16beta-O-acetyl-proscillaridin A - Compound Card

16beta-O-acetyl-proscillaridin A

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16beta-O-acetyl-proscillaridin A

Structure
Zoomed Structure
  • Family: Plantae - Hyacinthaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Bufadienolide
Canonical Smiles CC(=O)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/C32H44O10/c1-16-26(35)27(36)28(37)29(40-16)42-20-9-11-30(3)19(13-20)6-7-22-21(30)10-12-31(4)25(18-5-8-24(34)39-15-18)23(41-17(2)33)14-32(22,31)38/h5,8,13,15-16,20-23,25-29,35-38H,6-7,9-12,14H2,1-4H3/t16-,20-,21-,22+,23+,25-,26-,27+,28+,29-,30+,31+,32-/m0/s1
InChIKey VMLMEZINUVEFME-LORXWKFFSA-N
Formula C32H44O10
HBA 10
HBD 4
MW 588.69
Rotatable Bonds 4
TPSA 155.89
LogP 2.56
Number Rings 6
Number Aromatic Rings 1
Heavy Atom Count 42
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 588.29
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: 162986325
Nmrshiftdb2: 60070415

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 588.69 g/mol

Structure

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

Level: 1

Mol. Weight: 588.69 g/mol

Structure

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

Level: 1

Mol. Weight: 588.69 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CCC=4C3CCCC4

Level: 0

Mol. Weight: 588.69 g/mol

Structure

SMILES: O=c1cccco1

Level: 0

Mol. Weight: 588.69 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 588.69 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.86
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
3.87

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.75
Plasma Protein Binding
89.96
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
5.14
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.32
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.81
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.17
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Toxic
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
-10924.17
Rat (Acute)
5.26
Rat (Chronic Oral)
2.87
Fathead Minnow
27.42
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
334.78
Hydration Free Energy
-2.93
Log(D) at pH=7.4
2.84
Log(P)
1.95
Log S
-3.93
Log(Vapor Pressure)
-14.16
Melting Point
218.97
pKa Acid
6.37
pKa Basic
5.63
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 0.8792
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8792
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8295
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8295
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8166
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8166
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7830
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7830
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7608
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7608
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7488
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7488
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7478
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7478
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7462
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7462
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7442
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7442
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7422
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7422
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7419
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7419
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7414
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7414
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7350
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7350
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7316
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7316
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7294
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7294
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7256
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7256
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7231
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7231
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7228
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7228
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 2 0.7222
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 2 0.7222
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7176
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7176
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7164
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7164
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 2 0.7157
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 2 0.7157
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7128
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7128
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7113
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7113
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7108
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7108
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7101
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7101
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7098
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7098
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7062
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7062
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7008
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7008

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