8-epi-xanthanol - Compound Card

8-epi-xanthanol

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8-epi-xanthanol

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C[C@@H](C[C@@H](C1=CC[C@H]2[C@@H](C[C@@H]1C)OC(=O)C2=C)OC(=O)C)O
InChI InChI=1S/C17H24O5/c1-9-7-15-14(11(3)17(20)22-15)6-5-13(9)16(8-10(2)18)21-12(4)19/h5,9-10,14-16,18H,3,6-8H2,1-2,4H3/t9-,10-,14+,15+,16-/m0/s1
InChIKey JKIKMDJRHDXNEW-DYNNCCMVSA-N
Formula C17H24O5
HBA 5
HBD 1
MW 308.37
Rotatable Bonds 4
TPSA 72.83
LogP 2.14
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 308.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pulicaria undulata Asteraceae Plantae 119186

Showing of synonyms

  • Hegazy MEF, Matsuda H, et al. (2012). Sesquiterpenes from an Egyptian herbal medicine, Pulicaria undulate, with inhibitory effects on nitric oxide production in RAW264.7 macrophage cells. Chemical and Pharmaceutical Bulletin,2012,60(3),363-370. [View] [PubMed]
Pubchem: 56969895
Nmrshiftdb2: 70093927

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 308.37 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.58
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.47

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.54
Plasma Protein Binding
44.21
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
9.93
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.18
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.14
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.91
Micronucleos
Safe
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
-3.67
Rat (Acute)
2.75
Rat (Chronic Oral)
1.81
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
350.7
Hydration Free Energy
-6.47
Log(D) at pH=7.4
1.3
Log(P)
1.29
Log S
-2.99
Log(Vapor Pressure)
-6.22
Melting Point
84.59
pKa Acid
10.53
pKa Basic
5.84
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9145
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9145
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9108
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9108
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8938
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8938
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8865
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8865
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8844
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8844
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8814
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8814
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8719
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8719
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8623
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8623
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8451
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8451
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8208
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8208
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8176
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8176
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8102
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8102
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8048
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8048
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7923
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7923
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7788
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7788
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7745
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7745
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7702
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7702
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7623
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7623
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7498
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7498
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7495
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7495
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7411
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7411
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7411
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7411
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7370
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7370
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7316
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7316
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7288
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7288
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7253
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7253
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7251
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7251
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7221
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7221
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7197
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7197
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7181
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7181
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7137
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7137
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7134
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7134
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7105
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7105
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7079
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7079
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7037
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7037
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7032
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7032

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