11-hydroxydihydrousambarine - Compound Card

11-hydroxydihydrousambarine

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11-hydroxydihydrousambarine

Structure
Zoomed Structure
  • Family: Plantae - Loganiaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles CC[C@H]1CN2CCc3c([C@@H]2C[C@@H]1C[C@@H]1N(C)CCc2c1[nH]c1c2cccc1)[nH]c1c3ccc(c1)O
InChI InChI=1S/C30H36N4O/c1-3-18-17-34-13-11-24-22-9-8-20(35)16-26(22)32-30(24)28(34)15-19(18)14-27-29-23(10-12-33(27)2)21-6-4-5-7-25(21)31-29/h4-9,16,18-19,27-28,31-32,35H,3,10-15,17H2,1-2H3/t18-,19-,27-,28-/m0/s1
InChIKey KETKPZBETQITST-HVYZTVOGSA-N
Formula C30H36N4O
HBA 3
HBD 3
MW 468.65
Rotatable Bonds 3
TPSA 58.29
LogP 5.92
Number Rings 7
Number Aromatic Rings 4
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.47
Exact Mass 468.29
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Strychnos usambarensis Loganiaceae Plantae 992791

Showing of synonyms

  • Frederich M, Hayette MP, et al. (1999). In vitro activities of Strychnos alkaloids and extracts against Plasmodium falciparum.. Antimicrobial agents and chemotherapy,1999, 43(9), 2328-31. [View] [PubMed]
Pubchem: 49863369
Nmrshiftdb2: 70053776

No compound-protein relationship available.

Structure

SMILES: c1cccc2[nH]c(c3c12)C(NCC3)CC(C4)CCN(CC5)C4c(c5c67)[nH]c6cccc7

Level: 1

Mol. Weight: 468.65 g/mol

Structure

SMILES: C1CCCN(CC2)C1c(c2c34)[nH]c3cccc4

Level: 0

Mol. Weight: 468.65 g/mol

Structure

SMILES: C1CNCc(c1c23)[nH]c2cccc3

Level: 0

Mol. Weight: 468.65 g/mol

Antimalarial

Absorption

Caco-2 (logPapp)
-5.63
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.69
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.33

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.8
Plasma Protein Binding
89.75
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
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
9.66
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.62
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.19
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.54
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
Toxic
T. Pyriformis
-1382.32
Rat (Acute)
2.58
Rat (Chronic Oral)
1.89
Fathead Minnow
7.29
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
499.26
Hydration Free Energy
-2.98
Log(D) at pH=7.4
4.8
Log(P)
5.19
Log S
-4.8
Log(Vapor Pressure)
-9.08
Melting Point
253.98
pKa Acid
11.7
pKa Basic
7.14
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 0.9646
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.9586
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9540
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.9475
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.9456
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.9430
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9402
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 3 0.9276
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.9199
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9153
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.9139
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9089
clade A/E 93TH057 HIV-1 gp120 core A0A0M3KKW9 A0A0M3KKW9_9HIV1 Human immunodeficiency virus 1 3 0.9035
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9026
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.9024
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.9016
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9015
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8921
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8893
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8890
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8871
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8813
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8746
RAC-alpha serine/threonine-protein kinase P31749 AKT1_HUMAN Homo sapiens 3 0.8727
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8721
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8628
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8562
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8532
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8523
Naphthalene 1,2-dioxygenase system, large oxygenase component P0A110 NDOB_PSEPU Pseudomonas putida 3 0.8522
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8514
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8438
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.8414
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.8300
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8270
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 3 0.8178
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.8176
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.8169
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8060
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8058
Death-associated protein kinase 3 O43293 DAPK3_HUMAN Homo sapiens 3 0.8057
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8049
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7974
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7948
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7921
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7828
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7826
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7823
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7816
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7803
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7797
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7770
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7746
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7720
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7715
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 3 0.7702
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7693
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7688
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7684
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7644
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7638
Envelope glycoprotein gp160 C6G099 C6G099_9HIV1 Human immunodeficiency virus 1 3 0.7632
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 3 0.7602
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7598
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7595
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7572
Aklanonic acid methyl ester cyclase AcmA O52646 DNRD_STRGJ Streptomyces galilaeus 3 0.7562
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7533
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7520
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7520
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7514
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7509
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7466
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 2 0.7462
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7439
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7423
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7421
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7418
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7417
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7403
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7403
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7399
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7384
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7378
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 2 0.7374
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7371
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7368
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.7364
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7358
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 3 0.7356
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7354
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7353
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7345
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7336
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7314
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7276
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7268
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7261
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7258
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7254
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7250
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.7244
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7227
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7221
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7218
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7216
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7205
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7198
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7196
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7190
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7186
Cyclic nucleotide-binding domain-containing protein E0RR11 E0RR11_SPITD Spirochaeta thermophila 3 0.7185
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7182
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7175
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7171
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7171
Bromodomain protein, putative Q8I240 Q8I240_PLAF7 Plasmodium falciparum 4 0.7138
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7136
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7125
TGF-beta-activated kinase 1 and MAP3K7-binding protein 1 Q15750 TAB1_HUMAN Homo sapiens 3 0.7116
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7111
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7096
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.7089
tRNA (cytidine(34)-2'-O)-methyltransferase P44868 TRML_HAEIN Haemophilus influenzae 3 0.7076
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7076
Reticuline oxidase P30986 RETO_ESCCA Eschscholzia californica 4 0.7072
High affinity nerve growth factor receptor P04629 NTRK1_HUMAN Homo sapiens 3 0.7070
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7066
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7063
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7050
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7041
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7038
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7031
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7030
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7029
Sterol 14-alpha demethylase Q7Z1V1 CP51_TRYCC Trypanosoma cruzi 4 0.7021
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7021
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7018
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7016
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7009
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7007
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7006
DNA gyrase subunit B Q839Z1 GYRB_ENTFA Enterococcus faecalis 3 0.7006
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7005
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7001
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7001

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