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Proscillaridin
- Family: Plantae - Hyacinthaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Bufadienolide
| Canonical Smiles | O[C@H]1[C@H](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)O[C@H]([C@@H]([C@H]1O)O)C |
|---|---|
| InChI | InChI=1S/C30H42O8/c1-16-24(32)25(33)26(34)27(37-16)38-19-8-11-28(2)18(14-19)5-6-22-21(28)9-12-29(3)20(10-13-30(22,29)35)17-4-7-23(31)36-15-17/h4,7,14-16,19-22,24-27,32-35H,5-6,8-13H2,1-3H3/t16-,19-,20+,21-,22+,24-,25+,26+,27-,28-,29+,30-/m0/s1 |
| InChIKey | MYEJFUXQJGHEQK-ALRJYLEOSA-N |
| Formula | C30H42O8 |
| HBA | 8 |
| HBD | 4 |
| MW | 530.66 |
| Rotatable Bonds | 3 |
| TPSA | 129.59 |
| LogP | 3.01 |
| Number Rings | 6 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 38 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.77 |
| Exact Mass | 530.29 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Urginea maritima | Hyacinthaceae | Plantae | 82070 |
Showing of synonyms
Proscillaridin
Proscillaridin A
466-06-8
Proscillaridine
Talusin
Proscilaridina
Proscillaridina
Proscilardyna
Talucard
Herzo
Proscillaridinum
Scilla didier
Scillacrist
Desgluco-transvaalin
Scillarenin-rhamnose
Cardiovite
Procardin
Prostosin
Cardion
Coratol
Proscilardyna [Polish]
Proscillaridina [DCIT]
Scillarenin 3beta-rhamnoside
KC6BL281EN
Caradrine
Carmazon
Procilan
Proscillan
Proslladin
Proszin
Protasin
Solestril
Stellarid
Tradenal
Urgilan
Wirnesin
Proscilaridina [INN-Spanish]
Proscillaridine [INN-French]
Proscillaridinum [INN-Latin]
Scillarenin 3-beta-rhamnoside
Simeon
Talusin (TN)
Scillarenin-rhamnose [German]
Herzo proscillan
DTXSID5023532
Purosin-TC
Desglucotransvaaline
NSC 7521
NSC-7521
EINECS 207-370-4
Proscillaridin [USAN:INN:BAN:JAN]
PROSCILLARIDIN [MI]
Scillarenin, 3alpha-L-rhamnopyranoside
Transvaalin, degluco-
PROSCILLARIDIN [INN]
PROSCILLARIDIN [JAN]
Scillarenin, 3-alpha-L-rhamnopyranoside
PROSCILLARIDIN [USAN]
Rhamnopyranoside, scillarenin-3, alpha-L-
PROSCILLARIDIN [MART.]
DTXCID003532
PROSCILLARIDIN [WHO-DD]
5-[(3S,8R,9S,10R,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one
Bufa-4,20,22-trienolide, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-14-hydroxy-, (3beta)-
A-32686
14-Hydroxy-3-beta-(rhamnosyloxy)bufa-4,20,22-trienolide
14-Hydroxy-3beta-(rhamnosyloxy)bufa-4,20,22-trienolide
PSC-801
3-beta,14-beta-Dihydroxybufa-4,20,22-trienolide 3-rhamnoside
3-beta-Rhamnosido-14-beta-hydroxy-delta(sup 4,20,22)-bufatrienolide
((6-Deoxy-alpha-L-mannopyranosyl)oxy)-14-hydroxybufa-4,20,22-trienolide
Bufa-4,20,22-trienolide, 3-beta-((6-deoxy-alpha-L-mannosyl)oxy)-14-hydroxy-
3-beta-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-14-hydroxybufa-4,20,22-trienolide
Bufa-4,20,22-trienolide, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-14-hydroxy-, (3-beta)-
Proscilaridina (INN-Spanish)
Proscillaridine (INN-French)
Proscillaridinum (INN-Latin)
PROSCILLARIDIN (MART.)
((6-Deoxy-.alpha.-L-mannopyranosyl)oxy)-14-hydroxybufa-4,20,22-trienolide
BUFA-4,20,22-TRIENOLIDE, 3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-14-HYDROXY-, (3.BETA.)-
Scillarenin Rhamnoside
Rhamnoside, Scillarenin
5-((3S,8R,9S,10R,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta(a)phenanthren-17-yl)pyran-2-one
C01AB01
12041-88-2
207-370-4
Caradrin
Sandoscill
Bufa-4,20,22-trienolide,3-[(6-deoxy-a-L-mannopyranosyl)oxy]-14-hydroxy-, (3b)-
UNII-KC6BL281EN
Proscillaridin (JAN/USAN/INN)
NCGC00016447-01
CAS-466-06-8
Scillarenin 3b-rhamnoside
3-(6-Deoxy-a-L-mannopyranosyloxyl)-14-hydroxybufa-4,20,22-trienolide
MFCD00214065
C12816
Proscillaridin A (Standard)
SCHEMBL123759
CHEMBL600325
CHEBI:32065
HY-N2331R
BDBM430636
HMS3715E13
HY-N2331
Tox21_110442
Proscillaridin A - Bio-X trade mark
AKOS030622919
Tox21_110442_1
CCG-220986
DB13307
MP45299
NCGC00344555-01
BP300151
CS-0021123
D01379
G12494
Q7250550
(3beta)-3-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-14-hydroxybufa-4,20,22-trienolide
Pubchem:
5284613
Cas:
466-06-8
Zinc:
ZINC000008214665
Chebi:
32065
Nmrshiftdb2:
60070379
Chembl:
CHEMBL600325
Comptox:
DTXSID5023532
Drugbank:
DB13307
Bindingdb:
430636
CPRiL:
85812
SMILES: c1oc(=O)ccc1C2CCC(C23)C4C(CC3)C5C(CC4)=CC(CC5)OC6CCCCO6
Level: 2
Mol. Weight: 530.66 g/mol
SMILES: C1CCC(C12)CCC3C2CCC=4C3CCC(C4)OC5CCCCO5
Level: 1
Mol. Weight: 530.66 g/mol
SMILES: C1CCC=C(CC2)C1C(CC3)C2C(C34)CCC4c5ccc(=O)oc5
Level: 1
Mol. Weight: 530.66 g/mol
SMILES: C1CCC(C12)CCC3C2CCC=4C3CCCC4
Level: 0
Mol. Weight: 530.66 g/mol
SMILES: O=c1cccco1
Level: 0
Mol. Weight: 530.66 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 530.66 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.43
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.86
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.13
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.81
- Plasma Protein Binding
- 92.22
- 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
- 2.73
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.0
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.73
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.19
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Toxic
- NR-Aromatase
- Safe
- NR-ER
- Toxic
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -2096.77
- Rat (Acute)
- 4.63
- Rat (Chronic Oral)
- 2.72
- Fathead Minnow
- 6.39
- 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
- 486.29
- Hydration Free Energy
- -2.98
- Log(D) at pH=7.4
- 3.42
- Log(P)
- 2.54
- Log S
- -4.17
- Log(Vapor Pressure)
- -11.05
- Melting Point
- 239.07
- pKa Acid
- 7.3
- pKa Basic
- 6.8
| 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 | 0.9391 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.9391 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9357 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9357 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8378 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8378 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8158 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8158 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8062 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8062 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7948 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7948 |
| High affinity 3',5'-cyclic-AMP phosphodiesterase 7A | Q13946 | PDE7A_HUMAN | Homo sapiens | 3 | 0.7882 |
| High affinity 3',5'-cyclic-AMP phosphodiesterase 7A | Q13946 | PDE7A_HUMAN | Homo sapiens | 3 | 0.7882 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 2 | 0.7617 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 2 | 0.7617 |
| 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 | 0.7581 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7581 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7546 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7546 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7535 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7535 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7494 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7494 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7479 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7479 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7456 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7456 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7452 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7452 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7450 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7450 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7430 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7430 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.7428 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.7428 |
| 17-beta-hydroxysteroid dehydrogenase 14 | Q9BPX1 | DHB14_HUMAN | Homo sapiens | 2 | 0.7422 |
| 17-beta-hydroxysteroid dehydrogenase 14 | Q9BPX1 | DHB14_HUMAN | Homo sapiens | 2 | 0.7422 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7368 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7368 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7362 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7362 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7325 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7325 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7297 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7297 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 2 | 0.7267 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 2 | 0.7267 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 3 | 0.7216 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 3 | 0.7216 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 2 | 0.7153 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 2 | 0.7153 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7144 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7144 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.7129 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.7129 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7124 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7124 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 2 | 0.7111 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 2 | 0.7111 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7107 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7107 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7070 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7070 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7049 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7049 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 2 | 0.7040 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 2 | 0.7040 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7028 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7028 |