11-epi-21-hydroxytoonacilide - Compound Card

11-epi-21-hydroxytoonacilide

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11-epi-21-hydroxytoonacilide

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles COC(=O)C[C@H]1C(C)(C)C(=O)C=C[C@]1(C)[C@H]1[C@@H](OC(=O)C)[C@H](OC(=O)C)[C@@]2([C@]3(C1(C)C)O[C@@H]3C[C@H]2C1=CC(=O)OC1O)C
InChI InChI=1S/C32H42O11/c1-15(33)40-24-25(30(7)11-10-20(35)28(3,4)19(30)14-22(36)39-9)29(5,6)32-21(43-32)13-18(17-12-23(37)42-27(17)38)31(32,8)26(24)41-16(2)34/h10-12,18-19,21,24-27,38H,13-14H2,1-9H3/t18-,19-,21+,24+,25-,26-,27?,30-,31+,32-/m0/s1
InChIKey KNLQOXOBGHPAKT-BCUYAYFDSA-N
Formula C32H42O11
HBA 11
HBD 1
MW 602.68
Rotatable Bonds 6
TPSA 155.03
LogP 2.82
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 43
Formal Charge 0
Fraction CSP3 0.72
Exact Mass 602.27
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Turraea parvifolia Meliaceae Plantae 201020

Showing of synonyms

  • Cheplogoi PK, Mulholland DA. (2003). Tetranortriterpenoid derivatives from Turraea parvifolia (Meliaceae).. Phytochemistry,2003,62(8),1173-1178. [View] [PubMed]
Pubchem: 101243071

No compound-protein relationship available.

Structure

SMILES: C1OC(=O)C=C1C(CC(C234)O4)C2CCC(C3)C(CC5)C=CC5=O

Level: 2

Mol. Weight: 602.68 g/mol

Structure

SMILES: C123C(O3)CCC1CCC(C2)C(CC4)C=CC4=O

Level: 1

Mol. Weight: 602.68 g/mol

Structure

SMILES: C1CCCC2C(CC(C123)O3)C4=CC(=O)OC4

Level: 1

Mol. Weight: 602.68 g/mol

Structure

SMILES: C123C(O3)CCC1CCCC2

Level: 0

Mol. Weight: 602.68 g/mol

Structure

SMILES: O=C1C=CCCC1

Level: 0

Mol. Weight: 602.68 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 602.68 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.15
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.820
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
1.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.350
Plasma Protein Binding
66.68
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
10.770
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.590
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.050
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.800
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
-8500.180
Rat (Acute)
4.490
Rat (Chronic Oral)
2.420
Fathead Minnow
24.630
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
359.800
Hydration Free Energy
-2.920
Log(D) at pH=7.4
2.200
Log(P)
1.93
Log S
-5.13
Log(Vapor Pressure)
-12.66
Melting Point
190.84
pKa Acid
5.75
pKa Basic
2.05
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7887
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7887
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7661
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7661

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