6-oxoisoiguesterin - Compound Card

6-oxoisoiguesterin

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6-oxoisoiguesterin

Structure
Zoomed Structure
  • Family: Plantae - Celastraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Oxophenolic Triterpene
Canonical Smiles C=C1CC[C@]2([C@@H](C1)[C@]1(C)CC[C@@]3(C(=CC(=O)c4c3cc(O)c(c4C)O)[C@]1(CC2)C)C)C
InChI InChI=1S/C28H36O3/c1-16-7-8-25(3)9-11-28(6)22-15-19(29)23-17(2)24(31)20(30)14-18(23)26(22,4)10-12-27(28,5)21(25)13-16/h14-15,21,30-31H,1,7-13H2,2-6H3/t21-,25-,26+,27+,28-/m1/s1
InChIKey XVIQCCFXDXUXNE-JPJACQMESA-N
Formula C28H36O3
HBA 3
HBD 2
MW 420.59
Rotatable Bonds 0
TPSA 57.53
LogP 6.75
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.61
Exact Mass 420.27
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Salacia madagascariensis Celastraceae Plantae 670374

Showing of synonyms

  • Thiem DA, Sneden AT, et al. (2005). Bisnortriterpenes from Salacia madagascariensis. Journal of Natural Products,2005,68(2),251-254. [View] [PubMed]
Pubchem: 21575473
Nmrshiftdb2: 70060585
CPRiL: 410711
Structure

SMILES: C=C(C1)CCC(CC2)C1C(CC3)C2C(=CC4=O)C3c(c45)cccc5

Level: 0

Mol. Weight: 420.59 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.58
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.84

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.28
Plasma Protein Binding
95.88
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
Inhibitor
CYP 2C19 Substrate
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.03
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.71
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.27
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.71
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-37.11
Rat (Acute)
2.3
Rat (Chronic Oral)
2.42
Fathead Minnow
4.02
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
455.45
Hydration Free Energy
-4.14
Log(D) at pH=7.4
4.79
Log(P)
5.71
Log S
-6.34
Log(Vapor Pressure)
-9.0
Melting Point
257.39
pKa Acid
9.08
pKa Basic
5.39
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8989
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8989
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7446
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7446
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7401
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7401
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7352
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7352
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7201
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7201
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7117
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7117
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7116
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7116

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