3-angeloyl-3-detigloylruageanin B - Compound Card

3-angeloyl-3-detigloylruageanin B

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3-angeloyl-3-detigloylruageanin B

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles COC(=O)C[C@H]1C(C)(C)[C@H](OC(=O)/C(=C/C)/C)[C@]2(C(=O)[C@]1(C)[C@H]1CC[C@@]3([C@H]([C@]41[C@@H]2O4)CC(=O)O[C@H]3c1ccoc1)C)O
InChI InChI=1S/C32H40O10/c1-8-16(2)24(35)41-26-28(3,4)19(13-21(33)38-7)30(6)18-9-11-29(5)20(32(18)27(42-32)31(26,37)25(30)36)14-22(34)40-23(29)17-10-12-39-15-17/h8,10,12,15,18-20,23,26-27,37H,9,11,13-14H2,1-7H3/b16-8+/t18-,19+,20-,23+,26+,27-,29-,30-,31+,32-/m1/s1
InChIKey RHNVFPUACKXTEQ-DEBVYSQHSA-N
Formula C32H40O10
HBA 10
HBD 1
MW 584.66
Rotatable Bonds 5
TPSA 141.87
LogP 3.85
Number Rings 6
Number Aromatic Rings 1
Heavy Atom Count 42
Formal Charge 0
Fraction CSP3 0.69
Exact Mass 584.26
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: 11801433
Chebi: 68371
Nmrshiftdb2: 70024893
Metabolights: MTBLC68371

No compound-protein relationship available.

Structure

SMILES: C123C(O3)C4C(=O)C(CCC4)C1CCC5C2CC(=O)OC5c6ccoc6

Level: 1

Mol. Weight: 584.66 g/mol

Structure

SMILES: C123C(O3)C4C(=O)C(CCC4)C1CCC5C2CC(=O)OC5

Level: 0

Mol. Weight: 584.66 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 584.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.17
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.770
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
3.38

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.460
Plasma Protein Binding
67.48
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
11.690
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.550
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.050
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.590
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
-10094.440
Rat (Acute)
5.050
Rat (Chronic Oral)
2.370
Fathead Minnow
27.600
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
333.890
Hydration Free Energy
-2.920
Log(D) at pH=7.4
3.450
Log(P)
3.65
Log S
-5.36
Log(Vapor Pressure)
-13.08
Melting Point
222.24
pKa Acid
4.59
pKa Basic
2.78
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8290
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7848
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7818
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7790
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7631
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7580
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7572
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7539
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7473
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7454
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7379
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7364
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7299
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7281
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7255
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7216
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7203
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7181
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7160
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7140
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7117
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7098
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7059
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7004

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