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16beta-hydroxy-proscillaridin A

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

Canonical Smiles	O[C@H]1C[C@]2([C@]([C@H]1c1ccc(=O)oc1)(C)CC[C@@H]1[C@H]2CCC2=C[C@H](CC[C@]12C)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O
InChI	InChI=1S/C30H42O9/c1-15-24(33)25(34)26(35)27(38-15)39-18-8-10-28(2)17(12-18)5-6-20-19(28)9-11-29(3)23(21(31)13-30(20,29)36)16-4-7-22(32)37-14-16/h4,7,12,14-15,18-21,23-27,31,33-36H,5-6,8-11,13H2,1-3H3/t15-,18-,19+,20+,21-,23-,24-,25+,26+,27-,28-,29+,30-/m0/s1
InChIKey	FIPZUWCZGCGMNN-FZSLDBBZSA-N
Formula	C₃₀H₄₂O₉
HBA	9
HBD	5
MW	546.66
Rotatable Bonds	3
TPSA	149.82
LogP	1.98
Number Rings	6
Number Aromatic Rings	1
Heavy Atom Count	39
Formal Charge	0
Fraction CSP3	0.77
Exact Mass	546.28
Number of Lipinski Rule Violations	1

#	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: 162955699

Zinc: ZINC000255209271

Nmrshiftdb2: 60070404

No compound-protein relationship available.

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

Level: 2

Mol. Weight: 546.66 g/mol

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

Level: 1

Mol. Weight: 546.66 g/mol

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

Level: 1

Mol. Weight: 546.66 g/mol

SMILES: C1CCC(C12)CCC3C2CCC=4C3CCCC4

Level: 0

Mol. Weight: 546.66 g/mol

SMILES: O=c1cccco1

Level: 0

Mol. Weight: 546.66 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 546.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.8
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.94
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.64

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.84
Plasma Protein Binding: 91.92
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: 2.21
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.41
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.5
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.1
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -2898.87
Rat (Acute): 5.24
Rat (Chronic Oral): 2.99
Fathead Minnow: 7.67
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 486.21
Hydration Free Energy: -3.03
Log(D) at pH=7.4: 2.86
Log(P): 1.74
Log S: -3.62
Log(Vapor Pressure): -11.39
Melting Point: 252.63
pKa Acid: 6.87
pKa Basic: 6.44

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	0.9351
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.9351
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9092
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9092
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.8711
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.8711
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8642
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8642
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8617
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8617
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.8478
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.8478
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8332
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8332
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8221
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8221
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8125
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8125
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.8071
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.8071
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8046
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8046
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7684
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7684
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7598
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7598
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7546
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7546
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	3	0.7532
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	3	0.7532
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7503
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7503
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7498
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7498
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7495
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7495
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.7493
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	3	0.7493
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7475
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7475
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7456
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7456
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7450
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7450
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7441
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7441
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7394
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7394
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7369
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7369
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	3	0.7332
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	3	0.7332
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7301
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7301
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7301
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7301
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7298
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7298
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B	Q13370	PDE3B_HUMAN	Homo sapiens	3	0.7292
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B	Q13370	PDE3B_HUMAN	Homo sapiens	3	0.7292
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	2	0.7283
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	2	0.7283
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7278
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7278
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7269
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7269
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7260
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7260
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7199
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7199
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7194
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7194
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7184
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7184
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.7180
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.7180
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7176
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7176
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	2	0.7175
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	2	0.7175
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7128
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7128
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7114
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7114
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7092
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7092
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7088
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7088
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7088
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7088
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7082
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7082
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7080
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7080
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7073
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7073
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7071
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7071
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7069
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7069
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7059
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7059
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7042
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7042
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7001
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7001

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