1alpha,3beta-dihydroxy-7alpha,11betaH-germacra-4Z,9Z-dien-12,6alpha-olide - Compound Card

1alpha,3beta-dihydroxy-7alpha,11betaH-germacra-4Z,9Z-dien-12,6alpha-olide

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1alpha,3beta-dihydroxy-7alpha,11betaH-germacra-4Z,9Z-dien-12,6alpha-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O=C1O[C@H]2[C@H]([C@@H]1C)C/C=C(/C)\[C@H](C[C@@H](/C(=C\2)/C)O)O
InChI InChI=1S/C15H22O4/c1-8-4-5-11-10(3)15(18)19-14(11)6-9(2)13(17)7-12(8)16/h4,6,10-14,16-17H,5,7H2,1-3H3/b8-4-,9-6-/t10-,11-,12-,13-,14+/m0/s1
InChIKey PQCNNCMXLJZLIA-AQKQOQQPSA-N
Formula C15H22O4
HBA 4
HBD 2
MW 266.34
Rotatable Bonds 0
TPSA 66.76
LogP 1.57
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 266.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pyrethrum santolinoides Asteraceae Plantae 2072400
2 Pyrethrum santolinoides Asteraceae Plantae 2072400

Showing of synonyms

  • Mahmoud AA, Ahmed AA, et al. (1994). 2,3-secogermacranolides and germacranolides from Pyrethrum santolionoides. Phytochemistry,1994,36(2),393-398. [View]
  • Abdel-Mogib M, Jakupovic J, et al. (1989). Sesquiterpene lactones from Pyrethrum santolinoides. Phytochemistry,1989,28(1),268-271. [View]
Pubchem: 14194092
Nmrshiftdb2: 60061834

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 266.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.12
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.27

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.52
Plasma Protein Binding
39.25
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
5.64
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.31
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.18
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.58
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
-3.44
Rat (Acute)
2.22
Rat (Chronic Oral)
2.04
Fathead Minnow
3.78
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
354.71
Hydration Free Energy
-10.67
Log(D) at pH=7.4
0.68
Log(P)
1.27
Log S
-1.81
Log(Vapor Pressure)
-6.55
Melting Point
144.98
pKa Acid
9.07
pKa Basic
5.59
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8388
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8388
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7552
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7552
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7032
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7032

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