3-O-cinnamoylhosloppone - Compound Card

3-O-cinnamoylhosloppone

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3-O-cinnamoylhosloppone

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpene
Canonical Smiles O=C(O[C@H]1CC[C@]2(C(=CC=C3C2=C(O)C(=O)C(=C3)C(C)C)C1(C)C)C)/C=C/c1ccccc1
InChI InChI=1S/C29H32O4/c1-18(2)21-17-20-12-13-22-28(3,4)23(15-16-29(22,5)25(20)27(32)26(21)31)33-24(30)14-11-19-9-7-6-8-10-19/h6-14,17-18,23,32H,15-16H2,1-5H3/b14-11+/t23-,29-/m0/s1
InChIKey BLUKSJXOPCHNNT-FSJLORSQSA-N
Formula C29H32O4
HBA 4
HBD 1
MW 444.57
Rotatable Bonds 4
TPSA 63.6
LogP 6.28
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 444.23
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: 10049125
Nmrshiftdb2: 70085187

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 444.57 g/mol

Structure

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

Level: 0

Mol. Weight: 444.57 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 444.57 g/mol

Antimalarial

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.62
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.47

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.73
Plasma Protein Binding
101.42
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.92
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.01
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.33
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.78
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
-99.93
Rat (Acute)
2.71
Rat (Chronic Oral)
2.46
Fathead Minnow
5.23
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
485.05
Hydration Free Energy
-3.01
Log(D) at pH=7.4
4.68
Log(P)
6.25
Log S
-5.84
Log(Vapor Pressure)
-7.92
Melting Point
152.14
pKa Acid
8.25
pKa Basic
4.02
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8134
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8134
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7943
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7943
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7777
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7777
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7506
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7506
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7451
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7451
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 2 0.7283
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 2 0.7283
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7258
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7258
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7233
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7233
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7024
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7024
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 2 0.7017
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 2 0.7017

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