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Swertisin 2''-arabinoside

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

Canonical Smiles	OCC1O[C@H](C([C@H]([C@@H]1O)O)O[C@@H]1OC[C@@H]([C@@H](C1O)O)O)c1c(OC)cc2c(c1O)c(=O)cc(o2)c1ccc(cc1)O
InChI	InChI=1S/C27H30O14/c1-37-15-7-16-18(12(30)6-14(39-16)10-2-4-11(29)5-3-10)22(34)19(15)25-26(23(35)21(33)17(8-28)40-25)41-27-24(36)20(32)13(31)9-38-27/h2-7,13,17,20-21,23-29,31-36H,8-9H2,1H3/t13-,17?,20-,21+,23-,24?,25-,26?,27-/m0/s1
InChIKey	ITURUJYQEZMYRK-QBFOQREWSA-N
Formula	C₂₇H₃₀O₁₄
HBA	14
HBD	8
MW	578.52
Rotatable Bonds	6
TPSA	228.97
LogP	-1.14
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	41
Formal Charge	0
Fraction CSP3	0.44
Exact Mass	578.16
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Achillea fragrantissima	Asteraceae	Plantae	282738

Showing of synonyms

Ahmed AA (1988). Swertisin 2”-arabinoside, a new C-glycosylflavone from Achillea fragrantissima.. Journal of Natural Products,1988,51(5),971-972. [View] [PubMed]

Pubchem: 44258322

No compound-protein relationship available.

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

Level: 3

Mol. Weight: 578.52 g/mol

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

Level: 2

Mol. Weight: 578.52 g/mol

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

Level: 2

Mol. Weight: 578.52 g/mol

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

Level: 1

Mol. Weight: 578.52 g/mol

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

Level: 1

Mol. Weight: 578.52 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 578.52 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 578.52 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 578.52 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 578.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.66
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.28
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 4.96

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.91
Plasma Protein Binding: 54.0
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: 10.46
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.06
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.83
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.43
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: -6812.1
Rat (Acute): 2.65
Rat (Chronic Oral): 4.45
Fathead Minnow: 15.35
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 537.7
Hydration Free Energy: -2.95
Log(D) at pH=7.4: 0.25
Log(P): 0.22
Log S: -4.21
Log(Vapor Pressure): -11.84
Melting Point: 212.79
pKa Acid: 4.58
pKa Basic: 5.82

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9556
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9556
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9495
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9495
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.9181
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.9181
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8927
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8927
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8775
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8775
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8697
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8697
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8644
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8644
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8586
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8586
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.8382
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.8382
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.7866
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.7866
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7842
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7842
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7823
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7823
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7586
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7586
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7578
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7578
Beta sliding clamp	P0A988	DPO3B_ECOLI	Escherichia coli	3	0.7519
Beta sliding clamp	P0A988	DPO3B_ECOLI	Escherichia coli	3	0.7519
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7404
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7404
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7354
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7354
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7323
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7323
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7320
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7320
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7304
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7304
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7260
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7260
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7245
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7245
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7223
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7223
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7194
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7194
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7168
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7168
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7137
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7137
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7051
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7051
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7041
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7041
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7039
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7039
Isoleucine--tRNA ligase	P56690	SYI_THET8	Thermus thermophilus	3	0.7011
Isoleucine--tRNA ligase	P56690	SYI_THET8	Thermus thermophilus	3	0.7011
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7009
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7009
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7007
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7007

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