Obtusifoliol - Compound Card

Obtusifoliol

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Obtusifoliol

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Sterol
Canonical Smiles CC(C(=C)CC[C@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CC[C@@H]([C@H]2C)O)C)C)C
InChI InChI=1S/C30H50O/c1-19(2)20(3)9-10-21(4)23-13-17-30(8)26-12-11-24-22(5)27(31)15-16-28(24,6)25(26)14-18-29(23,30)7/h19,21-24,27,31H,3,9-18H2,1-2,4-8H3/t21-,22+,23-,24+,27+,28+,29-,30+/m1/s1
InChIKey MMNYKQIDRZNIKT-VSADUBDNSA-N
Formula C30H50O
HBA 1
HBD 1
MW 426.73
Rotatable Bonds 5
TPSA 20.23
LogP 8.34
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.87
Exact Mass 426.39
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia guyoniana Euphorbiaceae Plantae 1138347
2 Euphorbia officinarum Euphorbiaceae Plantae 1130835
3 Euphorbia bupleuroides Euphorbiaceae Plantae 1532838

Showing of synonyms

  • Mazoir N, Benharref A, et al. (2008). Bioactive triterpene derivatives from latex of two Euphorbia species. Phytochemistry,2008,69,1328-1338. [View] [PubMed]
  • Haba H, Lavaud C, et al. (2007). Diterpenoids and triterpenoids from Euphorbia guyoniana. Phytochemistry,2007,68,1255-1260. [View] [PubMed]
  • Aichour S, Haba H, et al. (2014). Terpenoids and other constituents from Euphorbia bupleuroides. Phytochemistry,2014,10,198-203. [View]
Pubchem: 65252
Kegg Ligand: C01943
Chebi: 17791
Nmrshiftdb2: 60018449
Metabolights: MTBLC17791
Pdb Ligand: DVE
CPRiL: 156788
Structure

SMILES: C1CCC(C12)CCC3=C2CCC4C3CCCC4

Level: 0

Mol. Weight: 426.73 g/mol

Anti-inflammatory
Antiviral

Absorption

Caco-2 (logPapp)
-4.86
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.53
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.86

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.6
Plasma Protein Binding
89.88
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
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-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
9.29
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.4
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.49
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.4
Micronucleos
Safe
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
Toxic
T. Pyriformis
-39.49
Rat (Acute)
2.15
Rat (Chronic Oral)
1.49
Fathead Minnow
3.94
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
410.06
Hydration Free Energy
-3.52
Log(D) at pH=7.4
6.7
Log(P)
8.9
Log S
-6.81
Log(Vapor Pressure)
-7.12
Melting Point
137.56
pKa Acid
13.27
pKa Basic
7.23
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8645
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8645
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 4 0.8256
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 4 0.8256
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.8233
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.8233
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8224
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8224
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.8099
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.8099
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8062
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8062
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7987
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7987
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7881
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7881
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7578
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7578
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7455
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7455
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7396
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7396
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7364
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7364
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7327
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7327
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7305
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7305
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7253
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7253
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7229
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7229
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7211
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7211
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7133
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7133
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7127
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7127
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7117
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7117
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7099
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7099
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7089
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7089

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