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Schaftoside

Family: Plantae - Moraceae
Kingdom: Plantae
Class: Flavonoid

Canonical Smiles	OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)c1c(O)c([C@@H]2OC[C@@H]([C@H]([C@H]2O)O)O)c2c(c1O)c(=O)cc(o2)c1ccc(cc1)O
InChI	InChI=1S/C26H28O14/c27-6-13-18(32)21(35)23(37)26(40-13)15-19(33)14-10(29)5-12(8-1-3-9(28)4-2-8)39-24(14)16(20(15)34)25-22(36)17(31)11(30)7-38-25/h1-5,11,13,17-18,21-23,25-28,30-37H,6-7H2/t11-,13+,17+,18+,21-,22+,23+,25-,26-/m0/s1
InChIKey	MMDUKUSNQNWVET-RJKGXTLSSA-N
Formula	C₂₆H₂₈O₁₄
HBA	14
HBD	10
MW	564.5
Rotatable Bonds	4
TPSA	250.97
LogP	-1.75
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	40
Formal Charge	0
Fraction CSP3	0.42
Exact Mass	564.15
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ficus asperifolia	Moraceae	Plantae	182103
2	Ficus variifolia	Moraceae	Plantae	425835
3	Ficus polita	Moraceae	Plantae	378027

Showing of synonyms

Greenham JR, Grayer RJ, et al. (2007). Intra-and interspecific variations in vacuolar flavonoids among Ficus species from the Budongo Forest, Uganda.. Biochemical systematics and ecology,2007,35(2),81-90. [View] [PubMed]

Pubchem: 442658

Cas: 51938-32-0

Gnps: CCMSLIB00006477844

Zinc: ZINC000004098602

Kegg Ligand: C10181

Chebi: 9047

Nmrshiftdb2: 60022857

CPRiL: 55004

SMILES: c1ccccc1-c(cc2=O)oc(c23)c(C4CCCCO4)cc(c3)C5CCCCO5

Level: 3

Mol. Weight: 564.5 g/mol

SMILES: O=c1ccoc(c12)c(C3CCCCO3)cc(c2)C4CCCCO4

Level: 2

Mol. Weight: 564.5 g/mol

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

Level: 2

Mol. Weight: 564.5 g/mol

SMILES: O1CCCCC1c(ccc2)c(c23)oc(cc3=O)-c4ccccc4

Level: 2

Mol. Weight: 564.5 g/mol

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

Level: 1

Mol. Weight: 564.5 g/mol

SMILES: O=c1ccoc(c12)c(ccc2)C3CCCCO3

Level: 1

Mol. Weight: 564.5 g/mol

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

Level: 1

Mol. Weight: 564.5 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 564.5 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 564.5 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 564.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.45
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -6.200
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 5.19

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.650
Plasma Protein Binding: 68.3
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: 8.300
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -3.770
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.740
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.380
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: -3787.170
Rat (Acute): 2.480
Rat (Chronic Oral): 4.890
Fathead Minnow: 7.540
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 681.370
Hydration Free Energy: -3.160
Log(D) at pH=7.4: -1.070
Log(P): -0.4
Log S: -3.43
Log(Vapor Pressure): -13.89
Melting Point: 211.34
pKa Acid: 2.1
pKa Basic: 10.42

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	4	0.8508
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	4	0.8508
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8469
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8469
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.8464
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.8464
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8443
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8443
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.8257
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.8257
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8048
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8048
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8017
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8017
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7909
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7909
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7884
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7884
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7668
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7668
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7657
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7657
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7576
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7576
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7522
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7522
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	4	0.7444
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	4	0.7444
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7393
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7393
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7281
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7281
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7270
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7270
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7266
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7266
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7225
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7225
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7159
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7159
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7159
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7159
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7144
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7144
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7121
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7121
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7106
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7106
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7077
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7077
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7055
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7055
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7042
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7042
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7022
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7022

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