Rubescin A - Compound Card

Rubescin A

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Rubescin A

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Limonoid
Canonical Smiles O=C1C2=C3[C@](CO2)(C)C=CC(=O)[C@@]3([C@@H]2[C@]1(C)C1=CC[C@H]([C@]1(C)CC2)c1cocc1)C
InChI InChI=1S/C26H28O4/c1-23-10-8-19(27)26(4)18-7-11-24(2)16(15-9-12-29-13-15)5-6-17(24)25(18,3)22(28)20(21(23)26)30-14-23/h6,8-10,12-13,16,18H,5,7,11,14H2,1-4H3/t16-,18-,23+,24-,25-,26-/m0/s1
InChIKey MHHWKYUSJKVZMV-ZUEMVNHCSA-N
Formula C26H28O4
HBA 4
HBD 0
MW 404.51
Rotatable Bonds 1
TPSA 56.51
LogP 5.13
Number Rings 6
Number Aromatic Rings 1
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.54
Exact Mass 404.2
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Trichilia rubescens Meliaceae Plantae 1672008

Showing of synonyms

  • Tsamo Tontsa A, Mkounga P, et al. (2013). Rubescins A, B and C: new havanensin type limonoids from root bark of Trichilia rubescens (Meliaceae).. Chemical & pharmaceutical bulletin,2013, 61(11), 1178-1183. [View] [PubMed]
Pubchem: 102125653

No compound-protein relationship available.

Structure

SMILES: c1occc1C(CC2)C(C=2C3C(=O)C4=C56)CCC3C6C(=O)C=CC5CO4

Level: 1

Mol. Weight: 404.51 g/mol

Structure

SMILES: C12=C3C(=O)C4C=5C(CCC5)CCC4C2C(=O)C=CC1CO3

Level: 0

Mol. Weight: 404.51 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 404.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.510
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.28

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.780
Plasma Protein Binding
83.59
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
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
11.110
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.680
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.330
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.840
Micronucleos
Safe
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
-58.750
Rat (Acute)
2.700
Rat (Chronic Oral)
2.110
Fathead Minnow
4.370
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
458.030
Hydration Free Energy
-3.690
Log(D) at pH=7.4
4.240
Log(P)
4.03
Log S
-5.33
Log(Vapor Pressure)
-8.13
Melting Point
221.5
pKa Acid
7.47
pKa Basic
3.39
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8225
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7711
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7644
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7407
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7375
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7292
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7108

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