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Glucoscillaren 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[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O)O
InChI	InChI=1S/C42H62O18/c1-18-35(59-39-34(52)31(49)36(26(16-44)58-39)60-38-32(50)29(47)28(46)25(15-43)57-38)30(48)33(51)37(55-18)56-21-8-11-40(2)20(14-21)5-6-24-23(40)9-12-41(3)22(10-13-42(24,41)53)19-4-7-27(45)54-17-19/h4,7,14,17-18,21-26,28-39,43-44,46-53H,5-6,8-13,15-16H2,1-3H3/t18-,21-,22+,23-,24+,25+,26+,28+,29-,30-,31+,32+,33+,34+,35-,36+,37-,38-,39-,40-,41+,42-/m0/s1
InChIKey	UHVXHHKIFHGLAJ-HFOYKOELSA-N
Formula	C₄₂H₆₂O₁₈
HBA	18
HBD	10
MW	854.94
Rotatable Bonds	9
TPSA	287.89
LogP	-1.34
Number Rings	8
Number Aromatic Rings	1
Heavy Atom Count	60
Formal Charge	0
Fraction CSP3	0.83
Exact Mass	854.39
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: 114585

Cas: 11003-96-6

Zinc: ZINC000255271443

Nmrshiftdb2: 60070399

Comptox: DTXSID80149123

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: 854.94 g/mol

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

Level: 3

Mol. Weight: 854.94 g/mol

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

Level: 3

Mol. Weight: 854.94 g/mol

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

Level: 2

Mol. Weight: 854.94 g/mol

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

Level: 2

Mol. Weight: 854.94 g/mol

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCCOC3

Level: 2

Mol. Weight: 854.94 g/mol

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

Level: 1

Mol. Weight: 854.94 g/mol

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

Level: 1

Mol. Weight: 854.94 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 854.94 g/mol

SMILES: C1CCC(C12)CCC3C2CCC=4C3CCCC4

Level: 0

Mol. Weight: 854.94 g/mol

SMILES: O=c1cccco1

Level: 0

Mol. Weight: 854.94 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 854.94 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.71
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 363.930
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 48393.83

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.850
Plasma Protein Binding: 81.45
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: 0.960
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -1119.560
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.900
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 5.130
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: -87831410.580
Rat (Acute): 3.640
Rat (Chronic Oral): 4.400
Fathead Minnow: 110875.110
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: 9874030.120
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 2.890
Log(P): 0.19
Log S: -2.29
Log(Vapor Pressure): -325004.52
Melting Point: 238.54
pKa Acid: -2295.89
pKa Basic: 6.28

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	0.9316
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9316
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8033
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8033
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7813
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7813
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7726
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7726
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7697
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7697
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7524
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7524
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7492
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7492
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7467
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7467
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7458
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7458
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7451
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7451
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7448
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7448
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7384
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7384
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7346
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7346
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7291
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7291
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7248
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7248
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	2	0.7145
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	2	0.7145
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7079
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7079
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7054
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7054

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