Retusolide C - Compound Card

Retusolide C

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Retusolide C

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]2C[C@@H]2C1=CC[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/h4,11,13-15H,5-9H2,1-3H3/t11?,13-,14-,15+,19+,20+/m1/s1
InChIKey KIQWNCGQYMBUGO-WQQVWZHOSA-N
Formula C20H24O3
HBA 3
HBD 0
MW 312.41
Rotatable Bonds 0
TPSA 43.37
LogP 3.59
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: 101485501
Nmrshiftdb2: 60062715

No compound-protein relationship available.

Structure

SMILES: C12C(C1)CCC3C2CC=C4C3CC5C(C4=O)=CC(=O)O5

Level: 0

Mol. Weight: 312.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.520
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.47

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.320
Plasma Protein Binding
63.46
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
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
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
15.030
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.290
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.330
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.750
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
Safe
T. Pyriformis
-0.560
Rat (Acute)
1.880
Rat (Chronic Oral)
1.670
Fathead Minnow
3.920
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
403.770
Hydration Free Energy
-3.660
Log(D) at pH=7.4
4.000
Log(P)
3.94
Log S
-4.68
Log(Vapor Pressure)
-6.31
Melting Point
170.48
pKa Acid
9.73
pKa Basic
6.05
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8826
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8826
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8251
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8251
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8001
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8001
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7963
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7963
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7875
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7875
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7825
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7825
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7769
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7769
Nuclear receptor coactivator 2 Q15596 NCOA2_HUMAN Homo sapiens 3 0.7536
Nuclear receptor coactivator 2 Q15596 NCOA2_HUMAN Homo sapiens 3 0.7536
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7501
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7501
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7492
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7492
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7427
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7427
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7336
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7336
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7299
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7299
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7207
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7207
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7167
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7167
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7131
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7131

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