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Habropetaline A
- Family: Plantae - Dioncophyllaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Naphthylisoquinoline Alkaloid
| Canonical Smiles | OCc1cc(OC)c2c(c1c1ccc3c(c1O)[C@@H](C)N[C@@H](C3)C)cccc2OC |
|---|---|
| InChI | InChI=1S/C24H27NO4/c1-13-10-15-8-9-18(24(27)21(15)14(2)25-13)22-16(12-26)11-20(29-4)23-17(22)6-5-7-19(23)28-3/h5-9,11,13-14,25-27H,10,12H2,1-4H3/t13-,14-/m1/s1 |
| InChIKey | UORJGZQGXAWGDM-ZIAGYGMSSA-N |
| Formula | C24H27NO4 |
| HBA | 5 |
| HBD | 3 |
| MW | 393.48 |
| Rotatable Bonds | 4 |
| TPSA | 70.95 |
| LogP | 4.32 |
| Number Rings | 4 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 29 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.33 |
| Exact Mass | 393.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Triphyophyllum peltatum | Dioncophyllaceae | Plantae | 63090 |
Showing of synonyms
Habropetaline A
76372-22-0
(1R,3R)-7-[2-(hydroxymethyl)-4,5-dimethoxynaphthalen-1-yl]-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol
DTXSID10997755
8-Isoquinolinol, 1,2,3,4-tetrahydro-7-(2-(hydroxymethyl)-4,5-dimethoxy-1-naphthalenyl)-1,3-dimethyl-, (1R,3R,7R)-
7-(2-Hydroxymethyl-4,5-dimethoxy-naphtalen-1-yl)-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol
7-[2-(hydroxymethyl)-4,5-dimethoxynaphthalen-1-yl]-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol
8-isoquinolinol, 1,2,3,4-tetrahydro-7-[2-(hydroxymethyl)-4,5-dimethoxy-1-naphthalenyl]-1,3-dimethyl-, (1R,3R)-
InChI=1/C24H27NO4/c1-13-10-15-8-9-18(24(27)21(15)14(2)25-13)22-16(12-26)11-20(29-4)23-17(22)6-5-7-19(23)28-3/h5-9,11,13-14,25-27H,10,12H2,1-4H3/t13-,14-/m1/s
Rel-(1R,3R)-7-[2-(hydroxymethyl)-4,5-dimethoxy-1-naphthyl]-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol
- Bringmann G, Messer K, et al. (2003). Habropetaline A, an antimalarial naphthylisoquinoline alkaloid from Triphyophyllum peltatum. Phytochemistry,2003,62(3),345-349. [View]
No compound-protein relationship available.
SMILES: c1cccc(c12)cccc2-c(c3)ccc(c34)CCNC4
Level: 1
Mol. Weight: 393.48 g/mol
SMILES: C1CNCc(c12)cccc2
Level: 0
Mol. Weight: 393.48 g/mol
SMILES: c1cccc(c12)cccc2
Level: 0
Mol. Weight: 393.48 g/mol
Anti-plasmodial
Absorption
- Caco-2 (logPapp)
- -5.05
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.88
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -0.83
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.08
- Plasma Protein Binding
- 81.26
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 8.39
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.55
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.48
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.46
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- 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
- -23.62
- Rat (Acute)
- 2.52
- Rat (Chronic Oral)
- 2.33
- Fathead Minnow
- 4.9
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 469.3
- Hydration Free Energy
- -7.22
- Log(D) at pH=7.4
- 3.37
- Log(P)
- 3.28
- Log S
- -3.87
- Log(Vapor Pressure)
- -8.87
- Melting Point
- 159.57
- pKa Acid
- 9.62
- pKa Basic
- 8.81
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9519 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9280 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.9102 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.9076 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8849 |
| Proliferating cell nuclear antigen | P12004 | PCNA_HUMAN | Homo sapiens | 3 | 0.8824 |
| Thymidylate synthase | P0A886 | TYSY_ECO57 | Escherichia coli O157:H7 | 3 | 0.8639 |
| GTPase KRas | P01116 | RASK_HUMAN | Homo sapiens | 3 | 0.8571 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8554 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8463 |
| Protoporphyrinogen oxidase | P50336 | PPOX_HUMAN | Homo sapiens | 3 | 0.8351 |
| DNA ligase | P43813 | DNLJ_HAEIN | Haemophilus influenzae | 3 | 0.8199 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8165 |
| Glycogen synthase | Q9V2J8 | Q9V2J8_PYRAB | Pyrococcus abyssi | 3 | 0.8144 |
| Endolysin | P00720 | ENLYS_BPT4 | Enterobacteria phage T4 | 3 | 0.8130 |
| Protein S100-A13 | Q99584 | S10AD_HUMAN | Homo sapiens | 3 | 0.8102 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8060 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8017 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8009 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7920 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7841 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.7834 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.7823 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 3 | 0.7813 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7767 |
| Endoplasmin | P14625 | ENPL_HUMAN | Homo sapiens | 3 | 0.7742 |
| Streptogramin A acetyltransferase | P50870 | VATD_ENTFC | Enterococcus faecium | 3 | 0.7694 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7678 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7650 |
| Glycogen synthase | Q9V2J8 | Q9V2J8_PYRAB | Pyrococcus abyssi | 3 | 0.7641 |
| Serine/threonine-protein kinase PLK2 | Q9NYY3 | PLK2_HUMAN | Homo sapiens | 3 | 0.7638 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7613 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7593 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7489 |
| Beta-galactosidase | P00722 | BGAL_ECOLI | Escherichia coli | 3 | 0.7460 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7455 |
| Cytohesin-2 | Q99418 | CYH2_HUMAN | Homo sapiens | 3 | 0.7452 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7445 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7444 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7437 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.7379 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7348 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7343 |
| Protoporphyrinogen oxidase | P50336 | PPOX_HUMAN | Homo sapiens | 3 | 0.7334 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7284 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7283 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7281 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7277 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 3 | 0.7269 |
| NAD(P)H dehydrogenase [quinone] 1 | P15559 | NQO1_HUMAN | Homo sapiens | 3 | 0.7261 |
| Thyroxine-binding globulin | P05543 | THBG_HUMAN | Homo sapiens | 3 | 0.7260 |
| Poly [ADP-ribose] polymerase 1 | P26446 | PARP1_CHICK | Gallus gallus | 3 | 0.7249 |
| Fatty acid-binding protein, intestinal | P12104 | FABPI_HUMAN | Homo sapiens | 3 | 0.7239 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7185 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 2 | 0.7179 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7162 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7159 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7153 |
| Type II methyltransferase M.TaqI | P14385 | MTTA_THEAQ | Thermus aquaticus | 3 | 0.7139 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 4 | 0.7118 |
| Prostaglandin F2a synthase | Q8I6L9 | Q8I6L9_TRYCR | Trypanosoma cruzi | 2 | 0.7106 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7102 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7100 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7098 |
| Carbonic anhydrase 12 | O43570 | CAH12_HUMAN | Homo sapiens | 2 | 0.7097 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7084 |
| Chloramphenicol 3-O phosphotransferase | Q56148 | CPT_STRVP | Streptomyces venezuelae | 3 | 0.7074 |
| Diamine acetyltransferase 1 | P21673 | SAT1_HUMAN | Homo sapiens | 2 | 0.7065 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7047 |
| Thymidylate synthase | P45352 | TYSY_RAT | Rattus norvegicus | 2 | 0.7038 |
| Aminoglycoside 3'-phosphotransferase | P0A3Y5 | KKA3_ENTFL | Enterococcus faecalis | 3 | 0.7033 |
| Serine/threonine-protein kinase PLK2 | Q9NYY3 | PLK2_HUMAN | Homo sapiens | 3 | 0.7009 |