6-O-tigloyl-8-O-isovaleryl-1alpha-6beta,8alpha,11-tetrahydroxygermacra-4E,10 (14)-diene - Compound Card

6-O-tigloyl-8-O-isovaleryl-1alpha-6beta,8alpha,11-tetrahydroxygermacra-4E,10 (14)-diene

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6-O-tigloyl-8-O-isovaleryl-1alpha-6beta,8alpha,11-tetrahydroxygermacra-4E,10 (14)-diene

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles C/C=C(/C(=O)O[C@H]1/C=C(\C)/CC[C@@H](C(=C)C[C@@H]([C@H]1C(O)(C)C)OC(=O)CC(C)C)O)\C
InChI InChI=1S/C25H40O6/c1-9-17(5)24(28)31-20-13-16(4)10-11-19(26)18(6)14-21(23(20)25(7,8)29)30-22(27)12-15(2)3/h9,13,15,19-21,23,26,29H,6,10-12,14H2,1-5,7-8H3/b16-13+,17-9+/t19-,20-,21-,23-/m0/s1
InChIKey XBDGHPZKGBZGMJ-TXBHCXQVSA-N
Formula C25H40O6
HBA 6
HBD 2
MW 436.59
Rotatable Bonds 6
TPSA 93.06
LogP 4.26
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.68
Exact Mass 436.28
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Daucus carota Apiaceae Plantae 4039

Showing of synonyms

  • Sirignano C, Hammami S, et al. (2021). Polyoxygenated germacranes from Daucus carota and their antimalarial transmission blocking activity. Phytochemistry, 2021, 183,112632.. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C=C1CCCC=CCCCC1

Level: 0

Mol. Weight: 436.59 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.5
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.67
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.85

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.4
Plasma Protein Binding
75.07
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
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.55
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.22
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.51
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.74
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
-11.54
Rat (Acute)
2.8
Rat (Chronic Oral)
2.13
Fathead Minnow
4.52
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
388.12
Hydration Free Energy
-5.5
Log(D) at pH=7.4
2.61
Log(P)
5.0
Log S
-4.52
Log(Vapor Pressure)
-6.97
Melting Point
107.99
pKa Acid
10.22
pKa Basic
4.55
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8192
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7641
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7478
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7467
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7295
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7221
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7060

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