NPASS Compound

Structure

NPC293658 OpenBabel07101719252D 37 42 0 0 1 0 0 0 0 0999 V2000 9.3933 -0.9759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2636 -0.7553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6730 0.9263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5499 2.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5633 1.2801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9505 1.6339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2488 -0.2187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9218 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5633 -0.8427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9505 -0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1761 0.2187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8630 0.4850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7879 2.4250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5499 -0.4889 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5633 0.5725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1761 -0.4889 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3377 1.2801 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5758 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3377 0.5725 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7064 0.9719 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5758 1.8525 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8630 -0.4889 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2749 0.9263 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.5499 0.4850 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9218 1.8525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7879 -0.5725 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9505 0.2187 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3010 0.9263 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3933 0.9719 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4942 2.6404 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7879 -1.5464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7064 1.9459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.8525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7064 -0.9759 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0195 -0.9759 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2488 2.0712 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 4 32 1 0 0 0 0 5 6 1 0 0 0 0 5 15 2 0 0 0 0 7 8 1 0 0 0 0 7 18 2 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 27 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 20 1 0 0 0 0 12 22 1 0 0 0 0 13 33 1 0 0 0 0 14 1 1 1 0 0 0 14 24 1 0 0 0 0 14 34 1 0 0 0 0 15 27 1 0 0 0 0 16 35 1 1 0 0 0 17 6 1 6 0 0 0 17 19 1 0 0 0 0 17 25 1 0 0 0 0 18 23 1 0 0 0 0 18 26 1 0 0 0 0 19 27 1 1 0 0 0 20 24 1 0 0 0 0 20 32 1 1 0 0 0 21 13 1 6 0 0 0 21 23 1 0 0 0 0 21 36 1 0 0 0 0 22 34 1 0 0 0 0 22 35 1 1 0 0 0 23 28 1 1 0 0 0 24 29 1 6 0 0 0 25 30 2 0 0 0 0 25 36 1 0 0 0 0 26 31 1 6 0 0 0 26 37 1 0 0 0 0 27 2 1 1 0 0 0 28 3 1 6 0 0 0 28 33 1 0 0 0 0 28 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	520.27
Volume:	512.708
LogP:	2.354
LogD:	1.918
LogS:	-4.626
# Rotatable Bonds:	3
TPSA:	112.91
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.428
Synthetic Accessibility Score:	5.916
Fsp3:	0.821
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.104
MDCK Permeability:	8.016266656341031e-05
Pgp-inhibitor:	0.039
Pgp-substrate:	0.98
Human Intestinal Absorption (HIA):	0.075
20% Bioavailability (F20%):	0.754
30% Bioavailability (F30%):	0.189

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	84.65882110595703%
Volume Distribution (VD):	1.108
Pgp-substrate:	4.470428466796875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.595
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.766
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.202
CYP3A4-inhibitor:	0.533
CYP3A4-substrate:	0.653

ADMET: Excretion

Clearance (CL):	3.773
Half-life (T1/2):	0.149

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.788
Drug-inuced Liver Injury (DILI):	0.902
AMES Toxicity:	0.934
Rat Oral Acute Toxicity:	0.623
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.604
Carcinogencity:	0.166
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.928

Download Data

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

Natural Product: NPC293658

Natural Product ID:	NPC293658
*Common Name:**	Paniculatumoside B
IUPAC Name:	n.a.
Synonyms:	paniculatumoside B
Standard InCHIKey:	RIZURMSYPNFAAV-QBJYZOITSA-N
Standard InCHI:	InChI=1S/C28H40O9/c1-14-24(29)20(32-4)12-22(34-14)35-16-9-10-27(2)15(11-16)5-6-17-19(27)8-7-18-23-21(36-25(17)30)13-33-28(23,3)37-26(18)31/h5,7,14,16-17,19-24,26,29,31H,6,8-13H2,1-4H3/b18-7+/t14-,16+,17-,19+,20-,21+,22+,23-,24-,26-,27+,28-/m1/s1
SMILES:	CO[C@@H]1C[C@H](O[C@H]2CC[C@]3(C(=CC[C@@H]4[C@@H]3C/C=C3/[C@H](O)O[C@@]5([C@H]3[C@@H](OC4=O)CO5)C)C2)C)O[C@@H]([C@H]1O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509742
PubChem CID:	44575541
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl 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
NPO31390	Cynanchum paniculatum	Species	Apocynaceae	Eukaryota	roots	n.a.	n.a.	PMID[14738392]
NPO31390	Cynanchum paniculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31390	Cynanchum paniculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	148.6	ug.mL-1	PMID[468257]

☑ 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 NPC293658 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	215
0.1-0.2	1217
0.2-0.3	4012
0.3-0.4	8847
0.4-0.5	12243
0.5-0.6	7359
0.6-0.7	6400
0.7-0.8	2308
0.8-0.85	82
0.85-0.9	12
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474410
0.8981	High Similarity	NPC127153
0.8879	High Similarity	NPC293512
0.885	High Similarity	NPC122971
0.8684	High Similarity	NPC477071
0.8661	High Similarity	NPC181145
0.8636	High Similarity	NPC119550
0.8636	High Similarity	NPC83005
0.8624	High Similarity	NPC177524
0.8624	High Similarity	NPC135015
0.8624	High Similarity	NPC48548
0.8624	High Similarity	NPC217921
0.8624	High Similarity	NPC392
0.8624	High Similarity	NPC128795
0.8624	High Similarity	NPC219900
0.8584	High Similarity	NPC189126
0.8571	High Similarity	NPC75167
0.8571	High Similarity	NPC311592
0.8545	High Similarity	NPC40728
0.8545	High Similarity	NPC316974
0.8532	High Similarity	NPC88013
0.8532	High Similarity	NPC125423
0.8532	High Similarity	NPC184512
0.8509	High Similarity	NPC473968
0.8496	Intermediate Similarity	NPC472274
0.8482	Intermediate Similarity	NPC174836
0.8462	Intermediate Similarity	NPC473231
0.8455	Intermediate Similarity	NPC295389
0.8455	Intermediate Similarity	NPC311223
0.844	Intermediate Similarity	NPC127609
0.844	Intermediate Similarity	NPC252296
0.8426	Intermediate Similarity	NPC127933
0.8426	Intermediate Similarity	NPC475889
0.8426	Intermediate Similarity	NPC7644
0.8426	Intermediate Similarity	NPC7613
0.8407	Intermediate Similarity	NPC264153
0.839	Intermediate Similarity	NPC41129
0.8378	Intermediate Similarity	NPC143706
0.8378	Intermediate Similarity	NPC118225
0.8378	Intermediate Similarity	NPC472534
0.8376	Intermediate Similarity	NPC476204
0.8376	Intermediate Similarity	NPC473250
0.8376	Intermediate Similarity	NPC170084
0.8364	Intermediate Similarity	NPC472390
0.8349	Intermediate Similarity	NPC470768
0.8349	Intermediate Similarity	NPC470321
0.8349	Intermediate Similarity	NPC264867
0.8349	Intermediate Similarity	NPC473207
0.8349	Intermediate Similarity	NPC81567
0.8349	Intermediate Similarity	NPC201880
0.8348	Intermediate Similarity	NPC474483
0.8348	Intermediate Similarity	NPC473405
0.8333	Intermediate Similarity	NPC238397
0.8333	Intermediate Similarity	NPC220293
0.8333	Intermediate Similarity	NPC470919
0.8333	Intermediate Similarity	NPC471363
0.8333	Intermediate Similarity	NPC469877
0.8319	Intermediate Similarity	NPC302146
0.8319	Intermediate Similarity	NPC318135
0.8304	Intermediate Similarity	NPC235014
0.8304	Intermediate Similarity	NPC129340
0.8304	Intermediate Similarity	NPC101450
0.8304	Intermediate Similarity	NPC274507
0.8302	Intermediate Similarity	NPC239547
0.8302	Intermediate Similarity	NPC125551
0.8302	Intermediate Similarity	NPC155319
0.8302	Intermediate Similarity	NPC309503
0.8302	Intermediate Similarity	NPC91197
0.8302	Intermediate Similarity	NPC96597
0.8291	Intermediate Similarity	NPC48692
0.8291	Intermediate Similarity	NPC470312
0.8276	Intermediate Similarity	NPC45475
0.8276	Intermediate Similarity	NPC473828
0.8276	Intermediate Similarity	NPC471548
0.8276	Intermediate Similarity	NPC473617
0.8273	Intermediate Similarity	NPC239961
0.8261	Intermediate Similarity	NPC474046
0.8261	Intermediate Similarity	NPC259306
0.8261	Intermediate Similarity	NPC470628
0.8257	Intermediate Similarity	NPC134270
0.8246	Intermediate Similarity	NPC251309
0.8241	Intermediate Similarity	NPC280991
0.823	Intermediate Similarity	NPC30397
0.823	Intermediate Similarity	NPC235841
0.823	Intermediate Similarity	NPC211798
0.823	Intermediate Similarity	NPC473481
0.823	Intermediate Similarity	NPC108748
0.823	Intermediate Similarity	NPC263827
0.823	Intermediate Similarity	NPC297208
0.823	Intermediate Similarity	NPC250481
0.823	Intermediate Similarity	NPC191763
0.823	Intermediate Similarity	NPC285410
0.822	Intermediate Similarity	NPC202051
0.8214	Intermediate Similarity	NPC237503
0.8214	Intermediate Similarity	NPC306746
0.8214	Intermediate Similarity	NPC204407
0.8214	Intermediate Similarity	NPC167383
0.8214	Intermediate Similarity	NPC265655
0.8214	Intermediate Similarity	NPC206618
0.8214	Intermediate Similarity	NPC57362
0.8214	Intermediate Similarity	NPC137917
0.8205	Intermediate Similarity	NPC475834
0.8205	Intermediate Similarity	NPC474179
0.8205	Intermediate Similarity	NPC475775
0.8205	Intermediate Similarity	NPC476529
0.819	Intermediate Similarity	NPC471547
0.8182	Intermediate Similarity	NPC470780
0.8182	Intermediate Similarity	NPC222161
0.8182	Intermediate Similarity	NPC121566
0.8182	Intermediate Similarity	NPC100955
0.8174	Intermediate Similarity	NPC473882
0.8165	Intermediate Similarity	NPC201191
0.8158	Intermediate Similarity	NPC470025
0.8158	Intermediate Similarity	NPC233003
0.8158	Intermediate Similarity	NPC128925
0.8158	Intermediate Similarity	NPC46388
0.8158	Intermediate Similarity	NPC321272
0.8158	Intermediate Similarity	NPC116794
0.8158	Intermediate Similarity	NPC328074
0.8158	Intermediate Similarity	NPC37739
0.8158	Intermediate Similarity	NPC317460
0.8158	Intermediate Similarity	NPC256798
0.8142	Intermediate Similarity	NPC68419
0.8142	Intermediate Similarity	NPC7870
0.8142	Intermediate Similarity	NPC476882
0.8142	Intermediate Similarity	NPC476883
0.8142	Intermediate Similarity	NPC476884
0.8142	Intermediate Similarity	NPC102914
0.8142	Intermediate Similarity	NPC108709
0.8142	Intermediate Similarity	NPC476880
0.8142	Intermediate Similarity	NPC110139
0.8142	Intermediate Similarity	NPC164194
0.8142	Intermediate Similarity	NPC56713
0.8142	Intermediate Similarity	NPC136877
0.8142	Intermediate Similarity	NPC78046
0.8142	Intermediate Similarity	NPC52241
0.8142	Intermediate Similarity	NPC279554
0.8142	Intermediate Similarity	NPC270667
0.8142	Intermediate Similarity	NPC476886
0.8142	Intermediate Similarity	NPC29069
0.8142	Intermediate Similarity	NPC476881
0.8142	Intermediate Similarity	NPC475296
0.8142	Intermediate Similarity	NPC59804
0.8142	Intermediate Similarity	NPC174679
0.8142	Intermediate Similarity	NPC474589
0.8142	Intermediate Similarity	NPC475317
0.8142	Intermediate Similarity	NPC75747
0.8142	Intermediate Similarity	NPC90856
0.8142	Intermediate Similarity	NPC199457
0.8142	Intermediate Similarity	NPC154856
0.8142	Intermediate Similarity	NPC220984
0.8142	Intermediate Similarity	NPC269095
0.8142	Intermediate Similarity	NPC476887
0.8142	Intermediate Similarity	NPC127056
0.8142	Intermediate Similarity	NPC476885
0.8136	Intermediate Similarity	NPC107338
0.8136	Intermediate Similarity	NPC109607
0.8136	Intermediate Similarity	NPC476150
0.8136	Intermediate Similarity	NPC476127
0.8131	Intermediate Similarity	NPC98112
0.8125	Intermediate Similarity	NPC476123
0.8125	Intermediate Similarity	NPC284807
0.8125	Intermediate Similarity	NPC473288
0.8125	Intermediate Similarity	NPC28198
0.8125	Intermediate Similarity	NPC38948
0.8125	Intermediate Similarity	NPC177246
0.8125	Intermediate Similarity	NPC195708
0.812	Intermediate Similarity	NPC234522
0.812	Intermediate Similarity	NPC475403
0.812	Intermediate Similarity	NPC475913
0.812	Intermediate Similarity	NPC291564
0.812	Intermediate Similarity	NPC160888
0.8115	Intermediate Similarity	NPC311534
0.8113	Intermediate Similarity	NPC230347
0.8113	Intermediate Similarity	NPC275310
0.8113	Intermediate Similarity	NPC286612
0.8108	Intermediate Similarity	NPC162033
0.8108	Intermediate Similarity	NPC95243
0.8108	Intermediate Similarity	NPC82251
0.8108	Intermediate Similarity	NPC470767
0.8108	Intermediate Similarity	NPC63023
0.8108	Intermediate Similarity	NPC210178
0.8108	Intermediate Similarity	NPC470763
0.8103	Intermediate Similarity	NPC207637
0.8091	Intermediate Similarity	NPC69171
0.8091	Intermediate Similarity	NPC474165
0.8087	Intermediate Similarity	NPC138334
0.8087	Intermediate Similarity	NPC269315
0.8087	Intermediate Similarity	NPC124296
0.8087	Intermediate Similarity	NPC157441
0.8087	Intermediate Similarity	NPC470027
0.8087	Intermediate Similarity	NPC47063
0.8087	Intermediate Similarity	NPC189884
0.8087	Intermediate Similarity	NPC258885
0.8087	Intermediate Similarity	NPC271138
0.8087	Intermediate Similarity	NPC204458
0.8083	Intermediate Similarity	NPC27363
0.8073	Intermediate Similarity	NPC198992
0.8073	Intermediate Similarity	NPC154127
0.807	Intermediate Similarity	NPC17791

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 NPC293658 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1419
0.2-0.3	3767
0.3-0.4	2503
0.4-0.5	757
0.5-0.6	309
0.6-0.7	173
0.7-0.8	40
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8624	High Similarity	NPD6686	Approved
0.7951	Intermediate Similarity	NPD7507	Approved
0.7876	Intermediate Similarity	NPD6412	Phase 2
0.7778	Intermediate Similarity	NPD8133	Approved
0.7769	Intermediate Similarity	NPD8513	Phase 3
0.7769	Intermediate Similarity	NPD8515	Approved
0.7769	Intermediate Similarity	NPD8517	Approved
0.7769	Intermediate Similarity	NPD8516	Approved
0.776	Intermediate Similarity	NPD7319	Approved
0.7739	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7327	Approved
0.7667	Intermediate Similarity	NPD7328	Approved
0.7623	Intermediate Similarity	NPD8033	Approved
0.7607	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD7516	Approved
0.7541	Intermediate Similarity	NPD8377	Approved
0.7541	Intermediate Similarity	NPD8294	Approved
0.748	Intermediate Similarity	NPD8380	Approved
0.748	Intermediate Similarity	NPD8378	Approved
0.748	Intermediate Similarity	NPD8379	Approved
0.748	Intermediate Similarity	NPD8335	Approved
0.748	Intermediate Similarity	NPD8296	Approved
0.7438	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD46	Approved
0.7407	Intermediate Similarity	NPD6698	Approved
0.736	Intermediate Similarity	NPD8328	Phase 3
0.7345	Intermediate Similarity	NPD7640	Approved
0.7345	Intermediate Similarity	NPD7639	Approved
0.7339	Intermediate Similarity	NPD7503	Approved
0.7288	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7638	Approved
0.7257	Intermediate Similarity	NPD4225	Approved
0.7188	Intermediate Similarity	NPD8293	Discontinued
0.7188	Intermediate Similarity	NPD8074	Phase 3
0.7154	Intermediate Similarity	NPD7115	Discovery
0.7143	Intermediate Similarity	NPD6370	Approved
0.7132	Intermediate Similarity	NPD7736	Approved
0.7117	Intermediate Similarity	NPD6399	Phase 3
0.7083	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7492	Approved
0.6984	Remote Similarity	NPD6054	Approved
0.6984	Remote Similarity	NPD6059	Approved
0.6977	Remote Similarity	NPD6616	Approved
0.6967	Remote Similarity	NPD6053	Discontinued
0.6957	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD6067	Discontinued
0.6923	Remote Similarity	NPD7078	Approved
0.6917	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7983	Approved
0.6852	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6882	Approved
0.6814	Remote Similarity	NPD5778	Approved
0.6814	Remote Similarity	NPD5779	Approved
0.6803	Remote Similarity	NPD6371	Approved
0.6797	Remote Similarity	NPD6015	Approved
0.6797	Remote Similarity	NPD6016	Approved
0.678	Remote Similarity	NPD7632	Discontinued
0.6746	Remote Similarity	NPD6009	Approved
0.6744	Remote Similarity	NPD5988	Approved
0.6726	Remote Similarity	NPD6411	Approved
0.6719	Remote Similarity	NPD6319	Approved
0.6697	Remote Similarity	NPD4786	Approved
0.6695	Remote Similarity	NPD5344	Discontinued
0.6694	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.664	Remote Similarity	NPD4632	Approved
0.6639	Remote Similarity	NPD7320	Approved
0.6637	Remote Similarity	NPD7838	Discovery
0.6612	Remote Similarity	NPD7128	Approved
0.6612	Remote Similarity	NPD6402	Approved
0.6612	Remote Similarity	NPD5739	Approved
0.6612	Remote Similarity	NPD6008	Approved
0.6612	Remote Similarity	NPD6675	Approved
0.6609	Remote Similarity	NPD7748	Approved
0.6585	Remote Similarity	NPD6372	Approved
0.6585	Remote Similarity	NPD6373	Approved
0.6581	Remote Similarity	NPD6083	Phase 2
0.6581	Remote Similarity	NPD6084	Phase 2
0.6581	Remote Similarity	NPD7902	Approved
0.6579	Remote Similarity	NPD7515	Phase 2
0.6579	Remote Similarity	NPD7637	Suspended
0.6549	Remote Similarity	NPD6101	Approved
0.6549	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD4251	Approved
0.6518	Remote Similarity	NPD4250	Approved
0.6514	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD6881	Approved
0.6504	Remote Similarity	NPD6899	Approved
0.6496	Remote Similarity	NPD7839	Suspended
0.6493	Remote Similarity	NPD6033	Approved
0.648	Remote Similarity	NPD6650	Approved
0.648	Remote Similarity	NPD6649	Approved
0.6471	Remote Similarity	NPD7260	Phase 2
0.6466	Remote Similarity	NPD8451	Approved
0.646	Remote Similarity	NPD6903	Approved
0.6439	Remote Similarity	NPD7829	Approved
0.6439	Remote Similarity	NPD7830	Approved
0.6429	Remote Similarity	NPD6684	Approved
0.6429	Remote Similarity	NPD6409	Approved
0.6429	Remote Similarity	NPD7521	Approved
0.6429	Remote Similarity	NPD5330	Approved
0.6429	Remote Similarity	NPD7334	Approved
0.6429	Remote Similarity	NPD4249	Approved
0.6429	Remote Similarity	NPD7146	Approved
0.6423	Remote Similarity	NPD5701	Approved
0.6423	Remote Similarity	NPD5697	Approved
0.6423	Remote Similarity	NPD6845	Suspended
0.6418	Remote Similarity	NPD8448	Approved
0.6412	Remote Similarity	NPD8444	Approved
0.6412	Remote Similarity	NPD6921	Approved
0.641	Remote Similarity	NPD5695	Phase 3
0.641	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7102	Approved
0.64	Remote Similarity	NPD6883	Approved
0.64	Remote Similarity	NPD7290	Approved
0.6397	Remote Similarity	NPD8392	Approved
0.6397	Remote Similarity	NPD8391	Approved
0.6397	Remote Similarity	NPD8390	Approved
0.6391	Remote Similarity	NPD8340	Approved
0.6391	Remote Similarity	NPD8342	Approved
0.6391	Remote Similarity	NPD8341	Approved
0.6391	Remote Similarity	NPD8299	Approved
0.6372	Remote Similarity	NPD7524	Approved
0.6349	Remote Similarity	NPD6847	Approved
0.6349	Remote Similarity	NPD8130	Phase 1
0.6349	Remote Similarity	NPD6617	Approved
0.6349	Remote Similarity	NPD6869	Approved
0.6339	Remote Similarity	NPD1694	Approved
0.6333	Remote Similarity	NPD6648	Approved
0.6325	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD7900	Approved
0.6325	Remote Similarity	NPD5282	Discontinued
0.632	Remote Similarity	NPD6012	Approved
0.632	Remote Similarity	NPD6014	Approved
0.632	Remote Similarity	NPD6013	Approved
0.6316	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7604	Phase 2
0.6316	Remote Similarity	NPD6672	Approved
0.6316	Remote Similarity	NPD5737	Approved
0.6306	Remote Similarity	NPD5362	Discontinued
0.6306	Remote Similarity	NPD7154	Phase 3
0.6304	Remote Similarity	NPD8449	Approved
0.6293	Remote Similarity	NPD8034	Phase 2
0.6293	Remote Similarity	NPD8035	Phase 2
0.6288	Remote Similarity	NPD5983	Phase 2
0.6283	Remote Similarity	NPD3618	Phase 1
0.6277	Remote Similarity	NPD5956	Approved
0.6277	Remote Similarity	NPD6914	Discontinued
0.6261	Remote Similarity	NPD5328	Approved
0.6261	Remote Similarity	NPD6051	Approved
0.6259	Remote Similarity	NPD8450	Suspended
0.625	Remote Similarity	NPD8336	Approved
0.625	Remote Similarity	NPD3668	Phase 3
0.625	Remote Similarity	NPD3665	Phase 1
0.625	Remote Similarity	NPD8337	Approved
0.625	Remote Similarity	NPD5696	Approved
0.625	Remote Similarity	NPD3666	Approved
0.625	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3133	Approved
0.6241	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.624	Remote Similarity	NPD6011	Approved
0.6239	Remote Similarity	NPD8171	Discontinued
0.6231	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5211	Phase 2
0.6222	Remote Similarity	NPD6336	Discontinued
0.622	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5785	Approved
0.6195	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD7122	Discontinued
0.6194	Remote Similarity	NPD7642	Approved
0.619	Remote Similarity	NPD7625	Phase 1
0.6183	Remote Similarity	NPD7641	Discontinued
0.6182	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.617	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD4755	Approved
0.6165	Remote Similarity	NPD8266	Approved
0.6165	Remote Similarity	NPD8267	Approved
0.6165	Remote Similarity	NPD8268	Approved
0.6165	Remote Similarity	NPD8269	Approved
0.6161	Remote Similarity	NPD6695	Phase 3
0.6154	Remote Similarity	NPD5693	Phase 1
0.6154	Remote Similarity	NPD6079	Approved
0.6147	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD4634	Approved
0.6134	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD5141	Approved
0.6121	Remote Similarity	NPD1695	Approved
0.6121	Remote Similarity	NPD4753	Phase 2
0.6111	Remote Similarity	NPD7228	Approved
0.6102	Remote Similarity	NPD4202	Approved
0.6087	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD5286	Approved
0.6066	Remote Similarity	NPD4700	Approved
0.6066	Remote Similarity	NPD4696	Approved
0.6066	Remote Similarity	NPD5285	Approved
0.6053	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6082	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