Saharanolide B - Compound Card

Saharanolide B

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Saharanolide B

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O=C1O[C@@H]2[C@H](C1=C)CCC(=C)[C@@]1([C@@H]2[C@@]2(C)C[C@@H]1O2)O
InChI InChI=1S/C15H18O4/c1-7-4-5-9-8(2)13(16)18-11(9)12-14(3)6-10(19-14)15(7,12)17/h9-12,17H,1-2,4-6H2,3H3/t9-,10-,11+,12-,14+,15+/m0/s1
InChIKey UTQNDJBAYYDNTJ-MDFWMIKMSA-N
Formula C15H18O4
HBA 4
HBD 1
MW 262.3
Rotatable Bonds 0
TPSA 55.76
LogP 1.34
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 262.12
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: 44566954
Nmrshiftdb2: 70082082

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC2C1CCC(=C)C(C(O3)C4)C2C34

Level: 0

Mol. Weight: 262.3 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.86
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.61
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.91

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.4
Plasma Protein Binding
42.86
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.6
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.54
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.73
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.73
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
Safe
T. Pyriformis
2.06
Rat (Acute)
3.82
Rat (Chronic Oral)
1.6
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
336.92
Hydration Free Energy
-7.06
Log(D) at pH=7.4
0.7
Log(P)
1.28
Log S
-2.41
Log(Vapor Pressure)
-6.12
Melting Point
158.64
pKa Acid
7.5
pKa Basic
5.81
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8277
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8277
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7689
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7689
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7312
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7312
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7245
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7245
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7222
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7222
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7161
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7161
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7141
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7141
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7045
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7045

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