22alpha-acetoxy-6-hydroxyneomacrolactone - Compound Card

22alpha-acetoxy-6-hydroxyneomacrolactone

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22alpha-acetoxy-6-hydroxyneomacrolactone

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@@]13C2C[C@@H](O)C2[C@]3(C1)C=CC(=O)O[C@H]2C)C
InChI InChI=1S/C34H48O8/c1-17(2)18(3)29(39)30(42-22(7)36)19(4)27-24(41-21(6)35)15-32(9)25-14-23(37)28-20(5)40-26(38)10-11-34(28)16-33(25,34)13-12-31(27,32)8/h10-11,17,19-20,23-25,27-28,30,37H,3,12-16H2,1-2,4-9H3/t19-,20-,23+,24-,25?,27-,28?,30+,31+,32-,33-,34+/m0/s1
InChIKey JRKQOFFGGDIQEU-QYMMCQLZSA-N
Formula C34H48O8
HBA 8
HBD 1
MW 584.75
Rotatable Bonds 7
TPSA 116.2
LogP 4.97
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 42
Formal Charge 0
Fraction CSP3 0.76
Exact Mass 584.33
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)CCC3C5C(CC4)CCC5

Level: 0

Mol. Weight: 584.75 g/mol

Anti-plasmodial
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.81
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.64

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.26
Plasma Protein Binding
91.06
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
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
5.98
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.94
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.58
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.71
Micronucleos
Toxic
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
-6329.92
Rat (Acute)
3.76
Rat (Chronic Oral)
2.27
Fathead Minnow
19.39
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
380.29
Hydration Free Energy
-2.88
Log(D) at pH=7.4
4.06
Log(P)
3.76
Log S
-5.79
Log(Vapor Pressure)
-11.11
Melting Point
225.93
pKa Acid
8.69
pKa Basic
3.59
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 0.8689
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8689
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7642
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7642
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7599
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7599
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7583
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7583
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7491
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7491
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7387
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7387
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7204
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7204
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7179
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7179
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7119
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7119
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7103
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7103
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7035
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7035

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