3,23-dioxotirucalla-7,24-dien-21-al - Compound Card

3,23-dioxotirucalla-7,24-dien-21-al

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3,23-dioxotirucalla-7,24-dien-21-al

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles O=C[C@H]([C@@H]1CC[C@]2([C@@]1(C)CC[C@H]1C2=CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)CC(=O)C=C(C)C
InChI InChI=1S/C30H44O3/c1-19(2)16-21(32)17-20(18-31)22-10-14-30(7)24-8-9-25-27(3,4)26(33)12-13-28(25,5)23(24)11-15-29(22,30)6/h8,16,18,20,22-23,25H,9-15,17H2,1-7H3/t20-,22+,23+,25+,28-,29+,30-/m1/s1
InChIKey UOWCRZCTJKGGKK-CGCXKXEYSA-N
Formula C30H44O3
HBA 3
HBD 0
MW 452.68
Rotatable Bonds 5
TPSA 51.21
LogP 6.9
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.77
Exact Mass 452.33
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Entandrophragma angolense Meliaceae Plantae 587577
2 Entandrophragma congoense Meliaceae Plantae 2590899

Showing of synonyms

  • Happi GM, Kouam SF, et al. (2015). Minor secondary metabolites from the bark of Entandrophragma congoënse (Meliaceae).. Fitoterapia,2015, 102, 35-40. [View] [PubMed]
  • Orisadipe AT, Adesomoju AA, et al. (2005). Tirucallane triterpenes from the leaf extract of Entandrophragma angolense. Phytochemistry,2005,66(19),2324-2328. [View]
Pubchem: 163028239
Nmrshiftdb2: 70063245

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2=CCC4C3CCC(=O)C4

Level: 0

Mol. Weight: 452.68 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.82
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.64
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.02

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.34
Plasma Protein Binding
85.24
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.92
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.02
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.55
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.4
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
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
-82.45
Rat (Acute)
2.42
Rat (Chronic Oral)
1.43
Fathead Minnow
4.01
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
483.47
Hydration Free Energy
-2.68
Log(D) at pH=7.4
5.73
Log(P)
5.89
Log S
-5.66
Log(Vapor Pressure)
-8.16
Melting Point
159.12
pKa Acid
9.67
pKa Basic
4.63
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9306
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9192
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9181
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8578
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8360
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.8359
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7924
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7922
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7900
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7671
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7670
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7496
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7445
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7425
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7372
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7080
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7062

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