Diazo derivative of Inuloxin A - Compound Card

Diazo derivative of Inuloxin A

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Diazo derivative of Inuloxin A

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C[C@@H]1CCC(=O)/C(=C/CC2[C@@H](C1)OC1=C2CCO1)/C
InChI InChI=1S/C16H22O3/c1-10-3-6-14(17)11(2)4-5-12-13-7-8-18-16(13)19-15(12)9-10/h4,10,12,15H,3,5-9H2,1-2H3/b11-4+/t10-,12?,15-/m1/s1
InChIKey ORTVZCQKJBVOMB-IOPLEKSJSA-N
Formula C16H22O3
HBA 3
HBD 0
MW 262.35
Rotatable Bonds 0
TPSA 35.53
LogP 3.36
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.69
Exact Mass 262.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Inula viscosa Asteraceae Plantae 56525

Showing of synonyms

  • Andolfi A, Zermane N, et al. (2013). Inuloxins A-D, phytotoxic bi-and tri-cyclic sesquiterpene lactones produced by Inula viscosa: potential for broomrapes and field dodder management. Phytochemistry,2013,86,112-120. [View]
Pubchem: 162817133

No compound-protein relationship available.

Structure

SMILES: C1COC(=C12)OC3C2CC=CC(=O)CCCC3

Level: 0

Mol. Weight: 262.35 g/mol

Phytotoxicity

Absorption

Caco-2 (logPapp)
-4.85
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.39
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.77
Plasma Protein Binding
52.06
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.56
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.04
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.49
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.63
Micronucleos
Safe
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
0.14
Rat (Acute)
1.88
Rat (Chronic Oral)
1.59
Fathead Minnow
4.22
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
344.79
Hydration Free Energy
-4.53
Log(D) at pH=7.4
2.88
Log(P)
2.54
Log S
-3.49
Log(Vapor Pressure)
-4.92
Melting Point
69.39
pKa Acid
10.36
pKa Basic
5.09
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7886
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7886
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7796
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7796
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7752
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7752
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7694
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7694
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7537
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7537
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7513
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7513
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7444
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7444
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7432
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7432
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7378
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7378
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7278
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7278
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7241
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7241
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7212
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7212
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7058
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7058
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7052
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7052
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7048
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7048
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7034
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7034

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