2alpha-hydroxyswietenolide - Compound Card

2alpha-hydroxyswietenolide

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2alpha-hydroxyswietenolide

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles COC(=O)[C@@H]([C@@H]1[C@@]2(C)[C@H]3CC[C@@]4(C(=C3C[C@](C2=O)([C@H](C1(C)C)O)O)CC(=O)O[C@H]4c1cocc1)C)O
InChI InChI=1S/C27H34O9/c1-24(2)19(18(29)21(30)34-5)26(4)15-6-8-25(3)16(14(15)11-27(33,22(24)31)23(26)32)10-17(28)36-20(25)13-7-9-35-12-13/h7,9,12,15,18-20,22,29,31,33H,6,8,10-11H2,1-5H3/t15-,18+,19-,20-,22-,25+,26+,27+/m0/s1
InChIKey ROELJMJDOPSYJR-KYWAYRNDSA-N
Formula C27H34O9
HBA 9
HBD 3
MW 502.56
Rotatable Bonds 3
TPSA 143.5
LogP 2.24
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 502.22
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: 101740824

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 502.56 g/mol

Structure

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

Level: 0

Mol. Weight: 502.56 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 502.56 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.42
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.940
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.92

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.700
Plasma Protein Binding
76.59
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
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.000
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.750
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.200
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.750
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
-507.300
Rat (Acute)
3.880
Rat (Chronic Oral)
2.920
Fathead Minnow
4.090
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
453.550
Hydration Free Energy
-2.770
Log(D) at pH=7.4
2.470
Log(P)
1.42
Log S
-3.57
Log(Vapor Pressure)
-10.21
Melting Point
244.9
pKa Acid
4.69
pKa Basic
3.68
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8855
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8819
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8724
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8680
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8665
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8635
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8575
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8521
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8452
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8424
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8007
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7890
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.7787
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7768
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7712
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7559
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7540
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7444
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7423
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7403
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7304
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7221
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7203
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7132
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7120
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7110
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7110
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7084
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7054
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7014

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