20+,21+/m1/s1
InChIKey	ODBRNZZJSYPIDI-RAFLFOFHSA-N
Formula	C₂₁H₂₀O₁₁
HBA	11
HBD	8
MW	448.38
Rotatable Bonds	3
TPSA	201.28
LogP	-0.2
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.29
Exact Mass	448.1
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Livistona australis	Arecaceae	Plantae	115491

Showing of synonyms

Kassem MES, Shoela S, et al. (2012). A sulphated flavone glycoside from Livistona australis and its antioxidant and cytotoxic activity. Natural Product Research,2012,26(15),1381-1387. [View] [PubMed]

Pubchem: 114776

Cas: 4261-42-1

Gnps: CCMSLIB00006417936

Zinc: ZINC000004349262

Kegg Ligand: C01821

Chebi: 17965

Nmrshiftdb2: 60022754

Chembl: CHEMBL239559

Pdb Ligand: H9R

Bindingdb: 50487756

CPRiL: 54727

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

Level: 2

Mol. Weight: 448.38 g/mol

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

Level: 1

Mol. Weight: 448.38 g/mol

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

Level: 1

Mol. Weight: 448.38 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 448.38 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 448.38 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 448.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.47
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.91
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 2.17

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.73
Plasma Protein Binding: 73.82
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: 13.12
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -2.1
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.9
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.68
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: -68.67
Rat (Acute): 2.42
Rat (Chronic Oral): 4.52
Fathead Minnow: 3.82
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: 658.09
Hydration Free Energy: -5.49
Log(D) at pH=7.4: -0.04
Log(P): 0.87
Log S: -3.78
Log(Vapor Pressure): -14.06
Melting Point: 244.08
pKa Acid: 3.65
pKa Basic: 9.02

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.9617
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.9617
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9380
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9380
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9316
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9316
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9004
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9004
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8950
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8950
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8936
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8936
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8926
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8926
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8860
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8860
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8758
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8758
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8728
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8728
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8696
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8696
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8645
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8645
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8511
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8511
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8423
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8423
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8340
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8340
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8200
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8200
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8161
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8161
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8141
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8141
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8129
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8129
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8126
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8126
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8031
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8031
GTP 3',8-cyclase	P69848	MOAA_STAA8	Staphylococcus aureus	4	0.7963
GTP 3',8-cyclase	P69848	MOAA_STAA8	Staphylococcus aureus	4	0.7963
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7902
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7902
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7865
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7865
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7685
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7685
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7669
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7669
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7617
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7617
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7587
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7587
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7470
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7470
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.7428
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.7428
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7422
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7422
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7419
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7419
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7358
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7358
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7358
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7358
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7314
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7314
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7285
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7285
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7276
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7276
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.7271
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.7271
Histone deacetylase 7	Q8WUI4	HDAC7_HUMAN	Homo sapiens	3	0.7242
Histone deacetylase 7	Q8WUI4	HDAC7_HUMAN	Homo sapiens	3	0.7242
Ribosomal RNA large subunit methyltransferase J	P37634	RLMJ_ECOLI	Escherichia coli	4	0.7218
Ribosomal RNA large subunit methyltransferase J	P37634	RLMJ_ECOLI	Escherichia coli	4	0.7218
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	4	0.7196
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	4	0.7196
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7193
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7193
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7184
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7184
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7158
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7158
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7137
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7137
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7120
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7120
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7119
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7119
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7117
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7117
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7103
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7103
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7065
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7065
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7049
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7049
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7027
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7027
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7026
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7026
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7015
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7015

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