NPASS Compound

Structure

NPC5262 OpenBabel07101718292D 41 43 0 0 1 0 0 0 0 0999 V2000 5.1962 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 36 1 0 0 0 0 2 37 1 0 0 0 0 3 38 1 0 0 0 0 4 39 1 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 14 2 0 0 0 0 7 18 1 0 0 0 0 8 14 1 0 0 0 0 8 19 2 0 0 0 0 9 15 2 0 0 0 0 9 20 1 0 0 0 0 10 15 1 0 0 0 0 10 21 2 0 0 0 0 11 16 1 0 0 0 0 11 29 1 0 0 0 0 12 30 1 0 0 0 0 13 17 1 0 0 0 0 13 40 1 0 0 0 0 16 5 1 6 0 0 0 16 17 1 0 0 0 0 17 6 1 6 0 0 0 18 23 2 0 0 0 0 18 36 1 0 0 0 0 19 23 1 0 0 0 0 19 37 1 0 0 0 0 20 24 2 0 0 0 0 20 38 1 0 0 0 0 21 24 1 0 0 0 0 21 39 1 0 0 0 0 22 12 1 6 0 0 0 22 25 1 0 0 0 0 22 41 1 0 0 0 0 23 31 1 0 0 0 0 24 32 1 0 0 0 0 25 26 1 0 0 0 0 25 33 1 1 0 0 0 26 27 1 0 0 0 0 26 34 1 6 0 0 0 27 28 1 0 0 0 0 27 35 1 1 0 0 0 28 40 1 6 0 0 0 28 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	584.25
Volume:	565.629
LogP:	0.214
LogD:	1.224
LogS:	-2.918
# Rotatable Bonds:	14
TPSA:	196.99
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.156
Synthetic Accessibility Score:	4.342
Fsp3:	0.571
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.283
MDCK Permeability:	2.2391730453819036e-05
Pgp-inhibitor:	0.107
Pgp-substrate:	0.979
Human Intestinal Absorption (HIA):	0.858
20% Bioavailability (F20%):	0.101
30% Bioavailability (F30%):	0.125

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.185
Plasma Protein Binding (PPB):	62.9680290222168%
Volume Distribution (VD):	0.384
Pgp-substrate:	40.559261322021484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.277
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.835
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.216
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.281
CYP3A4-inhibitor:	0.046
CYP3A4-substrate:	0.445

ADMET: Excretion

Clearance (CL):	9.352
Half-life (T1/2):	0.963

ADMET: Toxicity

hERG Blockers:	0.392
Human Hepatotoxicity (H-HT):	0.224
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.067
Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.946
Carcinogencity:	0.018
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.019

Download Data

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

Natural Product: NPC5262

Natural Product ID:	NPC5262
*Common Name:**	8,8'-Dimethoxy-1-O-(Beta-D-Glucopyranosyl) Secoisolariciresinol
IUPAC Name:	(2R,3R,4S,5S,6R)-2-[(2S,3S)-4-hydroxy-2,3-bis[(4-hydroxy-3,5-dimethoxyphenyl)methyl]butoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	OTSJYDFFIUXMJK-MICJZVNGSA-N
Standard InCHI:	InChI=1S/C28H40O13/c1-36-18-7-14(8-19(37-2)23(18)31)5-16(11-29)17(6-15-9-20(38-3)24(32)21(10-15)39-4)13-40-28-27(35)26(34)25(33)22(12-30)41-28/h7-10,16-17,22,25-35H,5-6,11-13H2,1-4H3/t16-,17-,22-,25-,26+,27-,28-/m1/s1
SMILES:	COc1cc(C[C@H](CO)[C@H](Cc2cc(c(c(c2)OC)O)OC)CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)cc(c1O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087036
PubChem CID:	10438279
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan glycosides

*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
NPO18521	Capparis flavicans	Species	Capparaceae	Eukaryota	aerial parts	Khon Kaen Province, Thailand	2006-Aug	PMID[19943620]
NPO18521	Capparis flavicans	Species	Capparaceae	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
NPT83	Cell Line	MCF7	Homo sapiens	Activity	<	0.1	uM	PMID[528399]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	0.8	uM	PMID[528399]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	93.0	uM	PMID[528399]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	0.6	uM	PMID[528399]
NPT396	Cell Line	T47D	Homo sapiens	Activity	>	100.0	uM	PMID[528399]

☑ 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 NPC5262 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	416
0.1-0.2	1454
0.2-0.3	3688
0.3-0.4	9539
0.4-0.5	9093
0.5-0.6	4980
0.6-0.7	7608
0.7-0.8	4276
0.8-0.85	1132
0.85-0.9	407
0.9-0.95	95
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472714
0.9853	High Similarity	NPC473046
0.9853	High Similarity	NPC187774
0.9853	High Similarity	NPC118385
0.9853	High Similarity	NPC472713
0.9853	High Similarity	NPC472712
0.964	High Similarity	NPC39657
0.9571	High Similarity	NPC130449
0.9571	High Similarity	NPC248132
0.9565	High Similarity	NPC25292
0.9565	High Similarity	NPC473045
0.9562	High Similarity	NPC469559
0.9562	High Similarity	NPC189115
0.9504	High Similarity	NPC55158
0.9504	High Similarity	NPC286235
0.9504	High Similarity	NPC51328
0.9496	High Similarity	NPC475096
0.9493	High Similarity	NPC473044
0.9489	High Similarity	NPC472711
0.9489	High Similarity	NPC469661
0.9481	High Similarity	NPC199459
0.9481	High Similarity	NPC177035
0.9481	High Similarity	NPC52277
0.9478	High Similarity	NPC107478
0.9437	High Similarity	NPC469707
0.9437	High Similarity	NPC9933
0.9437	High Similarity	NPC185955
0.9437	High Similarity	NPC469706
0.9437	High Similarity	NPC225815
0.9437	High Similarity	NPC214326
0.9437	High Similarity	NPC472709
0.9437	High Similarity	NPC260781
0.9437	High Similarity	NPC472710
0.9437	High Similarity	NPC218041
0.9437	High Similarity	NPC182368
0.9437	High Similarity	NPC145979
0.9429	High Similarity	NPC99515
0.9429	High Similarity	NPC190714
0.9412	High Similarity	NPC474039
0.9362	High Similarity	NPC227902
0.9357	High Similarity	NPC161700
0.9357	High Similarity	NPC277867
0.9353	High Similarity	NPC278961
0.9353	High Similarity	NPC185307
0.9353	High Similarity	NPC113680
0.9353	High Similarity	NPC477898
0.9353	High Similarity	NPC470950
0.9343	High Similarity	NPC98777
0.9343	High Similarity	NPC212770
0.9328	High Similarity	NPC470270
0.9296	High Similarity	NPC175976
0.9291	High Similarity	NPC125755
0.9286	High Similarity	NPC129417
0.9286	High Similarity	NPC84181
0.9286	High Similarity	NPC283995
0.9286	High Similarity	NPC470235
0.9281	High Similarity	NPC475084
0.9281	High Similarity	NPC476356
0.9275	High Similarity	NPC177868
0.927	High Similarity	NPC304152
0.927	High Similarity	NPC470413
0.927	High Similarity	NPC65530
0.927	High Similarity	NPC59324
0.927	High Similarity	NPC138738
0.9265	High Similarity	NPC236522
0.9259	High Similarity	NPC132895
0.922	High Similarity	NPC38041
0.922	High Similarity	NPC279298
0.922	High Similarity	NPC272619
0.922	High Similarity	NPC286245
0.922	High Similarity	NPC22150
0.9214	High Similarity	NPC185071
0.9214	High Similarity	NPC12728
0.9214	High Similarity	NPC37793
0.9214	High Similarity	NPC46092
0.9197	High Similarity	NPC203230
0.9197	High Similarity	NPC242028
0.9191	High Similarity	NPC251981
0.9191	High Similarity	NPC326095
0.9191	High Similarity	NPC48863
0.9191	High Similarity	NPC244983
0.9191	High Similarity	NPC13745
0.9191	High Similarity	NPC35731
0.9185	High Similarity	NPC201587
0.9185	High Similarity	NPC253105
0.9161	High Similarity	NPC270751
0.9155	High Similarity	NPC112861
0.9155	High Similarity	NPC212890
0.9149	High Similarity	NPC471065
0.9149	High Similarity	NPC469313
0.9149	High Similarity	NPC168579
0.9149	High Similarity	NPC76176
0.9149	High Similarity	NPC138227
0.9149	High Similarity	NPC253015
0.9143	High Similarity	NPC48309
0.9137	High Similarity	NPC291101
0.9137	High Similarity	NPC266197
0.9137	High Similarity	NPC106944
0.913	High Similarity	NPC283949
0.913	High Similarity	NPC195196
0.9124	High Similarity	NPC101624
0.9124	High Similarity	NPC184938
0.9118	High Similarity	NPC215833
0.9118	High Similarity	NPC69513
0.9111	High Similarity	NPC470095
0.9111	High Similarity	NPC65942
0.9111	High Similarity	NPC470096
0.9111	High Similarity	NPC475067
0.9111	High Similarity	NPC248307
0.9111	High Similarity	NPC474017
0.9097	High Similarity	NPC35877
0.9097	High Similarity	NPC95392
0.9097	High Similarity	NPC55715
0.9097	High Similarity	NPC106138
0.9091	High Similarity	NPC31325
0.9091	High Similarity	NPC213074
0.9091	High Similarity	NPC15538
0.9091	High Similarity	NPC224674
0.9091	High Similarity	NPC193473
0.9091	High Similarity	NPC15956
0.9091	High Similarity	NPC114505
0.9091	High Similarity	NPC473480
0.9091	High Similarity	NPC275284
0.9085	High Similarity	NPC18979
0.9085	High Similarity	NPC477702
0.9085	High Similarity	NPC307466
0.9078	High Similarity	NPC298317
0.9078	High Similarity	NPC252169
0.9078	High Similarity	NPC255566
0.9065	High Similarity	NPC156376
0.9058	High Similarity	NPC164857
0.9051	High Similarity	NPC187194
0.9051	High Similarity	NPC476411
0.9051	High Similarity	NPC287745
0.9051	High Similarity	NPC170694
0.9044	High Similarity	NPC204215
0.9044	High Similarity	NPC175067
0.9044	High Similarity	NPC299144
0.9041	High Similarity	NPC21902
0.9028	High Similarity	NPC280945
0.9007	High Similarity	NPC246947
0.9	High Similarity	NPC46591
0.9	High Similarity	NPC226547
0.9	High Similarity	NPC56091
0.8993	High Similarity	NPC185908
0.8986	High Similarity	NPC141765
0.8986	High Similarity	NPC24490
0.8986	High Similarity	NPC47398
0.8986	High Similarity	NPC234333
0.8986	High Similarity	NPC165155
0.8986	High Similarity	NPC34103
0.8986	High Similarity	NPC150534
0.8986	High Similarity	NPC470236
0.8986	High Similarity	NPC260898
0.898	High Similarity	NPC78809
0.8978	High Similarity	NPC115022
0.8978	High Similarity	NPC196937
0.8978	High Similarity	NPC158331
0.8978	High Similarity	NPC294166
0.8978	High Similarity	NPC49074
0.8973	High Similarity	NPC473621
0.8971	High Similarity	NPC309787
0.8966	High Similarity	NPC44452
0.8963	High Similarity	NPC307110
0.8963	High Similarity	NPC476968
0.8963	High Similarity	NPC170844
0.8951	High Similarity	NPC43508
0.8951	High Similarity	NPC189239
0.8951	High Similarity	NPC166506
0.8951	High Similarity	NPC110763
0.8951	High Similarity	NPC476301
0.8951	High Similarity	NPC197352
0.8944	High Similarity	NPC81638
0.8936	High Similarity	NPC210192
0.8936	High Similarity	NPC471908
0.8936	High Similarity	NPC471389
0.8929	High Similarity	NPC30951
0.8929	High Similarity	NPC22517
0.8929	High Similarity	NPC6369
0.8921	High Similarity	NPC172818
0.8921	High Similarity	NPC265433
0.8921	High Similarity	NPC270456
0.8921	High Similarity	NPC306441
0.8921	High Similarity	NPC197723
0.8921	High Similarity	NPC248727
0.8921	High Similarity	NPC40664
0.8921	High Similarity	NPC138350
0.8921	High Similarity	NPC162659
0.8921	High Similarity	NPC25695
0.8921	High Similarity	NPC165482
0.8921	High Similarity	NPC3293
0.8921	High Similarity	NPC16435
0.8913	High Similarity	NPC470881
0.8912	High Similarity	NPC302610
0.8905	High Similarity	NPC85799
0.8905	High Similarity	NPC184447
0.8905	High Similarity	NPC470752
0.8905	High Similarity	NPC106739
0.8905	High Similarity	NPC303422
0.8905	High Similarity	NPC35932

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 NPC5262 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	336
0.1-0.2	833
0.2-0.3	1884
0.3-0.4	2810
0.4-0.5	1696
0.5-0.6	974
0.6-0.7	524
0.7-0.8	82
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8963	High Similarity	NPD3027	Phase 3
0.8633	High Similarity	NPD1613	Approved
0.8633	High Similarity	NPD1612	Clinical (unspecified phase)
0.8535	High Similarity	NPD7228	Approved
0.8442	Intermediate Similarity	NPD6234	Discontinued
0.8406	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD7266	Discontinued
0.8355	Intermediate Similarity	NPD37	Approved
0.8345	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1653	Approved
0.8312	Intermediate Similarity	NPD4966	Approved
0.8312	Intermediate Similarity	NPD4965	Approved
0.8312	Intermediate Similarity	NPD4967	Phase 2
0.8288	Intermediate Similarity	NPD6674	Discontinued
0.8199	Intermediate Similarity	NPD7074	Phase 3
0.8137	Intermediate Similarity	NPD7054	Approved
0.8086	Intermediate Similarity	NPD7472	Approved
0.7988	Intermediate Similarity	NPD7240	Approved
0.7971	Intermediate Similarity	NPD3705	Approved
0.7963	Intermediate Similarity	NPD3818	Discontinued
0.7958	Intermediate Similarity	NPD4908	Phase 1
0.7879	Intermediate Similarity	NPD7251	Discontinued
0.7875	Intermediate Similarity	NPD7199	Phase 2
0.7847	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD1610	Phase 2
0.7842	Intermediate Similarity	NPD1091	Approved
0.7831	Intermediate Similarity	NPD7808	Phase 3
0.7818	Intermediate Similarity	NPD6797	Phase 2
0.7771	Intermediate Similarity	NPD1934	Approved
0.774	Intermediate Similarity	NPD3620	Phase 2
0.774	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2983	Phase 2
0.773	Intermediate Similarity	NPD2982	Phase 2
0.7725	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD5283	Phase 1
0.7688	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7685	Pre-registration
0.766	Intermediate Similarity	NPD2981	Phase 2
0.7639	Intermediate Similarity	NPD3018	Phase 2
0.7639	Intermediate Similarity	NPD2861	Phase 2
0.7626	Intermediate Similarity	NPD1357	Approved
0.7622	Intermediate Similarity	NPD6166	Phase 2
0.7622	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD4749	Approved
0.7556	Intermediate Similarity	NPD228	Approved
0.7529	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6559	Discontinued
0.7452	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7680	Approved
0.7429	Intermediate Similarity	NPD1548	Phase 1
0.7419	Intermediate Similarity	NPD5058	Phase 3
0.7415	Intermediate Similarity	NPD4625	Phase 3
0.7407	Intermediate Similarity	NPD3021	Approved
0.7407	Intermediate Similarity	NPD3022	Approved
0.7391	Intermediate Similarity	NPD2801	Approved
0.7391	Intermediate Similarity	NPD2977	Approved
0.7391	Intermediate Similarity	NPD2978	Approved
0.7391	Intermediate Similarity	NPD8455	Phase 2
0.7361	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4005	Discontinued
0.7355	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7157	Approved
0.7312	Intermediate Similarity	NPD4380	Phase 2
0.7303	Intermediate Similarity	NPD4108	Discontinued
0.7299	Intermediate Similarity	NPD6843	Phase 3
0.7299	Intermediate Similarity	NPD6841	Approved
0.7299	Intermediate Similarity	NPD6842	Approved
0.7294	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1465	Phase 2
0.7278	Intermediate Similarity	NPD5844	Phase 1
0.7267	Intermediate Similarity	NPD4060	Phase 1
0.7262	Intermediate Similarity	NPD7473	Discontinued
0.725	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7843	Approved
0.7244	Intermediate Similarity	NPD6190	Approved
0.7239	Intermediate Similarity	NPD3817	Phase 2
0.7237	Intermediate Similarity	NPD4536	Approved
0.7237	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4538	Approved
0.7226	Intermediate Similarity	NPD5177	Phase 3
0.7208	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5125	Phase 3
0.7203	Intermediate Similarity	NPD5126	Approved
0.7197	Intermediate Similarity	NPD7124	Phase 2
0.7195	Intermediate Similarity	NPD3882	Suspended
0.7186	Intermediate Similarity	NPD6232	Discontinued
0.7152	Intermediate Similarity	NPD7075	Discontinued
0.7152	Intermediate Similarity	NPD1558	Phase 1
0.7152	Intermediate Similarity	NPD1511	Approved
0.7143	Intermediate Similarity	NPD6099	Approved
0.7143	Intermediate Similarity	NPD6100	Approved
0.7133	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6111	Discontinued
0.7124	Intermediate Similarity	NPD7097	Phase 1
0.7115	Intermediate Similarity	NPD1652	Phase 2
0.7115	Intermediate Similarity	NPD3060	Approved
0.7105	Intermediate Similarity	NPD5124	Phase 1
0.7105	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5735	Approved
0.7105	Intermediate Similarity	NPD230	Phase 1
0.7099	Intermediate Similarity	NPD4678	Approved
0.7099	Intermediate Similarity	NPD4675	Approved
0.7097	Intermediate Similarity	NPD1375	Discontinued
0.7097	Intermediate Similarity	NPD3540	Phase 1
0.7083	Intermediate Similarity	NPD3787	Discontinued
0.708	Intermediate Similarity	NPD2684	Approved
0.7078	Intermediate Similarity	NPD5588	Approved
0.7078	Intermediate Similarity	NPD5960	Phase 3
0.7075	Intermediate Similarity	NPD8651	Approved
0.707	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7095	Approved
0.7066	Intermediate Similarity	NPD5494	Approved
0.7063	Intermediate Similarity	NPD1512	Approved
0.7039	Intermediate Similarity	NPD2238	Phase 2
0.7032	Intermediate Similarity	NPD3539	Phase 1
0.703	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD3384	Approved
0.7012	Intermediate Similarity	NPD3383	Approved
0.7012	Intermediate Similarity	NPD3382	Approved
0.7011	Intermediate Similarity	NPD7549	Discontinued
0.7007	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4237	Approved
0.7006	Intermediate Similarity	NPD4236	Phase 3
0.7	Intermediate Similarity	NPD7447	Phase 1
0.6993	Remote Similarity	NPD6355	Discontinued
0.6987	Remote Similarity	NPD5762	Approved
0.6987	Remote Similarity	NPD5763	Approved
0.6983	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6671	Approved
0.6971	Remote Similarity	NPD8313	Approved
0.6971	Remote Similarity	NPD8312	Approved
0.697	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7819	Suspended
0.6966	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4628	Phase 3
0.6962	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6331	Phase 2
0.6962	Remote Similarity	NPD4110	Phase 3
0.6951	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6653	Approved
0.6937	Remote Similarity	NPD7212	Phase 2
0.6937	Remote Similarity	NPD4357	Discontinued
0.6937	Remote Similarity	NPD7213	Phase 3
0.6932	Remote Similarity	NPD8053	Approved
0.6932	Remote Similarity	NPD8054	Approved
0.6923	Remote Similarity	NPD8127	Discontinued
0.6919	Remote Similarity	NPD3751	Discontinued
0.6918	Remote Similarity	NPD2219	Phase 1
0.6913	Remote Similarity	NPD3094	Phase 2
0.6906	Remote Similarity	NPD4750	Phase 3
0.6894	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD3657	Discovery
0.6879	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5536	Phase 2
0.6871	Remote Similarity	NPD422	Phase 1
0.6867	Remote Similarity	NPD6584	Phase 3
0.6863	Remote Similarity	NPD6233	Phase 2
0.6859	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD3892	Phase 2
0.6852	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD52	Approved
0.6852	Remote Similarity	NPD7526	Approved
0.6849	Remote Similarity	NPD5846	Approved
0.6849	Remote Similarity	NPD6516	Phase 2
0.6835	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1549	Phase 2
0.6829	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD5353	Approved
0.6826	Remote Similarity	NPD5402	Approved
0.6824	Remote Similarity	NPD6959	Discontinued
0.6818	Remote Similarity	NPD4140	Approved
0.6816	Remote Similarity	NPD7906	Approved
0.6815	Remote Similarity	NPD1242	Phase 1
0.6813	Remote Similarity	NPD2677	Approved
0.6813	Remote Similarity	NPD5241	Discontinued
0.6807	Remote Similarity	NPD6801	Discontinued
0.6802	Remote Similarity	NPD27	Approved
0.6802	Remote Similarity	NPD2489	Approved
0.6797	Remote Similarity	NPD5110	Phase 2

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