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Herbacetin 8-methyl ether 3-O- glucoside-7-O-rutinoside

Family: Plantae - Ephedraceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonol Glucoside

Canonical Smiles	OC[C@H]1OC(Oc2c(oc3c(c2=O)c(O)cc(c3OC)O[C@@H]2O[C@H](O)[C@H]([C@@H]([C@H]2O)CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C34H42O21/c1-10-18(38)23(43)25(45)32(50-10)49-9-13-19(39)31(47)55-33(20(13)40)51-15-7-14(37)17-22(42)30(54-34-26(46)24(44)21(41)16(8-35)52-34)27(53-29(17)28(15)48-2)11-3-5-12(36)6-4-11/h3-7,10,13,16,18-21,23-26,31-41,43-47H,8-9H2,1-2H3/t10-,13-,16+,18-,19-,20+,21+,23+,24-,25+,26+,31-,32+,33+,34?/m0/s1
InChIKey	WAYHGOVIRBUTLE-UOZZALNGSA-N
Formula	C₃₄H₄₂O₂₁
HBA	21
HBD	12
MW	786.69
Rotatable Bonds	10
TPSA	337.58
LogP	-3.71
Number Rings	6
Number Aromatic Rings	3
Heavy Atom Count	55
Formal Charge	0
Fraction CSP3	0.56
Exact Mass	786.22
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ephedra alata	Ephedraceae	Plantae	302006

Showing of synonyms

Nawwar MAM, El-Sissi HI, et al. (1984). Flavonoid constituents of Ephedra alata. Phytochemistry,1984,23(12),2937-2939. [View]

Pubchem: 162817296

Nmrshiftdb2: 60069875

No compound-protein relationship available.

SMILES: O1CCCCC1OCC2CC(OCC2)Oc(cc3)cc(c34)oc(-c5ccccc5)c(c4=O)OC6CCCCO6

Level: 4

Mol. Weight: 786.69 g/mol

SMILES: O1CCCCC1OCC2CC(OCC2)Oc(cc3)cc(c34)occ(c4=O)OC5CCCCO5

Level: 3

Mol. Weight: 786.69 g/mol

SMILES: O1CCCCC1OCC2CC(OCC2)Oc(cc3)cc(c34)oc(cc4=O)-c5ccccc5

Level: 3

Mol. Weight: 786.69 g/mol

SMILES: O1CCCCC1Oc(cc2)cc(c23)oc(-c4ccccc4)c(c3=O)OC5CCCCO5

Level: 3

Mol. Weight: 786.69 g/mol

SMILES: O1CCCCC1OCC2CC(OCC2)Oc(cc3)cc(c34)occc4=O

Level: 2

Mol. Weight: 786.69 g/mol

SMILES: O1CCCCC1Oc(cc2)cc(c23)occ(c3=O)OC4CCCCO4

Level: 2

Mol. Weight: 786.69 g/mol

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 786.69 g/mol

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

Level: 2

Mol. Weight: 786.69 g/mol

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

Level: 1

Mol. Weight: 786.69 g/mol

SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 786.69 g/mol

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

Level: 1

Mol. Weight: 786.69 g/mol

SMILES: C1COCCC1COC2CCCCO2

Level: 1

Mol. Weight: 786.69 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 786.69 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 786.69 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 786.69 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.46
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 13.9
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 2643.43

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.64
Plasma Protein Binding: 52.9
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: 5.22
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -60.2
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.05
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.46
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: -4793475.93
Rat (Acute): 2.63
Rat (Chronic Oral): 4.72
Fathead Minnow: 6059.13
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: 532507.78
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -1.54
Log(P): -1.78
Log S: -4.61
Log(Vapor Pressure): -17465.85
Melting Point: 219.84
pKa Acid: -90.26
pKa Basic: 4.39

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8732
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8732
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8549
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8549
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8435
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8435
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8342
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8342
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8337
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8337
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8269
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8269
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8051
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8051
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8039
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8039
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7822
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7822
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7754
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7754
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7575
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7575
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.7485
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.7485
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7482
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7482
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7407
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7407
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7406
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7406
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7369
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7369
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7321
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7321
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7318
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7318
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.7283
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.7283
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7212
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7212
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7133
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7133
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7130
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7130
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7100
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7100
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7078
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7078
Periplasmic pH-dependent serine endoprotease DegQ	P39099	DEGQ_ECOLI	Escherichia coli	4	0.7067
Periplasmic pH-dependent serine endoprotease DegQ	P39099	DEGQ_ECOLI	Escherichia coli	4	0.7067
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7015
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7015

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