Uncinatone - Compound Card

Uncinatone

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Uncinatone

Structure
Zoomed Structure
  • Family: Plantae - Verbenaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Abietane Diterpenoid
Canonical Smiles C[C@H]1Cc2c(O1)c(O)c1c(c2O)C(=O)C=C2[C@]1(C)CCC(=C2C)C
InChI InChI=1S/C20H22O4/c1-9-5-6-20(4)13(11(9)3)8-14(21)15-16(20)18(23)19-12(17(15)22)7-10(2)24-19/h8,10,22-23H,5-7H2,1-4H3/t10-,20-/m0/s1
InChIKey IQGPVLVWUUPQMQ-FVINQWEUSA-N
Formula C20H22O4
HBA 4
HBD 2
MW 326.39
Rotatable Bonds 0
TPSA 66.76
LogP 3.93
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.45
Exact Mass 326.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Clerodendrum eriophyllum Verbenaceae Plantae 54214

Showing of synonyms

  • Machumi F, Samoylenko V, et al. (2010). Antimicrobial and antiparasitic abietane diterpenoids from the roots of Clerodendrum eriophyllum. Natural Product Communication,2010,5(6),853-858. [View] [PubMed]
Pubchem: 442547
Kegg Ligand: C09976
Chebi: 9861
Nmrshiftdb2: 60029920
CPRiL: 64799
Structure

SMILES: C1COc(c12)cc3c(c2)C(=O)C=C4C3CCC=C4

Level: 0

Mol. Weight: 326.39 g/mol

Anti-leishmanial

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.54
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.52

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.66
Plasma Protein Binding
72.97
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
10.6
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.93
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-1.1
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.02
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
0.68
Rat (Acute)
2.51
Rat (Chronic Oral)
2.27
Fathead Minnow
4.25
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
414.61
Hydration Free Energy
-7.92
Log(D) at pH=7.4
3.21
Log(P)
4.08
Log S
-5.1
Log(Vapor Pressure)
-6.95
Melting Point
195.92
pKa Acid
8.57
pKa Basic
4.46
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9074
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9074
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8640
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8640
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8556
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8556
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8169
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8169
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7383
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7383
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7234
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7234
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7158
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7158

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