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

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

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6-O-isobutyryl-8-O-tigloyl-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]1CC(=C)[C@@H](O)CC/C(=C/[C@@H]([C@@H]1C(O)(C)C)OC(=O)C(C)C)/C)\C
InChI InChI=1S/C24H38O6/c1-9-16(5)23(27)30-20-13-17(6)18(25)11-10-15(4)12-19(21(20)24(7,8)28)29-22(26)14(2)3/h9,12,14,18-21,25,28H,6,10-11,13H2,1-5,7-8H3/b15-12+,16-9+/t18-,19-,20-,21-/m0/s1
InChIKey HTCFMTKXUAVUAC-JOYJVYBZSA-N
Formula C24H38O6
HBA 6
HBD 2
MW 422.56
Rotatable Bonds 5
TPSA 93.06
LogP 3.87
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 422.27
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: 422.56 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.53
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.67
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.72

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.38
Plasma Protein Binding
72.59
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.36
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.11
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.57
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.45
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
-8.48
Rat (Acute)
2.43
Rat (Chronic Oral)
2.06
Fathead Minnow
4.5
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
373.09
Hydration Free Energy
-6.42
Log(D) at pH=7.4
2.18
Log(P)
4.61
Log S
-4.23
Log(Vapor Pressure)
-6.89
Melting Point
119.28
pKa Acid
10.27
pKa Basic
4.37
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8677
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8648
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8155
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7973
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7941
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7873
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7823
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7717
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7622
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7604
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7549
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7532
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7474
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7430
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7401
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7378
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7321
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7263
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7239
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7236
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7184
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7131
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 3 0.7107
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7101
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7085
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7080
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7027
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7022
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7004

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