6alpha-hydroxy-1,4,1alpha,5alpha-diepoxyxanth-10(14)-ene - Compound Card

6alpha-hydroxy-1,4,1alpha,5alpha-diepoxyxanth-10(14)-ene

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6alpha-hydroxy-1,4,1alpha,5alpha-diepoxyxanth-10(14)-ene

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles CC([C@@H]1CCC(=C)[C@@]23[C@H]([C@H]1O)O[C@@](O3)(C)CC2)C
InChI InChI=1S/C15H24O3/c1-9(2)11-6-5-10(3)15-8-7-14(4,18-15)17-13(15)12(11)16/h9,11-13,16H,3,5-8H2,1-2,4H3/t11-,12-,13-,14+,15+/m0/s1
InChIKey RIAYYAJPMRTZCV-BTFPBAQTSA-N
Formula C15H24O3
HBA 3
HBD 1
MW 252.35
Rotatable Bonds 1
TPSA 38.69
LogP 2.63
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.87
Exact Mass 252.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pluchea dioscoridis Asteraceae Plantae —

Showing of synonyms

  • Mahmoud AA (1997). 7-Epi-eudesmanes, eudesmanoic acids, eudesmanolides and other sesquiterpenenes from Pluchea dioscoridis. Phytochemistry,1997,45(8),1633-1638. [View]
Pubchem: 101713148
Nmrshiftdb2: 60045971

No compound-protein relationship available.

Structure

SMILES: C=C1CCCCC(C123)OC(O3)CC2

Level: 0

Mol. Weight: 252.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.31
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.37

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.46
Plasma Protein Binding
35.6
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
14.17
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.32
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.37
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.51
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
-0.64
Rat (Acute)
2.46
Rat (Chronic Oral)
1.37
Fathead Minnow
3.66
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
296.21
Hydration Free Energy
-6.23
Log(D) at pH=7.4
2.42
Log(P)
3.5
Log S
-2.69
Log(Vapor Pressure)
-3.96
Melting Point
97.76
pKa Acid
9.98
pKa Basic
6.28
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.9321
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.9321
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8094
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8094
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8070
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8070
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8047
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8047
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7869
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7869
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7788
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7788
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7772
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7772
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7760
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7760
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7641
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7641
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7603
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7603
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7597
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7597
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7577
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7577
Thyroid hormone receptor alpha P04625 THA_CHICK Gallus gallus 3 0.7464
Thyroid hormone receptor alpha P04625 THA_CHICK Gallus gallus 3 0.7464
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7423
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7423
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7321
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7321
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7233
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7233
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7203
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7203
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7152
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7152
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7130
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7130
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7063
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7063
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7039
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7039
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7036
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7036
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7031
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7031
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7026
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7026

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