22alpha-acetoxyneomacrolactone - Compound Card

22alpha-acetoxyneomacrolactone

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22alpha-acetoxyneomacrolactone

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)OC(=O)C)C)(C)CC[C@@]13C2CCC2[C@]3(C1)C=CC(=O)O[C@H]2C)C
InChI InChI=1S/C34H48O7/c1-18(2)19(3)29(38)30(41-23(7)36)20(4)28-25(40-22(6)35)16-32(9)26-11-10-24-21(5)39-27(37)12-13-33(24)17-34(26,33)15-14-31(28,32)8/h12-13,18,20-21,24-26,28,30H,3,10-11,14-17H2,1-2,4-9H3/t20-,21-,24?,25-,26?,28-,30+,31+,32-,33+,34-/m0/s1
InChIKey VYYBKBSTKXKOIF-BZSFNVNSSA-N
Formula C34H48O7
HBA 7
HBD 0
MW 568.75
Rotatable Bonds 7
TPSA 95.97
LogP 6.0
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 41
Formal Charge 0
Fraction CSP3 0.76
Exact Mass 568.34
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]
Pubchem: 86276184

No compound-protein relationship available.

Structure

SMILES: C1=CC(=O)OCC(C1(C234)C2)CCC3C5C(CC4)CCC5

Level: 0

Mol. Weight: 568.75 g/mol

Anti-plasmodial
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.84
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.82
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.22

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.72
Plasma Protein Binding
93.49
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
6.39
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.37
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.36
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.7
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
-4433.32
Rat (Acute)
2.86
Rat (Chronic Oral)
2.25
Fathead Minnow
16.5
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
410.88
Hydration Free Energy
-2.79
Log(D) at pH=7.4
4.87
Log(P)
4.51
Log S
-6.51
Log(Vapor Pressure)
-8.91
Melting Point
220.69
pKa Acid
10.19
pKa Basic
4.11
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 0.8703
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8703
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8609
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8609
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8065
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8065
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7890
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7890
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7801
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7801
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7518
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7518
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7511
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7511
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7440
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7440
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7372
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7372
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7361
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7361

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