Retusolide B - Compound Card

Retusolide B

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Retusolide B

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Ent-Abietane Lactone
Canonical Smiles O=C1C2=C(C)C(=O)O[C@@H]2CC2=C1CC[C@H]1[C@@]2(C)CCC2[C@]1(C)C2
InChI InChI=1S/C20H24O3/c1-10-16-14(23-18(10)22)8-13-12(17(16)21)4-5-15-19(13,2)7-6-11-9-20(11,15)3/h11,14-15H,4-9H2,1-3H3/t11?,14-,15+,19+,20+/m1/s1
InChIKey ZRMFWYQIICGVKU-JYZFZSDMSA-N
Formula C20H24O3
HBA 3
HBD 0
MW 312.41
Rotatable Bonds 0
TPSA 43.37
LogP 3.73
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 312.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia retusa Euphorbiaceae Plantae 1091645

Showing of synonyms

  • Haba H, Lavaud C, et al. (2009). Diterpenoids and triterpenoids from Euphorbia retusa. Journal of Natural Products,2009,72(7),1258-1264. [View] [PubMed]
Pubchem: 101485500
Nmrshiftdb2: 60062700

No compound-protein relationship available.

Structure

SMILES: C12C(C1)CCC3C4=C(CCC23)C(=O)C=5C(C4)OC(=O)C5

Level: 0

Mol. Weight: 312.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.460
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.66

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.110
Plasma Protein Binding
64.11
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
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
15.610
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.080
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.140
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.960
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-0.360
Rat (Acute)
2.080
Rat (Chronic Oral)
1.850
Fathead Minnow
3.930
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
398.470
Hydration Free Energy
-3.660
Log(D) at pH=7.4
3.880
Log(P)
4.08
Log S
-4.32
Log(Vapor Pressure)
-6.03
Melting Point
168.58
pKa Acid
10.15
pKa Basic
5.67
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7975
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7975
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7332
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7332
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7293
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7293
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7222
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7222
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7109
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7109

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