NPASS Compound

Structure

NPC139783 OpenBabel07101718222D 43 50 0 0 1 0 0 0 0 0999 V2000 2.4185 -4.2224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5054 0.1318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1823 -5.0019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2805 -2.0338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3846 -3.1290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6587 -2.6652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1987 -2.8875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6149 -3.2951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2846 -1.7224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3387 -0.7153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2846 -2.7224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5348 -0.5144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1412 -3.9079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9574 -2.9201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1507 -3.3218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1676 -1.5171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4185 -0.2224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9320 -1.4178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6865 -1.2224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5595 -3.7356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1936 -2.2383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4185 -1.2224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4146 -0.9856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5525 -1.7224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8569 -3.8154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4908 -3.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5525 -2.7224 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8828 -0.8541 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7513 -3.1930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0951 -3.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5525 0.2776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6865 -0.2224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2931 -1.3100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3777 -0.3387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0209 -0.7432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7205 -0.0406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4185 -3.2224 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8068 -0.5838 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5669 -2.6144 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2495 -4.6416 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2848 -2.1261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0325 -0.6016 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 37 1 0 0 0 0 2 38 1 0 0 0 0 3 40 1 0 0 0 0 4 41 1 0 0 0 0 5 7 2 0 0 0 0 5 20 1 0 0 0 0 6 8 2 0 0 0 0 6 21 1 0 0 0 0 7 29 1 0 0 0 0 8 30 1 0 0 0 0 9 11 1 0 0 0 0 9 22 1 0 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 37 1 0 0 0 0 12 38 1 0 0 0 0 13 20 2 0 0 0 0 13 25 1 0 0 0 0 14 21 2 0 0 0 0 14 26 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 22 2 0 0 0 0 17 31 1 0 0 0 0 18 23 2 0 0 0 0 18 33 1 0 0 0 0 19 24 2 0 0 0 0 19 32 1 0 0 0 0 22 24 1 0 0 0 0 23 34 1 0 0 0 0 24 27 1 0 0 0 0 25 26 1 0 0 0 0 25 29 2 0 0 0 0 26 30 2 0 0 0 0 27 15 1 1 0 0 0 27 37 1 0 0 0 0 28 16 1 1 0 0 0 28 34 1 0 0 0 0 28 38 1 0 0 0 0 29 39 1 0 0 0 0 30 40 1 0 0 0 0 31 32 2 0 0 0 0 31 42 1 0 0 0 0 32 43 1 0 0 0 0 33 35 2 0 0 0 0 33 41 1 0 0 0 0 34 36 2 0 0 0 0 35 36 1 0 0 0 0 35 42 1 0 0 0 0 36 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.26
Volume:	597.067
LogP:	6.882
LogD:	3.955
LogS:	-7.358
# Rotatable Bonds:	2
TPSA:	63.63
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	8
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.247
Synthetic Accessibility Score:	5.794
Fsp3:	0.333
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.755
MDCK Permeability:	2.0571536879288033e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.89
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.517
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.383
Plasma Protein Binding (PPB):	78.6504135131836%
Volume Distribution (VD):	1.376
Pgp-substrate:	11.283672332763672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.09
CYP1A2-substrate:	0.957
CYP2C19-inhibitor:	0.073
CYP2C19-substrate:	0.954
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.586
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.96
CYP3A4-inhibitor:	0.073
CYP3A4-substrate:	0.949

ADMET: Excretion

Clearance (CL):	8.969
Half-life (T1/2):	0.109

ADMET: Toxicity

hERG Blockers:	0.945
Human Hepatotoxicity (H-HT):	0.026
Drug-inuced Liver Injury (DILI):	0.384
AMES Toxicity:	0.165
Rat Oral Acute Toxicity:	0.351
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.62
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.454

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC139783

Natural Product ID:	NPC139783
*Common Name:**	Tiliacorine
IUPAC Name:	n.a.
Synonyms:	Tiliacorine
Standard InCHIKey:	DQIJJKSVYLLDQW-WUFINQPMSA-N
Standard InCHI:	InChI=1S/C36H36N2O5/c1-37-11-9-22-17-31-32-19-24(22)27(37)15-20-5-7-29(39)25(13-20)26-14-21(6-8-30(26)40-3)16-28-34-23(10-12-38(28)2)18-33(41-4)35(42-31)36(34)43-32/h5-8,13-14,17-19,27-28,39H,9-12,15-16H2,1-4H3/t27-,28+/m0/s1
SMILES:	COc1cc2CCN([C@H]3c2c2c1Oc1cc4CCN([C@H](c4cc1O2)Cc1cc(c2cc(C3)ccc2OC)c(O)cc1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2017491
PubChem CID:	14527218
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO941	Tiliacora triandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22418278]
NPO941	Tiliacora triandra	Species	Menispermaceae	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	NP ID	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	1
MIC	5
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	3.87	ug.mL-1	PMID[480158]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	60.3	%	PMID[480159]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	3.1	ug.mL-1	PMID[480158]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	3.1	ug.mL-1	PMID[480158]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	6.2	ug.mL-1	PMID[480158]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC139783 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	1769
0.2-0.3	8543
0.3-0.4	9832
0.4-0.5	5277
0.5-0.6	8571
0.6-0.7	6823
0.7-0.8	1204
0.8-0.85	152
0.85-0.9	50
0.9-0.95	56
0.95-1	41

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC65312
0.994	High Similarity	NPC16357
0.994	High Similarity	NPC302245
0.994	High Similarity	NPC95426
0.9822	High Similarity	NPC275680
0.9822	High Similarity	NPC22115
0.9709	High Similarity	NPC256124
0.9645	High Similarity	NPC274716
0.9645	High Similarity	NPC254441
0.9645	High Similarity	NPC167116
0.9586	High Similarity	NPC49075
0.9586	High Similarity	NPC279228
0.9586	High Similarity	NPC285931
0.9586	High Similarity	NPC328155
0.9586	High Similarity	NPC217748
0.9586	High Similarity	NPC290582
0.9586	High Similarity	NPC42663
0.9586	High Similarity	NPC229373
0.9586	High Similarity	NPC290005
0.9586	High Similarity	NPC104196
0.9586	High Similarity	NPC8836
0.9586	High Similarity	NPC222661
0.9586	High Similarity	NPC7715
0.9586	High Similarity	NPC182052
0.9586	High Similarity	NPC258657
0.9586	High Similarity	NPC311973
0.9586	High Similarity	NPC15414
0.9586	High Similarity	NPC181796
0.9586	High Similarity	NPC223690
0.9586	High Similarity	NPC54654
0.9586	High Similarity	NPC271013
0.9586	High Similarity	NPC239824
0.9586	High Similarity	NPC90998
0.9586	High Similarity	NPC185639
0.9586	High Similarity	NPC251735
0.9535	High Similarity	NPC206900
0.9532	High Similarity	NPC116465
0.9532	High Similarity	NPC212237
0.9527	High Similarity	NPC286119
0.9471	High Similarity	NPC30779
0.9461	High Similarity	NPC12424
0.9461	High Similarity	NPC251580
0.9461	High Similarity	NPC129518
0.9461	High Similarity	NPC41376
0.9425	High Similarity	NPC478093
0.9401	High Similarity	NPC198498
0.9401	High Similarity	NPC227060
0.9401	High Similarity	NPC317145
0.9401	High Similarity	NPC63646
0.9401	High Similarity	NPC276890
0.9401	High Similarity	NPC76682
0.9401	High Similarity	NPC10908
0.9401	High Similarity	NPC317439
0.9401	High Similarity	NPC115284
0.9371	High Similarity	NPC478091
0.9371	High Similarity	NPC478092
0.9371	High Similarity	NPC30182
0.9371	High Similarity	NPC473589
0.9368	High Similarity	NPC60295
0.9368	High Similarity	NPC191132
0.9349	High Similarity	NPC293093
0.931	High Similarity	NPC82457
0.931	High Similarity	NPC175890
0.931	High Similarity	NPC274661
0.931	High Similarity	NPC48490
0.931	High Similarity	NPC11296
0.9278	High Similarity	NPC254581
0.9205	High Similarity	NPC24260
0.9191	High Similarity	NPC302275
0.9186	High Similarity	NPC239584
0.9128	High Similarity	NPC475479
0.9128	High Similarity	NPC243454
0.9086	High Similarity	NPC47077
0.9086	High Similarity	NPC14507
0.9023	High Similarity	NPC73492
0.9023	High Similarity	NPC299990
0.8939	High Similarity	NPC85381
0.8935	High Similarity	NPC256012
0.8935	High Similarity	NPC240841
0.8935	High Similarity	NPC317272
0.8935	High Similarity	NPC13916
0.8935	High Similarity	NPC268503
0.8935	High Similarity	NPC264850
0.8935	High Similarity	NPC250846
0.8935	High Similarity	NPC42549
0.8933	High Similarity	NPC41122
0.8933	High Similarity	NPC318805
0.8901	High Similarity	NPC475654
0.8876	High Similarity	NPC24465
0.884	High Similarity	NPC234318
0.883	High Similarity	NPC204908
0.883	High Similarity	NPC83198
0.8814	High Similarity	NPC249996
0.8786	High Similarity	NPC152680
0.8786	High Similarity	NPC190783
0.8786	High Similarity	NPC232386
0.8771	High Similarity	NPC281581
0.8757	High Similarity	NPC79402
0.8757	High Similarity	NPC80759
0.875	High Similarity	NPC257269
0.875	High Similarity	NPC230276
0.875	High Similarity	NPC195538
0.8743	High Similarity	NPC247639
0.8743	High Similarity	NPC25084
0.8743	High Similarity	NPC38964
0.8728	High Similarity	NPC239775
0.8722	High Similarity	NPC473716
0.8722	High Similarity	NPC475597
0.8701	High Similarity	NPC476202
0.8698	High Similarity	NPC235143
0.8698	High Similarity	NPC205255
0.8698	High Similarity	NPC230956
0.8698	High Similarity	NPC271388
0.8698	High Similarity	NPC119649
0.8693	High Similarity	NPC40496
0.8693	High Similarity	NPC119068
0.8671	High Similarity	NPC168753
0.8671	High Similarity	NPC118274
0.8639	High Similarity	NPC221864
0.8621	High Similarity	NPC108434
0.8621	High Similarity	NPC475215
0.8557	High Similarity	NPC82056
0.8555	High Similarity	NPC474931
0.8555	High Similarity	NPC306555
0.8555	High Similarity	NPC145832
0.8555	High Similarity	NPC81218
0.8555	High Similarity	NPC158376
0.8555	High Similarity	NPC12053
0.8555	High Similarity	NPC117188
0.8555	High Similarity	NPC205421
0.8538	High Similarity	NPC60186
0.8514	High Similarity	NPC10871
0.8488	Intermediate Similarity	NPC475393
0.8483	Intermediate Similarity	NPC474507
0.8475	Intermediate Similarity	NPC241704
0.8462	Intermediate Similarity	NPC204828
0.8462	Intermediate Similarity	NPC207757
0.8462	Intermediate Similarity	NPC193949
0.8462	Intermediate Similarity	NPC39701
0.8462	Intermediate Similarity	NPC172765
0.8462	Intermediate Similarity	NPC295691
0.8462	Intermediate Similarity	NPC54379
0.8462	Intermediate Similarity	NPC110416
0.8462	Intermediate Similarity	NPC189266
0.8462	Intermediate Similarity	NPC469817
0.8462	Intermediate Similarity	NPC5238
0.8462	Intermediate Similarity	NPC249797
0.8462	Intermediate Similarity	NPC127674
0.8462	Intermediate Similarity	NPC278799
0.8462	Intermediate Similarity	NPC2413
0.8462	Intermediate Similarity	NPC123323
0.8462	Intermediate Similarity	NPC276588
0.8462	Intermediate Similarity	NPC184026
0.8439	Intermediate Similarity	NPC196447
0.8439	Intermediate Similarity	NPC78222
0.8439	Intermediate Similarity	NPC212794
0.8439	Intermediate Similarity	NPC96603
0.8439	Intermediate Similarity	NPC477563
0.8439	Intermediate Similarity	NPC13504
0.8439	Intermediate Similarity	NPC306843
0.8439	Intermediate Similarity	NPC253043
0.8439	Intermediate Similarity	NPC136508
0.8391	Intermediate Similarity	NPC223077
0.8391	Intermediate Similarity	NPC56887
0.8391	Intermediate Similarity	NPC193853
0.8382	Intermediate Similarity	NPC324144
0.8382	Intermediate Similarity	NPC1229
0.838	Intermediate Similarity	NPC32154
0.8371	Intermediate Similarity	NPC173416
0.8371	Intermediate Similarity	NPC148709
0.8371	Intermediate Similarity	NPC476577
0.8363	Intermediate Similarity	NPC476572
0.8333	Intermediate Similarity	NPC209377
0.8333	Intermediate Similarity	NPC169743
0.827	Intermediate Similarity	NPC476565
0.8266	Intermediate Similarity	NPC166014
0.8266	Intermediate Similarity	NPC27410
0.8263	Intermediate Similarity	NPC51957
0.8263	Intermediate Similarity	NPC476151
0.8263	Intermediate Similarity	NPC476144
0.8263	Intermediate Similarity	NPC106295
0.8263	Intermediate Similarity	NPC16107
0.8263	Intermediate Similarity	NPC210437
0.8258	Intermediate Similarity	NPC66341
0.8258	Intermediate Similarity	NPC477020
0.8258	Intermediate Similarity	NPC192135
0.8251	Intermediate Similarity	NPC57036
0.8249	Intermediate Similarity	NPC109925
0.8246	Intermediate Similarity	NPC325871
0.8246	Intermediate Similarity	NPC99659
0.8239	Intermediate Similarity	NPC204947
0.8225	Intermediate Similarity	NPC151895
0.8225	Intermediate Similarity	NPC88249
0.8225	Intermediate Similarity	NPC220858
0.8225	Intermediate Similarity	NPC97221
0.8225	Intermediate Similarity	NPC192768
0.8222	Intermediate Similarity	NPC114364
0.8222	Intermediate Similarity	NPC320223
0.8216	Intermediate Similarity	NPC223236
0.8216	Intermediate Similarity	NPC259350

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC139783 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	783
0.2-0.3	1166
0.3-0.4	2216
0.4-0.5	2409
0.5-0.6	1561
0.6-0.7	662
0.7-0.8	126
0.8-0.85	4
0.85-0.9	0
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9586	High Similarity	NPD8054	Approved
0.9586	High Similarity	NPD8053	Approved
0.9401	High Similarity	NPD8251	Approved
0.9401	High Similarity	NPD8252	Approved
0.9401	High Similarity	NPD8099	Discontinued
0.9345	High Similarity	NPD8156	Discontinued
0.8693	High Similarity	NPD8453	Clinical (unspecified phase)
0.8441	Intermediate Similarity	NPD8095	Phase 1
0.8263	Intermediate Similarity	NPD4584	Approved
0.8208	Intermediate Similarity	NPD6788	Approved
0.8054	Intermediate Similarity	NPD7906	Approved
0.7989	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD4773	Phase 2
0.7977	Intermediate Similarity	NPD4772	Phase 2
0.7955	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD7833	Phase 2
0.7955	Intermediate Similarity	NPD7831	Phase 2
0.7931	Intermediate Similarity	NPD7298	Approved
0.7904	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD6071	Discontinued
0.7838	Intermediate Similarity	NPD7311	Approved
0.7838	Intermediate Similarity	NPD7312	Approved
0.7838	Intermediate Similarity	NPD7313	Approved
0.7838	Intermediate Similarity	NPD7310	Approved
0.7796	Intermediate Similarity	NPD7309	Approved
0.7778	Intermediate Similarity	NPD3051	Approved
0.7759	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD4578	Approved
0.7742	Intermediate Similarity	NPD4577	Approved
0.7735	Intermediate Similarity	NPD2970	Approved
0.7735	Intermediate Similarity	NPD2969	Approved
0.7733	Intermediate Similarity	NPD7447	Phase 1
0.7713	Intermediate Similarity	NPD4663	Approved
0.7692	Intermediate Similarity	NPD27	Approved
0.7692	Intermediate Similarity	NPD2489	Approved
0.7688	Intermediate Similarity	NPD7549	Discontinued
0.7667	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD2563	Approved
0.764	Intermediate Similarity	NPD2560	Approved
0.7572	Intermediate Similarity	NPD2420	Approved
0.7572	Intermediate Similarity	NPD2421	Approved
0.7572	Intermediate Similarity	NPD7213	Phase 3
0.7572	Intermediate Similarity	NPD7212	Phase 2
0.7558	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD4055	Discovery
0.7529	Intermediate Similarity	NPD1424	Approved
0.7529	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4675	Approved
0.7514	Intermediate Similarity	NPD4678	Approved
0.75	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2898	Approved
0.7473	Intermediate Similarity	NPD5677	Discontinued
0.7443	Intermediate Similarity	NPD6031	Approved
0.7443	Intermediate Similarity	NPD6030	Approved
0.7414	Intermediate Similarity	NPD7124	Phase 2
0.7414	Intermediate Similarity	NPD3845	Phase 1
0.7405	Intermediate Similarity	NPD4481	Phase 3
0.7391	Intermediate Similarity	NPD4010	Discontinued
0.7386	Intermediate Similarity	NPD6090	Discontinued
0.7371	Intermediate Similarity	NPD7598	Phase 2
0.736	Intermediate Similarity	NPD4017	Approved
0.7356	Intermediate Similarity	NPD5241	Discontinued
0.7345	Intermediate Similarity	NPD2122	Discontinued
0.7345	Intermediate Similarity	NPD3640	Phase 3
0.7345	Intermediate Similarity	NPD3639	Approved
0.7345	Intermediate Similarity	NPD3641	Approved
0.7337	Intermediate Similarity	NPD2494	Approved
0.7337	Intermediate Similarity	NPD7802	Discontinued
0.7337	Intermediate Similarity	NPD6107	Approved
0.7337	Intermediate Similarity	NPD3452	Approved
0.7337	Intermediate Similarity	NPD3450	Approved
0.7337	Intermediate Similarity	NPD2493	Approved
0.7321	Intermediate Similarity	NPD4474	Approved
0.7321	Intermediate Similarity	NPD4475	Approved
0.731	Intermediate Similarity	NPD2975	Approved
0.731	Intermediate Similarity	NPD2974	Approved
0.731	Intermediate Similarity	NPD2973	Approved
0.7309	Intermediate Similarity	NPD8153	Approved
0.7309	Intermediate Similarity	NPD8152	Approved
0.7293	Intermediate Similarity	NPD5772	Approved
0.7293	Intermediate Similarity	NPD5773	Approved
0.7287	Intermediate Similarity	NPD42	Phase 2
0.7287	Intermediate Similarity	NPD6042	Phase 2
0.7286	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6072	Discontinued
0.7268	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD4005	Discontinued
0.7251	Intermediate Similarity	NPD6997	Phase 2
0.7241	Intermediate Similarity	NPD5177	Phase 3
0.7236	Intermediate Similarity	NPD3837	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD4123	Phase 3
0.7231	Intermediate Similarity	NPD2488	Approved
0.7231	Intermediate Similarity	NPD2490	Approved
0.7228	Intermediate Similarity	NPD4582	Approved
0.7228	Intermediate Similarity	NPD4583	Approved
0.7214	Intermediate Similarity	NPD5005	Approved
0.7214	Intermediate Similarity	NPD5006	Approved
0.7212	Intermediate Similarity	NPD7047	Phase 3
0.72	Intermediate Similarity	NPD4580	Approved
0.72	Intermediate Similarity	NPD6748	Discontinued
0.7178	Intermediate Similarity	NPD4002	Approved
0.7178	Intermediate Similarity	NPD4004	Approved
0.7175	Intermediate Similarity	NPD3124	Discontinued
0.7167	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5718	Phase 2
0.7151	Intermediate Similarity	NPD2200	Suspended
0.715	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6666	Approved
0.7119	Intermediate Similarity	NPD6667	Approved
0.7105	Intermediate Similarity	NPD5312	Approved
0.7105	Intermediate Similarity	NPD5313	Approved
0.7104	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7466	Approved
0.7098	Intermediate Similarity	NPD2968	Approved
0.7098	Intermediate Similarity	NPD2971	Approved
0.7086	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6851	Approved
0.7062	Intermediate Similarity	NPD3692	Discontinued
0.7062	Intermediate Similarity	NPD6853	Approved
0.7052	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4908	Phase 1
0.7041	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6297	Approved
0.7022	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4420	Approved
0.7	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4625	Phase 3
0.6989	Remote Similarity	NPD7037	Approved
0.6986	Remote Similarity	NPD7827	Phase 1
0.6984	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7479	Phase 2
0.6977	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2238	Phase 2
0.6977	Remote Similarity	NPD1613	Approved
0.6971	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7590	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5976	Discontinued
0.6959	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6111	Discontinued
0.6954	Remote Similarity	NPD6896	Approved
0.6954	Remote Similarity	NPD6895	Approved
0.6952	Remote Similarity	NPD5709	Phase 3
0.6949	Remote Similarity	NPD4236	Phase 3
0.6949	Remote Similarity	NPD4237	Approved
0.6949	Remote Similarity	NPD3060	Approved
0.6944	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD4166	Phase 2
0.6927	Remote Similarity	NPD4873	Discontinued
0.6927	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4585	Approved
0.6915	Remote Similarity	NPD4666	Phase 3
0.6914	Remote Similarity	NPD1753	Discontinued
0.6911	Remote Similarity	NPD5938	Phase 3
0.6906	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD5090	Approved
0.6902	Remote Similarity	NPD7438	Suspended
0.6902	Remote Similarity	NPD5089	Approved
0.6901	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4040	Phase 1
0.6884	Remote Similarity	NPD7907	Approved
0.6881	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7177	Discontinued
0.6872	Remote Similarity	NPD2677	Approved
0.6869	Remote Similarity	NPD7291	Discontinued
0.6868	Remote Similarity	NPD7427	Discontinued
0.6854	Remote Similarity	NPD4162	Approved
0.6851	Remote Similarity	NPD7020	Approved
0.6851	Remote Similarity	NPD7019	Approved
0.6845	Remote Similarity	NPD7773	Phase 2
0.6839	Remote Similarity	NPD5844	Phase 1
0.6836	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD7030	Discontinued
0.6828	Remote Similarity	NPD2978	Approved
0.6828	Remote Similarity	NPD2977	Approved
0.6825	Remote Similarity	NPD2904	Discontinued
0.6821	Remote Similarity	NPD7477	Discontinued
0.6816	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6331	Phase 2
0.6816	Remote Similarity	NPD7125	Discontinued
0.6813	Remote Similarity	NPD7526	Approved
0.6813	Remote Similarity	NPD52	Approved
0.6813	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7527	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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