NPASS Compound

Structure

NPC469536 OpenBabel07101719252D 29 34 0 0 1 0 0 0 0 0999 V2000 -3.5842 -0.8452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4584 3.9084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5842 0.1275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0227 1.7455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1043 0.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9719 2.2581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1349 -0.0746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4398 1.1003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1319 0.3133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3635 1.3267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8994 2.0730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8994 0.1275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7418 0.6139 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7418 1.5866 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9131 0.7619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5756 1.3375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0026 1.6043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0841 0.4380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0570 1.5866 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7515 0.8957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0108 0.7879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2157 2.2412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1319 1.8872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0570 0.6139 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7762 1.5570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7469 2.3813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4527 -0.2747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8183 3.0047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 29 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 17 2 0 0 0 0 7 18 2 0 0 0 0 8 9 1 0 0 0 0 9 25 1 0 0 0 0 10 15 1 0 0 0 0 10 16 2 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 3 1 1 0 0 0 13 14 1 0 0 0 0 14 11 1 6 0 0 0 14 15 1 0 0 0 0 15 20 2 0 0 0 0 16 21 1 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 23 1 1 0 0 0 19 25 1 0 0 0 0 20 23 1 0 0 0 0 20 24 1 0 0 0 0 21 24 1 0 0 0 0 21 26 2 0 0 0 0 22 27 2 0 0 0 0 22 29 1 0 0 0 0 23 8 1 6 0 0 0 25 28 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.17
Volume:	393.725
LogP:	1.272
LogD:	0.878
LogS:	-2.347
# Rotatable Bonds:	3
TPSA:	71.36
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	5.801
Fsp3:	0.478
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.405
MDCK Permeability:	3.7971876736264676e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.933
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.814
Plasma Protein Binding (PPB):	52.16105651855469%
Volume Distribution (VD):	1.766
Pgp-substrate:	48.89424514770508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.755
CYP2C19-inhibitor:	0.077
CYP2C19-substrate:	0.929
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.593
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.198
CYP3A4-inhibitor:	0.319
CYP3A4-substrate:	0.935

ADMET: Excretion

Clearance (CL):	6.508
Half-life (T1/2):	0.9

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.187
Drug-inuced Liver Injury (DILI):	0.059
AMES Toxicity:	0.58
Rat Oral Acute Toxicity:	0.938
Maximum Recommended Daily Dose:	0.981
Skin Sensitization:	0.413
Carcinogencity:	0.928
Eye Corrosion:	0.003
Eye Irritation:	0.026
Respiratory Toxicity:	0.871

Download Data

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

Natural Product: NPC469536

Natural Product ID:	NPC469536
*Common Name:**	Leuconicine G
IUPAC Name:	n.a.
Synonyms:	Leuconicine G
Standard InCHIKey:	LSJSPFHZCPVBCN-BLLMQYLJSA-N
Standard InCHI:	InChI=1S/C23H24N2O4/c1-3-13-12-25(28)9-8-23-17-6-4-5-7-18(17)24-20(23)15(14(13)11-19(23)25)10-16(21(24)26)22(27)29-2/h4-7,10,13-14,19H,3,8-9,11-12H2,1-2H3/t13-,14+,19+,23-,25?/m1/s1
SMILES:	CC[C@@H]1CN2(=O)CC[C@@]34[C@@H]2C[C@@H]1c1cc(C(=O)OC)c(=O)n(c31)c1c4cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1086392
PubChem CID:	46881269
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

*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
NPO32945	leuconotis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20035556]
NPO32945	leuconotis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20515042]

☑ 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
IC50	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[508204]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[508204]

☑ 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 NPC469536 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	399
0.1-0.2	1833
0.2-0.3	7255
0.3-0.4	15958
0.4-0.5	11973
0.5-0.6	3065
0.6-0.7	1906
0.7-0.8	298
0.8-0.85	5
0.85-0.9	0
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9452	High Similarity	NPC243756
0.9128	High Similarity	NPC122106
0.8973	High Similarity	NPC469537
0.8933	High Similarity	NPC154602
0.8627	High Similarity	NPC285381
0.8514	High Similarity	NPC130251
0.8212	Intermediate Similarity	NPC301760
0.7964	Intermediate Similarity	NPC329338
0.7964	Intermediate Similarity	NPC469726
0.7742	Intermediate Similarity	NPC186284
0.7742	Intermediate Similarity	NPC22082
0.7683	Intermediate Similarity	NPC193410
0.7661	Intermediate Similarity	NPC260075
0.7636	Intermediate Similarity	NPC248117
0.753	Intermediate Similarity	NPC225319
0.7515	Intermediate Similarity	NPC224970
0.7515	Intermediate Similarity	NPC123241
0.7515	Intermediate Similarity	NPC61013
0.7515	Intermediate Similarity	NPC167724
0.7515	Intermediate Similarity	NPC223595
0.7485	Intermediate Similarity	NPC293458
0.7314	Intermediate Similarity	NPC6974
0.7299	Intermediate Similarity	NPC264482
0.7299	Intermediate Similarity	NPC203202
0.7283	Intermediate Similarity	NPC214626
0.7283	Intermediate Similarity	NPC251212
0.7283	Intermediate Similarity	NPC139085
0.7262	Intermediate Similarity	NPC36495
0.7216	Intermediate Similarity	NPC99043
0.7216	Intermediate Similarity	NPC218594
0.7209	Intermediate Similarity	NPC63047
0.7209	Intermediate Similarity	NPC475248
0.7176	Intermediate Similarity	NPC282339
0.7176	Intermediate Similarity	NPC99632
0.7175	Intermediate Similarity	NPC286994
0.7159	Intermediate Similarity	NPC186669
0.7152	Intermediate Similarity	NPC473329
0.7108	Intermediate Similarity	NPC475763
0.7056	Intermediate Similarity	NPC97584
0.7048	Intermediate Similarity	NPC318086
0.6977	Remote Similarity	NPC472117
0.6966	Remote Similarity	NPC14325
0.6966	Remote Similarity	NPC28848
0.6966	Remote Similarity	NPC476326
0.6954	Remote Similarity	NPC214960
0.6954	Remote Similarity	NPC279527
0.694	Remote Similarity	NPC14994
0.6937	Remote Similarity	NPC471123
0.6927	Remote Similarity	NPC329833
0.6915	Remote Similarity	NPC162440
0.6906	Remote Similarity	NPC159963
0.6905	Remote Similarity	NPC66936
0.6901	Remote Similarity	NPC113946
0.6893	Remote Similarity	NPC473743
0.6851	Remote Similarity	NPC476428
0.6842	Remote Similarity	NPC29285
0.6828	Remote Similarity	NPC25401
0.6824	Remote Similarity	NPC478076
0.6821	Remote Similarity	NPC201424
0.68	Remote Similarity	NPC472106
0.6798	Remote Similarity	NPC96901
0.6782	Remote Similarity	NPC472120
0.6782	Remote Similarity	NPC469741
0.6782	Remote Similarity	NPC472101
0.6774	Remote Similarity	NPC105055
0.6774	Remote Similarity	NPC22689
0.6748	Remote Similarity	NPC469560
0.6739	Remote Similarity	NPC52262
0.6724	Remote Similarity	NPC474058
0.6703	Remote Similarity	NPC311858
0.6686	Remote Similarity	NPC286871
0.6686	Remote Similarity	NPC161827
0.6684	Remote Similarity	NPC469732
0.6667	Remote Similarity	NPC264589
0.6649	Remote Similarity	NPC203628
0.6649	Remote Similarity	NPC22476
0.6649	Remote Similarity	NPC322621
0.6632	Remote Similarity	NPC221687
0.6629	Remote Similarity	NPC472102
0.6629	Remote Similarity	NPC309531
0.6611	Remote Similarity	NPC476425
0.6609	Remote Similarity	NPC222029
0.6597	Remote Similarity	NPC97100
0.6597	Remote Similarity	NPC473375
0.6596	Remote Similarity	NPC5630
0.6591	Remote Similarity	NPC176983
0.6588	Remote Similarity	NPC109787
0.6584	Remote Similarity	NPC53044
0.6571	Remote Similarity	NPC97380
0.6571	Remote Similarity	NPC63210
0.6571	Remote Similarity	NPC310403
0.6571	Remote Similarity	NPC263709
0.6571	Remote Similarity	NPC148468
0.6571	Remote Similarity	NPC243673
0.6568	Remote Similarity	NPC469735
0.6561	Remote Similarity	NPC129909
0.6546	Remote Similarity	NPC138830
0.6546	Remote Similarity	NPC67904
0.6529	Remote Similarity	NPC469740
0.6528	Remote Similarity	NPC218733
0.6528	Remote Similarity	NPC138615
0.6528	Remote Similarity	NPC100863
0.6528	Remote Similarity	NPC132874
0.6528	Remote Similarity	NPC265642
0.6517	Remote Similarity	NPC52059
0.6517	Remote Similarity	NPC471124
0.6517	Remote Similarity	NPC470069
0.6514	Remote Similarity	NPC104345
0.651	Remote Similarity	NPC303214
0.6494	Remote Similarity	NPC473297
0.6484	Remote Similarity	NPC13367
0.6478	Remote Similarity	NPC250476
0.6477	Remote Similarity	NPC471122
0.6467	Remote Similarity	NPC321211
0.6448	Remote Similarity	NPC476441
0.6448	Remote Similarity	NPC320147
0.6441	Remote Similarity	NPC143457
0.6429	Remote Similarity	NPC298851
0.6429	Remote Similarity	NPC21752
0.6429	Remote Similarity	NPC285622
0.6429	Remote Similarity	NPC471512
0.6429	Remote Similarity	NPC293255
0.6429	Remote Similarity	NPC210415
0.6429	Remote Similarity	NPC276993
0.6429	Remote Similarity	NPC232600
0.6429	Remote Similarity	NPC181138
0.642	Remote Similarity	NPC211525
0.642	Remote Similarity	NPC231382
0.642	Remote Similarity	NPC153694
0.6417	Remote Similarity	NPC470003
0.641	Remote Similarity	NPC192674
0.6407	Remote Similarity	NPC315051
0.6396	Remote Similarity	NPC1464
0.6393	Remote Similarity	NPC470548
0.6384	Remote Similarity	NPC469461
0.6383	Remote Similarity	NPC472209
0.6378	Remote Similarity	NPC127178
0.6369	Remote Similarity	NPC471164
0.6368	Remote Similarity	NPC61435
0.6364	Remote Similarity	NPC63370
0.6364	Remote Similarity	NPC36836
0.6359	Remote Similarity	NPC77777
0.6354	Remote Similarity	NPC473004
0.6337	Remote Similarity	NPC212799
0.6333	Remote Similarity	NPC475420
0.6332	Remote Similarity	NPC87714
0.6332	Remote Similarity	NPC475147
0.6325	Remote Similarity	NPC267508
0.6319	Remote Similarity	NPC472118
0.6308	Remote Similarity	NPC472541
0.6308	Remote Similarity	NPC472542
0.6304	Remote Similarity	NPC475097
0.6301	Remote Similarity	NPC242000
0.63	Remote Similarity	NPC246140
0.63	Remote Similarity	NPC195787
0.6298	Remote Similarity	NPC472114
0.6298	Remote Similarity	NPC472115
0.6294	Remote Similarity	NPC308197
0.6292	Remote Similarity	NPC276085
0.6289	Remote Similarity	NPC243626
0.6289	Remote Similarity	NPC474121
0.6284	Remote Similarity	NPC318183
0.6278	Remote Similarity	NPC328270
0.6266	Remote Similarity	NPC475915
0.6264	Remote Similarity	NPC33507
0.6263	Remote Similarity	NPC473615
0.6257	Remote Similarity	NPC68650
0.6257	Remote Similarity	NPC190945
0.6256	Remote Similarity	NPC472540
0.6256	Remote Similarity	NPC470787
0.6256	Remote Similarity	NPC472539
0.625	Remote Similarity	NPC288110
0.625	Remote Similarity	NPC185742
0.625	Remote Similarity	NPC473569
0.625	Remote Similarity	NPC177261
0.625	Remote Similarity	NPC475847
0.625	Remote Similarity	NPC473880
0.6242	Remote Similarity	NPC291962
0.6242	Remote Similarity	NPC177684
0.6235	Remote Similarity	NPC478079
0.6232	Remote Similarity	NPC15384
0.6232	Remote Similarity	NPC244425
0.6232	Remote Similarity	NPC126556
0.623	Remote Similarity	NPC229484
0.623	Remote Similarity	NPC21425
0.6212	Remote Similarity	NPC475489
0.6211	Remote Similarity	NPC470343
0.6211	Remote Similarity	NPC472244
0.6207	Remote Similarity	NPC475133
0.6205	Remote Similarity	NPC162417
0.6205	Remote Similarity	NPC230313
0.6205	Remote Similarity	NPC34717
0.6205	Remote Similarity	NPC316104
0.6203	Remote Similarity	NPC112373
0.6203	Remote Similarity	NPC161956
0.6203	Remote Similarity	NPC258531
0.6198	Remote Similarity	NPC292675
0.6196	Remote Similarity	NPC355
0.6195	Remote Similarity	NPC159815
0.619	Remote Similarity	NPC477159

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 NPC469536 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	586
0.2-0.3	656
0.3-0.4	1650
0.4-0.5	2903
0.5-0.6	2300
0.6-0.7	728
0.7-0.8	82
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
0.6842	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6395	Phase 2
0.6807	Remote Similarity	NPD6622	Phase 1
0.6788	Remote Similarity	NPD5527	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5526	Phase 2
0.675	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6489	Phase 3
0.6726	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD5427	Suspended
0.6711	Remote Similarity	NPD5179	Approved
0.6711	Remote Similarity	NPD5181	Approved
0.6711	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5180	Approved
0.671	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.671	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6017	Discontinued
0.6703	Remote Similarity	NPD5444	Phase 1
0.6687	Remote Similarity	NPD4430	Phase 2
0.6649	Remote Similarity	NPD6206	Phase 1
0.6649	Remote Similarity	NPD5075	Discontinued
0.6646	Remote Similarity	NPD5993	Phase 1
0.663	Remote Similarity	NPD5104	Approved
0.661	Remote Similarity	NPD2915	Discontinued
0.6573	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD2791	Discontinued
0.6561	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD3548	Approved
0.6543	Remote Similarity	NPD4334	Discontinued
0.6538	Remote Similarity	NPD4178	Approved
0.6538	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4176	Approved
0.6531	Remote Similarity	NPD3777	Phase 3
0.6514	Remote Similarity	NPD8630	Approved
0.6495	Remote Similarity	NPD6248	Phase 2
0.6495	Remote Similarity	NPD6249	Phase 2
0.6488	Remote Similarity	NPD2820	Phase 3
0.6474	Remote Similarity	NPD8400	Approved
0.6474	Remote Similarity	NPD8401	Approved
0.6474	Remote Similarity	NPD8402	Approved
0.6467	Remote Similarity	NPD2093	Discontinued
0.6463	Remote Similarity	NPD1065	Approved
0.6463	Remote Similarity	NPD1064	Approved
0.6452	Remote Similarity	NPD8281	Discontinued
0.6447	Remote Similarity	NPD5487	Phase 1
0.6443	Remote Similarity	NPD4116	Approved
0.6443	Remote Similarity	NPD6261	Phase 3
0.6441	Remote Similarity	NPD7244	Discontinued
0.6433	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD6878	Phase 2
0.6432	Remote Similarity	NPD6879	Phase 2
0.6429	Remote Similarity	NPD2365	Approved
0.6429	Remote Similarity	NPD6566	Discontinued
0.6425	Remote Similarity	NPD7036	Phase 3
0.6425	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD7035	Approved
0.6415	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD5932	Phase 3
0.6412	Remote Similarity	NPD5933	Phase 3
0.6412	Remote Similarity	NPD5931	Phase 3
0.641	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7881	Approved
0.6378	Remote Similarity	NPD6805	Discontinued
0.6364	Remote Similarity	NPD6570	Approved
0.6364	Remote Similarity	NPD6571	Approved
0.6354	Remote Similarity	NPD4315	Phase 2
0.6353	Remote Similarity	NPD7487	Discontinued
0.6343	Remote Similarity	NPD2790	Discontinued
0.6337	Remote Similarity	NPD7478	Approved
0.6333	Remote Similarity	NPD7633	Discontinued
0.6331	Remote Similarity	NPD6768	Approved
0.6328	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD7606	Phase 3
0.6304	Remote Similarity	NPD3422	Phase 3
0.6304	Remote Similarity	NPD3423	Phase 2
0.6304	Remote Similarity	NPD7940	Phase 3
0.6284	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7205	Discontinued
0.6279	Remote Similarity	NPD3278	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD2435	Approved
0.6257	Remote Similarity	NPD2506	Approved
0.6237	Remote Similarity	NPD5600	Discontinued
0.623	Remote Similarity	NPD7795	Phase 2
0.6222	Remote Similarity	NPD7220	Approved
0.6216	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5835	Phase 3
0.6207	Remote Similarity	NPD4682	Phase 2
0.6207	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5834	Phase 3
0.6201	Remote Similarity	NPD7599	Phase 2
0.6193	Remote Similarity	NPD2948	Discontinued
0.6188	Remote Similarity	NPD8008	Approved
0.6188	Remote Similarity	NPD8007	Approved
0.6185	Remote Similarity	NPD4041	Approved
0.6185	Remote Similarity	NPD1956	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4330	Approved
0.617	Remote Similarity	NPD4329	Approved
0.6169	Remote Similarity	NPD2914	Approved
0.6169	Remote Similarity	NPD2913	Approved
0.6168	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD5918	Discontinued
0.6162	Remote Similarity	NPD3377	Discontinued
0.6162	Remote Similarity	NPD7854	Phase 2
0.6159	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7142	Discontinued
0.6154	Remote Similarity	NPD6069	Approved
0.6154	Remote Similarity	NPD6070	Approved
0.6145	Remote Similarity	NPD1527	Phase 2
0.6144	Remote Similarity	NPD3865	Approved
0.614	Remote Similarity	NPD2923	Approved
0.6139	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD3277	Phase 3
0.6134	Remote Similarity	NPD5504	Discontinued
0.6131	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD6185	Discontinued
0.6127	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD5068	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD4942	Approved
0.6111	Remote Similarity	NPD2427	Approved
0.6108	Remote Similarity	NPD5182	Approved
0.6108	Remote Similarity	NPD5185	Approved
0.6108	Remote Similarity	NPD5184	Approved
0.6105	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5020	Approved
0.6102	Remote Similarity	NPD3248	Phase 1
0.6098	Remote Similarity	NPD4549	Discontinued
0.6089	Remote Similarity	NPD1663	Discontinued
0.6087	Remote Similarity	NPD2037	Approved
0.6082	Remote Similarity	NPD3625	Discontinued
0.6081	Remote Similarity	NPD708	Approved
0.6077	Remote Similarity	NPD7600	Phase 2
0.6075	Remote Similarity	NPD5997	Discontinued
0.6067	Remote Similarity	NPD4120	Approved
0.6067	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD4121	Phase 3
0.6065	Remote Similarity	NPD3387	Approved
0.6064	Remote Similarity	NPD3792	Approved
0.6061	Remote Similarity	NPD5131	Approved
0.6061	Remote Similarity	NPD4365	Phase 2
0.6059	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6057	Remote Similarity	NPD6758	Approved
0.6054	Remote Similarity	NPD5183	Approved
0.6054	Remote Similarity	NPD5186	Approved
0.6053	Remote Similarity	NPD3470	Approved
0.6053	Remote Similarity	NPD3471	Approved
0.6051	Remote Similarity	NPD5042	Phase 1
0.6048	Remote Similarity	NPD2949	Approved
0.6048	Remote Similarity	NPD2950	Approved
0.6045	Remote Similarity	NPD7670	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD2038	Approved
0.6039	Remote Similarity	NPD2039	Approved
0.6039	Remote Similarity	NPD7573	Discontinued
0.6036	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD5742	Approved
0.6034	Remote Similarity	NPD5743	Approved
0.6034	Remote Similarity	NPD7295	Approved
0.6034	Remote Similarity	NPD5741	Approved
0.6032	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD7775	Approved
0.6029	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD5631	Phase 3
0.6026	Remote Similarity	NPD5629	Discontinued
0.6024	Remote Similarity	NPD3118	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD2431	Approved
0.6022	Remote Similarity	NPD2432	Approved
0.6012	Remote Similarity	NPD7082	Approved
0.6012	Remote Similarity	NPD2129	Approved
0.6011	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD3399	Approved
0.6011	Remote Similarity	NPD6576	Discontinued
0.6011	Remote Similarity	NPD3789	Approved
0.6	Remote Similarity	NPD2455	Approved
0.6	Remote Similarity	NPD6358	Phase 2
0.6	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6457	Approved
0.6	Remote Similarity	NPD2670	Approved
0.6	Remote Similarity	NPD2454	Approved
0.6	Remote Similarity	NPD4499	Approved
0.6	Remote Similarity	NPD4607	Approved
0.6	Remote Similarity	NPD2351	Discontinued
0.599	Remote Similarity	NPD7595	Discontinued
0.5988	Remote Similarity	NPD2010	Phase 3
0.5988	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD1919	Approved
0.5988	Remote Similarity	NPD1920	Approved
0.5987	Remote Similarity	NPD4114	Approved
0.5987	Remote Similarity	NPD5253	Approved
0.5987	Remote Similarity	NPD4115	Approved
0.5981	Remote Similarity	NPD4897	Phase 2
0.5979	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD3793	Phase 3
0.5979	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD7612	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