6-O-tigloyl-8-O-2-methylbutyryl 1alpha,6beta,8alpha,11-tetrahydroxygermacra-4E,10(14)-diene - Compound Card

6-O-tigloyl-8-O-2-methylbutyryl 1alpha,6beta,8alpha,11-tetrahydroxygermacra-4E,10(14)-diene

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6-O-tigloyl-8-O-2-methylbutyryl 1alpha,6beta,8alpha,11-tetrahydroxygermacra-4E,10(14)-diene

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles CCC(C(=O)O[C@H]1CC(=C)[C@@H](O)CC/C(=C/[C@@H]([C@@H]1C(O)(C)C)OC(=O)/C(=C/C)/C)/C)C
InChI InChI=1S/C25H40O6/c1-9-16(4)23(27)30-20-13-15(3)11-12-19(26)18(6)14-21(22(20)25(7,8)29)31-24(28)17(5)10-2/h9,13,17,19-22,26,29H,6,10-12,14H2,1-5,7-8H3/b15-13+,16-9+/t17?,19-,20-,21-,22-/m0/s1
InChIKey RFDPOYRCIOLAIU-OFAWHFIGSA-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)
-4.53
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.68
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.65

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.39
Plasma Protein Binding
72.8
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
7.9
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.09
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.62
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.64
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
-13.54
Rat (Acute)
2.69
Rat (Chronic Oral)
1.98
Fathead Minnow
4.48
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
382.89
Hydration Free Energy
-5.11
Log(D) at pH=7.4
2.44
Log(P)
5.08
Log S
-4.4
Log(Vapor Pressure)
-7.04
Melting Point
107.73
pKa Acid
10.22
pKa Basic
4.3
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9473
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8961
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8335
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8301
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7992
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7928
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7788
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7693
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7595
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7532
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7487
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7479
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7460
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7394
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7367
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7335
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7306
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7245
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7184
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7163
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7153
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7144
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7089
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7035

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