4-hydroxy-8-epi-tomentosin - Compound Card

4-hydroxy-8-epi-tomentosin

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4-hydroxy-8-epi-tomentosin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)CC(C1=CC[C@H]2[C@H](C[C@@H]1C)OC(=O)C2=C)O
InChI InChI=1S/C15H20O4/c1-8-6-14-12(10(3)15(18)19-14)5-4-11(8)13(17)7-9(2)16/h4,8,12-14,17H,3,5-7H2,1-2H3/t8-,12+,13?,14-/m0/s1
InChIKey FVJAKCWZKUQZHO-WCBFBDHRSA-N
Formula C15H20O4
HBA 4
HBD 1
MW 264.32
Rotatable Bonds 3
TPSA 63.6
LogP 1.78
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 264.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Francoeuria crispa Asteraceae Plantae 1548540
2 Xanthium spinosum Asteraceae Plantae 1053410

Showing of synonyms

  • Abdel-Mogib M, Jakupovic J, et al. (1990). Sesquiterpene lactones and kaurane glycosides from Francoeuria crispa. Phytochemistry,1990,29(8),2581-2584. [View]
  • Abdei-Mogib M, Dawidar AM, et al. (1991). Xanthanolides from Xanthium spinosum. Phytochemistry,1991,30(10),3461-3462. [View]
Pubchem: 14633032

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 264.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.88
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.48
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.45

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.52
Plasma Protein Binding
40.9
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
8.53
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.22
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.24
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.31
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
1.31
Rat (Acute)
3.06
Rat (Chronic Oral)
1.88
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
336.43
Hydration Free Energy
-8.53
Log(D) at pH=7.4
0.75
Log(P)
0.31
Log S
-2.14
Log(Vapor Pressure)
-6.02
Melting Point
95.49
pKa Acid
8.89
pKa Basic
4.4
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9571
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9571
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8405
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8405
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 3 0.8315
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 3 0.8315
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8008
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8008
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 4 0.7937
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 4 0.7937
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.7878
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.7878
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7506
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7506
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7333
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7333
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7326
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7326
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7323
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7323
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7298
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7298
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7142
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7142
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7119
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7119
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7062
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7062
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7036
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7036

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