Dregeanin DM4 - Compound Card

Dregeanin DM4

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Dregeanin DM4

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Limonoid
    • Subclass: Limonin
Canonical Smiles CCC(C(C(=O)O[C@H]1[C@@H]2O[C@@H]3[C@@]([C@]2(C)C(=C)[C@@]24[C@]1(C)[C@@H](C[C@H]4O2)c1ccoc1)(C)C1CC(=O)OC[C@]1(OC(=O)C3)C)O)C
InChI InChI=1S/C33H42O10/c1-8-16(2)25(36)28(37)41-27-26-30(5,17(3)33-22(42-33)11-19(31(27,33)6)18-9-10-38-14-18)32(7)20-12-23(34)39-15-29(20,4)43-24(35)13-21(32)40-26/h9-10,14,16,19-22,25-27,36H,3,8,11-13,15H2,1-2,4-7H3/t16?,19-,20?,21-,22+,25?,26-,27-,29+,30+,31+,32+,33+/m0/s1
InChIKey FZOITJNSTPBUBS-XJPHJEKZSA-N
Formula C33H42O10
HBA 10
HBD 1
MW 598.69
Rotatable Bonds 5
TPSA 134.03
LogP 3.85
Number Rings 7
Number Aromatic Rings 1
Heavy Atom Count 43
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 598.28
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Trichilia welwitschii Meliaceae Plantae 2709005

Showing of synonyms

  • Dzoyem JP, Tsamo AT, et al. (2015). Cytotoxicity, nitric oxide and acetylcholinesterase inhibitory activity of three limonoids isolated from Trichilia welwitschii (Meliaceae).. Biological research,2015, 48, 57. [View] [PubMed]
CPRiL: 185986
Structure

SMILES: c1occc1C(CC(C234)O4)C2CC5C(C3=C)C6C(O5)CC(=O)OC7C6CC(=O)OC7

Level: 1

Mol. Weight: 598.69 g/mol

Structure

SMILES: C123C(O3)CCC1CC4C(C2=C)C5C(O4)CC(=O)OC6C5CC(=O)OC6

Level: 0

Mol. Weight: 598.69 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 598.69 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.2
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.83
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
8.21

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.6
Plasma Protein Binding
62.98
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
11.19
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.5
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.25
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
7.96
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
Toxic
T. Pyriformis
-18928.92
Rat (Acute)
6.17
Rat (Chronic Oral)
2.47
Fathead Minnow
40.78
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
281.68
Hydration Free Energy
-2.92
Log(D) at pH=7.4
3.37
Log(P)
3.16
Log S
-5.73
Log(Vapor Pressure)
-8.4
Melting Point
188.73
pKa Acid
4.58
pKa Basic
2.35
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9256
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8646
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8559
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8338
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8336
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8318
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8263
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7982
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7981
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7977
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7927
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7602
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7581
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7515
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7488
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7473
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7394
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7363
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7346
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7305
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7265
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7257
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7141
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7123
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 2 0.7112
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7060
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7051
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7042
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7014
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7013

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