2alpha-hydroxy-2R-xanthalongin - Compound Card

2alpha-hydroxy-2R-xanthalongin

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2alpha-hydroxy-2R-xanthalongin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)[C@@H](C1=CC[C@H]2[C@@H](C[C@@H]1C)OC(=O)C2=C)O
InChI InChI=1S/C14H18O4/c1-7-6-12-11(8(2)14(17)18-12)5-4-10(7)13(16)9(3)15/h4,7,11-13,16H,2,5-6H2,1,3H3/t7-,11+,12+,13-/m0/s1
InChIKey KQQJHYGPRJWZEY-LDICSKNTSA-N
Formula C14H18O4
HBA 4
HBD 1
MW 250.29
Rotatable Bonds 2
TPSA 63.6
LogP 1.39
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.57
Exact Mass 250.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Dittrichia graveolens Asteraceae Plantae 1532790

Showing of synonyms

  • Abou-Douh AM (2008). New eudesmane derivatives and other sesquiterpenes from the epigeal parts of Dittrichia graveolens. Chemical and Pharmaceutical Bulletin,2008,56(11),1535-1545. [View] [PubMed]
Pubchem: 162816934
Nmrshiftdb2: 70056005

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)CCC=CC2

Level: 0

Mol. Weight: 250.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.45
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.49
Plasma Protein Binding
39.9
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
7.63
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.11
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.35
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.03
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
-0.33
Rat (Acute)
2.56
Rat (Chronic Oral)
1.96
Fathead Minnow
3.92
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
321.64
Hydration Free Energy
-8.49
Log(D) at pH=7.4
1.07
Log(P)
0.6
Log S
-2.03
Log(Vapor Pressure)
-5.9
Melting Point
112.38
pKa Acid
7.8
pKa Basic
4.8
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.8990
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.8990
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8648
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8648
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8296
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8296
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8161
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8161
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 4 0.7989
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 4 0.7989
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7893
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7893
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7774
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7774
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7712
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7712
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7539
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7539
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7477
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7477
SKP1-like protein 1A Q39255 SKP1A_ARATH Arabidopsis thaliana 3 0.7417
SKP1-like protein 1A Q39255 SKP1A_ARATH Arabidopsis thaliana 3 0.7417
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7410
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7410
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7361
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7361
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7329
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7329
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7233
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7233
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7172
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7172
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7114
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7114
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7093
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7093
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7085
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7085
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.7014
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.7014
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7008
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7008
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7005
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7005

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