Azadirachtin - Compound Card

Azadirachtin

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Azadirachtin

Structure
Zoomed Structure
  • Family: Plantae - Canellaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Limonoid
Canonical Smiles C/C=C(/C(=O)O[C@H]1C[C@@H](OC(=O)C)[C@@]2(C3C41CO[C@]([C@H]4[C@@](C)([C@@H]([C@@H]3OC2)O)C12O[C@@]2(C)[C@H]2C[C@@H]1OC1[C@]2(O)C=CO1)(O)C(=O)OC)C(=O)OC)\C
InChI InChI=1S/C35H44O16/c1-8-15(2)24(38)49-18-12-19(48-16(3)36)32(26(39)43-6)13-46-21-22(32)31(18)14-47-34(42,27(40)44-7)25(31)29(4,23(21)37)35-20-11-17(30(35,5)51-35)33(41)9-10-45-28(33)50-20/h8-10,17-23,25,28,37,41-42H,11-14H2,1-7H3/b15-8+/t17-,18+,19-,20+,21-,22?,23-,25+,28?,29-,30+,31?,32+,33+,34+,35?/m1/s1
InChIKey FTNJWQUOZFUQQJ-WHWXNURTSA-N
Formula C35H44O16
HBA 16
HBD 3
MW 720.72
Rotatable Bonds 6
TPSA 215.34
LogP -0.2
Number Rings 8
Number Aromatic Rings 0
Heavy Atom Count 51
Formal Charge 0
Fraction CSP3 0.77
Exact Mass 720.26
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Warburgia ugandensis Canellaceae Plantae 549619

Showing of synonyms

  • Rugutt JK, Ngigi AN, et al. (2006). Native Kenyan plants as possible alternatives to methyl bromide in soil fumigation. Phytomedicine,2006,13(8),576-583. [View] [PubMed]
Pubchem: 5702264
CPRiL: 14017
Structure

SMILES: C1=COC(OC2C3)C1C3C(O4)C24C(C5COC6)CC7OCC(C7C568)CCC8

Level: 1

Mol. Weight: 720.72 g/mol

Structure

SMILES: C1CCC(C2C134)COC2CCC3COC4

Level: 0

Mol. Weight: 720.72 g/mol

Structure

SMILES: C12C(O2)C3CC1C4C(O3)OC=C4

Level: 0

Mol. Weight: 720.72 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.36
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-1.49
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
501.31

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.39
Plasma Protein Binding
47.76
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.73
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-8.26
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.57
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.08
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-912778.78
Rat (Acute)
5.15
Rat (Chronic Oral)
3.07
Fathead Minnow
1160.55
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
98430.26
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-0.02
Log(P)
1.18
Log S
-3.42
Log(Vapor Pressure)
-3217.15
Melting Point
145.98
pKa Acid
-3.88
pKa Basic
-2.38
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 0.8552
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8552

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