(1R,4S,8aR)-4,8a-dimethyl-6-(propan-2-yl)-1,2,3,4,4a,7,8,8a-octahydronaphthalene-1,4,5-triol - Compound Card

(1R,4S,8aR)-4,8a-dimethyl-6-(propan-2-yl)-1,2,3,4,4a,7,8,8a-octahydronaphthalene-1,4,5-triol

Select a section from the left sidebar

(1R,4S,8aR)-4,8a-dimethyl-6-(propan-2-yl)-1,2,3,4,4a,7,8,8a-octahydronaphthalene-1,4,5-triol

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles CC(C1=C(O)C2[C@](CC1)(C)[C@H](O)CC[C@]2(C)O)C
InChI InChI=1S/C15H26O3/c1-9(2)10-5-7-14(3)11(16)6-8-15(4,18)13(14)12(10)17/h9,11,13,16-18H,5-8H2,1-4H3/t11-,13?,14+,15+/m1/s1
InChIKey MCIPMASIVZSBIJ-JKRDAVGYSA-N
Formula C15H26O3
HBA 3
HBD 3
MW 254.37
Rotatable Bonds 1
TPSA 60.69
LogP 2.78
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.87
Exact Mass 254.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Chrysothamnus viscidiflorus Asteraceae Plantae 72914

Showing of synonyms

  • Ahmed AA, Hegazy MEF, et al. (2006). Constituents of Chrysothamnus viscidiflorus. Phytochemistry,2006,67,1547-1553. [View] [PubMed]
Pubchem: 162816962
Nmrshiftdb2: 60071001

No compound-protein relationship available.

Structure

SMILES: C1=CCCC(C12)CCCC2

Level: 0

Mol. Weight: 254.37 g/mol

Anticancer

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.09
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.49

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.5
Plasma Protein Binding
41.74
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
6.95
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.06
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.26
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.49
Micronucleos
Safe
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
-0.32
Rat (Acute)
2.26
Rat (Chronic Oral)
1.89
Fathead Minnow
3.45
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
334.04
Hydration Free Energy
-10.06
Log(D) at pH=7.4
1.71
Log(P)
2.13
Log S
-2.2
Log(Vapor Pressure)
-5.64
Melting Point
144.36
pKa Acid
9.54
pKa Basic
7.01
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8443
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8443
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8362
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8362
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8280
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8280
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8163
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8163
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7916
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7916
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7508
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7508
FKBP-type peptidyl-prolyl cis-trans isomerase FkpA P45523 FKBA_ECOLI Escherichia coli 4 0.7291
FKBP-type peptidyl-prolyl cis-trans isomerase FkpA P45523 FKBA_ECOLI Escherichia coli 4 0.7291
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7254
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7254
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7216
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7216
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7165
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7165
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7004
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7004

Download SDF