2alpha-hydroxy-3-acetylswietenolide - Compound Card

2alpha-hydroxy-3-acetylswietenolide

Select a section from the left sidebar

2alpha-hydroxy-3-acetylswietenolide

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles COC(=O)[C@@H]([C@H]1C(C)(C)[C@H](OC(=O)C)[C@]2(C(=O)[C@]1(C)C1CC[C@@]3(C(=C1C2)CC(=O)O[C@H]3c1ccoc1)C)O)O
InChI InChI=1S/C29H36O10/c1-14(30)38-25-26(2,3)21(20(32)23(33)36-6)28(5)17-7-9-27(4)18(16(17)12-29(25,35)24(28)34)11-19(31)39-22(27)15-8-10-37-13-15/h8,10,13,17,20-22,25,32,35H,7,9,11-12H2,1-6H3/t17?,20-,21+,22+,25+,27-,28-,29+/m1/s1
InChIKey JWYNOYIKTIPXBD-WUNLLSKDSA-N
Formula C29H36O10
HBA 10
HBD 2
MW 544.6
Rotatable Bonds 4
TPSA 149.57
LogP 2.81
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.66
Exact Mass 544.23
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Quivisia papinae Meliaceae Plantae —

Showing of synonyms

  • Coombes PH, Mulholland DA, et al. (2005). Mexicanolide limonoids from the Madagascan MeliaceaeQuivisia papinae. Phytochemistry, 2005, 66(10), 1100–1107. [View]
Pubchem: 23760110

No compound-protein relationship available.

Structure

SMILES: c1occc1C(OC(=O)C2)C3CCC(C4=C23)C5C(=O)C(C4)CCC5

Level: 1

Mol. Weight: 544.6 g/mol

Structure

SMILES: C1C(=O)OCC(C1=C23)CCC2C4C(=O)C(C3)CCC4

Level: 0

Mol. Weight: 544.6 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 544.6 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.41
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.850
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.51

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.620
Plasma Protein Binding
77.3
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
10.070
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.020
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.100
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.710
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-1849.910
Rat (Acute)
4.050
Rat (Chronic Oral)
2.650
Fathead Minnow
8.460
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
434.340
Hydration Free Energy
-2.830
Log(D) at pH=7.4
2.610
Log(P)
2.02
Log S
-4.36
Log(Vapor Pressure)
-9.61
Melting Point
253.85
pKa Acid
5.33
pKa Basic
2.99
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9176
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8936
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.8907
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8902
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8899
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8796
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8762
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8724
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8723
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8617
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8565
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.8048
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7920
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7846
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7829
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7750
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7744
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7726
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7700
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7641
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7622
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7580
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7558
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7462
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 2 0.7422
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7398
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7384
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7371
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7302
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7295
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7281
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7276
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7262
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7237
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7237
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7234
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7225
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7224
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7222
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7219
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7213
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7211
Albumin P14639 ALBU_SHEEP Ovis aries 2 0.7207
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7194
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7192
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7191
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7186
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 2 0.7181
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7165
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7143
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7108
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7095
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7090
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7080
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7059
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7052
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 2 0.7045
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7026
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7013
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7013

Download SDF