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Scutellarein-7-O-alpha-rhamnopyranosyl-(1→2)-alpha-rhamnopyranosyl-(1→2)-alpha-rhamnopyranoside

Family: Plantae - Chenopodiaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone Glycoside

Canonical Smiles	O[C@H]1[C@H](C)OC([C@@H]([C@@H]1O)OC1O[C@@H](C)[C@@H]([C@H]([C@H]1OC1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)O)Oc1cc2OC(CC(=O)c2c(c1O)O)c1ccc(cc1)O
InChI	InChI=1S/C33H42O18/c1-10-20(36)25(41)28(44)31(45-10)50-30-27(43)22(38)12(3)47-33(30)51-29-26(42)21(37)11(2)46-32(29)49-18-9-17-19(24(40)23(18)39)15(35)8-16(48-17)13-4-6-14(34)7-5-13/h4-7,9-12,16,20-22,25-34,36-44H,8H2,1-3H3/t10-,11-,12-,16?,20-,21-,22-,25+,26+,27+,28+,29+,30+,31?,32?,33?/m0/s1
InChIKey	MWCCJFOBHFRPCL-QRGSUYTJSA-N
Formula	C₃₃H₄₂O₁₈
HBA	18
HBD	10
MW	726.68
Rotatable Bonds	7
TPSA	283.98
LogP	-1.58
Number Rings	6
Number Aromatic Rings	2
Heavy Atom Count	51
Formal Charge	0
Fraction CSP3	0.61
Exact Mass	726.24
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Chenopodium ambrosioides	Chenopodiaceae	Plantae	330163

Showing of synonyms

Hammoda HM, Harraz FM, et al. (2015). Two new flavone glycosides from Chenopodium ambrosioides growing wildly in Egypt. Records of Natural Products,2015,9(4),609-613. [View]

Pubchem: 162817386

Nmrshiftdb2: 70037791

No compound-protein relationship available.

SMILES: c1ccccc1C(CC2=O)Oc(c23)cc(cc3)OC(OCCC4)C4OC(OCCC5)C5OC6CCCCO6

Level: 4

Mol. Weight: 726.68 g/mol

SMILES: O=C1CCOc(c12)cc(cc2)OC(OCCC3)C3OC(OCCC4)C4OC5CCCCO5

Level: 3

Mol. Weight: 726.68 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)cc(cc3)OC(OCCC4)C4OC5CCCCO5

Level: 3

Mol. Weight: 726.68 g/mol

SMILES: O=C1CCOc(c12)cc(cc2)OC(OCCC3)C3OC4CCCCO4

Level: 2

Mol. Weight: 726.68 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 726.68 g/mol

SMILES: O1CCCCC1OC2C(OCCC2)OC3CCCOC3

Level: 2

Mol. Weight: 726.68 g/mol

SMILES: O=C1CCOc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 726.68 g/mol

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 726.68 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 726.68 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 726.68 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 726.68 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 726.68 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.7
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -3.08
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 379.7

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.81
Plasma Protein Binding: 55.39
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: 8.91
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -5.69
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.52
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.58
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: -686905.46
Rat (Acute): 2.51
Rat (Chronic Oral): 4.32
Fathead Minnow: 877.85
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: 70641.64
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -0.24
Log(P): -0.34
Log S: -4.38
Log(Vapor Pressure): -2318.16
Melting Point: 200.76
pKa Acid: -1.55
pKa Basic: 5.53

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8885
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8885
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8814
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8814
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.8776
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.8776
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8507
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8507
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8456
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8456
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8293
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8293
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7857
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7857
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.7750
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.7750
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7712
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7712
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7464
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7464
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7423
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7423
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7415
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7415
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7367
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7367
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7277
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7277
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7250
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7250
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7227
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7227
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7205
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7205
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7187
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7187
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7155
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7155
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7147
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7147
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7106
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7106
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7059
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7059
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7016
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7016

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