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Pheophorbide A
- Family: Plantae - Cactaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Chlorophyll Derivative
| Canonical Smiles | COC(=O)[C@H]1C(=O)C2=C(C)C3=NC2=C1C1=N/C(=C\c2[nH]c(c(c2C)C=C)/C=c/2\[nH]/c(=C\3)/c(CC)c2C)/[C@H]([C@@H]1CCC(=O)O)C |
|---|---|
| InChI | InChI=1S/C35H36N4O5/c1-8-19-15(3)22-12-24-17(5)21(10-11-28(40)41)32(38-24)30-31(35(43)44-7)34(42)29-18(6)25(39-33(29)30)14-27-20(9-2)16(4)23(37-27)13-26(19)36-22/h8,12-14,17,21,31,36-37H,1,9-11H2,2-7H3,(H,40,41)/t17-,21-,31+/m0/s1 |
| InChIKey | OINDWIFDMFYGDX-LDCXZXNSSA-N |
| Formula | C35H36N4O5 |
| HBA | 6 |
| HBD | 3 |
| MW | 592.7 |
| Rotatable Bonds | 6 |
| TPSA | 138.03 |
| LogP | 6.66 |
| Number Rings | 6 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 44 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.34 |
| Exact Mass | 592.27 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Opuntia ficus indica | Cactaceae | Plantae | 371859 |
Showing of synonyms
Pheophorbide A
Pubchem:
5323510
CPRiL:
61430
SMILES: O=C1Cc(c2c13)c4nc(CC4)cc5ccc([nH]5)cc6ccc([nH]6)cc(n2)c3
Level: 0
Mol. Weight: 592.7 g/mol
Antiviral
Absorption
- Caco-2 (logPapp)
- -5.4
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.120
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 19.93
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.450
- Plasma Protein Binding
- 72.94
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 6.800
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -0.580
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.890
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.500
- Micronucleos
- Toxic
- 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
- Toxic
- T. Pyriformis
- -41536.430
- Rat (Acute)
- 3.040
- Rat (Chronic Oral)
- 3.440
- Fathead Minnow
- 69.540
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 175.070
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 3.050
- Log(P)
- 5.01
- Log S
- -4.36
- Log(Vapor Pressure)
- -44.17
- Melting Point
- 284.38
- pKa Acid
- 7.67
- pKa Basic
- 4.58
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.9053 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.9053 |
| ABC-type polar amino acid transport system, ATPase component | Q8RCC2 | Q8RCC2_CALS4 | Caldanaerobacter subterraneus subsp. tengcongensis | 3 | 0.8898 |
| ABC-type polar amino acid transport system, ATPase component | Q8RCC2 | Q8RCC2_CALS4 | Caldanaerobacter subterraneus subsp. tengcongensis | 3 | 0.8898 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8880 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8880 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.8704 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.8704 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q4WP27 | Q4WP27_ASPFU | Aspergillus fumigatus | 3 | 0.8646 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q4WP27 | Q4WP27_ASPFU | Aspergillus fumigatus | 3 | 0.8646 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 3 | 0.8604 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 3 | 0.8604 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8246 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8246 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.8124 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.8124 |
| Carbonic anhydrase 12 | O43570 | CAH12_HUMAN | Homo sapiens | 3 | 0.8040 |
| Carbonic anhydrase 12 | O43570 | CAH12_HUMAN | Homo sapiens | 3 | 0.8040 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8015 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8015 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 3 | 0.7950 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 3 | 0.7950 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.7785 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.7785 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7707 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7707 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7628 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7628 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7569 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7569 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7418 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7418 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 2 | 0.7324 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 2 | 0.7324 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7309 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7309 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7305 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7305 |
| Orf1a polyprotein | Q692E5 | Q692E5_CVHSA | SARS coronavirus TJF | 3 | 0.7273 |
| Orf1a polyprotein | Q692E5 | Q692E5_CVHSA | SARS coronavirus TJF | 3 | 0.7273 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7262 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7262 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 3 | 0.7246 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 3 | 0.7246 |
| Angiotensin-converting enzyme 2 | Q9BYF1 | ACE2_HUMAN | Homo sapiens | 2 | 0.7221 |
| Angiotensin-converting enzyme 2 | Q9BYF1 | ACE2_HUMAN | Homo sapiens | 2 | 0.7221 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7129 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7129 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7073 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7073 |
| CREB-binding protein | Q92793 | CBP_HUMAN | Homo sapiens | 2 | 0.7072 |
| CREB-binding protein | Q92793 | CBP_HUMAN | Homo sapiens | 2 | 0.7072 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 2 | 0.7071 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 2 | 0.7071 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 2 | 0.7040 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 2 | 0.7040 |
| Interleukin enhancer-binding factor 2 | Q9CXY6 | ILF2_MOUSE | Mus musculus | 2 | 0.7005 |
| Interleukin enhancer-binding factor 2 | Q9CXY6 | ILF2_MOUSE | Mus musculus | 2 | 0.7005 |