11-hydroxy rhazimanine - Compound Card

11-hydroxy rhazimanine

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11-hydroxy rhazimanine

Structure
Zoomed Structure
  • Family: Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles OCC(C1CC2N(C/C/1=C\C)CCc1c2[nH]c2c1ccc(c2)O)C(=O)OC
InChI InChI=1S/C21H26N2O4/c1-3-12-10-23-7-6-15-14-5-4-13(25)8-18(14)22-20(15)19(23)9-16(12)17(11-24)21(26)27-2/h3-5,8,16-17,19,22,24-25H,6-7,9-11H2,1-2H3/b12-3+
InChIKey FCUKPABXXVEFHR-KGVSQERTSA-N
Formula C21H26N2O4
HBA 5
HBD 3
MW 370.45
Rotatable Bonds 3
TPSA 85.79
LogP 2.52
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.48
Exact Mass 370.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pachypodium lamerei Apocynaceae Plantae 69385

Showing of synonyms

  • Mina S.A, Mohamed S.A, et al. (2020). LC-ESI-MS/MS profiling of alkaloids and antiproliferative activity of Pachypoduim lamerei drake leaves. Natural product research, 2020, 34(9), 1292-1296. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CC(=C)CN(CC2)C1c(c2c34)[nH]c3cccc4

Level: 0

Mol. Weight: 238.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.5
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.27
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.52

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.67
Plasma Protein Binding
3.45
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-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
15.41
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.24
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.75
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.58
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
-9.72
Rat (Acute)
2.7
Rat (Chronic Oral)
2.51
Fathead Minnow
4.36
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
463.41
Hydration Free Energy
-7.54
Log(D) at pH=7.4
2.11
Log(P)
2.11
Log S
-3.01
Log(Vapor Pressure)
-9.76
Melting Point
199.32
pKa Acid
8.53
pKa Basic
6.92
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9517
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9437
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9420
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.9402
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 3 0.9340
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9250
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9240
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9234
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9197
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9194
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9118
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9105
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9090
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9046
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9009
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9009
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8947
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8941
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8808
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8806
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8797
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8783
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8773
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8764
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8755
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8741
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8719
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8679
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8661
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8619
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8605
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8544
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8527
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.8508
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8508
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8494
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8374
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.8367
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8353
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8319
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.8282
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8276
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8275
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8266
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.8099
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8022
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7992
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 3 0.7973
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7947
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7928
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7910
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B Q13370 PDE3B_HUMAN Homo sapiens 3 0.7901
D-alanine--D-alanine ligase Q5HEB7 DDL_STAAC Staphylococcus aureus 3 0.7894
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7860
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7854
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7812
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7805
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7773
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7755
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7750
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7745
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7716
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7687
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7681
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7650
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7637
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.7627
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7618
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7601
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7591
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7585
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 4 0.7581
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7566
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7565
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7564
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7553
Naphthalene 1,2-dioxygenase system, large oxygenase component P0A110 NDOB_PSEPU Pseudomonas putida 3 0.7550
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7547
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7543
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7539
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7538
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7537
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7523
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7522
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7513
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7490
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7467
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7446
Casein kinase I isoform gamma-2 P78368 KC1G2_HUMAN Homo sapiens 3 0.7443
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7442
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7436
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7435
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7402
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7377
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7377
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7340
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7332
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7331
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7326
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7277
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7276
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7274
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 4 0.7272
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7272
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7261
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7246
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7232
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7228
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7225
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7222
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7189
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7184
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7171
Putative cytochrome P450 120 Q59990 CP120_SYNY3 Synechocystis sp 3 0.7149
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7141
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7113
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7083
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7082
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 2 0.7066
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7065
Trichosurin Q29147 TRIC_TRIVU Trichosurus vulpecula 3 0.7061
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7054
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 4 0.7046
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7040
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7028
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7024
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7018
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7016
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7008
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7006

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