3beta-hydroxy-1-oxo-7alpha,11beta-germacra-4Z,10(14)-dien-12,6alpha-olide - Compound Card

3beta-hydroxy-1-oxo-7alpha,11beta-germacra-4Z,10(14)-dien-12,6alpha-olide

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3beta-hydroxy-1-oxo-7alpha,11beta-germacra-4Z,10(14)-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)CCC(=C)[C@@H](CC(=O)/C(=C\2)/C)O
InChI InChI=1S/C15H20O4/c1-8-4-5-11-10(3)15(18)19-14(11)6-9(2)13(17)7-12(8)16/h6,10-12,14,16H,1,4-5,7H2,2-3H3/b9-6-/t10-,11-,12+,14+/m0/s1
InChIKey ZSWCIGXOGJAYMQ-PNDYUTCWSA-N
Formula C15H20O4
HBA 4
HBD 1
MW 264.32
Rotatable Bonds 0
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 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]
Pubchem: 162816865
Nmrshiftdb2: 70087153

No compound-protein relationship available.

Structure

SMILES: C1CC(=C)CCC(=O)C=CC(C12)OC(=O)C2

Level: 0

Mol. Weight: 264.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.46
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.23

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.55
Plasma Protein Binding
42.84
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
6.74
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.54
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.52
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.18
Micronucleos
Toxic
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
-1.59
Rat (Acute)
2.59
Rat (Chronic Oral)
1.94
Fathead Minnow
3.86
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
339.55
Hydration Free Energy
-8.65
Log(D) at pH=7.4
0.84
Log(P)
0.9
Log S
-1.84
Log(Vapor Pressure)
-6.32
Melting Point
132.92
pKa Acid
8.67
pKa Basic
4.99
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8534
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8534
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.8394
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.8394
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8365
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8365
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8024
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8024
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7898
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7898
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7770
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7770
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7734
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7734
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7645
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7645
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7626
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7626
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7576
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7576
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7499
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7499
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7267
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7267
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7110
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7110
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7092
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7092
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7041
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7041
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7017
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7017

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