22alpha-acetoxy-6,7-epoxyneomacrolactone - Compound Card

22alpha-acetoxy-6,7-epoxyneomacrolactone

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22alpha-acetoxy-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)OC(=O)C)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/C34H46O8/c1-16(2)17(3)26(38)27(41-21(7)36)18(4)24-22(40-20(6)35)14-32(9)30-29-28(42-29)25-19(5)39-23(37)10-11-33(25)15-34(30,33)13-12-31(24,32)8/h10-11,16,18-19,22,24-25,27-30H,3,12-15H2,1-2,4-9H3/t18-,19-,22-,24-,25?,27+,28-,29-,30?,31+,32-,33+,34-/m0/s1
InChIKey YETSACDYCZLWIT-YINPIIODSA-N
Formula C34H46O8
HBA 8
HBD 0
MW 582.73
Rotatable Bonds 7
TPSA 108.5
LogP 4.98
Number Rings 6
Number Aromatic Rings 0
Heavy Atom Count 42
Formal Charge 0
Fraction CSP3 0.76
Exact Mass 582.32
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: 582.73 g/mol

Anti-plasmodial
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.97
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.73
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
3.08

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.71
Plasma Protein Binding
73.08
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
9.37
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.25
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.3
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
8.0
Micronucleos
Toxic
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
-10688.94
Rat (Acute)
3.75
Rat (Chronic Oral)
2.2
Fathead Minnow
30.06
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
308.35
Hydration Free Energy
-2.91
Log(D) at pH=7.4
4.87
Log(P)
3.73
Log S
-6.43
Log(Vapor Pressure)
-14.05
Melting Point
211.32
pKa Acid
7.07
pKa Basic
2.95
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 0.8675
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8675
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8203
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8203
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8185
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8185
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7114
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7114
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7014
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7014

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