10-hydroxy-6-oxo-3,4,15,16-bis-epoxy-8H-cleroda-13(16),14-dien-20,12-olide - Compound Card

10-hydroxy-6-oxo-3,4,15,16-bis-epoxy-8H-cleroda-13(16),14-dien-20,12-olide

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10-hydroxy-6-oxo-3,4,15,16-bis-epoxy-8H-cleroda-13(16),14-dien-20,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Neo-Clerodane Diterpenoid
Canonical Smiles C1[C@H]2[C@@]([C@@]3([C@](C1)([C@]1([C@@H](CC3=O)C)C[C@H](OC1=O)c1ccoc1)O)C)(O2)C
InChI InChI=1S/C20H24O6/c1-11-8-14(21)17(2)18(3)15(26-18)4-6-20(17,23)19(11)9-13(25-16(19)22)12-5-7-24-10-12/h5,7,10-11,13,15,23H,4,6,8-9H2,1-3H3/t11-,13+,15+,17-,18+,19+,20-/m1/s1
InChIKey DCWMPDIKJVJVTN-XFLANZEOSA-N
Formula C20H24O6
HBA 6
HBD 1
MW 360.41
Rotatable Bonds 1
TPSA 89.27
LogP 2.55
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 360.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Conyza pyrrhopappa Asteraceae Plantae 72919

Showing of synonyms

  • Bitchagno GTM, Schüffler A, et al. (2021). Neo-clerodane diterpenoids from Conyza pyrrhopappa Sch.Bip. ex A.Rich.. Nat Prod Res. 2021, 35(19),3210-3219. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CC(O2)C2C(C(=O)CC3)C1C34C(=O)OC(C4)c5ccoc5

Level: 1

Mol. Weight: 360.41 g/mol

Structure

SMILES: C1CC(O2)C2C(C(=O)CC3)C1C34C(=O)OCC4

Level: 0

Mol. Weight: 360.41 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 360.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.22
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.8
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.24

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.46
Plasma Protein Binding
37.41
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.67
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.16
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.31
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.96
Micronucleos
Toxic
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
Toxic
T. Pyriformis
-5.66
Rat (Acute)
4.84
Rat (Chronic Oral)
1.66
Fathead Minnow
3.8
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
419.33
Hydration Free Energy
-6.03
Log(D) at pH=7.4
1.27
Log(P)
1.73
Log S
-3.3
Log(Vapor Pressure)
-8.24
Melting Point
208.79
pKa Acid
5.15
pKa Basic
4.23
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.9223
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9101
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8906
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8764
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7964
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7766
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7757
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7676
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7669
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7667
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7578
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7576
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7543
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7488
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7483
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7478
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7448
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7378
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7364
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7356
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7352
Virginiamycin A acetyltransferase P26839 VATA_STAAU Staphylococcus aureus 4 0.7320
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7291
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7253
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7249
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7172
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7093
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7085
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7059
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7037
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7023
Alanine racemase Q180W0 Q180W0_CLOD6 Clostridioides difficile 2 0.7018
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7005
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7001

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