8-deoxy-15-(3'-hydroxy-2'-methyl-propanoyl)-lactucin-3'-sulfate - Compound Card

8-deoxy-15-(3'-hydroxy-2'-methyl-propanoyl)-lactucin-3'-sulfate

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8-deoxy-15-(3'-hydroxy-2'-methyl-propanoyl)-lactucin-3'-sulfate

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O=C([C@H](COS(=O)(=O)[O-])C)OCC1=CC(=O)C2=C(C)CC[C@@H]3[C@@H](C12)OC(=O)C3=C
InChI InChI=1S/C19H22O9S/c1-9-4-5-13-11(3)19(22)28-17(13)16-12(6-14(20)15(9)16)8-26-18(21)10(2)7-27-29(23,24)25/h6,10,13,16-17H,3-5,7-8H2,1-2H3,(H,23,24,25)/p-1/t10-,13-,16?,17-/m0/s1
InChIKey SRHOHYYJDPEABB-WQASMUJBSA-M
Formula C19H21O9S-
HBA 9
HBD 0
MW 425.44
Rotatable Bonds 6
TPSA 136.1
LogP 0.98
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 29
Formal Charge -1
Fraction CSP3 0.53
Exact Mass 425.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Launaea arborescens Asteraceae Plantae 43199

Showing of synonyms

  • Bitam F, Ciavatta ML, et al. (2008). Chemical characterisation of the terpenoid constituents of the Algerian plant Launaea arborescens. Phytochemistry,2008,69,2984-2992. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CCC(C(=C)C(=O)O2)C2C(C=13)C=CC3=O

Level: 0

Mol. Weight: 425.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.6
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.01
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.53
Plasma Protein Binding
71.35
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
5.92
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.02
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.82
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.73
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
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
-3.72
Rat (Acute)
2.09
Rat (Chronic Oral)
1.98
Fathead Minnow
4.1
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
493.88
Hydration Free Energy
-4.37
Log(D) at pH=7.4
1.09
Log(P)
0.83
Log S
-2.27
Log(Vapor Pressure)
-9.64
Melting Point
185.52
pKa Acid
4.48
pKa Basic
3.86
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8828
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8828
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8529
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8529
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7827
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7827
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7118
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7118
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

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