Helioscopinolide A - Compound Card

Helioscopinolide A

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Helioscopinolide A

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles O=C1O[C@H]2C(=C1C)C=C1[C@@H](C2)[C@]2(C)CC[C@H](C([C@H]2CC1)(C)C)O
InChI InChI=1S/C20H28O3/c1-11-13-9-12-5-6-16-19(2,3)17(21)7-8-20(16,4)14(12)10-15(13)23-18(11)22/h9,14-17,21H,5-8,10H2,1-4H3/t14-,15-,16-,17-,20+/m1/s1
InChIKey KZIADLALQLRZIQ-RXFYRGCNSA-N
Formula C20H28O3
HBA 3
HBD 1
MW 316.44
Rotatable Bonds 0
TPSA 46.53
LogP 3.77
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 316.2
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia helioscopia Euphorbiaceae Plantae 154990

Showing of synonyms

  • Mohamed AH, Hegazy MF, et al. (2012). Euphorbia helioscopia: Chemical constituents and biological activities. International Journal of Phytopharmacology,2012,3(1),78-90. [View]
Pubchem: 10245246
Nmrshiftdb2: 70002226

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C=12)CC3C(=C2)CCC4C3CCCC4

Level: 0

Mol. Weight: 316.44 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.63
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.45
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.72

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.91
Plasma Protein Binding
56.96
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
13.35
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.45
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.71
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.7
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
Safe
T. Pyriformis
-3.38
Rat (Acute)
1.98
Rat (Chronic Oral)
1.71
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
397.93
Hydration Free Energy
-4.4
Log(D) at pH=7.4
3.8
Log(P)
3.68
Log S
-4.4
Log(Vapor Pressure)
-6.33
Melting Point
147.77
pKa Acid
10.38
pKa Basic
7.56
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8508
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8508
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8430
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8430
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8347
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8347
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8043
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8043
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8026
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8026
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7871
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7871
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7851
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7851
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7684
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7684
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7571
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7571
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7448
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7448
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 4 0.7436
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 4 0.7436
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7407
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7407
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7264
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7264
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7228
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7228
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7217
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7217

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