NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	1230.57
Volume:	1173.529
LogP:	0.249
LogD:	0.319
LogS:	-2.589
# Rotatable Bonds:	17
TPSA:	423.57
# H-Bond Aceptor:	27
# H-Bond Donor:	13
# Rings:	9
# Heavy Atoms:	27

MedChem Properties

QED Drug-Likeness Score:	0.028
Synthetic Accessibility Score:	7.408
Fsp3:	0.864
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.536
MDCK Permeability:	0.0003835026582237333
Pgp-inhibitor:	0.186
Pgp-substrate:	0.973
Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	0.206
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.203
Plasma Protein Binding (PPB):	45.26425552368164%
Volume Distribution (VD):	0.188
Pgp-substrate:	17.442365646362305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.037
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.019
CYP3A4-inhibitor:	0.115
CYP3A4-substrate:	0.006

ADMET: Excretion

Clearance (CL):	0.253
Half-life (T1/2):	0.787

ADMET: Toxicity

hERG Blockers:	0.132
Human Hepatotoxicity (H-HT):	0.23
Drug-inuced Liver Injury (DILI):	0.076
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.413
Skin Sensitization:	0.055
Carcinogencity:	0.014
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.342

Download Data

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

Natural Product: NPC476777

Natural Product ID:	NPC476777
*Common Name:**	theasaponins E1
IUPAC Name:	(2S,3S,4S,5R,6R)-6-[[(3S,4S,6aR,6bS,8R,8aR,9R,10R,14bR)-9-acetyloxy-4-formyl-8-hydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-5-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms:	Theasaponins E1
Standard InCHIKey:	WWVKOCDDDWJQLC-SEBBEXHUSA-N
Standard InCHI:	InChI=1S/C59H90O27/c1-10-24(2)49(76)86-46-47(79-25(3)63)59(23-62)27(17-54(46,4)5)26-11-12-32-55(6)15-14-34(56(7,22-61)31(55)13-16-57(32,8)58(26,9)18-33(59)66)81-53-45(85-51-40(72)38(70)37(69)30(19-60)80-51)42(41(73)43(83-53)48(74)75)82-52-44(36(68)29(65)21-78-52)84-50-39(71)35(67)28(64)20-77-50/h10-11,22,27-47,50-53,60,62,64-73H,12-21,23H2,1-9H3,(H,74,75)/b24-10-/t27?,28-,29+,30-,31?,32?,33-,34+,35+,36+,37+,38+,39-,40-,41+,42+,43+,44-,45-,46+,47+,50+,51-,52+,53-,55+,56+,57-,58-,59+/m1/s1
SMILES:	C/C=C(/C)\C(=O)O[C@H]1[C@@H]([C@@]2([C@@H](C[C@@]3(C(=CCC4[C@]3(CCC5[C@@]4(CC[C@@H]([C@@]5(C)C=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)O[C@@H]9[C@@H]([C@H]([C@H]([C@H](O9)CO)O)O)O)C)C)C2CC1(C)C)C)O)CO)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44566256
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.foodchem.2013.08.121]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[16180814]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	seeds	Shizuoka prefecture, Japan	n.a.	PMID[16499314]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18068204]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21434603]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	flower	n.a.	PMID[21922925]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[21925888]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22377672]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265489]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaves	Bandung, West Java, Indonesia		PMID[23621359]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Cotyledon	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Seed Oil	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8258	Camellia sinensis	Species	Theaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	71.4	%	PMID[16499314]

☑ 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 NPC476777 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	321
0.1-0.2	1966
0.2-0.3	4939
0.3-0.4	8436
0.4-0.5	11942
0.5-0.6	8262
0.6-0.7	4361
0.7-0.8	1667
0.8-0.85	281
0.85-0.9	314
0.9-0.95	138
0.95-1	70

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476778
0.9919	High Similarity	NPC110700
0.9919	High Similarity	NPC279915
0.9918	High Similarity	NPC476779
0.9836	High Similarity	NPC477195
0.9836	High Similarity	NPC476776
0.9754	High Similarity	NPC476775
0.9754	High Similarity	NPC476780
0.9754	High Similarity	NPC476774
0.9754	High Similarity	NPC271610
0.9675	High Similarity	NPC46823
0.9675	High Similarity	NPC312650
0.9675	High Similarity	NPC178264
0.9675	High Similarity	NPC30279
0.9675	High Similarity	NPC277212
0.9675	High Similarity	NPC71391
0.9675	High Similarity	NPC192765
0.9675	High Similarity	NPC473918
0.9672	High Similarity	NPC11577
0.9672	High Similarity	NPC252289
0.9672	High Similarity	NPC88311
0.9672	High Similarity	NPC1314
0.9672	High Similarity	NPC97918
0.9672	High Similarity	NPC252657
0.9672	High Similarity	NPC9470
0.9672	High Similarity	NPC470518
0.9672	High Similarity	NPC305793
0.9672	High Similarity	NPC472267
0.9672	High Similarity	NPC82380
0.9672	High Similarity	NPC115656
0.9672	High Similarity	NPC141600
0.9672	High Similarity	NPC269484
0.9672	High Similarity	NPC265841
0.9672	High Similarity	NPC244296
0.9672	High Similarity	NPC47995
0.9672	High Similarity	NPC273878
0.9672	High Similarity	NPC477196
0.9672	High Similarity	NPC107536
0.9672	High Similarity	NPC280029
0.9597	High Similarity	NPC225791
0.9593	High Similarity	NPC477197
0.959	High Similarity	NPC477192
0.959	High Similarity	NPC477193
0.959	High Similarity	NPC477191
0.959	High Similarity	NPC477194
0.9512	High Similarity	NPC470912
0.9512	High Similarity	NPC477079
0.9512	High Similarity	NPC477077
0.9512	High Similarity	NPC477076
0.9512	High Similarity	NPC470913
0.9435	High Similarity	NPC25998
0.9435	High Similarity	NPC478155
0.9431	High Similarity	NPC477078
0.9431	High Similarity	NPC477075
0.9431	High Similarity	NPC329923
0.9431	High Similarity	NPC475281
0.9431	High Similarity	NPC470475
0.9426	High Similarity	NPC284449
0.936	High Similarity	NPC478150
0.936	High Similarity	NPC478152
0.936	High Similarity	NPC478154
0.936	High Similarity	NPC478153
0.935	High Similarity	NPC470516
0.9344	High Similarity	NPC160452
0.9286	High Similarity	NPC478151
0.928	High Similarity	NPC262796
0.928	High Similarity	NPC173435
0.928	High Similarity	NPC476074
0.928	High Similarity	NPC329993
0.928	High Similarity	NPC172374
0.928	High Similarity	NPC478064
0.928	High Similarity	NPC301639
0.928	High Similarity	NPC475167
0.928	High Similarity	NPC45346
0.928	High Similarity	NPC264566
0.928	High Similarity	NPC134914
0.928	High Similarity	NPC475377
0.928	High Similarity	NPC478065
0.9274	High Similarity	NPC470476
0.9268	High Similarity	NPC475368
0.9262	High Similarity	NPC257211
0.9262	High Similarity	NPC44716
0.9262	High Similarity	NPC2370
0.9187	High Similarity	NPC471962
0.9187	High Similarity	NPC471963
0.9187	High Similarity	NPC247315
0.9187	High Similarity	NPC33068
0.918	High Similarity	NPC10607
0.918	High Similarity	NPC187290
0.918	High Similarity	NPC21691
0.918	High Similarity	NPC475591
0.918	High Similarity	NPC213952
0.918	High Similarity	NPC80986
0.918	High Similarity	NPC236870
0.918	High Similarity	NPC4749
0.9106	High Similarity	NPC200049
0.9106	High Similarity	NPC258617
0.9106	High Similarity	NPC471964
0.9106	High Similarity	NPC302543
0.9106	High Similarity	NPC262199
0.9106	High Similarity	NPC283417
0.9106	High Similarity	NPC14617
0.9106	High Similarity	NPC471961
0.9106	High Similarity	NPC202666
0.9098	High Similarity	NPC114484
0.9098	High Similarity	NPC171544
0.9098	High Similarity	NPC223301
0.9098	High Similarity	NPC62725
0.9098	High Similarity	NPC297263
0.9098	High Similarity	NPC22956
0.9098	High Similarity	NPC242840
0.9098	High Similarity	NPC187618
0.9098	High Similarity	NPC11242
0.9098	High Similarity	NPC159309
0.9098	High Similarity	NPC301449
0.9098	High Similarity	NPC31838
0.9098	High Similarity	NPC86222
0.9098	High Similarity	NPC64715
0.9098	High Similarity	NPC302887
0.9098	High Similarity	NPC31193
0.9098	High Similarity	NPC104372
0.9098	High Similarity	NPC222580
0.9032	High Similarity	NPC23275
0.9024	High Similarity	NPC471965
0.9024	High Similarity	NPC162574
0.9024	High Similarity	NPC131469
0.9024	High Similarity	NPC313110
0.9016	High Similarity	NPC294112
0.9016	High Similarity	NPC118440
0.9016	High Similarity	NPC236657
0.8976	High Similarity	NPC43589
0.8976	High Similarity	NPC311178
0.8976	High Similarity	NPC300655
0.8976	High Similarity	NPC222951
0.8968	High Similarity	NPC112492
0.8968	High Similarity	NPC23020
0.8968	High Similarity	NPC472269
0.8968	High Similarity	NPC472268
0.8968	High Similarity	NPC472270
0.896	High Similarity	NPC470218
0.896	High Similarity	NPC285091
0.896	High Similarity	NPC181066
0.896	High Similarity	NPC469947
0.8952	High Similarity	NPC281148
0.8952	High Similarity	NPC235405
0.8952	High Similarity	NPC30735
0.8934	High Similarity	NPC473884
0.8934	High Similarity	NPC475171
0.8934	High Similarity	NPC39211
0.8934	High Similarity	NPC180550
0.8934	High Similarity	NPC157868
0.8934	High Similarity	NPC472949
0.8934	High Similarity	NPC114441
0.8934	High Similarity	NPC192791
0.8934	High Similarity	NPC469945
0.8934	High Similarity	NPC208381
0.8934	High Similarity	NPC214484
0.8934	High Similarity	NPC309780
0.8934	High Similarity	NPC35405
0.8934	High Similarity	NPC6377
0.8934	High Similarity	NPC11551
0.8923	High Similarity	NPC190065
0.8923	High Similarity	NPC471089
0.8923	High Similarity	NPC141215
0.8906	High Similarity	NPC196874
0.8906	High Similarity	NPC322904
0.8906	High Similarity	NPC324933
0.8906	High Similarity	NPC475177
0.8906	High Similarity	NPC233223
0.8906	High Similarity	NPC319719
0.8906	High Similarity	NPC183816
0.8906	High Similarity	NPC475444
0.8906	High Similarity	NPC473679
0.888	High Similarity	NPC470477
0.8871	High Similarity	NPC40775
0.8871	High Similarity	NPC107966
0.8871	High Similarity	NPC249848
0.8871	High Similarity	NPC235438
0.8855	High Similarity	NPC295885
0.8855	High Similarity	NPC140045
0.8855	High Similarity	NPC596
0.8852	High Similarity	NPC471548
0.8852	High Similarity	NPC286347
0.8852	High Similarity	NPC470515
0.8852	High Similarity	NPC473459
0.8846	High Similarity	NPC262813
0.8819	High Similarity	NPC45606
0.8819	High Similarity	NPC220838
0.881	High Similarity	NPC297950
0.88	High Similarity	NPC478066
0.879	High Similarity	NPC75417
0.878	High Similarity	NPC470517
0.878	High Similarity	NPC470915
0.878	High Similarity	NPC473401
0.878	High Similarity	NPC473386
0.878	High Similarity	NPC470911
0.8779	High Similarity	NPC251998
0.877	High Similarity	NPC323359
0.877	High Similarity	NPC473405
0.877	High Similarity	NPC300419

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 NPC476777 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	2195
0.2-0.3	3746
0.3-0.4	1865
0.4-0.5	621
0.5-0.6	264
0.6-0.7	118
0.7-0.8	28
0.8-0.85	2
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9106	High Similarity	NPD8328	Phase 3
0.8618	High Similarity	NPD8295	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7319	Approved
0.8092	Intermediate Similarity	NPD7507	Approved
0.7923	Intermediate Similarity	NPD8517	Approved
0.7923	Intermediate Similarity	NPD8516	Approved
0.7923	Intermediate Similarity	NPD8515	Approved
0.7836	Intermediate Similarity	NPD7736	Approved
0.7823	Intermediate Similarity	NPD6686	Approved
0.7795	Intermediate Similarity	NPD8133	Approved
0.7786	Intermediate Similarity	NPD8513	Phase 3
0.776	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD8294	Approved
0.771	Intermediate Similarity	NPD8377	Approved
0.7652	Intermediate Similarity	NPD8296	Approved
0.7652	Intermediate Similarity	NPD8335	Approved
0.7652	Intermediate Similarity	NPD8379	Approved
0.7652	Intermediate Similarity	NPD8378	Approved
0.7652	Intermediate Similarity	NPD8380	Approved
0.7519	Intermediate Similarity	NPD8033	Approved
0.75	Intermediate Similarity	NPD8293	Discontinued
0.7463	Intermediate Similarity	NPD6370	Approved
0.7402	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7516	Approved
0.7353	Intermediate Similarity	NPD7492	Approved
0.7313	Intermediate Similarity	NPD6054	Approved
0.7313	Intermediate Similarity	NPD6319	Approved
0.7299	Intermediate Similarity	NPD6616	Approved
0.7293	Intermediate Similarity	NPD7328	Approved
0.7293	Intermediate Similarity	NPD7327	Approved
0.7259	Intermediate Similarity	NPD7503	Approved
0.7246	Intermediate Similarity	NPD7078	Approved
0.7231	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6412	Phase 2
0.7185	Intermediate Similarity	NPD6059	Approved
0.7176	Intermediate Similarity	NPD6882	Approved
0.7176	Intermediate Similarity	NPD8297	Approved
0.7132	Intermediate Similarity	NPD6016	Approved
0.7132	Intermediate Similarity	NPD6015	Approved
0.7097	Intermediate Similarity	NPD7902	Approved
0.709	Intermediate Similarity	NPD7115	Discovery
0.709	Intermediate Similarity	NPD6009	Approved
0.708	Intermediate Similarity	NPD5988	Approved
0.6992	Remote Similarity	NPD7748	Approved
0.697	Remote Similarity	NPD6650	Approved
0.697	Remote Similarity	NPD6649	Approved
0.6947	Remote Similarity	NPD6372	Approved
0.6947	Remote Similarity	NPD6373	Approved
0.6947	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4225	Approved
0.6905	Remote Similarity	NPD7638	Approved
0.6894	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD6921	Approved
0.6879	Remote Similarity	NPD8074	Phase 3
0.687	Remote Similarity	NPD6899	Approved
0.687	Remote Similarity	NPD6881	Approved
0.6866	Remote Similarity	NPD4632	Approved
0.6855	Remote Similarity	NPD7900	Approved
0.6855	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7640	Approved
0.685	Remote Similarity	NPD7639	Approved
0.6846	Remote Similarity	NPD6402	Approved
0.6846	Remote Similarity	NPD5739	Approved
0.6846	Remote Similarity	NPD7128	Approved
0.6846	Remote Similarity	NPD6675	Approved
0.6842	Remote Similarity	NPD8130	Phase 1
0.6829	Remote Similarity	NPD7515	Phase 2
0.6794	Remote Similarity	NPD5697	Approved
0.6767	Remote Similarity	NPD7290	Approved
0.6767	Remote Similarity	NPD6883	Approved
0.6767	Remote Similarity	NPD7102	Approved
0.6742	Remote Similarity	NPD7320	Approved
0.6716	Remote Similarity	NPD6617	Approved
0.6716	Remote Similarity	NPD6847	Approved
0.6716	Remote Similarity	NPD6869	Approved
0.6713	Remote Similarity	NPD6033	Approved
0.6692	Remote Similarity	NPD6013	Approved
0.6692	Remote Similarity	NPD6014	Approved
0.6692	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD8448	Approved
0.6643	Remote Similarity	NPD5983	Phase 2
0.6642	Remote Similarity	NPD4634	Approved
0.6641	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD8390	Approved
0.6621	Remote Similarity	NPD8392	Approved
0.6621	Remote Similarity	NPD8391	Approved
0.6617	Remote Similarity	NPD6011	Approved
0.6577	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6336	Discontinued
0.6573	Remote Similarity	NPD8451	Approved
0.6549	Remote Similarity	NPD7830	Approved
0.6549	Remote Similarity	NPD7829	Approved
0.6541	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.651	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7799	Discontinued
0.6484	Remote Similarity	NPD4697	Phase 3
0.648	Remote Similarity	NPD46	Approved
0.648	Remote Similarity	NPD6698	Approved
0.6471	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD7260	Phase 2
0.6443	Remote Similarity	NPD8415	Approved
0.6434	Remote Similarity	NPD7642	Approved
0.6403	Remote Similarity	NPD6274	Approved
0.6389	Remote Similarity	NPD8342	Approved
0.6389	Remote Similarity	NPD8340	Approved
0.6389	Remote Similarity	NPD8341	Approved
0.6389	Remote Similarity	NPD8299	Approved
0.6383	Remote Similarity	NPD7100	Approved
0.6383	Remote Similarity	NPD7101	Approved
0.6364	Remote Similarity	NPD7632	Discontinued
0.6364	Remote Similarity	NPD5211	Phase 2
0.6358	Remote Similarity	NPD8368	Discontinued
0.6336	Remote Similarity	NPD4696	Approved
0.6336	Remote Similarity	NPD5286	Approved
0.6336	Remote Similarity	NPD5285	Approved
0.6319	Remote Similarity	NPD6067	Discontinued
0.6312	Remote Similarity	NPD6335	Approved
0.6308	Remote Similarity	NPD6083	Phase 2
0.6308	Remote Similarity	NPD4755	Approved
0.6308	Remote Similarity	NPD6084	Phase 2
0.6306	Remote Similarity	NPD7625	Phase 1
0.6299	Remote Similarity	NPD8035	Phase 2
0.6299	Remote Similarity	NPD6411	Approved
0.6299	Remote Similarity	NPD7983	Approved
0.6299	Remote Similarity	NPD8034	Phase 2
0.6288	Remote Similarity	NPD5344	Discontinued
0.6286	Remote Similarity	NPD6868	Approved
0.6277	Remote Similarity	NPD6371	Approved
0.6269	Remote Similarity	NPD5141	Approved
0.625	Remote Similarity	NPD8080	Discontinued
0.625	Remote Similarity	NPD8407	Phase 2
0.625	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD5778	Approved
0.6241	Remote Similarity	NPD5226	Approved
0.6241	Remote Similarity	NPD5224	Approved
0.6241	Remote Similarity	NPD6317	Approved
0.6241	Remote Similarity	NPD4633	Approved
0.6241	Remote Similarity	NPD5225	Approved
0.624	Remote Similarity	NPD3573	Approved
0.6231	Remote Similarity	NPD5222	Approved
0.6231	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD5221	Approved
0.6222	Remote Similarity	NPD6008	Approved
0.6212	Remote Similarity	NPD4700	Approved
0.62	Remote Similarity	NPD6845	Suspended
0.6197	Remote Similarity	NPD7641	Discontinued
0.6197	Remote Similarity	NPD6314	Approved
0.6197	Remote Similarity	NPD6313	Approved
0.6194	Remote Similarity	NPD5175	Approved
0.6194	Remote Similarity	NPD5174	Approved
0.6187	Remote Similarity	NPD6053	Discontinued
0.6185	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD5173	Approved
0.6181	Remote Similarity	NPD8444	Approved
0.6181	Remote Similarity	NPD6908	Approved
0.6181	Remote Similarity	NPD6909	Approved
0.6174	Remote Similarity	NPD5956	Approved
0.6172	Remote Similarity	NPD6079	Approved
0.6165	Remote Similarity	NPD5223	Approved
0.6149	Remote Similarity	NPD8336	Approved
0.6149	Remote Similarity	NPD8337	Approved
0.6142	Remote Similarity	NPD5328	Approved
0.6142	Remote Similarity	NPD6101	Approved
0.6142	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD5696	Approved
0.6133	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD4730	Approved
0.6131	Remote Similarity	NPD4729	Approved
0.6124	Remote Similarity	NPD6399	Phase 3
0.6111	Remote Similarity	NPD8435	Approved
0.6103	Remote Similarity	NPD4767	Approved
0.6103	Remote Similarity	NPD4768	Approved
0.6094	Remote Similarity	NPD7838	Discovery
0.6093	Remote Similarity	NPD8338	Approved
0.6075	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD6672	Approved
0.6063	Remote Similarity	NPD5737	Approved
0.6043	Remote Similarity	NPD5247	Approved
0.6043	Remote Similarity	NPD5249	Phase 3
0.6043	Remote Similarity	NPD5251	Approved
0.6043	Remote Similarity	NPD5250	Approved
0.6043	Remote Similarity	NPD5248	Approved
0.6032	Remote Similarity	NPD3618	Phase 1
0.6032	Remote Similarity	NPD8319	Approved
0.6032	Remote Similarity	NPD8320	Phase 1
0.6031	Remote Similarity	NPD5695	Phase 3
0.6031	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD8360	Approved
0.6022	Remote Similarity	NPD8361	Approved
0.6016	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD5128	Approved
0.6011	Remote Similarity	NPD8312	Approved
0.6011	Remote Similarity	NPD8313	Approved
0.6	Remote Similarity	NPD6333	Approved

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