3,9-diacetoxy-13-hydroxy-1(10),4,7(11)-germacra-trien-12,6-olide - Compound Card

3,9-diacetoxy-13-hydroxy-1(10),4,7(11)-germacra-trien-12,6-olide

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3,9-diacetoxy-13-hydroxy-1(10),4,7(11)-germacra-trien-12,6-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OCC1=C2C[C@H](OC(=O)C)/C(=C/C[C@@H](/C(=C/[C@H]2OC1=O)/C)OC(=O)C)/C
InChI InChI=1S/C19H24O7/c1-10-5-6-16(24-12(3)21)11(2)7-18-14(8-17(10)25-13(4)22)15(9-20)19(23)26-18/h5,7,16-18,20H,6,8-9H2,1-4H3/b10-5+,11-7+/t16-,17-,18+/m0/s1
InChIKey HXCKNQXUYYXOEU-AUVZATJMSA-N
Formula C19H24O7
HBA 7
HBD 1
MW 364.39
Rotatable Bonds 3
TPSA 99.13
LogP 1.75
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 364.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Achillea santolina Asteraceae Plantae 1028379

Showing of synonyms

  • Balboul BAAA, Ahmed AA, et al. (1997). A guaianolide and a germacranolide from Achillea santolina.. Phytochemistry,1997,46(6),1045-1049. [View]
Pubchem: 101936581
Nmrshiftdb2: 60073254

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C=12)C=CCCC=CCC2

Level: 0

Mol. Weight: 364.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.63
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.98

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.33
Plasma Protein Binding
43.64
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
8.95
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.36
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.74
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.4
Micronucleos
Toxic
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
-3.41
Rat (Acute)
2.42
Rat (Chronic Oral)
2.17
Fathead Minnow
4.58
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
382.79
Hydration Free Energy
-8.16
Log(D) at pH=7.4
1.13
Log(P)
1.64
Log S
-3.05
Log(Vapor Pressure)
-6.98
Melting Point
135.21
pKa Acid
8.57
pKa Basic
4.38
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8905
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8905
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8013
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8013
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7326
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7326
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7128
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7128

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