NPASS Compound

Structure

NPC256227 OpenBabel07101718242D 26 29 0 0 1 0 0 0 0 0999 V2000 -2.9000 -1.3394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9017 0.2580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1970 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8440 -0.0812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0785 -0.3555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 2.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9892 0.7189 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4583 0.1703 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2024 3.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7422 -0.2151 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0685 2.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0685 1.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3689 1.2446 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6034 0.9703 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2024 1.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9306 1.0562 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 4.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7871 -1.2140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 3.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5475 2.2286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 1.1215 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 6 2 0 0 0 0 5 6 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 7 2 1 6 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 15 1 0 0 0 0 8 20 1 6 0 0 0 9 12 1 0 0 0 0 9 18 1 1 0 0 0 10 17 1 0 0 0 0 10 19 1 6 0 0 0 11 13 1 0 0 0 0 11 21 1 6 0 0 0 12 16 1 0 0 0 0 12 22 1 6 0 0 0 13 14 1 0 0 0 0 13 23 1 1 0 0 0 14 18 1 1 0 0 0 14 19 1 0 0 0 0 15 18 1 1 0 0 0 15 24 1 0 0 0 0 16 19 1 6 0 0 0 16 26 1 0 0 0 0 17 25 2 0 0 0 0 17 26 1 0 0 0 0 18 3 1 1 0 0 0 19 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.18
Volume:	359.213
LogP:	0.566
LogD:	0.08
LogS:	-2.69
# Rotatable Bonds:	0
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.28
Synthetic Accessibility Score:	5.427
Fsp3:	0.842
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.763
MDCK Permeability:	0.00011049044405808672
Pgp-inhibitor:	0.002
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.554
20% Bioavailability (F20%):	0.034
30% Bioavailability (F30%):	0.547

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.13
Plasma Protein Binding (PPB):	36.10641098022461%
Volume Distribution (VD):	0.36
Pgp-substrate:	64.37594604492188%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.159
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.681
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.032

ADMET: Excretion

Clearance (CL):	3.425
Half-life (T1/2):	0.534

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.259
Drug-inuced Liver Injury (DILI):	0.145
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.498
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.073
Carcinogencity:	0.004
Eye Corrosion:	0.004
Eye Irritation:	0.011
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC256227

Natural Product ID:	NPC256227
*Common Name:**	YEMMVDQCVABATJ-AQKHGAECSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YEMMVDQCVABATJ-AQKHGAECSA-N
Standard InCHI:	InChI=1S/C19H28O7/c1-6-5-8(20)15(24)18(3)9(6)12(22)16-19(4)10(17(25)26-16)7(2)11(21)13(23)14(18)19/h7-16,20-24H,1,5H2,2-4H3/t7-,8+,9-,10-,11-,12-,13+,14-,15-,16-,18+,19+/m1/s1
SMILES:	O[C@@H]1[C@H](C)[C@@H]2C(=O)O[C@H]3[C@@]2([C@H]([C@H]1O)[C@@]1(C)[C@H](O)[C@@H](O)CC(=C)[C@@H]1[C@H]3O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3317745
PubChem CID:	10067599
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	Roots	n.a.	n.a.	PMID[14575431]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	root	n.a.	PMID[1800638]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919052]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24467387]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[25066952]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25905468]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	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
Others	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	Activity	=	96.8	%	PMID[538821]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	101.0	%	PMID[538821]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	99.71	%	PMID[538821]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	101.0	%	PMID[538821]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	98.74	%	PMID[538821]

☑ 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 NPC256227 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	219
0.1-0.2	1510
0.2-0.3	5059
0.3-0.4	10456
0.4-0.5	10851
0.5-0.6	5496
0.6-0.7	5418
0.7-0.8	3201
0.8-0.85	389
0.85-0.9	84
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.898	High Similarity	NPC102352
0.8969	High Similarity	NPC277074
0.8969	High Similarity	NPC209298
0.8958	High Similarity	NPC252614
0.8889	High Similarity	NPC144854
0.8889	High Similarity	NPC230541
0.8889	High Similarity	NPC3316
0.8878	High Similarity	NPC301787
0.8854	High Similarity	NPC477655
0.8854	High Similarity	NPC477656
0.8854	High Similarity	NPC470388
0.8817	High Similarity	NPC147272
0.88	High Similarity	NPC154608
0.88	High Similarity	NPC277017
0.88	High Similarity	NPC273155
0.88	High Similarity	NPC192813
0.8788	High Similarity	NPC222833
0.8776	High Similarity	NPC225238
0.8776	High Similarity	NPC122811
0.8764	High Similarity	NPC97505
0.8737	High Similarity	NPC29410
0.8737	High Similarity	NPC200054
0.8737	High Similarity	NPC104568
0.8713	High Similarity	NPC141350
0.8713	High Similarity	NPC154906
0.87	High Similarity	NPC186054
0.87	High Similarity	NPC166993
0.8632	High Similarity	NPC98639
0.8627	High Similarity	NPC471093
0.8614	High Similarity	NPC231278
0.8614	High Similarity	NPC63841
0.8614	High Similarity	NPC112895
0.8614	High Similarity	NPC218123
0.86	High Similarity	NPC138908
0.86	High Similarity	NPC181357
0.86	High Similarity	NPC200957
0.8586	High Similarity	NPC61442
0.8557	High Similarity	NPC162459
0.8557	High Similarity	NPC20479
0.8557	High Similarity	NPC38296
0.8557	High Similarity	NPC471038
0.8557	High Similarity	NPC28864
0.8557	High Similarity	NPC98837
0.8557	High Similarity	NPC38471
0.8557	High Similarity	NPC89099
0.8544	High Similarity	NPC29505
0.8529	High Similarity	NPC143706
0.8529	High Similarity	NPC472534
0.8515	High Similarity	NPC471474
0.8495	Intermediate Similarity	NPC77001
0.8495	Intermediate Similarity	NPC253618
0.8495	Intermediate Similarity	NPC194642
0.8469	Intermediate Similarity	NPC293866
0.8454	Intermediate Similarity	NPC470425
0.8454	Intermediate Similarity	NPC10864
0.8447	Intermediate Similarity	NPC210005
0.8438	Intermediate Similarity	NPC259042
0.8438	Intermediate Similarity	NPC470232
0.8438	Intermediate Similarity	NPC157686
0.8431	Intermediate Similarity	NPC55973
0.8431	Intermediate Similarity	NPC471094
0.8431	Intermediate Similarity	NPC37628
0.8431	Intermediate Similarity	NPC469984
0.8431	Intermediate Similarity	NPC473410
0.8427	Intermediate Similarity	NPC223330
0.8427	Intermediate Similarity	NPC209318
0.8421	Intermediate Similarity	NPC291373
0.8416	Intermediate Similarity	NPC56656
0.84	Intermediate Similarity	NPC87927
0.8384	Intermediate Similarity	NPC163963
0.8384	Intermediate Similarity	NPC52899
0.8384	Intermediate Similarity	NPC289148
0.8384	Intermediate Similarity	NPC46848
0.8384	Intermediate Similarity	NPC253886
0.8384	Intermediate Similarity	NPC121218
0.8381	Intermediate Similarity	NPC49451
0.8381	Intermediate Similarity	NPC471252
0.8367	Intermediate Similarity	NPC476806
0.8367	Intermediate Similarity	NPC476807
0.8365	Intermediate Similarity	NPC56025
0.8365	Intermediate Similarity	NPC201992
0.8365	Intermediate Similarity	NPC213320
0.8365	Intermediate Similarity	NPC188738
0.8365	Intermediate Similarity	NPC157476
0.8365	Intermediate Similarity	NPC94650
0.8351	Intermediate Similarity	NPC329910
0.8351	Intermediate Similarity	NPC219353
0.835	Intermediate Similarity	NPC102741
0.8333	Intermediate Similarity	NPC475118
0.8333	Intermediate Similarity	NPC225474
0.8333	Intermediate Similarity	NPC59530
0.8333	Intermediate Similarity	NPC284732
0.8333	Intermediate Similarity	NPC469596
0.8333	Intermediate Similarity	NPC470386
0.8333	Intermediate Similarity	NPC277399
0.8333	Intermediate Similarity	NPC67745
0.8333	Intermediate Similarity	NPC471461
0.8333	Intermediate Similarity	NPC148000
0.8333	Intermediate Similarity	NPC470385
0.8333	Intermediate Similarity	NPC78966
0.8317	Intermediate Similarity	NPC471293
0.8317	Intermediate Similarity	NPC475036
0.8316	Intermediate Similarity	NPC198054
0.8302	Intermediate Similarity	NPC117712
0.83	Intermediate Similarity	NPC304832
0.83	Intermediate Similarity	NPC76866
0.83	Intermediate Similarity	NPC246736
0.83	Intermediate Similarity	NPC88203
0.83	Intermediate Similarity	NPC214946
0.83	Intermediate Similarity	NPC148628
0.83	Intermediate Similarity	NPC275990
0.83	Intermediate Similarity	NPC170615
0.83	Intermediate Similarity	NPC286519
0.8298	Intermediate Similarity	NPC116620
0.8286	Intermediate Similarity	NPC302146
0.8286	Intermediate Similarity	NPC472002
0.8286	Intermediate Similarity	NPC474927
0.8286	Intermediate Similarity	NPC473397
0.8286	Intermediate Similarity	NPC289312
0.8286	Intermediate Similarity	NPC474516
0.8286	Intermediate Similarity	NPC473352
0.8286	Intermediate Similarity	NPC11252
0.8283	Intermediate Similarity	NPC287676
0.8283	Intermediate Similarity	NPC267921
0.8269	Intermediate Similarity	NPC473324
0.8269	Intermediate Similarity	NPC85391
0.8269	Intermediate Similarity	NPC100908
0.8269	Intermediate Similarity	NPC474786
0.8269	Intermediate Similarity	NPC320383
0.8269	Intermediate Similarity	NPC137104
0.8265	Intermediate Similarity	NPC473963
0.8265	Intermediate Similarity	NPC111348
0.8265	Intermediate Similarity	NPC43686
0.8265	Intermediate Similarity	NPC253586
0.8252	Intermediate Similarity	NPC275539
0.8252	Intermediate Similarity	NPC189075
0.8252	Intermediate Similarity	NPC19412
0.8252	Intermediate Similarity	NPC293850
0.8252	Intermediate Similarity	NPC189663
0.8252	Intermediate Similarity	NPC89860
0.8247	Intermediate Similarity	NPC90014
0.8247	Intermediate Similarity	NPC41070
0.8247	Intermediate Similarity	NPC470229
0.8235	Intermediate Similarity	NPC307660
0.8235	Intermediate Similarity	NPC472655
0.8235	Intermediate Similarity	NPC37600
0.8235	Intermediate Similarity	NPC130511
0.8235	Intermediate Similarity	NPC470587
0.8229	Intermediate Similarity	NPC244356
0.8229	Intermediate Similarity	NPC224060
0.8229	Intermediate Similarity	NPC294263
0.8229	Intermediate Similarity	NPC199543
0.8224	Intermediate Similarity	NPC474734
0.8224	Intermediate Similarity	NPC96312
0.8224	Intermediate Similarity	NPC328374
0.8224	Intermediate Similarity	NPC251236
0.8224	Intermediate Similarity	NPC179626
0.8224	Intermediate Similarity	NPC207217
0.8224	Intermediate Similarity	NPC40632
0.8218	Intermediate Similarity	NPC139347
0.8218	Intermediate Similarity	NPC471005
0.8218	Intermediate Similarity	NPC99510
0.8218	Intermediate Similarity	NPC216114
0.8218	Intermediate Similarity	NPC72842
0.8211	Intermediate Similarity	NPC472146
0.8211	Intermediate Similarity	NPC153853
0.8211	Intermediate Similarity	NPC185529
0.8208	Intermediate Similarity	NPC51978
0.8208	Intermediate Similarity	NPC132668
0.82	Intermediate Similarity	NPC39683
0.82	Intermediate Similarity	NPC475958
0.82	Intermediate Similarity	NPC295276
0.82	Intermediate Similarity	NPC54909
0.82	Intermediate Similarity	NPC233012
0.819	Intermediate Similarity	NPC474846
0.819	Intermediate Similarity	NPC97939
0.819	Intermediate Similarity	NPC100329
0.819	Intermediate Similarity	NPC247031
0.819	Intermediate Similarity	NPC132790
0.819	Intermediate Similarity	NPC122339
0.819	Intermediate Similarity	NPC469655
0.819	Intermediate Similarity	NPC469656
0.8182	Intermediate Similarity	NPC78427
0.8182	Intermediate Similarity	NPC260149
0.8182	Intermediate Similarity	NPC474724
0.8182	Intermediate Similarity	NPC16911
0.8182	Intermediate Similarity	NPC58942
0.8182	Intermediate Similarity	NPC474793
0.8173	Intermediate Similarity	NPC252679
0.8173	Intermediate Similarity	NPC118721
0.8173	Intermediate Similarity	NPC310546
0.8173	Intermediate Similarity	NPC274827
0.8173	Intermediate Similarity	NPC131903
0.8173	Intermediate Similarity	NPC478210
0.8163	Intermediate Similarity	NPC473964
0.8163	Intermediate Similarity	NPC13949
0.8163	Intermediate Similarity	NPC470387
0.8163	Intermediate Similarity	NPC475785
0.8163	Intermediate Similarity	NPC93245
0.8155	Intermediate Similarity	NPC110496

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 NPC256227 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	1938
0.2-0.3	3896
0.3-0.4	2005
0.4-0.5	609
0.5-0.6	247
0.6-0.7	183
0.7-0.8	72
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7938	Intermediate Similarity	NPD8035	Phase 2
0.7938	Intermediate Similarity	NPD8034	Phase 2
0.7905	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6008	Approved
0.7545	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD6399	Phase 3
0.75	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD7638	Approved
0.7404	Intermediate Similarity	NPD7640	Approved
0.7404	Intermediate Similarity	NPD7639	Approved
0.7387	Intermediate Similarity	NPD8133	Approved
0.7379	Intermediate Similarity	NPD7902	Approved
0.7312	Intermediate Similarity	NPD6118	Approved
0.7312	Intermediate Similarity	NPD6115	Approved
0.7312	Intermediate Similarity	NPD6114	Approved
0.7312	Intermediate Similarity	NPD6697	Approved
0.7308	Intermediate Similarity	NPD4225	Approved
0.7304	Intermediate Similarity	NPD6319	Approved
0.7273	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD8328	Phase 3
0.7255	Intermediate Similarity	NPD7748	Approved
0.7228	Intermediate Similarity	NPD7515	Phase 2
0.7222	Intermediate Similarity	NPD5739	Approved
0.7222	Intermediate Similarity	NPD6402	Approved
0.7222	Intermediate Similarity	NPD7128	Approved
0.7222	Intermediate Similarity	NPD6675	Approved
0.7204	Intermediate Similarity	NPD6116	Phase 1
0.7193	Intermediate Similarity	NPD6009	Approved
0.7182	Intermediate Similarity	NPD6372	Approved
0.7182	Intermediate Similarity	NPD6373	Approved
0.7174	Intermediate Similarity	NPD3703	Phase 2
0.7156	Intermediate Similarity	NPD5701	Approved
0.7156	Intermediate Similarity	NPD5697	Approved
0.7143	Intermediate Similarity	NPD7507	Approved
0.7143	Intermediate Similarity	NPD8297	Approved
0.7097	Intermediate Similarity	NPD6117	Approved
0.7094	Intermediate Similarity	NPD5983	Phase 2
0.7094	Intermediate Similarity	NPD6921	Approved
0.7091	Intermediate Similarity	NPD6686	Approved
0.7091	Intermediate Similarity	NPD7320	Approved
0.7091	Intermediate Similarity	NPD6899	Approved
0.7091	Intermediate Similarity	NPD6011	Approved
0.7091	Intermediate Similarity	NPD6881	Approved
0.7087	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7900	Approved
0.7071	Intermediate Similarity	NPD3618	Phase 1
0.7059	Intermediate Similarity	NPD7492	Approved
0.7054	Intermediate Similarity	NPD6649	Approved
0.7054	Intermediate Similarity	NPD6650	Approved
0.703	Intermediate Similarity	NPD5328	Approved
0.7027	Intermediate Similarity	NPD6013	Approved
0.7027	Intermediate Similarity	NPD6014	Approved
0.7027	Intermediate Similarity	NPD6012	Approved
0.7025	Intermediate Similarity	NPD7736	Approved
0.701	Intermediate Similarity	NPD3667	Approved
0.7009	Intermediate Similarity	NPD6059	Approved
0.7009	Intermediate Similarity	NPD6054	Approved
0.7	Intermediate Similarity	NPD6412	Phase 2
0.7	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6616	Approved
0.6975	Remote Similarity	NPD7604	Phase 2
0.6967	Remote Similarity	NPD7319	Approved
0.6964	Remote Similarity	NPD7102	Approved
0.6964	Remote Similarity	NPD6883	Approved
0.6964	Remote Similarity	NPD7290	Approved
0.6952	Remote Similarity	NPD4697	Phase 3
0.6949	Remote Similarity	NPD6016	Approved
0.6949	Remote Similarity	NPD6015	Approved
0.6944	Remote Similarity	NPD7632	Discontinued
0.6942	Remote Similarity	NPD7078	Approved
0.6942	Remote Similarity	NPD8293	Discontinued
0.6903	Remote Similarity	NPD8130	Phase 1
0.6903	Remote Similarity	NPD6617	Approved
0.6903	Remote Similarity	NPD6847	Approved
0.6903	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6869	Approved
0.6897	Remote Similarity	NPD7115	Discovery
0.6893	Remote Similarity	NPD6411	Approved
0.6893	Remote Similarity	NPD6079	Approved
0.6891	Remote Similarity	NPD5988	Approved
0.6891	Remote Similarity	NPD6370	Approved
0.6887	Remote Similarity	NPD4755	Approved
0.6882	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4786	Approved
0.686	Remote Similarity	NPD6336	Discontinued
0.6842	Remote Similarity	NPD6882	Approved
0.6818	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD4634	Approved
0.6792	Remote Similarity	NPD5222	Approved
0.6792	Remote Similarity	NPD5221	Approved
0.6792	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD4700	Approved
0.6759	Remote Similarity	NPD5286	Approved
0.6759	Remote Similarity	NPD4696	Approved
0.6759	Remote Similarity	NPD5285	Approved
0.6729	Remote Similarity	NPD5173	Approved
0.6699	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6101	Approved
0.6697	Remote Similarity	NPD5223	Approved
0.6697	Remote Similarity	NPD1700	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6639	Remote Similarity	NPD7516	Approved
0.6636	Remote Similarity	NPD4633	Approved
0.6636	Remote Similarity	NPD5226	Approved
0.6636	Remote Similarity	NPD5211	Phase 2
0.6636	Remote Similarity	NPD5225	Approved
0.6636	Remote Similarity	NPD5224	Approved
0.6633	Remote Similarity	NPD7525	Registered
0.663	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6033	Approved
0.661	Remote Similarity	NPD6317	Approved
0.6602	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4788	Approved
0.6577	Remote Similarity	NPD5175	Approved
0.6577	Remote Similarity	NPD4754	Approved
0.6577	Remote Similarity	NPD5174	Approved
0.6574	Remote Similarity	NPD6084	Phase 2
0.6574	Remote Similarity	NPD6083	Phase 2
0.6571	Remote Similarity	NPD7983	Approved
0.6569	Remote Similarity	NPD7146	Approved
0.6569	Remote Similarity	NPD7521	Approved
0.6569	Remote Similarity	NPD6409	Approved
0.6569	Remote Similarity	NPD5330	Approved
0.6569	Remote Similarity	NPD6684	Approved
0.6569	Remote Similarity	NPD7334	Approved
0.6557	Remote Similarity	NPD6067	Discontinued
0.6555	Remote Similarity	NPD6335	Approved
0.6555	Remote Similarity	NPD6313	Approved
0.6555	Remote Similarity	NPD7327	Approved
0.6555	Remote Similarity	NPD6314	Approved
0.6555	Remote Similarity	NPD7328	Approved
0.6542	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD3666	Approved
0.6535	Remote Similarity	NPD3665	Phase 1
0.6535	Remote Similarity	NPD3668	Phase 3
0.6535	Remote Similarity	NPD3133	Approved
0.6529	Remote Similarity	NPD8033	Approved
0.6525	Remote Similarity	NPD6868	Approved
0.6518	Remote Similarity	NPD5141	Approved
0.6514	Remote Similarity	NPD5696	Approved
0.65	Remote Similarity	NPD7101	Approved
0.65	Remote Similarity	NPD7100	Approved
0.6489	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6698	Approved
0.6476	Remote Similarity	NPD46	Approved
0.646	Remote Similarity	NPD4768	Approved
0.646	Remote Similarity	NPD4767	Approved
0.6458	Remote Similarity	NPD3702	Approved
0.6446	Remote Similarity	NPD8294	Approved
0.6446	Remote Similarity	NPD8377	Approved
0.6442	Remote Similarity	NPD6672	Approved
0.6442	Remote Similarity	NPD6903	Approved
0.6442	Remote Similarity	NPD5737	Approved
0.641	Remote Similarity	NPD6053	Discontinued
0.64	Remote Similarity	NPD1779	Approved
0.64	Remote Similarity	NPD1780	Approved
0.64	Remote Similarity	NPD8074	Phase 3
0.6396	Remote Similarity	NPD5344	Discontinued
0.6393	Remote Similarity	NPD8379	Approved
0.6393	Remote Similarity	NPD6909	Approved
0.6393	Remote Similarity	NPD8296	Approved
0.6393	Remote Similarity	NPD8335	Approved
0.6393	Remote Similarity	NPD8380	Approved
0.6393	Remote Similarity	NPD8378	Approved
0.6393	Remote Similarity	NPD6908	Approved
0.6389	Remote Similarity	NPD5695	Phase 3
0.6389	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7645	Phase 2
0.6348	Remote Similarity	NPD4730	Approved
0.6348	Remote Similarity	NPD4729	Approved
0.6348	Remote Similarity	NPD5128	Approved
0.6346	Remote Similarity	NPD7524	Approved
0.6337	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5777	Approved
0.6311	Remote Similarity	NPD1694	Approved
0.6304	Remote Similarity	NPD4224	Phase 2
0.6296	Remote Similarity	NPD5282	Discontinued
0.6296	Remote Similarity	NPD6001	Approved
0.6277	Remote Similarity	NPD3698	Phase 2
0.6275	Remote Similarity	NPD3669	Approved
0.6275	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5281	Approved
0.6262	Remote Similarity	NPD5284	Approved
0.6262	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD3574	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