3-O-acetyl greenwayodendrin - Compound Card

3-O-acetyl greenwayodendrin

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3-O-acetyl greenwayodendrin

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles CC(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2Cc2n1c1c(c2)cccc1)C)C
InChI InChI=1S/C25H33NO2/c1-16(27)28-22-11-12-24(4)20(23(22,2)3)10-13-25(5)21(24)15-18-14-17-8-6-7-9-19(17)26(18)25/h6-9,14,20-22H,10-13,15H2,1-5H3/t20-,21+,22-,24-,25+/m0/s1
InChIKey DRMMGUOJBQDCMO-LJDQNPOQSA-N
Formula C25H33NO2
HBA 3
HBD 0
MW 379.54
Rotatable Bonds 1
TPSA 31.23
LogP 5.7
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.64
Exact Mass 379.25
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Polyalthia suaveolens Annonaceae Plantae 235734

Showing of synonyms

  • Ngantchou I, Nyasse B, et al. (2010). Antitrypanosomal alkaloids from Polyalthia suaveolens (Annonaceae): their effects on three selected glycolytic enzymes of Trypanosoma brucei.. Bioorganic & medicinal chemistry letters,2010, 20(12), 3495-8. [View] [PubMed]
Pubchem: 46891355
Nmrshiftdb2: 70032695
Bindingdb: 50320386

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)n3c(c2)CC4C3CCC5C4CCCC5

Level: 0

Mol. Weight: 379.54 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.47
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.72

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.41
Plasma Protein Binding
91.08
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.89
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.28
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.33
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.88
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-14.95
Rat (Acute)
2.1
Rat (Chronic Oral)
1.31
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
456.81
Hydration Free Energy
-4.83
Log(D) at pH=7.4
4.94
Log(P)
6.14
Log S
-5.52
Log(Vapor Pressure)
-7.62
Melting Point
168.5
pKa Acid
12.17
pKa Basic
6.82
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 0.8201
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8188
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7863
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7756
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 3 0.7746
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7464
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7411
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7285
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7283
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7280
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7207
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7180
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7094
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7087
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7041

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