Ugandensolide - Compound Card

Ugandensolide

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Ugandensolide

Structure
Zoomed Structure
  • Family: Plantae - Canellaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles CC(=O)O[C@@H]1[C@@H](O)C2=C([C@@]3([C@@H]1C(C)(C)CCC3)C)C(=O)OC2
InChI InChI=1S/C17H24O5/c1-9(18)22-13-12(19)10-8-21-15(20)11(10)17(4)7-5-6-16(2,3)14(13)17/h12-14,19H,5-8H2,1-4H3/t12-,13+,14-,17+/m0/s1
InChIKey NYFWOFCJTJKPJY-QDEZUTFSSA-N
Formula C17H24O5
HBA 5
HBD 1
MW 308.37
Rotatable Bonds 1
TPSA 72.83
LogP 1.98
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.76
Exact Mass 308.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Warburgia ugandensis Canellaceae Plantae 549619
2 Warburgia ugandensis Canellaceae Plantae 549619
3 Warburgia ugandensis Canellaceae Plantae 549619
4 Warburgia ugandensis Canellaceae Plantae 549619

Showing of synonyms

  • Opiyo SA, Manguro LOA, et al. (2011). 7alpha-Acetylugandensolide and antimicrobial properties of Warburgia ugandensis extracts and isolates against sweet potato pathogens. Phytochemistry Letters,2011,4(2),161-165. [View] [PubMed]
  • Wube AA, Bucar F, et al. (2010). Antiprotozoal activity of drimane and coloratane sesquiterpenes towards Trypanosoma brucei rhodesiense and Plasmodium falciparum in vitro. Phytotherapy Research,2010,24(10),1468-1472. [View] [PubMed]
  • Rugutt JK, Ngigi AN, et al. (2006). Native Kenyan plants as possible alternatives to methyl bromide in soil fumigation. Phytomedicine,2006,13(8),576-583. [View] [PubMed]
  • Wube AA, Bucar F, et al. (2005). Sesquiterpenes from Warburgia ugandensis and their antimycobacterial activity. Phytochemistry,2005,66(19),2309-2315. [View] [PubMed]
Pubchem: 12444581
Nmrshiftdb2: 60059018

No compound-protein relationship available.

Structure

SMILES: O=C1OCC(=C12)CCC3C2CCCC3

Level: 0

Mol. Weight: 308.37 g/mol

Antibacterial
Antifungal
Antimycobacterial
Antitrypanosomal

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.85
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.99

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.6
Plasma Protein Binding
44.73
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
Non-Substrate
CYP 2C9 Inhibitor
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
12.69
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.13
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.87
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.72
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
Safe
T. Pyriformis
-0.06
Rat (Acute)
2.47
Rat (Chronic Oral)
1.98
Fathead Minnow
3.95
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
351.09
Hydration Free Energy
-6.64
Log(D) at pH=7.4
1.59
Log(P)
1.63
Log S
-3.59
Log(Vapor Pressure)
-6.06
Melting Point
174.48
pKa Acid
8.28
pKa Basic
5.48

No predicted protein targets found for this compound.

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