NPASS Compound

Structure

NPC254581 OpenBabel07101719402D 44 51 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 -2.6587 -2.6652 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 -1.9574 -2.9201 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 0.3846 -3.1290 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 1.1507 -3.3218 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 -2.1936 -2.2383 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 2.4185 -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 -1.4908 -3.4706 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 -0.1987 -2.8875 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 1 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 -0.7513 -3.1930 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 -0.2550 -1.8890 0.0000 Br 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 38 1 0 0 0 0 2 39 1 0 0 0 0 3 41 1 0 0 0 0 4 42 1 0 0 0 0 5 6 2 0 0 0 0 5 19 1 0 0 0 0 6 29 1 0 0 0 0 7 9 1 0 0 0 0 7 21 1 0 0 0 0 8 10 1 0 0 0 0 8 22 1 0 0 0 0 9 38 1 0 0 0 0 10 39 1 0 0 0 0 11 19 2 0 0 0 0 11 24 1 0 0 0 0 12 20 2 0 0 0 0 12 25 1 0 0 0 0 13 20 1 0 0 0 0 13 26 2 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 16 30 1 0 0 0 0 17 22 2 0 0 0 0 17 32 1 0 0 0 0 18 23 2 0 0 0 0 18 31 1 0 0 0 0 21 23 1 0 0 0 0 22 33 1 0 0 0 0 23 27 1 0 0 0 0 24 25 1 0 0 0 0 24 29 2 0 0 0 0 25 34 2 0 0 0 0 26 34 1 0 0 0 0 26 37 1 0 0 0 0 27 15 1 1 0 0 0 27 38 1 0 0 0 0 28 14 1 6 0 0 0 28 33 1 0 0 0 0 28 39 1 0 0 0 0 29 41 1 0 0 0 0 30 31 2 0 0 0 0 30 43 1 0 0 0 0 31 44 1 0 0 0 0 32 35 2 0 0 0 0 32 42 1 0 0 0 0 33 36 2 0 0 0 0 34 40 1 0 0 0 0 35 36 1 0 0 0 0 35 43 1 0 0 0 0 36 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	654.17
Volume:	616.351
LogP:	7.117
LogD:	3.944
LogS:	-7.281
# Rotatable Bonds:	2
TPSA:	63.63
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	8
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.21
Synthetic Accessibility Score:	5.903
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:	-5.875
MDCK Permeability:	2.1528347133425996e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.787
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.161
30% Bioavailability (F30%):	0.881

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.296
Plasma Protein Binding (PPB):	88.39096069335938%
Volume Distribution (VD):	1.34
Pgp-substrate:	9.361848831176758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.098
CYP1A2-substrate:	0.964
CYP2C19-inhibitor:	0.181
CYP2C19-substrate:	0.96
CYP2C9-inhibitor:	0.055
CYP2C9-substrate:	0.55
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.956
CYP3A4-inhibitor:	0.077
CYP3A4-substrate:	0.951

ADMET: Excretion

Clearance (CL):	7.57
Half-life (T1/2):	0.087

ADMET: Toxicity

hERG Blockers:	0.958
Human Hepatotoxicity (H-HT):	0.04
Drug-inuced Liver Injury (DILI):	0.772
AMES Toxicity:	0.068
Rat Oral Acute Toxicity:	0.458
Maximum Recommended Daily Dose:	0.995
Skin Sensitization:	0.847
Carcinogencity:	0.038
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.575

Download Data

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

Natural Product: NPC254581

Natural Product ID:	NPC254581
*Common Name:**	FWGCIVBZBPEQOD-NSOVKSMOSA-N
IUPAC Name:	n.a.
Synonyms:	13'-Bromo-Tiliacorinine
Standard InCHIKey:	FWGCIVBZBPEQOD-NSOVKSMOSA-N
Standard InCHI:	InChI=1S/C36H35BrN2O5/c1-38-9-7-21-16-30-31-18-23(21)27(38)15-20-12-25(34(40)26(37)13-20)24-11-19(5-6-29(24)41-3)14-28-33-22(8-10-39(28)2)17-32(42-4)35(43-30)36(33)44-31/h5-6,11-13,16-18,27-28,40H,7-10,14-15H2,1-4H3/t27-,28-/m0/s1
SMILES:	CN1CCc2cc3c4cc2[C@@H]1Cc1cc(-c2cc(ccc2OC)C[C@H]2c5c(CCN2C)cc(c(c5O4)O3)OC)c(c(c1)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2017492
PubChem CID:	57404336
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

Activity Type	# Activity
Cell Line	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	=	20.0	ug.mL-1	PMID[506460]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	6.2	ug.mL-1	PMID[506460]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	3.1	ug.mL-1	PMID[506460]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	1.5	ug.mL-1	PMID[506460]

☑ 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 NPC254581 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	471
0.1-0.2	2172
0.2-0.3	10556
0.3-0.4	8266
0.4-0.5	6528
0.5-0.6	10782
0.6-0.7	3297
0.7-0.8	496
0.8-0.85	46
0.85-0.9	76
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9278	High Similarity	NPC139783
0.9278	High Similarity	NPC65312
0.9222	High Similarity	NPC16357
0.9222	High Similarity	NPC95426
0.9222	High Similarity	NPC302245
0.9121	High Similarity	NPC22115
0.9121	High Similarity	NPC275680
0.9027	High Similarity	NPC256124
0.8956	High Similarity	NPC274716
0.8956	High Similarity	NPC167116
0.8956	High Similarity	NPC254441
0.8901	High Similarity	NPC182052
0.8901	High Similarity	NPC290582
0.8901	High Similarity	NPC185639
0.8901	High Similarity	NPC223690
0.8901	High Similarity	NPC54654
0.8901	High Similarity	NPC279228
0.8901	High Similarity	NPC285931
0.8901	High Similarity	NPC271013
0.8901	High Similarity	NPC8836
0.8901	High Similarity	NPC42663
0.8901	High Similarity	NPC258657
0.8901	High Similarity	NPC311973
0.8901	High Similarity	NPC90998
0.8901	High Similarity	NPC181796
0.8901	High Similarity	NPC7715
0.8901	High Similarity	NPC217748
0.8901	High Similarity	NPC104196
0.8901	High Similarity	NPC222661
0.8901	High Similarity	NPC49075
0.8901	High Similarity	NPC229373
0.8901	High Similarity	NPC239824
0.8901	High Similarity	NPC251735
0.8901	High Similarity	NPC15414
0.8901	High Similarity	NPC290005
0.8901	High Similarity	NPC328155
0.8865	High Similarity	NPC206900
0.8859	High Similarity	NPC212237
0.8859	High Similarity	NPC116465
0.8846	High Similarity	NPC286119
0.8798	High Similarity	NPC30779
0.8778	High Similarity	NPC12424
0.8778	High Similarity	NPC251580
0.8778	High Similarity	NPC129518
0.8778	High Similarity	NPC41376
0.877	High Similarity	NPC478093
0.8723	High Similarity	NPC473589
0.8723	High Similarity	NPC478092
0.8723	High Similarity	NPC478091
0.8723	High Similarity	NPC30182
0.8722	High Similarity	NPC276890
0.8722	High Similarity	NPC115284
0.8722	High Similarity	NPC198498
0.8722	High Similarity	NPC317439
0.8722	High Similarity	NPC76682
0.8722	High Similarity	NPC227060
0.8722	High Similarity	NPC317145
0.8722	High Similarity	NPC63646
0.8722	High Similarity	NPC10908
0.8717	High Similarity	NPC60295
0.8717	High Similarity	NPC191132
0.8681	High Similarity	NPC293093
0.8663	High Similarity	NPC82457
0.8663	High Similarity	NPC48490
0.8663	High Similarity	NPC175890
0.8663	High Similarity	NPC274661
0.8663	High Similarity	NPC11296
0.8571	High Similarity	NPC24260
0.8548	High Similarity	NPC302275
0.8541	High Similarity	NPC239584
0.8486	Intermediate Similarity	NPC243454
0.8486	Intermediate Similarity	NPC475479
0.8457	Intermediate Similarity	NPC14507
0.8457	Intermediate Similarity	NPC47077
0.8396	Intermediate Similarity	NPC73492
0.8396	Intermediate Similarity	NPC299990
0.8333	Intermediate Similarity	NPC85381
0.8325	Intermediate Similarity	NPC318805
0.8325	Intermediate Similarity	NPC41122
0.8308	Intermediate Similarity	NPC475654
0.8297	Intermediate Similarity	NPC42549
0.8297	Intermediate Similarity	NPC240841
0.8297	Intermediate Similarity	NPC268503
0.8297	Intermediate Similarity	NPC317272
0.8297	Intermediate Similarity	NPC13916
0.8297	Intermediate Similarity	NPC250846
0.8297	Intermediate Similarity	NPC264850
0.8297	Intermediate Similarity	NPC256012
0.8247	Intermediate Similarity	NPC234318
0.8242	Intermediate Similarity	NPC24465
0.8211	Intermediate Similarity	NPC249996
0.8207	Intermediate Similarity	NPC204908
0.8207	Intermediate Similarity	NPC83198
0.8186	Intermediate Similarity	NPC38964
0.8177	Intermediate Similarity	NPC281581
0.8172	Intermediate Similarity	NPC152680
0.8172	Intermediate Similarity	NPC190783
0.8172	Intermediate Similarity	NPC232386
0.8148	Intermediate Similarity	NPC257269
0.8148	Intermediate Similarity	NPC195538
0.8148	Intermediate Similarity	NPC230276
0.8135	Intermediate Similarity	NPC473716
0.8135	Intermediate Similarity	NPC475597
0.8132	Intermediate Similarity	NPC80759
0.8132	Intermediate Similarity	NPC79402
0.8118	Intermediate Similarity	NPC239775
0.8111	Intermediate Similarity	NPC247639
0.8111	Intermediate Similarity	NPC25084
0.8105	Intermediate Similarity	NPC476202
0.8095	Intermediate Similarity	NPC119068
0.8095	Intermediate Similarity	NPC40496
0.8077	Intermediate Similarity	NPC205255
0.8077	Intermediate Similarity	NPC235143
0.8077	Intermediate Similarity	NPC271388
0.8077	Intermediate Similarity	NPC119649
0.8077	Intermediate Similarity	NPC230956
0.8065	Intermediate Similarity	NPC118274
0.8065	Intermediate Similarity	NPC168753
0.8022	Intermediate Similarity	NPC221864
0.8021	Intermediate Similarity	NPC475215
0.8021	Intermediate Similarity	NPC108434
0.8019	Intermediate Similarity	NPC82056
0.7957	Intermediate Similarity	NPC474931
0.7957	Intermediate Similarity	NPC145832
0.7957	Intermediate Similarity	NPC12053
0.7957	Intermediate Similarity	NPC158376
0.7957	Intermediate Similarity	NPC306555
0.7957	Intermediate Similarity	NPC81218
0.7957	Intermediate Similarity	NPC205421
0.7957	Intermediate Similarity	NPC117188
0.7935	Intermediate Similarity	NPC60186
0.7926	Intermediate Similarity	NPC10871
0.7906	Intermediate Similarity	NPC474507
0.7895	Intermediate Similarity	NPC241704
0.7892	Intermediate Similarity	NPC475393
0.7857	Intermediate Similarity	NPC189266
0.7857	Intermediate Similarity	NPC110416
0.7857	Intermediate Similarity	NPC2413
0.7857	Intermediate Similarity	NPC207757
0.7857	Intermediate Similarity	NPC184026
0.7857	Intermediate Similarity	NPC204828
0.7857	Intermediate Similarity	NPC39701
0.7857	Intermediate Similarity	NPC276588
0.7857	Intermediate Similarity	NPC54379
0.7857	Intermediate Similarity	NPC193949
0.7857	Intermediate Similarity	NPC249797
0.7857	Intermediate Similarity	NPC5238
0.7857	Intermediate Similarity	NPC127674
0.7857	Intermediate Similarity	NPC123323
0.7857	Intermediate Similarity	NPC295691
0.7857	Intermediate Similarity	NPC469817
0.7857	Intermediate Similarity	NPC278799
0.7857	Intermediate Similarity	NPC172765
0.7849	Intermediate Similarity	NPC477563
0.7849	Intermediate Similarity	NPC13504
0.7849	Intermediate Similarity	NPC78222
0.7849	Intermediate Similarity	NPC306843
0.7849	Intermediate Similarity	NPC196447
0.7849	Intermediate Similarity	NPC253043
0.7849	Intermediate Similarity	NPC136508
0.7849	Intermediate Similarity	NPC96603
0.7849	Intermediate Similarity	NPC212794
0.7812	Intermediate Similarity	NPC32154
0.7807	Intermediate Similarity	NPC56887
0.7807	Intermediate Similarity	NPC193853
0.7807	Intermediate Similarity	NPC223077
0.7801	Intermediate Similarity	NPC148709
0.7801	Intermediate Similarity	NPC476577
0.7801	Intermediate Similarity	NPC173416
0.7796	Intermediate Similarity	NPC324144
0.7796	Intermediate Similarity	NPC1229
0.7772	Intermediate Similarity	NPC476572
0.7754	Intermediate Similarity	NPC169743
0.7754	Intermediate Similarity	NPC209377
0.7727	Intermediate Similarity	NPC476565
0.7704	Intermediate Similarity	NPC57036
0.7696	Intermediate Similarity	NPC192135
0.7696	Intermediate Similarity	NPC66341
0.7696	Intermediate Similarity	NPC477020
0.7688	Intermediate Similarity	NPC27410
0.7688	Intermediate Similarity	NPC166014
0.7684	Intermediate Similarity	NPC109925
0.7677	Intermediate Similarity	NPC259350
0.7677	Intermediate Similarity	NPC223236
0.7672	Intermediate Similarity	NPC204947
0.7668	Intermediate Similarity	NPC320223
0.7668	Intermediate Similarity	NPC114364
0.7667	Intermediate Similarity	NPC476151
0.7667	Intermediate Similarity	NPC476144
0.7667	Intermediate Similarity	NPC210437
0.7667	Intermediate Similarity	NPC106295
0.7667	Intermediate Similarity	NPC51957
0.7667	Intermediate Similarity	NPC16107
0.7663	Intermediate Similarity	NPC99659
0.7663	Intermediate Similarity	NPC325871
0.7644	Intermediate Similarity	NPC19520
0.7644	Intermediate Similarity	NPC149090
0.7637	Intermediate Similarity	NPC88249
0.7637	Intermediate Similarity	NPC192768
0.7637	Intermediate Similarity	NPC151895

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 NPC254581 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	879
0.2-0.3	1338
0.3-0.4	2642
0.4-0.5	2236
0.5-0.6	1406
0.6-0.7	349
0.7-0.8	46
0.8-0.85	0
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.914	High Similarity	NPD8095	Phase 1
0.8901	High Similarity	NPD8054	Approved
0.8901	High Similarity	NPD8053	Approved
0.8722	High Similarity	NPD8251	Approved
0.8722	High Similarity	NPD8252	Approved
0.8722	High Similarity	NPD8099	Discontinued
0.8674	High Similarity	NPD8156	Discontinued
0.8095	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD4010	Discontinued
0.7667	Intermediate Similarity	NPD4584	Approved
0.7634	Intermediate Similarity	NPD6788	Approved
0.7525	Intermediate Similarity	NPD7906	Approved
0.7433	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4773	Phase 2
0.7419	Intermediate Similarity	NPD4772	Phase 2
0.7407	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7833	Phase 2
0.7407	Intermediate Similarity	NPD7831	Phase 2
0.7389	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD7298	Approved
0.7344	Intermediate Similarity	NPD6071	Discontinued
0.7333	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7310	Approved
0.7323	Intermediate Similarity	NPD7311	Approved
0.7323	Intermediate Similarity	NPD7313	Approved
0.7323	Intermediate Similarity	NPD7312	Approved
0.7286	Intermediate Similarity	NPD7309	Approved
0.7254	Intermediate Similarity	NPD3051	Approved
0.7236	Intermediate Similarity	NPD4577	Approved
0.7236	Intermediate Similarity	NPD4578	Approved
0.7219	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD2969	Approved
0.7216	Intermediate Similarity	NPD2970	Approved
0.7214	Intermediate Similarity	NPD4663	Approved
0.7189	Intermediate Similarity	NPD7447	Phase 1
0.7186	Intermediate Similarity	NPD7549	Discontinued
0.7179	Intermediate Similarity	NPD2489	Approved
0.7179	Intermediate Similarity	NPD27	Approved
0.715	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD2563	Approved
0.712	Intermediate Similarity	NPD2560	Approved
0.7047	Intermediate Similarity	NPD4055	Discovery
0.7043	Intermediate Similarity	NPD7213	Phase 3
0.7043	Intermediate Similarity	NPD7212	Phase 2
0.7043	Intermediate Similarity	NPD2420	Approved
0.7043	Intermediate Similarity	NPD2421	Approved
0.7041	Intermediate Similarity	NPD6688	Approved
0.7041	Intermediate Similarity	NPD6687	Approved
0.7027	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD1424	Approved
0.7005	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD2898	Approved
0.7	Intermediate Similarity	NPD4675	Approved
0.7	Intermediate Similarity	NPD4678	Approved
0.6995	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5677	Discontinued
0.6931	Remote Similarity	NPD6030	Approved
0.6931	Remote Similarity	NPD6031	Approved
0.6919	Remote Similarity	NPD4481	Phase 3
0.6907	Remote Similarity	NPD8153	Approved
0.6907	Remote Similarity	NPD8152	Approved
0.6898	Remote Similarity	NPD3845	Phase 1
0.6898	Remote Similarity	NPD7124	Phase 2
0.6887	Remote Similarity	NPD3450	Approved
0.6887	Remote Similarity	NPD2494	Approved
0.6887	Remote Similarity	NPD2493	Approved
0.6887	Remote Similarity	NPD3452	Approved
0.6878	Remote Similarity	NPD6090	Discontinued
0.6862	Remote Similarity	NPD7598	Phase 2
0.6859	Remote Similarity	NPD4017	Approved
0.6857	Remote Similarity	NPD2975	Approved
0.6857	Remote Similarity	NPD2973	Approved
0.6857	Remote Similarity	NPD2974	Approved
0.6853	Remote Similarity	NPD7802	Discontinued
0.6853	Remote Similarity	NPD6107	Approved
0.6845	Remote Similarity	NPD5241	Discontinued
0.6842	Remote Similarity	NPD2122	Discontinued
0.6842	Remote Similarity	NPD3641	Approved
0.6842	Remote Similarity	NPD3640	Phase 3
0.6842	Remote Similarity	NPD3639	Approved
0.684	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.683	Remote Similarity	NPD6997	Phase 2
0.6816	Remote Similarity	NPD42	Phase 2
0.6816	Remote Similarity	NPD6042	Phase 2
0.6804	Remote Similarity	NPD5773	Approved
0.6804	Remote Similarity	NPD5772	Approved
0.6796	Remote Similarity	NPD4474	Approved
0.6796	Remote Similarity	NPD4475	Approved
0.6792	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD4583	Approved
0.6791	Remote Similarity	NPD4582	Approved
0.6788	Remote Similarity	NPD6072	Discontinued
0.6787	Remote Similarity	NPD7047	Phase 3
0.6786	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2488	Approved
0.6779	Remote Similarity	NPD2490	Approved
0.6776	Remote Similarity	NPD5006	Approved
0.6776	Remote Similarity	NPD5005	Approved
0.6771	Remote Similarity	NPD4005	Discontinued
0.6761	Remote Similarity	NPD4580	Approved
0.6744	Remote Similarity	NPD4002	Approved
0.6744	Remote Similarity	NPD4004	Approved
0.6738	Remote Similarity	NPD5177	Phase 3
0.6737	Remote Similarity	NPD4123	Phase 3
0.6702	Remote Similarity	NPD6748	Discontinued
0.6699	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD3124	Discontinued
0.6667	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.665	Remote Similarity	NPD5312	Approved
0.665	Remote Similarity	NPD2971	Approved
0.665	Remote Similarity	NPD5313	Approved
0.665	Remote Similarity	NPD2968	Approved
0.665	Remote Similarity	NPD3337	Discontinued
0.6649	Remote Similarity	NPD2200	Suspended
0.6648	Remote Similarity	NPD5718	Phase 2
0.6648	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6666	Approved
0.6632	Remote Similarity	NPD6667	Approved
0.663	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD7671	Approved
0.6621	Remote Similarity	NPD7672	Approved
0.662	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD6853	Approved
0.6618	Remote Similarity	NPD6851	Approved
0.6615	Remote Similarity	NPD2183	Approved
0.6615	Remote Similarity	NPD2184	Approved
0.6614	Remote Similarity	NPD7466	Approved
0.6602	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD4420	Approved
0.6585	Remote Similarity	NPD6297	Approved
0.6582	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD3692	Discontinued
0.6577	Remote Similarity	NPD7827	Phase 1
0.6559	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD7590	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4908	Phase 1
0.6538	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD7479	Phase 2
0.6535	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.652	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD7037	Approved
0.6503	Remote Similarity	NPD4625	Phase 3
0.65	Remote Similarity	NPD8398	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5709	Phase 3
0.6495	Remote Similarity	NPD5976	Discontinued
0.6492	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7907	Approved
0.649	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD4873	Discontinued
0.6486	Remote Similarity	NPD1613	Approved
0.6486	Remote Similarity	NPD2238	Phase 2
0.6486	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD4166	Phase 2
0.6484	Remote Similarity	NPD4040	Phase 1
0.6484	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4236	Phase 3
0.6474	Remote Similarity	NPD3060	Approved
0.6474	Remote Similarity	NPD4237	Approved
0.6471	Remote Similarity	NPD6895	Approved
0.6471	Remote Similarity	NPD6896	Approved
0.6471	Remote Similarity	NPD6111	Discontinued
0.6471	Remote Similarity	NPD5938	Phase 3
0.6468	Remote Similarity	NPD4666	Phase 3
0.6467	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4585	Approved
0.6465	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.645	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5090	Approved
0.6447	Remote Similarity	NPD5089	Approved
0.6447	Remote Similarity	NPD7438	Suspended
0.6445	Remote Similarity	NPD7291	Discontinued
0.6443	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD7177	Discontinued
0.6436	Remote Similarity	NPD1753	Discontinued
0.6413	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7427	Discontinued
0.6408	Remote Similarity	NPD5844	Phase 1
0.6406	Remote Similarity	NPD2677	Approved
0.6402	Remote Similarity	NPD7125	Discontinued
0.64	Remote Similarity	NPD7773	Phase 2
0.6396	Remote Similarity	NPD7701	Phase 2
0.6392	Remote Similarity	NPD7020	Approved
0.6392	Remote Similarity	NPD7019	Approved
0.6387	Remote Similarity	NPD4162	Approved
0.6386	Remote Similarity	NPD2904	Discontinued
0.6385	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD5525	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