3-O-benzoylhinokiol - Compound Card

3-O-benzoylhinokiol

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3-O-benzoylhinokiol

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpene
Canonical Smiles O=C(c1ccccc1)O[C@H]1CC[C@]2([C@H](C1(C)C)CCc1c2cc(O)c(c1)C(C)C)C
InChI InChI=1S/C27H34O3/c1-17(2)20-15-19-11-12-23-26(3,4)24(30-25(29)18-9-7-6-8-10-18)13-14-27(23,5)21(19)16-22(20)28/h6-10,15-17,23-24,28H,11-14H2,1-5H3/t23-,24-,27+/m0/s1
InChIKey HFAMSEZTLMXOQW-NLJOTIRTSA-N
Formula C27H34O3
HBA 3
HBD 1
MW 406.57
Rotatable Bonds 3
TPSA 46.53
LogP 6.38
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.52
Exact Mass 406.25
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: 101635422
Nmrshiftdb2: 70085185

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC(C2)CCC3C2CCc(c34)cccc4

Level: 1

Mol. Weight: 406.57 g/mol

Structure

SMILES: c1cccc(c12)CCC3C2CCCC3

Level: 0

Mol. Weight: 406.57 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 406.57 g/mol

Antimalarial

Absorption

Caco-2 (logPapp)
-4.97
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
-2.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.39
Plasma Protein Binding
107.21
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
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
5.89
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.26
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.14
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.79
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-23.65
Rat (Acute)
1.8
Rat (Chronic Oral)
2.42
Fathead Minnow
4.56
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
445.76
Hydration Free Energy
-3.97
Log(D) at pH=7.4
5.77
Log(P)
6.97
Log S
-6.89
Log(Vapor Pressure)
-7.84
Melting Point
131.29
pKa Acid
10.34
pKa Basic
6.72
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7736
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7736
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7575
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7575
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7326
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7326
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7294
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7294
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.7261
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.7261
Acetyl-CoA carboxylase 2 O00763 ACACB_HUMAN Homo sapiens 3 0.7249
Acetyl-CoA carboxylase 2 O00763 ACACB_HUMAN Homo sapiens 3 0.7249
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7239
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7239
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7195
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7195
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7132
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7132
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7109
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7109
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7084
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7084
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7044
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7044
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7034
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7034

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