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Scillrubrosidin-3-O-beta-D-rhamnosido-1''→4'-beta-D-glucosido-1'''→4''-beta-D-glucoside

Family: Plantae - Hyacinthaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Bufadienolide

Canonical Smiles	OC[C@H]1O[C@@H](O[C@H]2[C@H](C)O[C@H]([C@@H]([C@@H]2O)O)O[C@H]2CC[C@]3(C(=C2)CC[C@@H]2[C@]3(O)CC[C@]3([C@]2(O)CC[C@@H]3c2ccc(=O)oc2)C)C)[C@@H]([C@H]([C@@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O)O
InChI	InChI=1S/C42H62O19/c1-18-34(60-38-33(52)30(49)35(24(16-44)59-38)61-37-31(50)28(47)27(46)23(15-43)58-37)29(48)32(51)36(56-18)57-21-8-10-39(2)20(14-21)5-6-25-41(53)11-9-22(19-4-7-26(45)55-17-19)40(41,3)12-13-42(25,39)54/h4,7,14,17-18,21-25,27-38,43-44,46-54H,5-6,8-13,15-16H2,1-3H3/t18-,21-,22+,23+,24+,25-,27+,28-,29-,30+,31+,32+,33+,34-,35+,36-,37-,38-,39-,40+,41-,42+/m0/s1
InChIKey	OKURYBVFXBJNKP-DFZBEENSSA-N
Formula	C₄₂H₆₂O₁₉
HBA	19
HBD	11
MW	870.94
Rotatable Bonds	9
TPSA	308.12
LogP	-2.22
Number Rings	8
Number Aromatic Rings	1
Heavy Atom Count	61
Formal Charge	0
Fraction CSP3	0.83
Exact Mass	870.39
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Urginea maritima	Hyacinthaceae	Plantae	82070

Showing of synonyms

Kopp B, Krenn L, et al. (1996). Bufadienolides from Urginea maritima from Egypt. Phytochemistry,1996,42(2),513-522. [View] [PubMed]

Pubchem: 162817186

Nmrshiftdb2: 60070384

No compound-protein relationship available.

SMILES: c1oc(=O)ccc1C2CCC(C23)C4C(CC3)C5C(CC4)=CC(CC5)OC(OC6)CCC6OC(OC7)CCC7OC8CCCCO8

Level: 4

Mol. Weight: 870.94 g/mol

SMILES: C1CCC(C12)CCC3C2CCC=4C3CCC(C4)OC(OC5)CCC5OC(OC6)CCC6OC7CCCCO7

Level: 3

Mol. Weight: 870.94 g/mol

SMILES: c1oc(=O)ccc1C2CCC(C23)C4C(CC3)C5C(CC4)=CC(CC5)OC(OC6)CCC6OC7CCCCO7

Level: 3

Mol. Weight: 870.94 g/mol

SMILES: C1CCC(C12)CCC3C2CCC=4C3CCC(C4)OC(OC5)CCC5OC6CCCCO6

Level: 2

Mol. Weight: 870.94 g/mol

SMILES: c1oc(=O)ccc1C2CCC(C23)C4C(CC3)C5C(CC4)=CC(CC5)OC6CCCCO6

Level: 2

Mol. Weight: 870.94 g/mol

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCCOC3

Level: 2

Mol. Weight: 870.94 g/mol

SMILES: C1CCC(C12)CCC3C2CCC=4C3CCC(C4)OC5CCCCO5

Level: 1

Mol. Weight: 870.94 g/mol

SMILES: C1CCC=C(CC2)C1C(CC3)C2C(C34)CCC4c5ccc(=O)oc5

Level: 1

Mol. Weight: 870.94 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 870.94 g/mol

SMILES: C1CCC(C12)CCC3C2CCC=4C3CCCC4

Level: 0

Mol. Weight: 870.94 g/mol

SMILES: O=c1cccco1

Level: 0

Mol. Weight: 870.94 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 870.94 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.78
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 507.810
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 67213.01

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.820
Plasma Protein Binding: 75.42
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: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 1.230
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -1557.110
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.620
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 4.760
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Toxic
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Toxic
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -121986873.860
Rat (Acute): 3.820
Rat (Chronic Oral): 4.120
Fathead Minnow: 153989.110
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 13715374.130
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 1.580
Log(P): -0.75
Log S: -1.99
Log(Vapor Pressure): -451494.02
Melting Point: 239.53
pKa Acid: -3214.46
pKa Basic: 4.18

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	0.9515
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9515
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.9101
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.9101
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8680
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8680
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8163
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8163
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7966
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7966
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.7819
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.7819
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7740
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7740
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7740
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7740
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7707
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7707
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7610
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7610
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7604
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7604
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7578
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7578
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7542
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7542
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7538
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7538
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7457
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7457
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7454
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7454
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7404
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7404
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	2	0.7285
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	2	0.7285
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7279
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7279
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7274
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7274
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7233
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7233
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7229
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7229
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7213
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7213
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7205
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7205
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7179
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7179
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7149
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7149
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7129
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7129
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7116
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7116
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7090
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7090
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7051
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7051
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	2	0.7048
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	2	0.7048
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7024
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7024
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7022
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7022
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	2	0.7018
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	2	0.7018
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	2	0.7005
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	2	0.7005

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