5alpha-hydroxy-10,14alphaH-dihydroinuviscolide - Compound Card

5alpha-hydroxy-10,14alphaH-dihydroinuviscolide

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5alpha-hydroxy-10,14alphaH-dihydroinuviscolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C[C@H]1C[C@@H]2OC(=O)C(=C)[C@H]2C[C@@]2([C@@H]1CC[C@]2(C)O)O
InChI InChI=1S/C15H22O4/c1-8-6-12-10(9(2)13(16)19-12)7-15(18)11(8)4-5-14(15,3)17/h8,10-12,17-18H,2,4-7H2,1,3H3/t8-,10+,11+,12-,14-,15-/m0/s1
InChIKey WEHLZWJUGYFTKK-FPBWHMEOSA-N
Formula C15H22O4
HBA 4
HBD 2
MW 266.34
Rotatable Bonds 0
TPSA 66.76
LogP 1.41
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 266.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Jasonia candicans Asteraceae Plantae 557631

Showing of synonyms

  • Ahmed AA, Mahmoud AA (1998). Jasonol, a rare tricyclic eudesmane sesquiterpene and six other new sesquiterpenoids from Jasonia candicans. Tetrahedron,1998,54,8141-8152. [View]
Pubchem: 23241669
Nmrshiftdb2: 70028516

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)CCC3C(C2)CCC3

Level: 0

Mol. Weight: 266.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.8
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.56
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.12

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.46
Plasma Protein Binding
44.98
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
6.97
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.61
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.85
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.61
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
0.57
Rat (Acute)
3.07
Rat (Chronic Oral)
1.62
Fathead Minnow
3.82
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
334.2
Hydration Free Energy
-7.84
Log(D) at pH=7.4
1.22
Log(P)
1.15
Log S
-2.22
Log(Vapor Pressure)
-6.08
Melting Point
162.96
pKa Acid
8.09
pKa Basic
7.18
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8776
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8776
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7925
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7925
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7895
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7895
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7832
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7832
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7685
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7685
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7294
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7294
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7193
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7193
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7130
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7130
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7096
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7096
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7027
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7027

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