NPASS Compound

Natural Product: NPC489234

Natural Product ID	NPC489234
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YRXOQXUDKDCXME-YIVRLKKSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5282309
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004707] Organic nitrogen compounds [CHEMONTID:0000278] Organonitrogen compounds [CHEMONTID:0002449] Amines [CHEMONTID:0002460] Alkanolamines [CHEMONTID:0001897] 1,2-aminoalcohols

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 64 63 0 0 0 0 0 0 0 0999 V2000 9.3379 1.0833 0.9701 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2143 0.2937 0.2822 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2749 1.2752 -0.3713 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1458 0.5873 -1.0782 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3440 -0.2281 -0.1203 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1845 -0.9321 -0.8110 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2444 0.0488 -1.4530 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1259 -0.6928 -2.1172 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3218 -1.5325 -1.1647 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6857 -0.7058 -0.0729 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2509 0.3371 -0.6486 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8406 1.1150 0.4846 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6271 0.2693 1.4578 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7578 -0.4227 0.8315 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9876 -0.1808 1.2684 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2013 -0.8322 0.6990 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9050 0.1954 -0.1541 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1696 1.4612 0.6087 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6574 2.4047 -0.3068 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1123 -0.2701 -0.7520 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9740 -1.3932 -1.6214 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2668 -0.2794 0.0843 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9590 -1.2904 1.7566 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9452 2.0593 1.3127 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1255 1.2681 0.2054 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7170 0.4406 1.7744 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6868 -0.2720 1.0882 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6296 -0.3668 -0.5050 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8770 1.9975 0.3924 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9051 1.8674 -1.0940 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5578 -0.0686 -1.8764 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5075 1.3973 -1.5180 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9561 0.4297 0.6749 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9802 -1.0236 0.3373 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6329 -1.4535 0.0091 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5434 -1.6624 -1.5355 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9003 0.8213 -0.7533 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8133 0.5624 -2.2824 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5219 0.0110 -2.6922 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6029 -1.4114 -2.8410 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4609 -1.9809 -1.7400 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9363 -2.3161 -0.7068 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0777 -1.4178 0.5414 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4249 -0.2571 0.6188 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3789 1.0394 -1.2352 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9861 -0.0849 -1.3318 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4159 2.0063 0.1740 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0296 1.5259 1.0766 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0036 0.9620 2.2353 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9695 -0.4478 1.9939 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6663 -1.1367 0.0167 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1538 0.5233 2.0823 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8495 -1.6625 0.0534 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2020 0.4542 -0.9733 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8016 1.3458 1.4919 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1755 1.8697 0.9404 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9972 2.4441 -1.0479 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5030 -1.1328 -2.5821 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9177 -1.5821 -1.8991 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4603 -2.3182 -1.2517 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9968 -1.0743 -0.1686 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8101 0.6907 -0.0880 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9735 -0.2835 1.1434 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4981 -2.0736 2.1337 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 17 20 1 0 20 21 1 0 20 22 1 0 16 23 1 0 1 24 1 0 1 25 1 0 1 26 1 0 2 27 1 0 2 28 1 0 3 29 1 0 3 30 1 0 4 31 1 0 4 32 1 0 5 33 1 0 5 34 1 0 6 35 1 0 6 36 1 0 7 37 1 0 7 38 1 0 8 39 1 0 8 40 1 0 9 41 1 0 9 42 1 0 10 43 1 0 10 44 1 0 11 45 1 0 11 46 1 0 12 47 1 0 12 48 1 0 13 49 1 0 13 50 1 0 14 51 1 0 15 52 1 0 16 53 1 6 17 54 1 6 18 55 1 0 18 56 1 0 19 57 1 0 21 58 1 0 21 59 1 0 21 60 1 0 22 61 1 0 22 62 1 0 22 63 1 0 23 64 1 0 M END

Standard InCHIKey	YRXOQXUDKDCXME-YIVRLKKSSA-N
Standard InCHI	InChI=1S/C20H41NO2/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)19(18-22)21(2)3/h16-17,19-20,22-23H,4-15,18H2,1-3H3/b17-16+/t19-,20+/m0/s1
SMILES	CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N(C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	327.31	Volume:	380.417 ? Van der Waals volume.
Dense:	0.86	LogP:	4.19 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.249 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.592 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	1.0
TPSA:	43.7 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	0.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.323	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.253	Fsp³:	0.9
MCE-18:	3.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.339	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.276	Promiscuous compounds:	0.246

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.162	MDCK Permeability:	-4.771
Pgp-inhibitor:	0.0	Pgp-substrate:	0.261
PAMPA:	0.006 ? 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):	0.956
20% Bioavailability (F20%):	0.992	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.058
Plasma Protein Binding (PPB):	98.31%	Volume Distribution (VD):	0.864
Fu:	2.563% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.593
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.676
BSEP inhibitor:	0.406

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.61	CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.943	CYP2D6-substrate:	0.005
CYP3A4-inhibitor:	0.083	CYP3A4-substrate:	0.758
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.59 ? 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):

5.033

Half-life (T1/2):

0.87

ADMET: Toxicity

hERG Blockers:	0.158	hERG Blockers (10um):	0.422
Human Hepatotoxicity (H-HT):	0.885	Drug-induced Liver Injury (DILI):	0.492
AMES Toxicity:	0.02	Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.114	Skin Sensitization:	0.999
Carcinogencity:	0.075	Eye Corrosion:	0.126
Eye Irritation:	0.921	Respiratory Toxicity:	0.904
Drug-induced Neurotoxicity:	0.045	Ototoxicity:	0.762
Hematotoxicity:	0.41	Drug-induced Nephrotoxicity:	0.572
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.113
A549 Cytotoxicity:	0.56	Hek293 Cytotoxicity:	0.133
BCF:	1.587 ? 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:	4.831 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.043 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.025 ? 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
NPO33030	Haliclona koremella	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9644076]

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
FC	1
IC50	12
Activity	4
Inhibition	15
Ki	6

Activity Type	# Activity
Individual protein	34
Cell line	3
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT150	Individual protein	Anthrax lethal factor	Bacillus anthracis	FC	=	6.4	n.a.	PMID[17485504]
NPT150	Individual protein	Anthrax lethal factor	Bacillus anthracis	IC50	=	2300.0	nM	PMID[17485504]
NPT3193	Individual protein	Sphingosine kinase 1	Homo sapiens	IC50	=	5700.0	nM	PMID[19469544]
NPT3194	Individual protein	Sphingosine kinase 2	Homo sapiens	Activity	=	66.97	%	PMID[19469544]
NPT3193	Individual protein	Sphingosine kinase 1	Homo sapiens	Activity	=	58.04	%	PMID[19469544]
NPT3194	Individual protein	Sphingosine kinase 2	Homo sapiens	Inhibition	=	33.03	%	PMID[19469544]
NPT3193	Individual protein	Sphingosine kinase 1	Homo sapiens	Inhibition	=	41.96	%	PMID[19469544]
NPT3193	Individual protein	Sphingosine kinase 1	Homo sapiens	Ki	=	6000.0	nM	PMID[19469544]
NPT3194	Individual protein	Sphingosine kinase 2	Homo sapiens	Ki	=	12500.0	nM	PMID[19469544]
NPT3193	Individual protein	Sphingosine kinase 1	Homo sapiens	IC50	=	2170.0	nM	PMID[19467599]
NPT3194	Individual protein	Sphingosine kinase 2	Homo sapiens	IC50	>	80000.0	nM	PMID[19467599]
NPT3193	Individual protein	Sphingosine kinase 1	Homo sapiens	IC50	=	5700.0	nM	PMID[19800228]
NPT3455	Individual protein	Protein kinase C zeta	Homo sapiens	Inhibition	=	99.1	%	PMID[21868240]
NPT3124	Individual protein	Protein kinase C eta	Homo sapiens	Inhibition	=	43.8	%	PMID[21868240]
NPT3124	Individual protein	Protein kinase C eta	Homo sapiens	Inhibition	=	100.4	%	PMID[21868240]
NPT182	Individual protein	Protein kinase C alpha	Homo sapiens	Inhibition	=	35.0	%	PMID[21868240]
NPT3194	Individual protein	Sphingosine kinase 2	Homo sapiens	Inhibition	=	50.0	%	PMID[21868240]
NPT3193	Individual protein	Sphingosine kinase 1	Homo sapiens	Inhibition	=	50.0	%	PMID[21868240]
NPT3193	Individual protein	Sphingosine kinase 1	Homo sapiens	Ki	=	5000.0	nM	PMID[24471412]
NPT3194	Individual protein	Sphingosine kinase 2	Homo sapiens	Ki	=	12000.0	nM	PMID[24471412]
NPT3193	Individual protein	Sphingosine kinase 1	Homo sapiens	IC50	=	35790.0	nM	DOI[10.1039/C4MD00312H]
NPT3194	Individual protein	Sphingosine kinase 2	Homo sapiens	IC50	=	16300.0	nM	DOI[10.1039/C4MD00312H]
NPT3194	Individual protein	Sphingosine kinase 2	Homo sapiens	Ki	=	14000.0	nM	PMID[27255176]
NPT3193	Individual protein	Sphingosine kinase 1	Homo sapiens	Ki	=	16000.0	nM	PMID[27255176]
NPT3193	Individual protein	Sphingosine kinase 1	Homo sapiens	IC50	=	50560.0	nM	PMID[27255176]
NPT3194	Individual protein	Sphingosine kinase 2	Homo sapiens	IC50	=	26290.0	nM	PMID[27255176]
NPT3193	Individual protein	Sphingosine kinase 1	Homo sapiens	IC50	=	60000.0	nM	PMID[28408190]
NPT3194	Individual protein	Sphingosine kinase 2	Homo sapiens	IC50	=	20000.0	nM	PMID[28408190]
NPT880	Individual protein	Protein kinase C gamma	Homo sapiens	Inhibition	=	49.2	%	PMID[21868240]
NPT761	Individual protein	Protein kinase C epsilon	Homo sapiens	Inhibition	=	40.4	%	PMID[21868240]
NPT881	Individual protein	Protein kinase C delta	Homo sapiens	Inhibition	=	83.9	%	PMID[21868240]
NPT887	Individual protein	Protein kinase C theta	Homo sapiens	Inhibition	=	47.1	%	PMID[21868240]
NPT760	Individual protein	Protein kinase C beta	Homo sapiens	Inhibition	=	44.3	%	PMID[21868240]
NPT760	Individual protein	Protein kinase C beta	Homo sapiens	Inhibition	=	68.5	%	PMID[21868240]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT21880	Cell line	FL5.12	Mus musculus	IC50	=	800.0	nM	PMID[27475534]
NPT21880	Cell line	FL5.12	Mus musculus	Activity	=	69.0	%	PMID[27475534]
NPT21880	Cell line	FL5.12	Mus musculus	Activity	=	72.0	n.a.	PMID[27475534]
NPT2	Others	Unspecified	n.a.	Inhibition	~	47.0	%	PMID[10560747]

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 NPC489234 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	35040
0.1-0.2	13648
0.2-0.3	958
0.3-0.4	189
0.4-0.5	23
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	Natural Product ID
		NPC

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC489234 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7319
0.1-0.2	1765
0.2-0.3	59
0.3-0.4	6
0.4-0.5	1
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