6,7-epoxyneomacrolactone - Compound Card

6,7-epoxyneomacrolactone

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6,7-epoxyneomacrolactone

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles CC(=O)O[C@H]1C[C@@]2([C@]([C@H]1[C@@H]([C@H](C(=O)C(=C)C(C)C)O)C)(C)CC[C@@]13C2[C@H]2O[C@H]2C2[C@]3(C1)C=CC(=O)O[C@H]2C)C
InChI InChI=1S/C32H44O7/c1-15(2)16(3)24(35)25(36)17(4)22-20(38-19(6)33)13-30(8)28-27-26(39-27)23-18(5)37-21(34)9-10-31(23)14-32(28,31)12-11-29(22,30)7/h9-10,15,17-18,20,22-23,25-28,36H,3,11-14H2,1-2,4-8H3/t17-,18-,20-,22-,23?,25+,26-,27-,28?,29+,30-,31+,32-/m0/s1
InChIKey DWXUAGGKLHZLHE-BQHMTOEGSA-N
Formula C32H44O7
HBA 7
HBD 1
MW 540.7
Rotatable Bonds 6
TPSA 102.43
LogP 4.41
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.78
Exact Mass 540.31
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Neoboutonia macrocalyx Euphorbiaceae Plantae 1260343

Showing of synonyms

  • Namukobe J, Kiremire BT, et al. (2014). Cycloartane triterpenes from the leaves of Neoboutonia macrocalyx L.. Phytochemistry,2014,102,189-196. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1=CC(=O)OCC(C1(C234)C2)C5C(O5)C3C6C(CC4)CCC6

Level: 0

Mol. Weight: 540.7 g/mol

Anti-plasmodial
Cytotoxic

Absorption

Caco-2 (logPapp)
-5.06
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.8
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.25

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.79
Plasma Protein Binding
69.92
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
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
9.67
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.36
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.21
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.92
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-2906.69
Rat (Acute)
3.96
Rat (Chronic Oral)
2.14
Fathead Minnow
11.49
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
444.91
Hydration Free Energy
-2.83
Log(D) at pH=7.4
4.37
Log(P)
3.12
Log S
-5.93
Log(Vapor Pressure)
-8.54
Melting Point
215.22
pKa Acid
5.97
pKa Basic
3.55
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9103
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9103
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8126
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8126
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7917
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7917
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7506
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7506
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7430
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7430
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7265
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7265
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7254
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7254
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7135
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7135
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7092
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7092
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7090
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7090
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7043
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7043
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7012
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7012

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