4-methylen-neomacrolactone - Compound Card

4-methylen-neomacrolactone

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4-methylen-neomacrolactone

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@@]13C2CCC2[C@]3(C1)C=CC(=O)OC2=C)C
InChI InChI=1S/C32H44O6/c1-17(2)18(3)27(35)28(36)19(4)26-23(38-21(6)33)15-30(8)24-10-9-22-20(5)37-25(34)11-12-31(22)16-32(24,31)14-13-29(26,30)7/h11-12,17,19,22-24,26,28,36H,3,5,9-10,13-16H2,1-2,4,6-8H3/t19-,22?,23-,24?,26-,28+,29+,30-,31+,32-/m0/s1
InChIKey NZDPEZMEKAYSPC-YBXXQLIUSA-N
Formula C32H44O6
HBA 6
HBD 1
MW 524.7
Rotatable Bonds 6
TPSA 89.9
LogP 5.55
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.72
Exact Mass 524.31
Number of Lipinski Rule Violations 2
# 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)OC(=C)C(C1(C234)C2)CCC3C5C(CC4)CCC5

Level: 0

Mol. Weight: 524.7 g/mol

Anti-plasmodial
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.86
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.86
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.96

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.89
Plasma Protein Binding
91.8
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
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
6.38
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.8
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.33
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.89
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-1204.21
Rat (Acute)
3.29
Rat (Chronic Oral)
2.31
Fathead Minnow
6.33
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
469.72
Hydration Free Energy
-2.89
Log(D) at pH=7.4
4.81
Log(P)
3.66
Log S
-6.23
Log(Vapor Pressure)
-8.69
Melting Point
217.79
pKa Acid
7.93
pKa Basic
4.32
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9199
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9199
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8612
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8612
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.8355
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.8355
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8300
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8300
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8219
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8219
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8056
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8056
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7757
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7757
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7734
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7734
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7507
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7507
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7466
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7466
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7456
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7456
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7435
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7435
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7381
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7381
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7253
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7253
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7239
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7239
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7221
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7221
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7195
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7195
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7098
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7098

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