3-beta,4-beta-15,16-diepoxy- 20,12(R)-olide ent-cleroda-13(16),14-dien-19-oic acid methyl ester - Compound Card

3-beta,4-beta-15,16-diepoxy- 20,12(R)-olide ent-cleroda-13(16),14-dien-19-oic acid methyl ester

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3-beta,4-beta-15,16-diepoxy- 20,12(R)-olide ent-cleroda-13(16),14-dien-19-oic acid methyl ester

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Ent-Clerodane Diterpenoid
Canonical Smiles COC(=O)[C@@]12CC[C@H]([C@@]3([C@H]1CC[C@H]1[C@]2(C)O1)C[C@@H](OC3=O)c1ccoc1)C
InChI InChI=1S/C21H26O6/c1-12-6-8-21(18(23)24-3)15(4-5-16-19(21,2)27-16)20(12)10-14(26-17(20)22)13-7-9-25-11-13/h7,9,11-12,14-16H,4-6,8,10H2,1-3H3/t12-,14-,15-,16+,19+,20-,21-/m1/s1
InChIKey TWTZURAMYVFYIA-QOZVVDAXSA-N
Formula C21H26O6
HBA 6
HBD 0
MW 374.43
Rotatable Bonds 2
TPSA 78.27
LogP 3.41
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.71
Exact Mass 374.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Croton dictyophlebodes Euphorbiaceae Plantae 100370

Showing of synonyms

  • Munissi JJE, Isyaka SM, et al. (2020). Ent-clerodane and ent-trachylobane diterpenoids from Croton dictyophlebodes. Phytochemistry, 2020, 179, 112487. [View]

No compound-protein relationship available.

Structure

SMILES: C1CC(O2)C2C(CCC3)C1C34C(=O)OC(C4)c5ccoc5

Level: 1

Mol. Weight: 374.43 g/mol

Structure

SMILES: C1CC(O2)C2C(CCC3)C1C34C(=O)OCC4

Level: 0

Mol. Weight: 374.43 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 374.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.13
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.900
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.45

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.550
Plasma Protein Binding
37.33
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
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.800
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.820
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.510
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.020
Micronucleos
Toxic
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
-11.090
Rat (Acute)
4.080
Rat (Chronic Oral)
1.860
Fathead Minnow
3.930
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
435.330
Hydration Free Energy
-5.350
Log(D) at pH=7.4
3.070
Log(P)
2.88
Log S
-4.38
Log(Vapor Pressure)
-7.28
Melting Point
153.92
pKa Acid
7.03
pKa Basic
5.15
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.9283
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7621
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7446
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7339

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