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Scillaren A

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@@H]3CC[C@]3([C@]2(O)CC[C@@H]3c2ccc(=O)oc2)C)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C36H52O13/c1-17-31(49-33-29(42)27(40)26(39)24(15-37)48-33)28(41)30(43)32(46-17)47-20-8-11-34(2)19(14-20)5-6-23-22(34)9-12-35(3)21(10-13-36(23,35)44)18-4-7-25(38)45-16-18/h4,7,14,16-17,20-24,26-33,37,39-44H,5-6,8-13,15H2,1-3H3/t17-,20-,21+,22-,23+,24+,26+,27-,28+,29+,30+,31-,32-,33-,34-,35+,36-/m0/s1
InChIKey	NXJOCELNFPGKIV-QQHFKTCASA-N
Formula	C₃₆H₅₂O₁₃
HBA	13
HBD	7
MW	692.8
Rotatable Bonds	6
TPSA	208.74
LogP	0.84
Number Rings	7
Number Aromatic Rings	1
Heavy Atom Count	49
Formal Charge	0
Fraction CSP3	0.81
Exact Mass	692.34
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: 163016836

Zinc: ZINC000261521322

Nmrshiftdb2: 60070386

No compound-protein relationship available.

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

Level: 3

Mol. Weight: 692.8 g/mol

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

Level: 2

Mol. Weight: 692.8 g/mol

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

Level: 2

Mol. Weight: 692.8 g/mol

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

Level: 1

Mol. Weight: 692.8 g/mol

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

Level: 1

Mol. Weight: 692.8 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 692.8 g/mol

SMILES: C1CCC(C12)CCC3C2CCC=4C3CCCC4

Level: 0

Mol. Weight: 692.8 g/mol

SMILES: O=c1cccco1

Level: 0

Mol. Weight: 692.8 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 692.8 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.58
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -3.850
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 236.57

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.900
Plasma Protein Binding: 94.8
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: 0.730
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -4.200
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.340
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 6.550
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Toxic
NR-Aromatase: Toxic
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -430716.630
Rat (Acute): 4.570
Rat (Chronic Oral): 3.800
Fathead Minnow: 554.020
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 44201.010
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 2.690
Log(P): 1.21
Log S: -2.66
Log(Vapor Pressure): -1399.91
Melting Point: 230.02
pKa Acid: 3.9
pKa Basic: 6.25

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.9501
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.9501
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9372
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9372
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8289
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8289
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8098
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8098
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7818
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7818
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7768
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7768
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7655
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7655
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7605
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7605
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7572
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7572
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7564
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7564
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7563
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7563
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7523
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7523
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7503
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7503
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7501
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7501
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7486
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7486
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7471
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7471
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7447
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7447
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7384
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7384
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7362
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7362
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7336
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7336
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7313
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7313
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7303
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7303
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7295
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7295
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7266
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7266
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	2	0.7252
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	2	0.7252
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7250
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7250
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7160
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7160
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7153
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7153
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7142
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7142
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7113
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7113
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7110
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7110
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7067
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7067
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7057
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7057
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.7055
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.7055
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	2	0.7048
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7048
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	2	0.7048
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7048
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7038
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7038
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7024
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7024

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