Desacyl laurenobiolide angelate - Compound Card

Desacyl laurenobiolide angelate

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Desacyl laurenobiolide angelate

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C/C=C(\C(=O)O[C@H]1/C=C(\C)/CC/C=C(/C[C@H]2[C@H]1C(=C)C(=O)O2)\C)/C
InChI InChI=1S/C20H26O4/c1-6-14(4)19(21)23-16-10-12(2)8-7-9-13(3)11-17-18(16)15(5)20(22)24-17/h6,9-10,16-18H,5,7-8,11H2,1-4H3/b12-10+,13-9+,14-6-/t16-,17-,18-/m0/s1
InChIKey TVZVGKUKJBIRJK-VUQQRKDTSA-N
Formula C20H26O4
HBA 4
HBD 0
MW 330.42
Rotatable Bonds 2
TPSA 52.6
LogP 4.04
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 330.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cotula cinerea Asteraceae Plantae —

Showing of synonyms

  • Metwally MA, El-dahmy S, et al. (1986). Glaucolide-like sesquiterpene lactones from Cotula cinerea. Phytochemistry,1986,25(1),255-257. [View]
Pubchem: 163013632
Nmrshiftdb2: 70018559

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)CC=CCCC=CC2

Level: 0

Mol. Weight: 330.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.56
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.64
Plasma Protein Binding
60.72
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
6.99
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.33
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.19
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.71
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
-2.12
Rat (Acute)
2.09
Rat (Chronic Oral)
2.05
Fathead Minnow
4.82
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
351.33
Hydration Free Energy
-4.41
Log(D) at pH=7.4
3.63
Log(P)
4.41
Log S
-4.94
Log(Vapor Pressure)
-5.79
Melting Point
89.3
pKa Acid
10.0
pKa Basic
4.73
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8573
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8573
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8347
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8347
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8018
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8018
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7884
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7884
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7725
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7725
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7695
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7695
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7686
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7686
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7629
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7629
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7580
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7580
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7531
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7531
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7516
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7516
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7511
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7511
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7443
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7443
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7331
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7331
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7323
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7323
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7212
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7212
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7197
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7197
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7079
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7079
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7059
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7059
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7020
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7020
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7018
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7018

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