Muzigadiolide - Compound Card

Muzigadiolide

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Muzigadiolide

Structure
Zoomed Structure
  • Family: Plantae - Canellaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles C=C1[C@@H](C)CC[C@]2([C@H]1CC=C1[C@]2(O)COC1=O)C
InChI InChI=1S/C15H20O3/c1-9-6-7-14(3)11(10(9)2)4-5-12-13(16)18-8-15(12,14)17/h5,9,11,17H,2,4,6-8H2,1,3H3/t9-,11-,14-,15+/m0/s1
InChIKey OUBGLUCJLDERNN-LHAJWOIZSA-N
Formula C15H20O3
HBA 3
HBD 1
MW 248.32
Rotatable Bonds 0
TPSA 46.53
LogP 2.21
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 248.14
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: 636559
Nmrshiftdb2: 60059021

No compound-protein relationship available.

Structure

SMILES: C1CCC(=C)C(CC2)C1C(C=23)COC3=O

Level: 0

Mol. Weight: 248.32 g/mol

Anti-plasmodial
Antibacterial
Antifungal
Antimycobacterial
Antitrypanosomal

Absorption

Caco-2 (logPapp)
-4.82
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.65
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.92
Plasma Protein Binding
44.34
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
6.22
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.39
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.64
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.5
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
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
-0.77
Rat (Acute)
2.5
Rat (Chronic Oral)
1.59
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
329.47
Hydration Free Energy
-5.73
Log(D) at pH=7.4
1.92
Log(P)
2.32
Log S
-3.93
Log(Vapor Pressure)
-5.7
Melting Point
152.16
pKa Acid
7.88
pKa Basic
6.11
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8763
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8763
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8588
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8588
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8473
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8473
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8416
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8416
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8181
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8181
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8049
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8049
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8037
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8037
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7838
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7838
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7745
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7745
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7706
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7706
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7683
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7683
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7661
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7661
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7515
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7515
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7257
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7257
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7222
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7222
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7017
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7017
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7010
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7010

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