8alpha-(2-methylacrolyloyloxy)salonitenolide - Compound Card

8alpha-(2-methylacrolyloyloxy)salonitenolide

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8alpha-(2-methylacrolyloyloxy)salonitenolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OC/C/1=C\[C@H]2OC(=O)C(=C)[C@@H]2[C@H](C/C(=C/CC1)/C)OC(=O)C(=C)C
InChI InChI=1S/C19H24O5/c1-11(2)18(21)23-15-8-12(3)6-5-7-14(10-20)9-16-17(15)13(4)19(22)24-16/h6,9,15-17,20H,1,4-5,7-8,10H2,2-3H3/b12-6+,14-9-/t15-,16+,17+/m0/s1
InChIKey HMWGYLUJHPBFQV-YUZWDKKQSA-N
Formula C19H24O5
HBA 5
HBD 1
MW 332.4
Rotatable Bonds 3
TPSA 72.83
LogP 2.62
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.47
Exact Mass 332.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cheirolophus intybaceus Asteraceae Plantae 64995
2 Cheirolophus x hortigenus Asteraceae Plantae 41544

Showing of synonyms

  • Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones, lignans and aromatic esters ftrom Cheirolophus species. Phytochemistry,1994,37(4),1101-1107. [View]
Pubchem: 162972447
Nmrshiftdb2: 60072555

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)C=CCCC=CCC2

Level: 0

Mol. Weight: 332.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.61
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.89

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.5
Plasma Protein Binding
51.34
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.16
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.3
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.08
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.1
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
1.35
Rat (Acute)
2.54
Rat (Chronic Oral)
1.99
Fathead Minnow
4.42
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
357.67
Hydration Free Energy
-7.29
Log(D) at pH=7.4
1.96
Log(P)
2.71
Log S
-3.71
Log(Vapor Pressure)
-6.79
Melting Point
119.51
pKa Acid
8.33
pKa Basic
4.94
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8597
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8597
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8422
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8422
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.8379
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.8379
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8176
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8176
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8091
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8091
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7834
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7834
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7547
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7547
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7432
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7432
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7332
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7332
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.7327
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.7327
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7319
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7319
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7303
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7303
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7184
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7184
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7150
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7150
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7091
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7091
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7066
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7066
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7064
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7064

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