Retusolide A - Compound Card

Retusolide A

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Retusolide A

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Ent-Abietane Lactone
Canonical Smiles O=C1O[C@H]2C(=C1C)C(=O)[C@]1([C@@H](C2)[C@]2(C)CCC3[C@]([C@H]2CC1)(C)C3)O
InChI InChI=1S/C20H26O4/c1-10-15-12(24-17(10)22)8-14-18(2)6-4-11-9-19(11,3)13(18)5-7-20(14,23)16(15)21/h11-14,23H,4-9H2,1-3H3/t11?,12-,13+,14+,18-,19+,20+/m1/s1
InChIKey YCQMGTFAKICNOS-MZYCLFAISA-N
Formula C20H26O4
HBA 4
HBD 1
MW 330.42
Rotatable Bonds 0
TPSA 63.6
LogP 2.78
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 330.18
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: 101485499
Nmrshiftdb2: 60062706

No compound-protein relationship available.

Structure

SMILES: C12C(C1)CCC3C2CCC4C3CC5C(C4=O)=CC(=O)O5

Level: 0

Mol. Weight: 330.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.42
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.5
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.55

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.88
Plasma Protein Binding
62.2
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
14.83
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.69
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.31
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.04
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
-2.79
Rat (Acute)
1.88
Rat (Chronic Oral)
1.64
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
396.23
Hydration Free Energy
-5.16
Log(D) at pH=7.4
3.71
Log(P)
3.18
Log S
-4.19
Log(Vapor Pressure)
-7.22
Melting Point
211.17
pKa Acid
7.96
pKa Basic
5.54
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 0.8994
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8994
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8854
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8854
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7999
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7999
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7953
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7953
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7828
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7828
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7766
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7766
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7754
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7754
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7637
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7637
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7629
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7629
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7610
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7610
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7595
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7595
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7583
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7583
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7559
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7559
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7387
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7387
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7294
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7294
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7278
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7278
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7206
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7206
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7133
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7133
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7105
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7105
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7099
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7099

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