3-O-benzoylhosloppone - Compound Card

3-O-benzoylhosloppone

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3-O-benzoylhosloppone

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpene
Canonical Smiles OC1=C2C(=CC=C3[C@]2(C)CC[C@@H](C3(C)C)OC(=O)c2ccccc2)C=C(C1=O)C(C)C
InChI InChI=1S/C27H30O4/c1-16(2)19-15-18-11-12-20-26(3,4)21(31-25(30)17-9-7-6-8-10-17)13-14-27(20,5)22(18)24(29)23(19)28/h6-12,15-16,21,29H,13-14H2,1-5H3/t21-,27-/m0/s1
InChIKey KCFFKDXTABUTPF-IDISGSTGSA-N
Formula C27H30O4
HBA 4
HBD 1
MW 418.53
Rotatable Bonds 3
TPSA 63.6
LogP 5.88
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.41
Exact Mass 418.21
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: 10477133
Nmrshiftdb2: 70085184

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC(CC2)CC(=CC3)C2C(C=34)=CC(=O)C=C4

Level: 1

Mol. Weight: 418.53 g/mol

Structure

SMILES: C1C(=O)C=CC(C=12)=CC=C3C2CCCC3

Level: 0

Mol. Weight: 418.53 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 418.53 g/mol

Antimalarial

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.620
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.56

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.590
Plasma Protein Binding
100.35
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-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
3.970
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.870
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.420
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.050
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
-36.800
Rat (Acute)
2.690
Rat (Chronic Oral)
2.400
Fathead Minnow
4.800
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
458.950
Hydration Free Energy
-4.200
Log(D) at pH=7.4
4.390
Log(P)
6.13
Log S
-5.74
Log(Vapor Pressure)
-7.53
Melting Point
145.44
pKa Acid
7.68
pKa Basic
3.85
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7646
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7646
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7119
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7119
Acetyl-CoA carboxylase 2 O00763 ACACB_HUMAN Homo sapiens 3 0.7102
Acetyl-CoA carboxylase 2 O00763 ACACB_HUMAN Homo sapiens 3 0.7102
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7094
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7094
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7087
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7087
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7065
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7065

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