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Spinacetin 3-O-rutinoside

Family: Asteraceae-Compositae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonol Glycoside

Canonical Smiles	COc1cc(ccc1O)c1oc2cc(O)c(c(c2c(=O)c1OC1OC(COC2OC(C)C(C(C2O)O)O)C(C(C1O)O)O)O)OC
InChI	InChI=1S/C29H34O17/c1-9-17(32)21(36)23(38)28(43-9)42-8-15-18(33)22(37)24(39)29(45-15)46-27-20(35)16-14(7-12(31)26(41-3)19(16)34)44-25(27)10-4-5-11(30)13(6-10)40-2/h4-7,9,15,17-18,21-24,28-34,36-39H,8H2,1-3H3
InChIKey	GYMVARJSAYZGSZ-UHFFFAOYSA-N
Formula	C₂₉H₃₄O₁₇
HBA	17
HBD	9
MW	654.57
Rotatable Bonds	8
TPSA	267.66
LogP	-1.38
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	46
Formal Charge	0
Fraction CSP3	0.48
Exact Mass	654.18
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Asteriscus graveolens	Asteraceae-Compositae	Plantae	73976

Showing of synonyms

Achoub H, Mencherini T, et al. (2021). New sesquiterpenes from Asteriscus graveolens. Natural product research, 2021, 35(13), 2190-2198. [View] [PubMed]

Pubchem: 131752195

Chebi: 192459

No compound-protein relationship available.

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 436.5 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 360.41 g/mol

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

Level: 2

Mol. Weight: 322.36 g/mol

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

Level: 1

Mol. Weight: 246.26 g/mol

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

Level: 1

Mol. Weight: 222.24 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 200.28 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 146.14 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 86.13 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.63
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.190
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 33.27

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.810
Plasma Protein Binding: -6.48
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: 12.060
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.890
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.920
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.000
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: -58048.170
Rat (Acute): 2.250
Rat (Chronic Oral): 4.520
Fathead Minnow: 91.460
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: 767.930
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -0.340
Log(P): -0.48
Log S: -5.01
Log(Vapor Pressure): -65.78
Melting Point: 206.36
pKa Acid: 3.71
pKa Basic: 5.16

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9352
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9000
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8864
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8778
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8769
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8636
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8631
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8473
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8472
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	3	0.8448
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8334
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8328
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8262
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8214
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8196
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8167
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8161
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8062
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.8055
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8055
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8010
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7980
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	3	0.7960
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.7933
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7898
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7714
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7698
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7685
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7648
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7606
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7585
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7520
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7516
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7513
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7491
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7468
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7455
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7386
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7369
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7366
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7302
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7275
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7262
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7260
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7197
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7169
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7096
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7042
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7017
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7016
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7002
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7001

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