NPASS Compound

Natural Product: NPC479095

Natural Product ID	NPC479095
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OYJUPQUBVKLDQY-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	129762063
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 29 31 0 0 0 0 0 0 0 0999 V2000 4.6115 0.2018 -1.5778 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2180 0.2098 -0.2267 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9068 0.1776 0.1996 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6292 0.1883 1.5638 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3151 0.1559 1.9927 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2750 0.1131 1.0861 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0859 0.0757 1.2666 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9037 0.0674 2.3818 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2705 0.0250 2.2003 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7834 -0.0075 0.9551 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0077 -0.0003 -0.1567 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6054 -0.0379 -1.5153 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4466 -1.3293 -2.0052 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6371 0.0418 -0.0053 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6327 0.0589 -0.9027 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5606 0.1026 -0.2811 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8727 0.1350 -0.7077 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0022 -0.4486 -2.2160 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5522 1.2334 -2.0296 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6828 -0.0926 -1.6060 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4342 0.2221 2.3025 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1436 0.1662 3.0630 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5089 0.0934 3.3824 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9199 0.0184 3.0756 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6785 0.1915 -1.5092 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0909 0.7200 -2.1465 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0027 -1.3584 -2.8820 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7392 0.0412 -1.9422 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1094 0.1282 -1.7596 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 11 14 2 0 14 15 1 0 15 16 1 0 16 17 2 0 17 3 1 0 16 6 1 0 14 7 1 0 1 18 1 0 1 19 1 0 1 20 1 0 4 21 1 0 5 22 1 0 8 23 1 0 9 24 1 0 12 25 1 0 12 26 1 0 13 27 1 0 15 28 1 0 17 29 1 0 M END

Standard InCHIKey	OYJUPQUBVKLDQY-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C13H12N2O2/c1-17-8-2-3-9-10-4-5-14-12(7-16)13(10)15-11(9)6-8/h2-6,15-16H,7H2,1H3
SMILES	COc1ccc2c3ccnc(CO)c3[nH]c2c1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	228.09	Volume:	231.49 ? Van der Waals volume.
Dense:	0.985	LogP:	2.336 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.442 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.491 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	15.0
TPSA:	58.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.707	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.324	Fsp³:	0.154
MCE-18:	15.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.134	Fluc inhibitor:	0.719 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.877 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.204 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.017	Promiscuous compounds:	0.812

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.827	MDCK Permeability:	-4.627
Pgp-inhibitor:	0.013	Pgp-substrate:	0.216
PAMPA:	0.227 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.061
20% Bioavailability (F20%):	0.051	30% Bioavailability (F30%):	0.344
50% Bioavailability (F50%):	0.761

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.123	MRP1:	0.561
Plasma Protein Binding (PPB):	87.281%	Volume Distribution (VD):	0.112
Fu:	14.238% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.789
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.626
BSEP inhibitor:	0.816

ADMET: Metabolism

CYP1A2-inhibitor:	0.215	CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.98	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.957	CYP2C9-substrate:	0.723
CYP2D6-inhibitor:	0.952	CYP2D6-substrate:	0.727
CYP3A4-inhibitor:	0.608	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.118
HLM stability:	0.164 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

8.745

Half-life (T1/2):

0.86

ADMET: Toxicity

hERG Blockers:	0.272	hERG Blockers (10um):	0.449
Human Hepatotoxicity (H-HT):	0.634	Drug-induced Liver Injury (DILI):	0.8
AMES Toxicity:	0.859	Rat Oral Acute Toxicity:	0.472
Maximum Recommended Daily Dose:	0.627	Skin Sensitization:	0.166
Carcinogencity:	0.884	Eye Corrosion:	0.0
Eye Irritation:	0.868	Respiratory Toxicity:	0.857
Drug-induced Neurotoxicity:	0.778	Ototoxicity:	0.76
Hematotoxicity:	0.59	Drug-induced Nephrotoxicity:	0.867
Genotoxicity:	0.532	RPMI-8226 Immunitoxicity:	0.13
A549 Cytotoxicity:	0.209	Hek293 Cytotoxicity:	0.466
BCF:	0.338 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.009 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.369 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.588 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO1085	Peganum harmala	Species	Nitrariaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[28128938]
NPO1085	Peganum harmala	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38971075]
NPO1085	Peganum harmala	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6736972]
NPO1085	Peganum harmala	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1085	Peganum harmala	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1085	Peganum harmala	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1085	Peganum harmala	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1085	Peganum harmala	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Inhibition	2
IC50	5
Activity	54

Activity Type	# Activity
Individual protein	58
Cell line	1
Single protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3114	Individual protein	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Homo sapiens	Inhibition	=	75.0	%	PMID[30059217]
NPT3114	Individual protein	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Homo sapiens	Inhibition	=	49.0	%	PMID[30059217]
NPT3114	Individual protein	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Homo sapiens	IC50	=	54.8	nM	PMID[30059217]
NPT3114	Individual protein	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Homo sapiens	IC50	=	106.0	nM	PMID[30059217]
NPT3323	Individual protein	Cell division cycle 2-like protein kinase 6	Homo sapiens	Activity	=	98.0	%	PMID[30059217]
NPT3346	Individual protein	Cyclin-dependent kinase 7	Homo sapiens	Activity	=	27.0	%	PMID[30059217]
NPT3324	Individual protein	Cell division protein kinase 8	Homo sapiens	Activity	=	94.0	%	PMID[30059217]
NPT3397	Individual protein	Cyclin-dependent kinase-like 5	Homo sapiens	Activity	=	100.0	%	PMID[30059217]
NPT3334	Individual protein	Citron Rho-interacting kinase	Homo sapiens	Activity	=	44.0	%	PMID[30059217]
NPT1681	Individual protein	Dual specificty protein kinase CLK1	Homo sapiens	Activity	=	3.5	%	PMID[30059217]
NPT1682	Individual protein	Dual specificity protein kinase CLK2	Homo sapiens	Activity	=	5.5	%	PMID[30059217]
NPT3231	Individual protein	Dual specificity protein kinase CLK4	Homo sapiens	Activity	=	17.0	%	PMID[30059217]
NPT3168	Individual protein	Casein kinase I alpha	Homo sapiens	Activity	=	10.0	%	PMID[30059217]
NPT3266	Individual protein	Casein kinase I delta	Homo sapiens	Activity	=	17.0	%	PMID[30059217]
NPT3226	Individual protein	Casein kinase I epsilon	Homo sapiens	Activity	=	6.5	%	PMID[30059217]
NPT1685	Individual protein	Casein kinase I gamma 2	Homo sapiens	Activity	=	30.0	%	PMID[30059217]
NPT1598	Individual protein	Casein kinase II alpha	Homo sapiens	Activity	=	34.0	%	PMID[30059217]
NPT3273	Individual protein	Casein kinase II alpha (prime)	Homo sapiens	Activity	=	37.0	%	PMID[30059217]
NPT1721	Individual protein	Death-associated protein kinase 1	Homo sapiens	Activity	=	85.0	%	PMID[30059217]
NPT3236	Individual protein	Death-associated protein kinase 2	Homo sapiens	Activity	=	80.0	%	PMID[30059217]
NPT1687	Individual protein	Death-associated protein kinase 3	Homo sapiens	Activity	=	81.0	%	PMID[30059217]
NPT3230	Individual protein	Serine/threonine-protein kinase 17B	Homo sapiens	Activity	=	88.0	%	PMID[30059217]
NPT3114	Individual protein	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Homo sapiens	Activity	=	0.0	%	PMID[30059217]
NPT3274	Individual protein	Dual specificity tyrosine-phosphorylation-regulated kinase 1B	Homo sapiens	Activity	=	66.0	%	PMID[30059217]
NPT3399	Individual protein	Dual-specificity tyrosine-phosphorylation regulated kinase 2	Homo sapiens	Activity	=	6.5	%	PMID[30059217]
NPT3444	Individual protein	Homeodomain-interacting protein kinase 1	Homo sapiens	Activity	=	30.0	%	PMID[30059217]
NPT3432	Individual protein	Homeodomain-interacting protein kinase 2	Homo sapiens	Activity	=	30.0	%	PMID[30059217]
NPT3409	Individual protein	Homeodomain-interacting protein kinase 3	Homo sapiens	Activity	=	21.0	%	PMID[30059217]
NPT3386	Individual protein	Interleukin-1 receptor-associated kinase 1	Homo sapiens	Activity	=	32.0	%	PMID[30059217]
NPT3288	Individual protein	Interleukin-1 receptor-associated kinase 3	Homo sapiens	Activity	=	39.0	%	PMID[30059217]
NPT3393	Individual protein	PI4-kinase beta subunit	Homo sapiens	Activity	=	3.7	%	PMID[30059217]
NPT1265	Individual protein	Serine/threonine-protein kinase PIM1	Homo sapiens	Activity	=	65.0	%	PMID[30059217]
NPT1700	Individual protein	Serine/threonine-protein kinase PIM2	Homo sapiens	Activity	=	58.0	%	PMID[30059217]
NPT3433	Individual protein	Phosphatidylinositol-5-phosphate 4-kinase type-2 gamma	Homo sapiens	Activity	=	28.0	%	PMID[30059217]
NPT3374	Individual protein	Ribosomal protein S6 kinase alpha 4	Homo sapiens	Activity	=	54.0	%	PMID[30059217]
NPT3355	Individual protein	TGF-beta receptor type II	Homo sapiens	Activity	=	91.0	%	PMID[30059217]
NPT3346	Individual protein	Cyclin-dependent kinase 7	Homo sapiens	Activity	=	27.0	%	PMID[32003560]
NPT1681	Individual protein	Dual specificty protein kinase CLK1	Homo sapiens	Activity	=	3.5	%	PMID[32003560]
NPT1682	Individual protein	Dual specificity protein kinase CLK2	Homo sapiens	Activity	=	5.5	%	PMID[32003560]
NPT3231	Individual protein	Dual specificity protein kinase CLK4	Homo sapiens	Activity	=	17.0	%	PMID[32003560]
NPT3168	Individual protein	Casein kinase I alpha	Homo sapiens	Activity	=	10.0	%	PMID[32003560]
NPT3266	Individual protein	Casein kinase I delta	Homo sapiens	Activity	=	17.0	%	PMID[32003560]
NPT3226	Individual protein	Casein kinase I epsilon	Homo sapiens	Activity	=	6.5	%	PMID[32003560]
NPT1685	Individual protein	Casein kinase I gamma 2	Homo sapiens	Activity	=	30.0	%	PMID[32003560]
NPT1598	Individual protein	Casein kinase II alpha	Homo sapiens	Activity	=	34.0	%	PMID[32003560]
NPT3114	Individual protein	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Homo sapiens	Activity	=	0.0	%	PMID[32003560]
NPT3274	Individual protein	Dual specificity tyrosine-phosphorylation-regulated kinase 1B	Homo sapiens	Activity	=	66.0	%	PMID[32003560]
NPT3399	Individual protein	Dual-specificity tyrosine-phosphorylation regulated kinase 2	Homo sapiens	Activity	=	6.5	%	PMID[32003560]
NPT3432	Individual protein	Homeodomain-interacting protein kinase 2	Homo sapiens	Activity	=	30.0	%	PMID[32003560]
NPT3409	Individual protein	Homeodomain-interacting protein kinase 3	Homo sapiens	Activity	=	20.0	%	PMID[32003560]
NPT3386	Individual protein	Interleukin-1 receptor-associated kinase 1	Homo sapiens	Activity	=	32.0	%	PMID[32003560]
NPT3288	Individual protein	Interleukin-1 receptor-associated kinase 3	Homo sapiens	Activity	=	39.0	%	PMID[32003560]
NPT1445	Individual protein	PI3-kinase p110-gamma subunit	Homo sapiens	Activity	=	44.0	%	PMID[32003560]
NPT3393	Individual protein	PI4-kinase beta subunit	Homo sapiens	Activity	=	3.7	%	PMID[32003560]
NPT3114	Individual protein	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Homo sapiens	IC50	=	56.0	nM	PMID[33528252]
NPT4093	Individual protein	Serine/threonine-protein kinase haspin	Homo sapiens	Activity	=	4.8	%	PMID[30059217]
NPT4093	Individual protein	Serine/threonine-protein kinase haspin	Homo sapiens	Activity	=	4.8	%	PMID[32003560]
NPT591	Individual protein	Glycogen synthase kinase-3 beta	Homo sapiens	IC50	>	8300.0	nM	PMID[33682417]
NPT24177	Single protein	Phosphatidylinositol 3-kinase catalytic subunit type 3	Homo sapiens	Activity	=	53.0	%	PMID[30059217]
NPT24177	Single protein	Phosphatidylinositol 3-kinase catalytic subunit type 3	Homo sapiens	Activity	=	53.0	%	PMID[32003560]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	4360.0	nM	PMID[28128938]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC479095 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	30530
0.1-0.2	18479
0.2-0.3	731
0.3-0.4	83
0.4-0.5	23
0.5-0.6	4
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.74	Intermediate Similarity	NPC232727
0.717	Intermediate Similarity	NPC146472
0.7115	Intermediate Similarity	NPC122436
0.7115	Intermediate Similarity	NPC479097
0.6981	Remote Similarity	NPC260434
0.6333	Remote Similarity	NPC60621
0.6154	Remote Similarity	NPC48938
0.5873	Remote Similarity	NPC101350
0.5522	Remote Similarity	NPC235685
0.5507	Remote Similarity	NPC91868
0.507	Remote Similarity	NPC63971

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC479095 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4598
0.1-0.2	4454
0.2-0.3	98
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data