(±)-8-oxohypecorinine - Compound Card

(±)-8-oxohypecorinine

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(±)-8-oxohypecorinine

Structure
Zoomed Structure
  • Family: Plantae - Hypecoaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Aporphine Alkaloid
Canonical Smiles O=C1OC2(N(C)CCc3c2cc2OCOc2c3)C(=O)c2c1c1OCOc1cc2
InChI InChI=1S/C20H15NO7/c1-21-5-4-10-6-14-15(26-8-25-14)7-12(10)20(21)18(22)11-2-3-13-17(27-9-24-13)16(11)19(23)28-20/h2-3,6-7H,4-5,8-9H2,1H3
InChIKey BWYHFNMQBBIIDP-UHFFFAOYSA-N
Formula C20H15NO7
HBA 8
HBD 0
MW 381.34
Rotatable Bonds 0
TPSA 83.53
LogP 1.84
Number Rings 6
Number Aromatic Rings 2
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.3
Exact Mass 381.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Hypecoum procumbens Hypecoaceae Plantae 391933

Showing of synonyms

  • Saad HEA (1995). (±)-8-oxohypecorinine from Hypecoum procumbens Var. Glaucescens. Phytochemistry,1995,38(4),1049-1051. [View]
Pubchem: 162817182
Nmrshiftdb2: 60069878

No compound-protein relationship available.

Structure

SMILES: O1COc(cc2)c1c(C(=O)O3)c2C(=O)C34c5c(CCN4)cc6c(c5)OCO6

Level: 0

Mol. Weight: 381.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.02
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.56
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.26

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.06
Plasma Protein Binding
49.37
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-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
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.65
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.1
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.51
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.62
Micronucleos
Toxic
NR-AhR
Safe
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
-30.17
Rat (Acute)
2.27
Rat (Chronic Oral)
1.22
Fathead Minnow
4.73
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
450.54
Hydration Free Energy
-4.71
Log(D) at pH=7.4
2.4
Log(P)
2.76
Log S
-4.52
Log(Vapor Pressure)
-10.1
Melting Point
214.22
pKa Acid
6.48
pKa Basic
3.6
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.9316
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.9316
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8960
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8960
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8577
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8577
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8364
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8364
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8168
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8168
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8159
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8159
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8112
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8112
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7842
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7842
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7829
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7829
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7688
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7688
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7683
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7683
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7578
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7578
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7448
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7448
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7402
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7402
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7344
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7344
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7331
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7331
Cytochrome P450 2C19 P33261 CP2CJ_HUMAN Homo sapiens 3 0.7312
Cytochrome P450 2C19 P33261 CP2CJ_HUMAN Homo sapiens 3 0.7312
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7307
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7307
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7297
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7297
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7258
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7258
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7138
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7138
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7088
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7088
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7083
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7083
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 4 0.7067
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 4 0.7067
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 3 0.7041
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 3 0.7041

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