N4-methyl-10-hydroxygeissoschizol - Compound Card

N4-methyl-10-hydroxygeissoschizol

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N4-methyl-10-hydroxygeissoschizol

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Monoterpenoid Indole Alkaloid
Canonical Smiles OCC[C@H]1C[C@H]2c3[nH]c4c(c3CC[N@+]2(C/C/1=C/C)C)cc(cc4)O
InChI InChI=1S/C20H26N2O2/c1-3-13-12-22(2)8-6-16-17-11-15(24)4-5-18(17)21-20(16)19(22)10-14(13)7-9-23/h3-5,11,14,19,21,23H,6-10,12H2,1-2H3/p+1/b13-3-/t14-,19-,22-/m0/s1
InChIKey SJZVPGIUGNSWTN-AQGAXGGASA-O
Formula C20H27N2O2+
HBA 2
HBD 3
MW 327.45
Rotatable Bonds 2
TPSA 56.25
LogP 3.27
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 24
Formal Charge 1
Fraction CSP3 0.5
Exact Mass 327.21
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pleiocarpa pycnantha Apocynaceae Plantae 1220085

Showing of synonyms

  • Ndongo JT, Mbing JN, et al. (2018). Carbazole-, aspidofractinine-, and aspidocarpamine-type alkaloids from Pleiocarpa pycnantha.. Journal of natural products,2018, 81(5), 1193-1202. [View] [PubMed]

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 327.45 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.56
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.030
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.300
Plasma Protein Binding
59.38
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-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
15.040
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.100
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.530
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.210
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
-1.110
Rat (Acute)
2.700
Rat (Chronic Oral)
1.880
Fathead Minnow
4.180
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
449.100
Hydration Free Energy
-9.650
Log(D) at pH=7.4
1.240
Log(P)
-1.03
Log S
-0.95
Log(Vapor Pressure)
-11.26
Melting Point
272.52
pKa Acid
9.73
pKa Basic
6.83
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9547
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9410
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8901
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.8828
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.8734
Naphthalene 1,2-dioxygenase system, large oxygenase component P0A110 NDOB_PSEPU Pseudomonas putida 3 0.8587
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8348
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8188
Cytochrome P450 2E1 P05181 CP2E1_HUMAN Homo sapiens 3 0.7721
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.7715
Cytochrome b-c1 complex subunit 1, mitochondrial P31800 QCR1_BOVIN Bos taurus 3 0.7670
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7644
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 2 0.7633
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7621
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7605
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7568
Benzoylformate decarboxylase P20906 MDLC_PSEPU Pseudomonas putida 3 0.7555
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7494
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7440
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7406
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 3 0.7395
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7358
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7353
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7318
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7290
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7275
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7256
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7239
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7236
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 2 0.7233
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7227
(R)-S-adenosyl-L-methionine hydrolase O58212 O58212_PYRHO Pyrococcus horikoshii OT3 3 0.7212
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7197
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7168
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7160
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7157
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7150
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7134
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7125
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7122
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7118
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7118
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7094
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7074
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7065
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7049
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7045
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7035
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7028
Phosphoglycerate kinase Q83AU6 PGK_COXBU Coxiella burnetii 3 0.7027
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 2 0.7022
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7012
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7009

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