3-O-benzoylhosloquinone - Compound Card

3-O-benzoylhosloquinone

Select a section from the left sidebar

3-O-benzoylhosloquinone

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpene
Canonical Smiles O=C(c1ccccc1)O[C@@H]1CC=C2[C@@](C1(C)C)(C)C=CC1=C2C(=O)C(=O)C(=C1)C(C)C
InChI InChI=1S/C27H28O4/c1-16(2)19-15-18-13-14-27(5)20(22(18)24(29)23(19)28)11-12-21(26(27,3)4)31-25(30)17-9-7-6-8-10-17/h6-11,13-16,21H,12H2,1-5H3/t21-,27-/m1/s1
InChIKey SZHPWLGMFBCELK-JIPXPUAJSA-N
Formula C27H28O4
HBA 4
HBD 0
MW 416.52
Rotatable Bonds 3
TPSA 60.44
LogP 5.18
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.37
Exact Mass 416.2
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Hoslundia opposita Lamiaceae Plantae 204228

Showing of synonyms

  • Achenbach H, Waibel R, et al. (1992). Antimalarial compounds from Hoslundia opposita.. Phytochemistry,1992,31(11),3781-3784. [View] [PubMed]
Pubchem: 101635423

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC(C2)CC=C3C2C=CC(=C34)C=CC(=O)C4=O

Level: 1

Mol. Weight: 416.52 g/mol

Structure

SMILES: O=C1C(=O)C=CC(=C12)C=CC3C2=CCCC3

Level: 0

Mol. Weight: 416.52 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 416.52 g/mol

Antimalarial

Absorption

Caco-2 (logPapp)
-4.66
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.64
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.72
Plasma Protein Binding
95.72
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
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
3.79
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.95
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.71
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.43
Micronucleos
Safe
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Toxic
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-39.07
Rat (Acute)
2.68
Rat (Chronic Oral)
2.41
Fathead Minnow
5.0
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
456.28
Hydration Free Energy
-3.99
Log(D) at pH=7.4
4.67
Log(P)
6.09
Log S
-5.8
Log(Vapor Pressure)
-7.02
Melting Point
144.33
pKa Acid
7.04
pKa Basic
3.56
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8987
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8987
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7877
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7877
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7679
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7679
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7461
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7461
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7367
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7367
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7090
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7090
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7077
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7077
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7056
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7056
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 2 0.7042
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 2 0.7042
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7038
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7038

Download SDF