6-O-angeloyl-8-O-tigloyl-beta,8alpha,11-trihydroxygermacra-1(10)E,4E-diene - Compound Card

6-O-angeloyl-8-O-tigloyl-beta,8alpha,11-trihydroxygermacra-1(10)E,4E-diene

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6-O-angeloyl-8-O-tigloyl-beta,8alpha,11-trihydroxygermacra-1(10)E,4E-diene

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles C/C=C(/C(=O)O[C@H]1C/C(=C/CC/C(=C/[C@@H]([C@@H]1C(O)(C)C)OC(=O)/C(=C\C)/C)/C)/C)\C
InChI InChI=1S/C25H38O5/c1-9-18(5)23(26)29-20-14-16(3)12-11-13-17(4)15-21(22(20)25(7,8)28)30-24(27)19(6)10-2/h9-10,12,15,20-22,28H,11,13-14H2,1-8H3/b16-12+,17-15+,18-9+,19-10-/t20-,21-,22+/m0/s1
InChIKey WLUZYQDSHYPPAK-PCOXHAPDSA-N
Formula C25H38O5
HBA 5
HBD 1
MW 418.57
Rotatable Bonds 5
TPSA 72.83
LogP 5.21
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 418.27
Number of Lipinski Rule Violations 1
# 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: C1=CCCCCC=CCC1

Level: 0

Mol. Weight: 418.57 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.6
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.61
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.86

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.54
Plasma Protein Binding
74.56
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.22
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.52
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.61
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.16
Micronucleos
Safe
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
-9.82
Rat (Acute)
2.03
Rat (Chronic Oral)
1.92
Fathead Minnow
5.13
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
373.27
Hydration Free Energy
-5.47
Log(D) at pH=7.4
3.46
Log(P)
6.37
Log S
-5.18
Log(Vapor Pressure)
-6.15
Melting Point
106.85
pKa Acid
10.72
pKa Basic
4.33
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8538
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8165
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7843
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7801
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 4 0.7786
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7652
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7563
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7421
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7311
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7055
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7016
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7009

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