NPASS Compound

Natural Product: NPC136768

Natural Product ID	NPC136768
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-Beta-D-Xylopyranosyl-(1->3)-Alpha-L-Rhamnopyranosyl-(1->2)-[Beta-D-Glucopyranosyl-(1->4)]-Alpha-L-Arabinopyranosyl Siaresinolic Acid 28-O-Alpha-L-Rhamnopyranosyl-(1->4)-Beta-D-Glucopyranosyl-(1->6)-Beta-D-Glucopyranosyl Ester
IUPAC Name	[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (1S,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-1-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2430035
PubChem CID	72189540
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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

Chemical Representations

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105219 1 0 M END

Standard InCHIKey	FRALZQPZQJMQEK-MKSLBANYSA-N
Standard InCHI	InChI=1S/C70H114O35/c1-25-37(74)43(80)48(85)59(95-25)102-53-30(21-72)98-57(51(88)46(53)83)93-23-31-41(78)45(82)50(87)61(99-31)105-64(91)70-18-16-65(3,4)56(90)36(70)27-10-11-34-67(7)14-13-35(66(5,6)33(67)12-15-69(34,9)68(27,8)17-19-70)101-63-55(42(79)32(24-94-63)100-60-49(86)44(81)40(77)29(20-71)97-60)104-62-52(89)54(38(75)26(2)96-62)103-58-47(84)39(76)28(73)22-92-58/h10,25-26,28-63,71-90H,11-24H2,1-9H3/t25-,26-,28+,29+,30+,31+,32-,33-,34+,35-,36+,37-,38-,39-,40+,41+,42-,43+,44-,45-,46+,47+,48+,49+,50+,51+,52+,53+,54+,55+,56-,57+,58-,59-,60-,61-,62-,63-,67-,68+,69+,70-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC(=O)[C@@]12CCC(C)(C)[C@H]([C@H]2C2=CC[C@@H]3[C@@]4(C)CC[C@@H](C(C)(C)[C@@H]4CC[C@@]3(C)[C@]2(C)CC1)O[C@H]1[C@@H]([C@H]([C@H](CO1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1514.71	Volume:	1418.983 ? Van der Waals volume.
Dense:	1.067	LogP:	0.18 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.977 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.987 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	18.0	Rigid Bonds:	69.0
TPSA:	550.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	35.0
H-Bond Donor:	20.0	Rings:	12.0
Heavy Atoms:	35.0

MedChem Properties

QED Drug-Likeness Score:	0.037	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.348	Fsp³:	0.957
MCE-18:	263.474 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.693	Fluc inhibitor:	0.007 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.022 ? 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:	0.432	Promiscuous compounds:	0.048

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.501	MDCK Permeability:	-4.896
Pgp-inhibitor:	0.0	Pgp-substrate:	0.99
PAMPA:	1.0 ? 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):	0.999
20% Bioavailability (F20%):	0.922	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.001
Plasma Protein Binding (PPB):	41.535%	Volume Distribution (VD):	-0.258
Fu:	23.873% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.066
HLM stability:	0.017 ? 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):

-1.777

Half-life (T1/2):

5.518

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.574	Drug-induced Liver Injury (DILI):	0.99
AMES Toxicity:	0.993	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.001	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.559	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	0.049	RPMI-8226 Immunitoxicity:	0.657
A549 Cytotoxicity:	0.914	Hek293 Cytotoxicity:	0.265
BCF:	0.947 ? 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:	3.363 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.844 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.766 ? 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
NPO32682	anemone taipaiensis	Species	Ranunculaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23992864]
NPO32682	anemone taipaiensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
IC50	5

Activity Type	# Activity
Cell line	4
Non-molecular	1

Molecular-level activity

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

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	80000.0	nM	PMID[18676884]
NPT81	Cell line	A549	Homo sapiens	IC50	>	80000.0	nM	DrugMatrix in vitro pharmacology data
NPT116	Cell line	HL-60	Homo sapiens	IC50	>	80000.0	nM	PMID[18077363]
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	80000.0	nM	DrugMatrix in vitro pharmacology data
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	43560.0	nM	PMID[23992864]

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 NPC136768 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	26137
0.1-0.2	19952
0.2-0.3	2489
0.3-0.4	696
0.4-0.5	371
0.5-0.6	134
0.6-0.7	35
0.7-0.8	0
0.8-0.85	4
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9196	High Similarity	NPC110633
0.8814	High Similarity	NPC250247
0.839	Intermediate Similarity	NPC43550
0.8017	Intermediate Similarity	NPC236638
0.8017	Intermediate Similarity	NPC294453
0.8017	Intermediate Similarity	NPC305981
0.7951	Intermediate Similarity	NPC261506
0.7951	Intermediate Similarity	NPC4328
0.7851	Intermediate Similarity	NPC41061
0.7851	Intermediate Similarity	NPC227551
0.7838	Intermediate Similarity	NPC148417
0.7787	Intermediate Similarity	NPC65105
0.775	Intermediate Similarity	NPC481080
0.744	Intermediate Similarity	NPC202828
0.744	Intermediate Similarity	NPC119592
0.7381	Intermediate Similarity	NPC298034
0.7381	Intermediate Similarity	NPC71065
0.7355	Intermediate Similarity	NPC135904
0.7355	Intermediate Similarity	NPC123199
0.7266	Intermediate Similarity	NPC220160
0.719	Intermediate Similarity	NPC79643
0.7107	Intermediate Similarity	NPC60557
0.7107	Intermediate Similarity	NPC67857
0.7097	Intermediate Similarity	NPC488560
0.7059	Intermediate Similarity	NPC295823
0.7059	Intermediate Similarity	NPC174720
0.7059	Intermediate Similarity	NPC475467
0.7031	Intermediate Similarity	NPC481081
0.7016	Intermediate Similarity	NPC475160
0.7016	Intermediate Similarity	NPC473714
0.6992	Remote Similarity	NPC165204
0.6984	Remote Similarity	NPC476068
0.686	Remote Similarity	NPC481078
0.6829	Remote Similarity	NPC475287
0.6727	Remote Similarity	NPC128925
0.672	Remote Similarity	NPC471384
0.6692	Remote Similarity	NPC293330
0.6615	Remote Similarity	NPC258617
0.6565	Remote Similarity	NPC471385
0.6562	Remote Similarity	NPC54636
0.656	Remote Similarity	NPC76972
0.656	Remote Similarity	NPC469782
0.656	Remote Similarity	NPC204414
0.6504	Remote Similarity	NPC241909
0.6441	Remote Similarity	NPC161674
0.6439	Remote Similarity	NPC161717
0.6424	Remote Similarity	NPC481323
0.6424	Remote Similarity	NPC469778
0.6406	Remote Similarity	NPC166422
0.6376	Remote Similarity	NPC469776
0.6364	Remote Similarity	NPC63159
0.6358	Remote Similarity	NPC32723
0.6346	Remote Similarity	NPC295941
0.6336	Remote Similarity	NPC57484
0.629	Remote Similarity	NPC481079
0.6241	Remote Similarity	NPC475514
0.6234	Remote Similarity	NPC135334
0.614	Remote Similarity	NPC256798
0.6131	Remote Similarity	NPC224381
0.6116	Remote Similarity	NPC112352
0.6107	Remote Similarity	NPC100639
0.609	Remote Similarity	NPC481324
0.6066	Remote Similarity	NPC160415
0.6058	Remote Similarity	NPC70809
0.6031	Remote Similarity	NPC251263
0.5954	Remote Similarity	NPC323341
0.5949	Remote Similarity	NPC469777
0.5948	Remote Similarity	NPC469775
0.5938	Remote Similarity	NPC469772
0.5935	Remote Similarity	NPC469774
0.5909	Remote Similarity	NPC219180
0.5909	Remote Similarity	NPC155410
0.5902	Remote Similarity	NPC469946
0.5887	Remote Similarity	NPC101744
0.5882	Remote Similarity	NPC48499
0.5878	Remote Similarity	NPC192600
0.5864	Remote Similarity	NPC469773
0.5823	Remote Similarity	NPC100925
0.5806	Remote Similarity	NPC104071
0.5806	Remote Similarity	NPC309714
0.576	Remote Similarity	NPC102439
0.5746	Remote Similarity	NPC470218
0.5725	Remote Similarity	NPC185466
0.5714	Remote Similarity	NPC470911
0.5692	Remote Similarity	NPC473826
0.5691	Remote Similarity	NPC295371
0.5669	Remote Similarity	NPC475504
0.5669	Remote Similarity	NPC297263
0.5667	Remote Similarity	NPC78046
0.5652	Remote Similarity	NPC470876
0.5635	Remote Similarity	NPC173859
0.5635	Remote Similarity	NPC148603
0.563	Remote Similarity	NPC191827
0.5629	Remote Similarity	NPC45606
0.5625	Remote Similarity	NPC134835
0.5625	Remote Similarity	NPC480422
0.5597	Remote Similarity	NPC133818
0.5583	Remote Similarity	NPC204458
0.5583	Remote Similarity	NPC90856
0.5573	Remote Similarity	NPC31838
0.5548	Remote Similarity	NPC478559
0.5548	Remote Similarity	NPC478560
0.5547	Remote Similarity	NPC257468
0.5538	Remote Similarity	NPC301449
0.5538	Remote Similarity	NPC601290
0.5532	Remote Similarity	NPC309223
0.5532	Remote Similarity	NPC302543
0.5512	Remote Similarity	NPC46665
0.5512	Remote Similarity	NPC480475
0.549	Remote Similarity	NPC220838
0.5486	Remote Similarity	NPC102505
0.5486	Remote Similarity	NPC488514
0.5469	Remote Similarity	NPC68175
0.5468	Remote Similarity	NPC286457
0.5462	Remote Similarity	NPC73318
0.5455	Remote Similarity	NPC207738
0.5455	Remote Similarity	NPC187290
0.5448	Remote Similarity	NPC610204
0.5441	Remote Similarity	NPC475209
0.542	Remote Similarity	NPC324875
0.542	Remote Similarity	NPC292677
0.5407	Remote Similarity	NPC123522
0.5403	Remote Similarity	NPC475516
0.5391	Remote Similarity	NPC473459
0.5385	Remote Similarity	NPC469821
0.5379	Remote Similarity	NPC488564
0.5374	Remote Similarity	NPC33012
0.536	Remote Similarity	NPC58448
0.5354	Remote Similarity	NPC223301
0.5354	Remote Similarity	NPC171544
0.5344	Remote Similarity	NPC104372
0.5338	Remote Similarity	NPC36831
0.5338	Remote Similarity	NPC609281
0.5333	Remote Similarity	NPC473824
0.5317	Remote Similarity	NPC470512
0.5308	Remote Similarity	NPC123796
0.5306	Remote Similarity	NPC8524
0.5299	Remote Similarity	NPC470915
0.5294	Remote Similarity	NPC472268
0.529	Remote Similarity	NPC471550
0.529	Remote Similarity	NPC475140
0.5267	Remote Similarity	NPC601659
0.5248	Remote Similarity	NPC13998
0.5238	Remote Similarity	NPC473373
0.5231	Remote Similarity	NPC105800
0.5231	Remote Similarity	NPC470515
0.5229	Remote Similarity	NPC297950
0.5227	Remote Similarity	NPC114484
0.5224	Remote Similarity	NPC475486
0.5221	Remote Similarity	NPC268184
0.5217	Remote Similarity	NPC191763
0.5217	Remote Similarity	NPC603137
0.5214	Remote Similarity	NPC85154
0.5212	Remote Similarity	NPC488203
0.5194	Remote Similarity	NPC30735
0.5191	Remote Similarity	NPC481082
0.5191	Remote Similarity	NPC222580
0.5191	Remote Similarity	NPC164419
0.5188	Remote Similarity	NPC606145
0.5185	Remote Similarity	NPC606553
0.5159	Remote Similarity	NPC235405
0.5157	Remote Similarity	NPC311178
0.5156	Remote Similarity	NPC213674
0.5155	Remote Similarity	NPC472269
0.5154	Remote Similarity	NPC251768
0.5152	Remote Similarity	NPC471435
0.5152	Remote Similarity	NPC471434
0.5152	Remote Similarity	NPC484832
0.5132	Remote Similarity	NPC489208
0.513	Remote Similarity	NPC484831
0.513	Remote Similarity	NPC484830
0.5118	Remote Similarity	NPC249848
0.5118	Remote Similarity	NPC107966
0.5115	Remote Similarity	NPC258885
0.5115	Remote Similarity	NPC139044
0.5115	Remote Similarity	NPC235438
0.5113	Remote Similarity	NPC37134
0.5111	Remote Similarity	NPC104137
0.5111	Remote Similarity	NPC26626
0.5109	Remote Similarity	NPC607904
0.5109	Remote Similarity	NPC610461
0.5108	Remote Similarity	NPC309907
0.5097	Remote Similarity	NPC329893
0.5096	Remote Similarity	NPC233223
0.5096	Remote Similarity	NPC183816
0.5096	Remote Similarity	NPC43589
0.509	Remote Similarity	NPC488202
0.5081	Remote Similarity	NPC189884
0.5081	Remote Similarity	NPC138334
0.5075	Remote Similarity	NPC323359
0.507	Remote Similarity	NPC21691
0.5066	Remote Similarity	NPC475368
0.5042	Remote Similarity	NPC116794
0.504	Remote Similarity	NPC29069
0.5039	Remote Similarity	NPC263756
0.5038	Remote Similarity	NPC10607
0.5038	Remote Similarity	NPC164389
0.5037	Remote Similarity	NPC480473
0.5037	Remote Similarity	NPC80986

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC136768 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7955
0.1-0.2	1137
0.2-0.3	49
0.3-0.4	9
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