NPASS Compound

Structure

NPC2933 OpenBabel07101718182D 35 42 0 0 1 0 0 0 0 0999 V2000 -2.5305 -4.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9227 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0567 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6167 2.1694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9796 -3.3345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7575 -1.8611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2435 -1.2826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9793 1.8209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3802 1.1828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0134 -1.7295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9855 -0.5724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2304 1.9053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8346 -1.5509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5685 -2.5149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7554 -1.0193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2414 -0.4407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6974 1.3724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9814 -3.3943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1906 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1906 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4199 0.6451 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7818 -1.6235 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0567 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0921 0.3000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0712 1.3313 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4305 -2.5597 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 -1.4010 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.5340 -4.2887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0567 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 4 31 1 0 0 0 0 5 21 1 0 0 0 0 6 7 2 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 9 2 0 0 0 0 8 12 1 0 0 0 0 9 17 1 0 0 0 0 10 18 2 0 0 0 0 11 19 2 0 0 0 0 12 20 2 0 0 0 0 13 15 1 0 0 0 0 13 28 1 0 0 0 0 14 16 1 0 0 0 0 15 32 1 0 0 0 0 16 33 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 0 0 0 0 19 30 1 0 0 0 0 20 22 1 0 0 0 0 20 31 1 0 0 0 0 21 32 1 0 0 0 0 21 34 2 0 0 0 0 22 29 1 0 0 0 0 23 24 1 0 0 0 0 23 33 1 1 0 0 0 24 27 1 0 0 0 0 24 35 1 1 0 0 0 25 29 1 6 0 0 0 25 30 1 0 0 0 0 25 31 1 0 0 0 0 26 28 1 1 0 0 0 26 32 1 0 0 0 0 26 33 1 0 0 0 0 27 35 1 0 0 0 0 28 29 1 1 0 0 0 29 14 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.27
Volume:	484.801
LogP:	4.005
LogD:	3.096
LogS:	-5.004
# Rotatable Bonds:	3
TPSA:	51.35
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	8
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.673
Synthetic Accessibility Score:	6.33
Fsp3:	0.552
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.33
MDCK Permeability:	2.5463781639700755e-05
Pgp-inhibitor:	0.871
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.859
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.745
Plasma Protein Binding (PPB):	74.31401824951172%
Volume Distribution (VD):	2.739
Pgp-substrate:	18.352487564086914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.126
CYP2C19-inhibitor:	0.611
CYP2C19-substrate:	0.925
CYP2C9-inhibitor:	0.591
CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.642
CYP3A4-inhibitor:	0.908
CYP3A4-substrate:	0.855

ADMET: Excretion

Clearance (CL):	7.431
Half-life (T1/2):	0.115

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.701
Drug-inuced Liver Injury (DILI):	0.124
AMES Toxicity:	0.197
Rat Oral Acute Toxicity:	0.99
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.811
Carcinogencity:	0.686
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.902

Download Data

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

Natural Product: NPC2933

Natural Product ID:	NPC2933
*Common Name:**	Communesin G
IUPAC Name:	n.a.
Synonyms:	Communesin G
Standard InCHIKey:	OMFQPKNORYZBSJ-HLYNDKHPSA-N
Standard InCHI:	InChI=1S/C29H34N4O2/c1-5-21(34)32-15-13-28-18-10-6-7-11-19(18)30-25-29(28)14-16-33(26(28)32)23(24-27(2,3)35-24)17-9-8-12-20(22(17)29)31(25)4/h6-12,23-26,30H,5,13-16H2,1-4H3/t23-,24+,25+,26+,28-,29-/m1/s1
SMILES:	CCC(=O)N1CC[C@@]23c4ccccc4N[C@@H]4[C@@]53CCN([C@H](c3cccc(c53)N4C)[C@H]3C(C)(C)O3)[C@H]12
Synthetic Gene Cluster:	BGC0001205;
ChEMBL Identifier:	CHEMBL500121
PubChem CID:	11476943
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001913] Alpha carbolines

*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
NPO32528	penicillium rivulum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730257]

☑ 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
NPT168	Cell Line	P388	Mus musculus	ID50	>	12.5	ug ml-1	PMID[567263]

☑ 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 NPC2933 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	299
0.1-0.2	1440
0.2-0.3	7190
0.3-0.4	23801
0.4-0.5	6305
0.5-0.6	3190
0.6-0.7	403
0.7-0.8	61
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9939	High Similarity	NPC256288
0.9939	High Similarity	NPC259626
0.9759	High Similarity	NPC473615
0.9701	High Similarity	NPC229484
0.9643	High Similarity	NPC292675
0.8466	Intermediate Similarity	NPC109787
0.7966	Intermediate Similarity	NPC285622
0.7692	Intermediate Similarity	NPC477173
0.767	Intermediate Similarity	NPC286871
0.7653	Intermediate Similarity	NPC470488
0.7571	Intermediate Similarity	NPC176983
0.75	Intermediate Similarity	NPC477179
0.7473	Intermediate Similarity	NPC251212
0.7473	Intermediate Similarity	NPC139085
0.7473	Intermediate Similarity	NPC214626
0.7462	Intermediate Similarity	NPC477178
0.7462	Intermediate Similarity	NPC254850
0.7462	Intermediate Similarity	NPC477180
0.7462	Intermediate Similarity	NPC477181
0.7458	Intermediate Similarity	NPC471122
0.7443	Intermediate Similarity	NPC29285
0.7437	Intermediate Similarity	NPC475259
0.7437	Intermediate Similarity	NPC471945
0.7437	Intermediate Similarity	NPC470491
0.7437	Intermediate Similarity	NPC471950
0.7424	Intermediate Similarity	NPC477174
0.7424	Intermediate Similarity	NPC470490
0.7416	Intermediate Similarity	NPC472102
0.7416	Intermediate Similarity	NPC309531
0.7416	Intermediate Similarity	NPC68650
0.7401	Intermediate Similarity	NPC113946
0.74	Intermediate Similarity	NPC471951
0.74	Intermediate Similarity	NPC471946
0.7389	Intermediate Similarity	NPC471124
0.7389	Intermediate Similarity	NPC472106
0.738	Intermediate Similarity	NPC477159
0.7377	Intermediate Similarity	NPC473743
0.7374	Intermediate Similarity	NPC470489
0.7348	Intermediate Similarity	NPC279527
0.7348	Intermediate Similarity	NPC214960
0.7316	Intermediate Similarity	NPC285841
0.7303	Intermediate Similarity	NPC222029
0.7302	Intermediate Similarity	NPC307396
0.7283	Intermediate Similarity	NPC264589
0.7283	Intermediate Similarity	NPC177261
0.7278	Intermediate Similarity	NPC472101
0.7278	Intermediate Similarity	NPC472120
0.7277	Intermediate Similarity	NPC475359
0.7277	Intermediate Similarity	NPC191817
0.7273	Intermediate Similarity	NPC471436
0.7263	Intermediate Similarity	NPC276085
0.7189	Intermediate Similarity	NPC242269
0.7182	Intermediate Similarity	NPC282339
0.7182	Intermediate Similarity	NPC85651
0.7182	Intermediate Similarity	NPC99632
0.7166	Intermediate Similarity	NPC260075
0.715	Intermediate Similarity	NPC22689
0.715	Intermediate Similarity	NPC105055
0.715	Intermediate Similarity	NPC473298
0.712	Intermediate Similarity	NPC476095
0.7119	Intermediate Similarity	NPC66936
0.7113	Intermediate Similarity	NPC25401
0.7107	Intermediate Similarity	NPC162440
0.7105	Intermediate Similarity	NPC159963
0.7059	Intermediate Similarity	NPC471123
0.7047	Intermediate Similarity	NPC181928
0.7033	Intermediate Similarity	NPC225319
0.7026	Intermediate Similarity	NPC276430
0.7022	Intermediate Similarity	NPC475763
0.7011	Intermediate Similarity	NPC475420
0.7005	Intermediate Similarity	NPC473006
0.6995	Remote Similarity	NPC472117
0.6974	Remote Similarity	NPC128582
0.6968	Remote Similarity	NPC475097
0.6966	Remote Similarity	NPC318086
0.6966	Remote Similarity	NPC473329
0.6959	Remote Similarity	NPC14994
0.6952	Remote Similarity	NPC248601
0.6952	Remote Similarity	NPC355
0.6927	Remote Similarity	NPC285192
0.6923	Remote Similarity	NPC284706
0.6915	Remote Similarity	NPC473880
0.6915	Remote Similarity	NPC96901
0.6915	Remote Similarity	NPC138830
0.6915	Remote Similarity	NPC67904
0.6905	Remote Similarity	NPC471197
0.6879	Remote Similarity	NPC469560
0.6872	Remote Similarity	NPC471198
0.6856	Remote Similarity	NPC52262
0.6848	Remote Similarity	NPC143457
0.6842	Remote Similarity	NPC203202
0.6842	Remote Similarity	NPC320147
0.6842	Remote Similarity	NPC264482
0.6842	Remote Similarity	NPC471663
0.6834	Remote Similarity	NPC34717
0.6829	Remote Similarity	NPC225400
0.6825	Remote Similarity	NPC476425
0.6823	Remote Similarity	NPC11149
0.6802	Remote Similarity	NPC473569
0.68	Remote Similarity	NPC22082
0.68	Remote Similarity	NPC186284
0.6796	Remote Similarity	NPC472538
0.6796	Remote Similarity	NPC471155
0.6796	Remote Similarity	NPC470786
0.6793	Remote Similarity	NPC193410
0.6791	Remote Similarity	NPC472115
0.6791	Remote Similarity	NPC472114
0.6789	Remote Similarity	NPC470548
0.6782	Remote Similarity	NPC106118
0.678	Remote Similarity	NPC329833
0.678	Remote Similarity	NPC472103
0.6766	Remote Similarity	NPC90967
0.6763	Remote Similarity	NPC270241
0.676	Remote Similarity	NPC212799
0.6758	Remote Similarity	NPC478076
0.6757	Remote Similarity	NPC248117
0.675	Remote Similarity	NPC230313
0.675	Remote Similarity	NPC243626
0.6743	Remote Similarity	NPC130251
0.6739	Remote Similarity	NPC61013
0.6726	Remote Similarity	NPC252794
0.672	Remote Similarity	NPC472118
0.6719	Remote Similarity	NPC186669
0.6712	Remote Similarity	NPC470729
0.6712	Remote Similarity	NPC477175
0.6712	Remote Similarity	NPC477176
0.6712	Remote Similarity	NPC470730
0.6704	Remote Similarity	NPC472100
0.6686	Remote Similarity	NPC145754
0.6684	Remote Similarity	NPC6974
0.6684	Remote Similarity	NPC218594
0.6684	Remote Similarity	NPC473007
0.6684	Remote Similarity	NPC99043
0.6683	Remote Similarity	NPC473005
0.6682	Remote Similarity	NPC475969
0.6682	Remote Similarity	NPC475859
0.6682	Remote Similarity	NPC474877
0.6667	Remote Similarity	NPC224970
0.6667	Remote Similarity	NPC476441
0.6667	Remote Similarity	NPC167724
0.6667	Remote Similarity	NPC33507
0.6667	Remote Similarity	NPC223595
0.6667	Remote Similarity	NPC221687
0.6652	Remote Similarity	NPC165743
0.665	Remote Similarity	NPC100863
0.6649	Remote Similarity	NPC469428
0.6634	Remote Similarity	NPC470787
0.6634	Remote Similarity	NPC472539
0.6634	Remote Similarity	NPC472540
0.6631	Remote Similarity	NPC472121
0.6627	Remote Similarity	NPC475915
0.6617	Remote Similarity	NPC470485
0.6615	Remote Similarity	NPC13367
0.6613	Remote Similarity	NPC36495
0.6601	Remote Similarity	NPC472541
0.6601	Remote Similarity	NPC472542
0.66	Remote Similarity	NPC470483
0.6599	Remote Similarity	NPC322621
0.6598	Remote Similarity	NPC475094
0.6598	Remote Similarity	NPC321211
0.6592	Remote Similarity	NPC311330
0.6582	Remote Similarity	NPC19679
0.6571	Remote Similarity	NPC477160
0.6559	Remote Similarity	NPC123241
0.6558	Remote Similarity	NPC77777
0.6556	Remote Similarity	NPC116519
0.6552	Remote Similarity	NPC473375
0.6552	Remote Similarity	NPC97100
0.655	Remote Similarity	NPC473008
0.6546	Remote Similarity	NPC476326
0.6545	Remote Similarity	NPC469915
0.6543	Remote Similarity	NPC469741
0.6543	Remote Similarity	NPC293458
0.6542	Remote Similarity	NPC251936
0.6517	Remote Similarity	NPC301760
0.6512	Remote Similarity	NPC244425
0.6512	Remote Similarity	NPC15384
0.6505	Remote Similarity	NPC475489
0.6495	Remote Similarity	NPC129624
0.6492	Remote Similarity	NPC63047
0.6492	Remote Similarity	NPC475248
0.649	Remote Similarity	NPC295548
0.6489	Remote Similarity	NPC201424
0.6485	Remote Similarity	NPC473004
0.6479	Remote Similarity	NPC159815
0.6477	Remote Similarity	NPC267508
0.6473	Remote Similarity	NPC471512
0.6467	Remote Similarity	NPC243756
0.6465	Remote Similarity	NPC97584
0.6465	Remote Similarity	NPC245741
0.6457	Remote Similarity	NPC477177
0.6444	Remote Similarity	NPC469537
0.6439	Remote Similarity	NPC471199
0.6429	Remote Similarity	NPC277350
0.6422	Remote Similarity	NPC272174
0.6421	Remote Similarity	NPC313757
0.6419	Remote Similarity	NPC478157
0.6417	Remote Similarity	NPC477157
0.6417	Remote Similarity	NPC477156
0.6414	Remote Similarity	NPC472109

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 NPC2933 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	504
0.2-0.3	704
0.3-0.4	1610
0.4-0.5	3649
0.5-0.6	2327
0.6-0.7	183
0.7-0.8	1
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
0.7126	Intermediate Similarity	NPD7785	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD8240	Discontinued
0.7006	Intermediate Similarity	NPD5942	Approved
0.7006	Intermediate Similarity	NPD5941	Approved
0.6965	Remote Similarity	NPD6238	Discontinued
0.6911	Remote Similarity	NPD6878	Phase 2
0.6911	Remote Similarity	NPD6879	Phase 2
0.6906	Remote Similarity	NPD5742	Approved
0.6906	Remote Similarity	NPD5743	Approved
0.6906	Remote Similarity	NPD5741	Approved
0.6895	Remote Similarity	NPD5600	Discontinued
0.6851	Remote Similarity	NPD4121	Phase 3
0.6851	Remote Similarity	NPD4120	Approved
0.6789	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5997	Discontinued
0.6724	Remote Similarity	NPD5318	Discontinued
0.6649	Remote Similarity	NPD7593	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7824	Approved
0.6629	Remote Similarity	NPD5024	Approved
0.6613	Remote Similarity	NPD7599	Phase 2
0.6606	Remote Similarity	NPD7271	Approved
0.6599	Remote Similarity	NPD6557	Phase 2
0.6579	Remote Similarity	NPD7890	Discontinued
0.6578	Remote Similarity	NPD7600	Phase 2
0.6545	Remote Similarity	NPD7731	Approved
0.6545	Remote Similarity	NPD7730	Approved
0.6536	Remote Similarity	NPD4430	Phase 2
0.6534	Remote Similarity	NPD6358	Phase 2
0.6533	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD1949	Approved
0.6529	Remote Similarity	NPD1950	Approved
0.6529	Remote Similarity	NPD3240	Phase 2
0.6517	Remote Similarity	NPD3625	Discontinued
0.6505	Remote Similarity	NPD7105	Phase 1
0.6497	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8630	Approved
0.6471	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD5185	Approved
0.6457	Remote Similarity	NPD5184	Approved
0.6457	Remote Similarity	NPD5182	Approved
0.6444	Remote Similarity	NPD6301	Phase 2
0.6425	Remote Similarity	NPD2093	Discontinued
0.6416	Remote Similarity	NPD4365	Phase 2
0.6416	Remote Similarity	NPD8263	Discontinued
0.641	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7789	Approved
0.64	Remote Similarity	NPD7791	Approved
0.64	Remote Similarity	NPD7790	Approved
0.64	Remote Similarity	NPD7951	Approved
0.64	Remote Similarity	NPD7953	Approved
0.64	Remote Similarity	NPD7952	Approved
0.64	Remote Similarity	NPD7950	Approved
0.6393	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7854	Phase 2
0.6389	Remote Similarity	NPD6768	Approved
0.6381	Remote Similarity	NPD6644	Discontinued
0.638	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5060	Phase 1
0.6368	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.635	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6342	Discontinued
0.6348	Remote Similarity	NPD6294	Approved
0.6348	Remote Similarity	NPD6295	Approved
0.6341	Remote Similarity	NPD5179	Approved
0.6341	Remote Similarity	NPD5181	Approved
0.6341	Remote Similarity	NPD5180	Approved
0.6337	Remote Similarity	NPD7444	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD3790	Phase 2
0.633	Remote Similarity	NPD1663	Discontinued
0.6328	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6070	Approved
0.6325	Remote Similarity	NPD6069	Approved
0.6323	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD6978	Phase 2
0.6321	Remote Similarity	NPD3983	Phase 3
0.6321	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD2387	Approved
0.6319	Remote Similarity	NPD7487	Discontinued
0.6305	Remote Similarity	NPD5758	Clinical (unspecified phase)
0.6305	Remote Similarity	NPD4499	Approved
0.6304	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD5993	Phase 1
0.6296	Remote Similarity	NPD8060	Phase 1
0.6289	Remote Similarity	NPD5531	Discontinued
0.6287	Remote Similarity	NPD6483	Approved
0.6287	Remote Similarity	NPD6484	Approved
0.6286	Remote Similarity	NPD4781	Approved
0.6286	Remote Similarity	NPD4783	Approved
0.6279	Remote Similarity	NPD8128	Discontinued
0.6277	Remote Similarity	NPD7072	Phase 2
0.6275	Remote Similarity	NPD6272	Phase 1
0.6275	Remote Similarity	NPD5042	Phase 1
0.627	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD8402	Approved
0.6257	Remote Similarity	NPD8400	Approved
0.6257	Remote Similarity	NPD8401	Approved
0.6244	Remote Similarity	NPD7726	Phase 1
0.6242	Remote Similarity	NPD2913	Approved
0.6242	Remote Similarity	NPD2914	Approved
0.6239	Remote Similarity	NPD7688	Phase 1
0.6231	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5918	Discontinued
0.6225	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD4796	Discontinued
0.6218	Remote Similarity	NPD4976	Discontinued
0.6216	Remote Similarity	NPD2426	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD1769	Discontinued
0.6205	Remote Similarity	NPD5186	Approved
0.6205	Remote Similarity	NPD5183	Approved
0.6204	Remote Similarity	NPD7595	Discontinued
0.6199	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD7717	Approved
0.6188	Remote Similarity	NPD7716	Approved
0.6186	Remote Similarity	NPD6037	Discontinued
0.6183	Remote Similarity	NPD4644	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD7775	Approved
0.6178	Remote Similarity	NPD3388	Phase 1
0.6178	Remote Similarity	NPD4393	Approved
0.6178	Remote Similarity	NPD4514	Approved
0.6178	Remote Similarity	NPD33	Approved
0.6175	Remote Similarity	NPD2820	Phase 3
0.617	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6345	Approved
0.6154	Remote Similarity	NPD5830	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6343	Approved
0.615	Remote Similarity	NPD7780	Approved
0.615	Remote Similarity	NPD7781	Approved
0.615	Remote Similarity	NPD8114	Approved
0.615	Remote Similarity	NPD8115	Approved
0.6149	Remote Similarity	NPD2840	Approved
0.6145	Remote Similarity	NPD2791	Discontinued
0.6143	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD6995	Phase 1
0.6141	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.614	Remote Similarity	NPD5579	Approved
0.614	Remote Similarity	NPD5576	Approved
0.6138	Remote Similarity	NPD2790	Discontinued
0.6134	Remote Similarity	NPD7036	Phase 3
0.6134	Remote Similarity	NPD7035	Approved
0.6131	Remote Similarity	NPD4317	Approved
0.6127	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD7578	Phase 2
0.6124	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD2039	Approved
0.6121	Remote Similarity	NPD2038	Approved
0.6121	Remote Similarity	NPD2999	Approved
0.6121	Remote Similarity	NPD3001	Approved
0.612	Remote Similarity	NPD2365	Approved
0.6119	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD1922	Discontinued
0.6114	Remote Similarity	NPD6259	Discontinued
0.6114	Remote Similarity	NPD1743	Approved
0.6114	Remote Similarity	NPD4600	Approved
0.6114	Remote Similarity	NPD19	Approved
0.6114	Remote Similarity	NPD4601	Approved
0.6114	Remote Similarity	NPD1742	Approved
0.6111	Remote Similarity	NPD6544	Discontinued
0.6108	Remote Similarity	NPD5931	Phase 3
0.6108	Remote Similarity	NPD5933	Phase 3
0.6108	Remote Similarity	NPD5932	Phase 3
0.6108	Remote Similarity	NPD8167	Discontinued
0.6102	Remote Similarity	NPD6489	Phase 3
0.61	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7479	Phase 2
0.6099	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD7939	Discontinued
0.6098	Remote Similarity	NPD8025	Phase 2
0.6096	Remote Similarity	NPD4682	Phase 2
0.6095	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD8322	Phase 2
0.6091	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD7543	Phase 2
0.6091	Remote Similarity	NPD5633	Discontinued
0.6089	Remote Similarity	NPD5596	Phase 2
0.6087	Remote Similarity	NPD7570	Approved
0.6087	Remote Similarity	NPD7569	Approved
0.6085	Remote Similarity	NPD3248	Phase 1
0.6085	Remote Similarity	NPD7921	Approved
0.608	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6073	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6073	Remote Similarity	NPD6395	Phase 2
0.607	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD519	Approved
0.6067	Remote Similarity	NPD5581	Approved
0.6062	Remote Similarity	NPD5989	Phase 1

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