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Diosmetin 7-O-(2”,6”-di-O-alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside

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

Canonical Smiles	COc1ccc(cc1O)c1oc2cc(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@@H]([C@H]([C@H]4O)O)O)[C@H]([C@@H]([C@H]3O[C@@H]3O[C@@H](C)[C@@H]([C@H]([C@H]3O)O)O)O)O)cc(c2c(=O)c1)O
InChI	InChI=1S/C34H42O19/c1-11-23(38)26(41)29(44)32(48-11)47-10-21-25(40)28(43)31(53-33-30(45)27(42)24(39)12(2)49-33)34(52-21)50-14-7-16(36)22-17(37)9-19(51-20(22)8-14)13-4-5-18(46-3)15(35)6-13/h4-9,11-12,21,23-36,38-45H,10H2,1-3H3/t11-,12-,21+,23-,24-,25+,26+,27+,28-,29+,30+,31+,32+,33-,34+/m0/s1
InChIKey	NLOYJTQYMYDUFN-BYWVGFEBSA-N
Formula	C₃₄H₄₂O₁₉
HBA	19
HBD	10
MW	754.69
Rotatable Bonds	9
TPSA	297.12
LogP	-2.24
Number Rings	6
Number Aromatic Rings	3
Heavy Atom Count	53
Formal Charge	0
Fraction CSP3	0.56
Exact Mass	754.23
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Buddleja madagascariensis L.	Loganiaceae	Plantae	26473

Showing of synonyms

Emam A.M, Elias R, et al. (1998). Two flavonoid triglycosides from Buddleja madagascariensis. Phytochemistry, 1998, 48(4), 739-42. [View] [PubMed]

Pubchem: 21721988

Zinc: ZINC000255246672

Nmrshiftdb2: 70051501

No compound-protein relationship available.

SMILES: O1CCCCC1OCC2CCC(OC3CCCCO3)C(O2)Oc(cc4)cc(c45)oc(cc5=O)-c6ccccc6

Level: 4

Mol. Weight: 754.69 g/mol

SMILES: O1CCCCC1OCC2CCC(OC3CCCCO3)C(O2)Oc(cc4)cc(c45)occc5=O

Level: 3

Mol. Weight: 754.69 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(cc3)cc(c34)oc(cc4=O)-c5ccccc5

Level: 3

Mol. Weight: 754.69 g/mol

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC(OCCC4)C4OC5CCCCO5

Level: 3

Mol. Weight: 754.69 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(cc3)cc(c34)occc4=O

Level: 2

Mol. Weight: 754.69 g/mol

SMILES: O=c1ccoc(c12)cc(cc2)OC(OCCC3)C3OC4CCCCO4

Level: 2

Mol. Weight: 754.69 g/mol

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

Level: 2

Mol. Weight: 754.69 g/mol

SMILES: O1CCCCC1OCC2CCC(CO2)OC3CCCCO3

Level: 2

Mol. Weight: 754.69 g/mol

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

Level: 1

Mol. Weight: 754.69 g/mol

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

Level: 1

Mol. Weight: 754.69 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 754.69 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 754.69 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 754.69 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 754.69 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 754.69 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.58
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 1.630
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 1007.81

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.800
Plasma Protein Binding: 64.97
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: 7.790
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -21.960
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.640
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.790
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: -1827236.520
Rat (Acute): 2.490
Rat (Chronic Oral): 4.570
Fathead Minnow: 2314.420
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: 199308.490
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -0.080
Log(P): -0.1
Log S: -5.16
Log(Vapor Pressure): -6520.43
Melting Point: 232.56
pKa Acid: -14.33
pKa Basic: 3.89

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9678
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9442
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9407
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9327
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9270
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.9238
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.9153
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9132
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8974
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8881
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	3	0.8814
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8792
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8768
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8660
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8624
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.8610
GTP 3',8-cyclase	P69848	MOAA_STAA8	Staphylococcus aureus	4	0.8587
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8553
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8539
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8530
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8520
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8463
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8436
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8361
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.8342
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8141
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8107
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8106
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.8106
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.8094
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8072
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8013
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7941
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7918
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7915
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7895
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7807
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7803
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7782
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7779
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.7760
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	3	0.7744
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7724
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7720
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7708
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7679
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7651
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7640
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7623
Cell division cycle 7-related protein kinase	O00311	CDC7_HUMAN	Homo sapiens	4	0.7604
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7558
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7513
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7502
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7482
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7464
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7449
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7432
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7428
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7421
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7415
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7401
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7383
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7359
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7359
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7340
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7329
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7323
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7304
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	3	0.7270
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7265
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7264
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7220
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7202
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7194
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7144
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7142
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7113
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7106
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7102
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7092
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7089
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7089
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7086
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7085
dTDP-4-dehydrorhamnose 3,5-epimerase	A0A6L7H6N0	A0A1S0QLH9_BACAN	Bacillus anthracis	3	0.7064
Ribosomal protein L11 methyltransferase, putative	C3MWA1	C3MWA1_SULIM	Sulfolobus islandicus	4	0.7047
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7046
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7044
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7025
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7018
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7017
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.7013
Genome polyprotein	P12823	POLG_DEN2P	Dengue virus type 2	3	0.7012
F420-dependent NADP reductase	O29370	FNO_ARCFU	Archaeoglobus fulgidus	3	0.7008
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.7004

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