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10'-hydroxydihydrousambarine

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]c1c3cc(cc1)O
InChI	InChI=1S/C30H36N4O/c1-3-18-17-34-13-11-23-24-16-20(35)8-9-26(24)32-30(23)28(34)15-19(18)14-27-29-22(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	LJLFWHVFRNHBRP-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: 49863342

Zinc: ZINC000014616160

Nmrshiftdb2: 70053777

Chembl: CHEMBL1213086

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 468.65 g/mol

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

Level: 0

Mol. Weight: 468.65 g/mol

SMILES: C1CNCc(c1c23)[nH]c2cccc3

Level: 0

Mol. Weight: 468.65 g/mol

Antimalarial

Absorption

Caco-2 (logPapp): -5.63
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.67
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 0.46

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.83
Plasma Protein Binding: 90.11
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: 9.59
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: -1.14
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 5.55
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: -1390.1
Rat (Acute): 2.58
Rat (Chronic Oral): 1.82
Fathead Minnow: 7.3
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: 499.84
Hydration Free Energy: -2.98
Log(D) at pH=7.4: 4.82
Log(P): 5.04
Log S: -4.81
Log(Vapor Pressure): -9.11
Melting Point: 253.98
pKa Acid: 11.84
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	0.9547
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.9451
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.9385
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.9314
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.9177
clade A/E 93TH057 HIV-1 gp120 core	A0A0M3KKW9	A0A0M3KKW9_9HIV1	Human immunodeficiency virus 1	3	0.9041
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	3	0.8976
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.8953
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8821
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.8727
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8696
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8646
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.8539
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8538
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.8454
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8333
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.8312
Genome polyprotein	Q99AU2	Q99AU2_9HEPC	Hepatitis C virus subtype 1b	3	0.8228
Naphthalene 1,2-dioxygenase system, large oxygenase component	P0A110	NDOB_PSEPU	Pseudomonas putida	3	0.8227
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8159
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.8129
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8055
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.8034
Orf1a polyprotein	Q692E5	Q692E5_CVHSA	SARS coronavirus TJF	3	0.8019
Aklanonic acid methyl ester cyclase AcmA	O52646	DNRD_STRGJ	Streptomyces galilaeus	3	0.7999
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7993
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7986
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7981
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	4	0.7908
Death-associated protein kinase 3	O43293	DAPK3_HUMAN	Homo sapiens	3	0.7904
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7855
Beta-galactoside-specific lectin 1	P81446	ML1_VISAL	Viscum album	3	0.7818
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7779
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7737
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	2	0.7737
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.7721
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7708
Antitumor antibiotic C-1027 apoprotein	Q06110	CAGA_STRGL	Streptomyces globisporus	2	0.7696
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7687
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase	O33877	FABA_PSEAE	Pseudomonas aeruginosa	3	0.7684
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7674
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7674
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7656
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7653
Threonine synthase 1, chloroplastic	Q9S7B5	THRC1_ARATH	Arabidopsis thaliana	3	0.7652
3',5'-cyclic-AMP phosphodiesterase 4B	Q07343	PDE4B_HUMAN	Homo sapiens	4	0.7640
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7625
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7623
Troponin C, slow skeletal and cardiac muscles	P09860	TNNC1_CHICK	Gallus gallus	3	0.7591
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7565
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7553
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	2	0.7550
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7500
Glycogen phosphorylase, liver form	P06737	PYGL_HUMAN	Homo sapiens	3	0.7497
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7484
Integrin alpha-IIb	P08514	ITA2B_HUMAN	Homo sapiens	3	0.7479
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7438
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7391
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7387
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7385
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	3	0.7384
CRP-like cAMP-activated global transcriptional regulator	P9WMH3	CRPL_MYCTU	Mycobacterium tuberculosis	3	0.7365
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7344
Prenyltransferase	Q4R2T2	Q4R2T2_STRC1	Streptomyces sp	3	0.7338
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7333
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7331
Cyclic nucleotide-gated potassium channel mll3241	Q98GN8	CNGK1_RHILO	Mesorhizobium japonicum)	3	0.7330
Dipeptidyl peptidase 4	P14740	DPP4_RAT	Rattus norvegicus	3	0.7328
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7324
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7296
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7293
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7281
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7253
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7248
HD domain protein	Q836G9	Q836G9_ENTFA	Enterococcus faecalis	3	0.7245
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.7236
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7236
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7236
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	3	0.7215
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	2	0.7205
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7198
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7197
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7192
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.7183
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7170
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7164
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7159
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.7139
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7131
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7129
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7111
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	2	0.7110
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7110
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7108
Class 10 plant pathogenesis-related protein 2B	Q9LLQ2	P102B_LUPLU	Lupinus luteus	2	0.7106
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7102
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7099
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7098
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7091
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7085
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7085
Nucleoside 2-deoxyribosyltransferase	Q8RLY5	Q8RLY5_LACHE	Lactobacillus helveticus	2	0.7081
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.7077
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	3	0.7076
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7065
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	2	0.7062
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 1	O88704	HCN1_MOUSE	Mus musculus	3	0.7061
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7045
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.7042
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	2	0.7039
Proto-oncogene tyrosine-protein kinase receptor Ret	P07949	RET_HUMAN	Homo sapiens	3	0.7035
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	2	0.7030
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7027
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.7025
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7015
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	2	0.7015
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	2	0.7013
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7008
Carbonic anhydrase 13	Q8N1Q1	CAH13_HUMAN	Homo sapiens	3	0.7002

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