NPASS Compound

Structure

NPC274695 OpenBabel07101718322D 40 46 0 0 1 0 0 0 0 0999 V2000 7.4706 1.0528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1228 -1.7670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3084 -0.8681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6967 -0.0770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6611 -2.3964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3484 0.4404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1871 0.1113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7106 0.7741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6616 0.4651 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6228 -0.9010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5682 -0.0101 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1228 -0.0349 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4527 -0.7497 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6228 -0.9010 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1228 -0.0349 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9888 -2.9512 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7568 -0.4010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1362 0.5517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4963 -2.2068 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6616 -0.5349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1239 -2.6986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0467 -1.5614 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3175 -1.0023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 -1.4010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4339 -0.9010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9451 -1.4941 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9749 0.2225 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6228 0.8311 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3261 -3.8926 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0128 1.5405 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4706 -1.1227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3329 -3.3103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6814 -2.4923 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8690 0.6704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7106 -0.8440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3445 -1.9029 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0970 -1.7980 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 3 25 1 0 0 0 0 4 25 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 26 1 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 11 1 1 1 0 0 0 11 22 1 0 0 0 0 12 2 1 1 0 0 0 12 16 1 0 0 0 0 12 17 1 0 0 0 0 13 20 1 0 0 0 0 13 27 1 1 0 0 0 14 17 1 6 0 0 0 14 37 1 0 0 0 0 15 25 1 0 0 0 0 15 28 1 6 0 0 0 16 19 1 0 0 0 0 16 26 1 1 0 0 0 17 30 1 6 0 0 0 18 21 1 0 0 0 0 18 23 1 0 0 0 0 18 31 1 6 0 0 0 19 26 1 1 0 0 0 19 29 1 0 0 0 0 20 29 1 0 0 0 0 20 32 2 0 0 0 0 21 28 1 1 0 0 0 21 38 1 0 0 0 0 22 33 2 0 0 0 0 22 37 1 0 0 0 0 23 34 2 0 0 0 0 23 39 1 0 0 0 0 24 27 1 6 0 0 0 24 28 1 0 0 0 0 24 35 1 0 0 0 0 25 38 1 0 0 0 0 26 5 1 6 0 0 0 27 9 1 6 0 0 0 27 40 1 0 0 0 0 28 39 1 1 0 0 0 29 36 1 1 0 0 0 29 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.25
Volume:	338.244
LogP:	6.917
LogD:	5.472
LogS:	-5.543
# Rotatable Bonds:	4
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.698
Synthetic Accessibility Score:	4.435
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.565
MDCK Permeability:	1.45086432894459e-05
Pgp-inhibitor:	0.513
Pgp-substrate:	0.167
Human Intestinal Absorption (HIA):	0.172
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087
Plasma Protein Binding (PPB):	88.192626953125%
Volume Distribution (VD):	5.03
Pgp-substrate:	4.05806303024292%

ADMET: Metabolism

CYP1A2-inhibitor:	0.709
CYP1A2-substrate:	0.319
CYP2C19-inhibitor:	0.281
CYP2C19-substrate:	0.818
CYP2C9-inhibitor:	0.324
CYP2C9-substrate:	0.693
CYP2D6-inhibitor:	0.052
CYP2D6-substrate:	0.197
CYP3A4-inhibitor:	0.675
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	16.328
Half-life (T1/2):	0.087

ADMET: Toxicity

hERG Blockers:	0.23
Human Hepatotoxicity (H-HT):	0.754
Drug-inuced Liver Injury (DILI):	0.168
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.897
Carcinogencity:	0.113
Eye Corrosion:	0.247
Eye Irritation:	0.47
Respiratory Toxicity:	0.073

Download Data

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

Natural Product: NPC274695

Natural Product ID:	NPC274695
*Common Name:**	LLEMQBRGGMFRMI-PMAKBTIZSA-N
IUPAC Name:	n.a.
Synonyms:	2Beta-Hydroxyarisanlactone C
Standard InCHIKey:	LLEMQBRGGMFRMI-PMAKBTIZSA-N
Standard InCHI:	InChI=1S/C29H40O11/c1-11-10-14(37-22(11)33)17(30)12(2)16-19-26(16,5)8-9-27-13(20(32)29(19,36)40-27)6-7-15-25(3,4)38-21-18(31)23(34)39-28(15,21)24(27)35/h11-19,21,24,30-31,35-36H,6-10H2,1-5H3/t11-,12+,13+,14+,15+,16-,17+,18-,19+,21-,24+,26-,27-,28-,29+/m1/s1
SMILES:	C[C@@H]1C[C@@H]([C@H]([C@@H](C)[C@@H]2[C@H]3[C@]2(C)CC[C@@]24[C@@H](CC[C@H]5C(C)(C)O[C@@H]6[C@H](C(=O)O[C@]56[C@H]2O)O)C(=O)[C@@]3(O)O4)O)OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1171984
PubChem CID:	46872939
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001816] Furofurans

*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
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19673515]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[20536188]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[23265871]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2740	Cell Line	Neutrophils		Inhibition	=	18.47	%	PMID[476440]

☑ 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 NPC274695 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	806
0.1-0.2	5604
0.2-0.3	13435
0.3-0.4	12136
0.4-0.5	7707
0.5-0.6	2634
0.6-0.7	312
0.7-0.8	44
0.8-0.85	6
0.85-0.9	10
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC329876
0.899	High Similarity	NPC168890
0.899	High Similarity	NPC469441
0.899	High Similarity	NPC41674
0.899	High Similarity	NPC228311
0.89	High Similarity	NPC290247
0.89	High Similarity	NPC469787
0.89	High Similarity	NPC469788
0.8812	High Similarity	NPC278693
0.8812	High Similarity	NPC220773
0.8725	High Similarity	NPC217041
0.8713	High Similarity	NPC176756
0.8654	High Similarity	NPC98870
0.8641	High Similarity	NPC182185
0.8627	High Similarity	NPC167044
0.8416	Intermediate Similarity	NPC469350
0.8039	Intermediate Similarity	NPC162024
0.7981	Intermediate Similarity	NPC177518
0.7981	Intermediate Similarity	NPC123070
0.7981	Intermediate Similarity	NPC88890
0.7981	Intermediate Similarity	NPC114365
0.7981	Intermediate Similarity	NPC18433
0.7981	Intermediate Similarity	NPC18044
0.7981	Intermediate Similarity	NPC132304
0.7981	Intermediate Similarity	NPC169089
0.7981	Intermediate Similarity	NPC154962
0.7789	Intermediate Similarity	NPC473791
0.7788	Intermediate Similarity	NPC292803
0.7745	Intermediate Similarity	NPC328180
0.7745	Intermediate Similarity	NPC278028
0.7732	Intermediate Similarity	NPC314364
0.7586	Intermediate Similarity	NPC186339
0.7527	Intermediate Similarity	NPC475616
0.7477	Intermediate Similarity	NPC473526
0.7477	Intermediate Similarity	NPC473701
0.7473	Intermediate Similarity	NPC125164
0.7455	Intermediate Similarity	NPC475463
0.7436	Intermediate Similarity	NPC1538
0.7426	Intermediate Similarity	NPC469627
0.7391	Intermediate Similarity	NPC228411
0.7379	Intermediate Similarity	NPC470191
0.7374	Intermediate Similarity	NPC51662
0.7373	Intermediate Similarity	NPC144625
0.735	Intermediate Similarity	NPC192309
0.7333	Intermediate Similarity	NPC211087
0.7327	Intermediate Similarity	NPC65359
0.73	Intermediate Similarity	NPC470009
0.7281	Intermediate Similarity	NPC475490
0.7273	Intermediate Similarity	NPC13071
0.7273	Intermediate Similarity	NPC476717
0.725	Intermediate Similarity	NPC11732
0.7236	Intermediate Similarity	NPC224623
0.7204	Intermediate Similarity	NPC179922
0.7172	Intermediate Similarity	NPC478111
0.7157	Intermediate Similarity	NPC477444
0.7157	Intermediate Similarity	NPC477442
0.7157	Intermediate Similarity	NPC477433
0.7143	Intermediate Similarity	NPC157328
0.7143	Intermediate Similarity	NPC476009
0.7143	Intermediate Similarity	NPC42747
0.7115	Intermediate Similarity	NPC76136
0.7115	Intermediate Similarity	NPC217567
0.7115	Intermediate Similarity	NPC329713
0.7091	Intermediate Similarity	NPC166079
0.7087	Intermediate Similarity	NPC474699
0.7073	Intermediate Similarity	NPC469351
0.7059	Intermediate Similarity	NPC477443
0.7059	Intermediate Similarity	NPC477440
0.7053	Intermediate Similarity	NPC474003
0.7049	Intermediate Similarity	NPC172823
0.7048	Intermediate Similarity	NPC475900
0.7043	Intermediate Similarity	NPC470115
0.7043	Intermediate Similarity	NPC470116
0.7041	Intermediate Similarity	NPC212340
0.7034	Intermediate Similarity	NPC317635
0.7034	Intermediate Similarity	NPC329008
0.7	Intermediate Similarity	NPC100078
0.6989	Remote Similarity	NPC475260
0.6989	Remote Similarity	NPC473699
0.6989	Remote Similarity	NPC474100
0.6989	Remote Similarity	NPC51249
0.6989	Remote Similarity	NPC475232
0.6989	Remote Similarity	NPC473775
0.6979	Remote Similarity	NPC470014
0.6972	Remote Similarity	NPC213528
0.6972	Remote Similarity	NPC244969
0.697	Remote Similarity	NPC474266
0.6961	Remote Similarity	NPC471221
0.6937	Remote Similarity	NPC306776
0.6931	Remote Similarity	NPC469626
0.6931	Remote Similarity	NPC475491
0.693	Remote Similarity	NPC473062
0.6923	Remote Similarity	NPC216137
0.6916	Remote Similarity	NPC470632
0.6916	Remote Similarity	NPC74466
0.6915	Remote Similarity	NPC215030
0.6882	Remote Similarity	NPC470243
0.6869	Remote Similarity	NPC475849
0.6857	Remote Similarity	NPC472238
0.6857	Remote Similarity	NPC472237
0.6857	Remote Similarity	NPC475788
0.6832	Remote Similarity	NPC51267
0.6832	Remote Similarity	NPC476715
0.6822	Remote Similarity	NPC158416
0.6822	Remote Similarity	NPC470883
0.6822	Remote Similarity	NPC475765
0.6822	Remote Similarity	NPC76862
0.6822	Remote Similarity	NPC475785
0.6822	Remote Similarity	NPC39859
0.6813	Remote Similarity	NPC469925
0.6796	Remote Similarity	NPC476435
0.6796	Remote Similarity	NPC53158
0.6792	Remote Similarity	NPC470424
0.6783	Remote Similarity	NPC287311
0.678	Remote Similarity	NPC471146
0.6768	Remote Similarity	NPC216941
0.6765	Remote Similarity	NPC477441
0.675	Remote Similarity	NPC147635
0.675	Remote Similarity	NPC163693
0.6733	Remote Similarity	NPC115995
0.6733	Remote Similarity	NPC477434
0.6731	Remote Similarity	NPC474951
0.6731	Remote Similarity	NPC173926
0.6729	Remote Similarity	NPC322188
0.6702	Remote Similarity	NPC96322
0.6698	Remote Similarity	NPC474379
0.6697	Remote Similarity	NPC472144
0.6697	Remote Similarity	NPC253995
0.6696	Remote Similarity	NPC88469
0.6667	Remote Similarity	NPC471254
0.6667	Remote Similarity	NPC225353
0.6667	Remote Similarity	NPC472754
0.6667	Remote Similarity	NPC470172
0.6667	Remote Similarity	NPC97002
0.6667	Remote Similarity	NPC477445
0.6667	Remote Similarity	NPC474747
0.664	Remote Similarity	NPC188291
0.6639	Remote Similarity	NPC179429
0.6639	Remote Similarity	NPC471145
0.6638	Remote Similarity	NPC157476
0.6637	Remote Similarity	NPC474101
0.6637	Remote Similarity	NPC478038
0.6636	Remote Similarity	NPC247877
0.6636	Remote Similarity	NPC190294
0.6636	Remote Similarity	NPC470423
0.6636	Remote Similarity	NPC289004
0.6636	Remote Similarity	NPC309127
0.6636	Remote Similarity	NPC206878
0.6635	Remote Similarity	NPC221993
0.6634	Remote Similarity	NPC476721
0.663	Remote Similarity	NPC286842
0.661	Remote Similarity	NPC308858
0.661	Remote Similarity	NPC79193
0.661	Remote Similarity	NPC475537
0.6607	Remote Similarity	NPC110989
0.6607	Remote Similarity	NPC475871
0.6607	Remote Similarity	NPC472755
0.6607	Remote Similarity	NPC475945
0.6607	Remote Similarity	NPC473406
0.6607	Remote Similarity	NPC471253
0.6606	Remote Similarity	NPC328562
0.6606	Remote Similarity	NPC323421
0.6606	Remote Similarity	NPC472145
0.6606	Remote Similarity	NPC474313
0.6604	Remote Similarity	NPC475878
0.6604	Remote Similarity	NPC474065
0.6604	Remote Similarity	NPC329952
0.6602	Remote Similarity	NPC92139
0.6602	Remote Similarity	NPC472745
0.6602	Remote Similarity	NPC470657
0.6593	Remote Similarity	NPC476330
0.6579	Remote Similarity	NPC194620
0.6579	Remote Similarity	NPC324327
0.6579	Remote Similarity	NPC474421
0.6579	Remote Similarity	NPC72813
0.6579	Remote Similarity	NPC203974
0.6579	Remote Similarity	NPC326994
0.6577	Remote Similarity	NPC178853
0.6577	Remote Similarity	NPC472753
0.6577	Remote Similarity	NPC478181
0.6574	Remote Similarity	NPC287354
0.6574	Remote Similarity	NPC17336
0.6574	Remote Similarity	NPC62407
0.6571	Remote Similarity	NPC92974
0.6569	Remote Similarity	NPC65133
0.6569	Remote Similarity	NPC475689
0.6562	Remote Similarity	NPC477867
0.6552	Remote Similarity	NPC470622
0.6552	Remote Similarity	NPC477103
0.6549	Remote Similarity	NPC203659
0.6549	Remote Similarity	NPC474741
0.6549	Remote Similarity	NPC472748
0.6549	Remote Similarity	NPC472756
0.6542	Remote Similarity	NPC475307
0.6538	Remote Similarity	NPC31349
0.6538	Remote Similarity	NPC239938
0.6538	Remote Similarity	NPC197333
0.6535	Remote Similarity	NPC148740
0.6535	Remote Similarity	NPC102156
0.6531	Remote Similarity	NPC108014

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 NPC274695 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1069
0.1-0.2	4568
0.2-0.3	2413
0.3-0.4	716
0.4-0.5	325
0.5-0.6	51
0.6-0.7	6
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7981	Intermediate Similarity	NPD4057	Clinical (unspecified phase)
0.7981	Intermediate Similarity	NPD4056	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD1700	Approved
0.641	Remote Similarity	NPD6371	Approved
0.6293	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD8138	Approved
0.6228	Remote Similarity	NPD8083	Approved
0.6228	Remote Similarity	NPD8084	Approved
0.6228	Remote Similarity	NPD8082	Approved
0.6228	Remote Similarity	NPD8085	Approved
0.6228	Remote Similarity	NPD8086	Approved
0.6228	Remote Similarity	NPD8139	Approved
0.6211	Remote Similarity	NPD229	Approved
0.6174	Remote Similarity	NPD8276	Approved
0.6174	Remote Similarity	NPD8275	Approved
0.616	Remote Similarity	NPD8266	Approved
0.616	Remote Similarity	NPD8269	Approved
0.616	Remote Similarity	NPD8268	Approved
0.616	Remote Similarity	NPD8267	Approved
0.6139	Remote Similarity	NPD4238	Approved
0.6139	Remote Similarity	NPD4802	Phase 2
0.6121	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD8081	Approved
0.6098	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD8393	Approved
0.6047	Remote Similarity	NPD7078	Approved
0.6016	Remote Similarity	NPD7492	Approved
0.5982	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD6616	Approved
0.5957	Remote Similarity	NPD7909	Approved
0.5952	Remote Similarity	NPD6059	Approved
0.5952	Remote Similarity	NPD6054	Approved
0.5948	Remote Similarity	NPD8300	Approved
0.5948	Remote Similarity	NPD8301	Approved
0.5938	Remote Similarity	NPD897	Approved
0.5938	Remote Similarity	NPD8328	Phase 3
0.5938	Remote Similarity	NPD896	Approved
0.5938	Remote Similarity	NPD898	Approved
0.5923	Remote Similarity	NPD8293	Discontinued
0.5922	Remote Similarity	NPD7329	Approved
0.5895	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD5282	Discontinued
0.5878	Remote Similarity	NPD7736	Approved
0.5859	Remote Similarity	NPD6370	Approved
0.5856	Remote Similarity	NPD7983	Approved
0.5827	Remote Similarity	NPD6319	Approved
0.5781	Remote Similarity	NPD6016	Approved
0.5781	Remote Similarity	NPD6015	Approved
0.5781	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD6921	Approved
0.575	Remote Similarity	NPD8307	Discontinued
0.575	Remote Similarity	NPD8140	Approved
0.5736	Remote Similarity	NPD5988	Approved
0.5736	Remote Similarity	NPD8080	Discontinued
0.5714	Remote Similarity	NPD73	Approved
0.5701	Remote Similarity	NPD3669	Approved
0.5701	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD8961	Approved
0.566	Remote Similarity	NPD1779	Approved
0.566	Remote Similarity	NPD1780	Approved
0.5656	Remote Similarity	NPD8306	Approved
0.5656	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD8305	Approved
0.5644	Remote Similarity	NPD3181	Approved
0.561	Remote Similarity	NPD8087	Discontinued
0.56	Remote Similarity	NPD7532	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