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Isoorientin 2''-O-alpha-rhamnopyranoside

Family: Plantae - Neuradaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonoid Glycoside

Canonical Smiles	OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)c1c(O)cc2c(c1O)c(=O)cc(o2)c1ccc(c(c1)O)O
InChI	InChI=1S/C27H30O15/c1-8-19(33)22(36)24(38)27(39-8)42-26-23(37)20(34)16(7-28)41-25(26)18-13(32)6-15-17(21(18)35)12(31)5-14(40-15)9-2-3-10(29)11(30)4-9/h2-6,8,16,19-20,22-30,32-38H,7H2,1H3/t8-,16+,19-,20+,22+,23-,24+,25-,26+,27-/m0/s1
InChIKey	IUYFTHKQEWZTHY-QMVGNYJJSA-N
Formula	C₂₇H₃₀O₁₅
HBA	15
HBD	10
MW	594.52
Rotatable Bonds	5
TPSA	260.2
LogP	-1.35
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	42
Formal Charge	0
Fraction CSP3	0.44
Exact Mass	594.16
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Neurada procumbens	Neuradaceae	Plantae	32215
2	Neurada procumbens	Neuradaceae	Plantae	32215

Showing of synonyms

Marzouk MM, Hussein SR, et al. (2014). Flavonoids from Neurada procumbens L. (Neuradaceae) in Egypt. Biochemical Systematics and Ecology,2014,57,67-68. [View]
Marzouk M, Hussein SR, et al. (2013). Flavonoids from Neurada procumbens L. (Neuradaceae) in Egypt. Planta Medica,2013,79-PI46. [View]

Pubchem: 50993776

Zinc: ZINC000060179028

Chebi: 70203

Nmrshiftdb2: 60071080

Metabolights: MTBLC70203

Chembl: CHEMBL1651280

No compound-protein relationship available.

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4C(CCCO4)OC5CCCCO5

Level: 3

Mol. Weight: 594.52 g/mol

SMILES: O=c1ccoc(c12)ccc(c2)C3C(CCCO3)OC4CCCCO4

Level: 2

Mol. Weight: 594.52 g/mol

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

Level: 2

Mol. Weight: 594.52 g/mol

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

Level: 1

Mol. Weight: 594.52 g/mol

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

Level: 1

Mol. Weight: 594.52 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 594.52 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 594.52 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 594.52 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 594.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.42
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.770
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 7.17

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.700
Plasma Protein Binding: 68.07
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: 11.390
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -3.430
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.770
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.900
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: -8528.280
Rat (Acute): 2.380
Rat (Chronic Oral): 4.330
Fathead Minnow: 17.950
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 550.960
Hydration Free Energy: -2.970
Log(D) at pH=7.4: -0.710
Log(P): 0.36
Log S: -4.32
Log(Vapor Pressure): -12.11
Melting Point: 207.65
pKa Acid: 3.5
pKa Basic: 9.47

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	0.9621
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.9621
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9440
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9440
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9365
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9365
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9112
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9112
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9052
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9052
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9006
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9006
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8808
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8808
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8722
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8722
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8664
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8664
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.8606
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.8606
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8561
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8561
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8550
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8550
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8378
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8378
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8360
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8360
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8335
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8335
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8313
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8313
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8244
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8244
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8012
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8012
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7861
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7861
GTP 3',8-cyclase	P69848	MOAA_STAA8	Staphylococcus aureus	4	0.7810
GTP 3',8-cyclase	P69848	MOAA_STAA8	Staphylococcus aureus	4	0.7810
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7749
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7749
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7718
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7718
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7708
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7708
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7611
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7611
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.7607
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.7607
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7558
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7558
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7539
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7539
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7528
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7528
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7522
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7522
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7500
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7500
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7500
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7500
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7406
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7406
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7386
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7386
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7343
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7343
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7330
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7330
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7322
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7322
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7295
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7295
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7291
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7291
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.7271
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.7271
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7261
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7261
Tubulin--tyrosine ligase	F6Z895	A9ULH4_XENTR	Xenopus tropicalis	4	0.7238
Tubulin--tyrosine ligase	F6Z895	A9ULH4_XENTR	Xenopus tropicalis	4	0.7238
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7208
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7208
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7147
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7147
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7138
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7138
Histone deacetylase 7	Q8WUI4	HDAC7_HUMAN	Homo sapiens	3	0.7123
Histone deacetylase 7	Q8WUI4	HDAC7_HUMAN	Homo sapiens	3	0.7123
14-3-3 protein gamma	P61981	1433G_HUMAN	Homo sapiens	3	0.7106
14-3-3 protein gamma	P61981	1433G_HUMAN	Homo sapiens	3	0.7106
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7086
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7086
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7082
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7082
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7082
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7082
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7041
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7041
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7018
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7018
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7018
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7018
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7003
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	3	0.7003
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7000
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7000

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