8-desoxy-3alpha,4alpha-epoxyrupiculin-A - Compound Card

8-desoxy-3alpha,4alpha-epoxyrupiculin-A

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8-desoxy-3alpha,4alpha-epoxyrupiculin-A

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CCC(C(=O)O[C@H]1[C@H]2O[C@]1(C)[C@H]1C2=C(C)CC[C@@H]2[C@H]1OC(=O)C2=C)C
InChI InChI=1S/C20H26O5/c1-6-9(2)18(21)24-17-16-13-10(3)7-8-12-11(4)19(22)23-15(12)14(13)20(17,5)25-16/h9,12,14-17H,4,6-8H2,1-3,5H3/t9?,12-,14-,15+,16-,17-,20+/m0/s1
InChIKey FPLUWNGZVAMKNR-UWBBWCMESA-N
Formula C20H26O5
HBA 5
HBD 0
MW 346.42
Rotatable Bonds 3
TPSA 61.83
LogP 2.94
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 346.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Warionia saharae Asteraceae Plantae 40727

Showing of synonyms

  • Hilmi F, Sticher O, et al. (2002). New cytotoxic 6,7-cis and 6,7-trans configured guaianolides from Warionia saharae. Journal of Natural Products,2002,65,523-526. [View] [PubMed]
Pubchem: 11046234
Nmrshiftdb2: 20173406

No compound-protein relationship available.

Structure

SMILES: C1CCC(C(=C)C(=O)O2)C2C(C(O3)C4)C=1C34

Level: 0

Mol. Weight: 346.42 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.72
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.99

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.71
Plasma Protein Binding
55.32
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.76
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.16
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.8
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.35
Micronucleos
Toxic
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
-0.67
Rat (Acute)
3.32
Rat (Chronic Oral)
2.06
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
376.07
Hydration Free Energy
-4.19
Log(D) at pH=7.4
2.77
Log(P)
3.53
Log S
-4.38
Log(Vapor Pressure)
-6.7
Melting Point
116.98
pKa Acid
8.77
pKa Basic
4.99
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8660
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8660
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8302
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8302
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7845
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7845
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7628
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7628
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7534
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7534
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7436
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7436
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7413
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7413
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7399
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7399
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7358
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7358
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7299
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7299
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7279
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7279
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7149
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7149
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7061
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7061

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