NPASS Compound

Structure

NPC285381 OpenBabel07101719152D 27 32 0 0 1 0 0 0 0 0999 V2000 3.5784 0.8438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5784 -0.1273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0179 -1.7427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0993 -0.5782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9687 -2.2545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1315 0.0745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4391 -1.0985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1317 -0.3128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3613 -1.3245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8964 -2.0696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8964 -0.1273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7374 -0.6129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7374 -1.5841 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9100 -0.7607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5746 -1.3353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0009 -1.6017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0823 -0.4373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0553 -1.5841 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7503 -0.8942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0108 -0.7867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2153 -2.2375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1317 -1.8842 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0553 -0.6129 0.0000 N 0 0 0 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 -1.7733 -1.5544 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7457 -2.3775 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8170 -2.9999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 12 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 16 2 0 0 0 0 6 17 2 0 0 0 0 7 8 1 0 0 0 0 8 23 1 0 0 0 0 9 14 1 0 0 0 0 9 15 2 0 0 0 0 10 18 1 0 0 0 0 11 12 2 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 13 10 1 6 0 0 0 13 14 1 0 0 0 0 14 19 2 0 0 0 0 15 20 1 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 22 1 0 0 0 0 17 24 1 0 0 0 0 18 22 1 1 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 19 24 1 0 0 0 0 20 24 1 0 0 0 0 20 25 2 0 0 0 0 21 26 2 0 0 0 0 21 27 1 0 0 0 0 22 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.15
Volume:	365.002
LogP:	2.1
LogD:	1.092
LogS:	-3.115
# Rotatable Bonds:	2
TPSA:	62.54
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.894
Synthetic Accessibility Score:	5.475
Fsp3:	0.364
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:	-4.968
MDCK Permeability:	2.6457992134965025e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.809
Human Intestinal Absorption (HIA):	0.039
20% Bioavailability (F20%):	0.045
30% Bioavailability (F30%):	0.863

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.644
Plasma Protein Binding (PPB):	68.51652526855469%
Volume Distribution (VD):	0.417
Pgp-substrate:	34.56376647949219%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.165
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.584
CYP2C9-inhibitor:	0.098
CYP2C9-substrate:	0.758
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.138
CYP3A4-inhibitor:	0.034
CYP3A4-substrate:	0.886

ADMET: Excretion

Clearance (CL):	1.041
Half-life (T1/2):	0.766

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.256
Drug-inuced Liver Injury (DILI):	0.865
AMES Toxicity:	0.049
Rat Oral Acute Toxicity:	0.946
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.12
Carcinogencity:	0.7
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC285381

Natural Product ID:	NPC285381
*Common Name:**	Leuconicine E
IUPAC Name:	n.a.
Synonyms:	Leuconicine E
Standard InCHIKey:	AEHQXGJWNFLWOF-KVYZTJHFSA-N
Standard InCHI:	InChI=1S/C22H20N2O3/c1-2-12-11-23-8-7-22-16-5-3-4-6-17(16)24-19(22)14(13(12)10-18(22)23)9-15(20(24)25)21(26)27/h3-6,9,11,13,18H,2,7-8,10H2,1H3,(H,26,27)/t13-,18-,22+/m0/s1
SMILES:	CCC1=CN2CC[C@@]34c5ccccc5-n5c4c(cc(c5=O)C(=O)O)[C@H]1C[C@H]23
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1085415
PubChem CID:	46881261
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	4

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	3

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[486128]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[486128]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	13.52	ug.mL-1	PMID[486128]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	37560.0	nM	PMID[486128]

☑ 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 NPC285381 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	364
0.1-0.2	1782
0.2-0.3	8051
0.3-0.4	16797
0.4-0.5	10577
0.5-0.6	2797
0.6-0.7	2098
0.7-0.8	223
0.8-0.85	2
0.85-0.9	1
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.965	High Similarity	NPC154602
0.9448	High Similarity	NPC122106
0.9116	High Similarity	NPC243756
0.9021	High Similarity	NPC301760
0.869	High Similarity	NPC130251
0.8627	High Similarity	NPC469536
0.8267	Intermediate Similarity	NPC469537
0.8133	Intermediate Similarity	NPC186284
0.8133	Intermediate Similarity	NPC22082
0.7826	Intermediate Similarity	NPC36495
0.7706	Intermediate Similarity	NPC286994
0.7545	Intermediate Similarity	NPC475248
0.7545	Intermediate Similarity	NPC63047
0.7515	Intermediate Similarity	NPC472117
0.7439	Intermediate Similarity	NPC123241
0.741	Intermediate Similarity	NPC293458
0.7394	Intermediate Similarity	NPC193410
0.7349	Intermediate Similarity	NPC225319
0.7349	Intermediate Similarity	NPC248117
0.7241	Intermediate Similarity	NPC99043
0.7241	Intermediate Similarity	NPC218594
0.7235	Intermediate Similarity	NPC223595
0.7235	Intermediate Similarity	NPC167724
0.7235	Intermediate Similarity	NPC224970
0.7229	Intermediate Similarity	NPC61013
0.7175	Intermediate Similarity	NPC97584
0.7135	Intermediate Similarity	NPC52262
0.7101	Intermediate Similarity	NPC99632
0.7101	Intermediate Similarity	NPC282339
0.707	Intermediate Similarity	NPC471123
0.7044	Intermediate Similarity	NPC315051
0.7029	Intermediate Similarity	NPC203202
0.7029	Intermediate Similarity	NPC264482
0.7024	Intermediate Similarity	NPC104345
0.7018	Intermediate Similarity	NPC471124
0.7018	Intermediate Similarity	NPC472106
0.7011	Intermediate Similarity	NPC139085
0.7011	Intermediate Similarity	NPC214626
0.7011	Intermediate Similarity	NPC251212
0.7	Intermediate Similarity	NPC472101
0.7	Intermediate Similarity	NPC472120
0.6994	Remote Similarity	NPC264589
0.6989	Remote Similarity	NPC186669
0.6982	Remote Similarity	NPC471122
0.6951	Remote Similarity	NPC469740
0.6949	Remote Similarity	NPC6974
0.6941	Remote Similarity	NPC309531
0.6941	Remote Similarity	NPC472102
0.694	Remote Similarity	NPC203628
0.6928	Remote Similarity	NPC66936
0.6928	Remote Similarity	NPC475763
0.6923	Remote Similarity	NPC53044
0.6901	Remote Similarity	NPC469741
0.6893	Remote Similarity	NPC260075
0.6885	Remote Similarity	NPC5630
0.6882	Remote Similarity	NPC97100
0.6882	Remote Similarity	NPC473375
0.6879	Remote Similarity	NPC279527
0.6879	Remote Similarity	NPC214960
0.6875	Remote Similarity	NPC469726
0.6875	Remote Similarity	NPC469560
0.6875	Remote Similarity	NPC329338
0.6875	Remote Similarity	NPC470548
0.6867	Remote Similarity	NPC473329
0.6863	Remote Similarity	NPC470343
0.6863	Remote Similarity	NPC472244
0.6859	Remote Similarity	NPC329833
0.6857	Remote Similarity	NPC318183
0.6848	Remote Similarity	NPC212799
0.6842	Remote Similarity	NPC201424
0.6842	Remote Similarity	NPC68650
0.6824	Remote Similarity	NPC113946
0.6818	Remote Similarity	NPC473743
0.6798	Remote Similarity	NPC28848
0.6798	Remote Similarity	NPC14325
0.6793	Remote Similarity	NPC105055
0.6793	Remote Similarity	NPC22689
0.6791	Remote Similarity	NPC303214
0.6766	Remote Similarity	NPC318086
0.6761	Remote Similarity	NPC355
0.6746	Remote Similarity	NPC478076
0.6744	Remote Similarity	NPC474058
0.6743	Remote Similarity	NPC33507
0.6738	Remote Similarity	NPC221687
0.6725	Remote Similarity	NPC222029
0.6707	Remote Similarity	NPC109787
0.6705	Remote Similarity	NPC476231
0.6704	Remote Similarity	NPC474081
0.6703	Remote Similarity	NPC470003
0.6687	Remote Similarity	NPC471164
0.6687	Remote Similarity	NPC469735
0.6685	Remote Similarity	NPC475097
0.6667	Remote Similarity	NPC472541
0.6667	Remote Similarity	NPC162440
0.6667	Remote Similarity	NPC129909
0.6667	Remote Similarity	NPC475761
0.6667	Remote Similarity	NPC472542
0.6648	Remote Similarity	NPC475607
0.6648	Remote Similarity	NPC159963
0.6648	Remote Similarity	NPC476441
0.6646	Remote Similarity	NPC267508
0.6628	Remote Similarity	NPC211525
0.6628	Remote Similarity	NPC153694
0.6615	Remote Similarity	NPC232600
0.6614	Remote Similarity	NPC472540
0.6614	Remote Similarity	NPC472539
0.6614	Remote Similarity	NPC470787
0.661	Remote Similarity	NPC472118
0.6595	Remote Similarity	NPC14994
0.6592	Remote Similarity	NPC475594
0.6591	Remote Similarity	NPC472115
0.6591	Remote Similarity	NPC472114
0.6579	Remote Similarity	NPC177684
0.6579	Remote Similarity	NPC291962
0.6578	Remote Similarity	NPC22476
0.6578	Remote Similarity	NPC25401
0.6576	Remote Similarity	NPC307396
0.6575	Remote Similarity	NPC474041
0.6573	Remote Similarity	NPC292265
0.6571	Remote Similarity	NPC313757
0.657	Remote Similarity	NPC29285
0.6566	Remote Similarity	NPC314186
0.6552	Remote Similarity	NPC315368
0.6546	Remote Similarity	NPC295548
0.6545	Remote Similarity	NPC138615
0.6545	Remote Similarity	NPC132874
0.6545	Remote Similarity	NPC218733
0.6545	Remote Similarity	NPC265642
0.6541	Remote Similarity	NPC231382
0.6536	Remote Similarity	NPC161956
0.6536	Remote Similarity	NPC96901
0.6536	Remote Similarity	NPC112373
0.6536	Remote Similarity	NPC258531
0.6531	Remote Similarity	NPC472538
0.6528	Remote Similarity	NPC471512
0.6522	Remote Similarity	NPC316104
0.6522	Remote Similarity	NPC162417
0.6519	Remote Similarity	NPC150863
0.6514	Remote Similarity	NPC286871
0.651	Remote Similarity	NPC192674
0.651	Remote Similarity	NPC106118
0.6505	Remote Similarity	NPC473815
0.6494	Remote Similarity	NPC148468
0.6494	Remote Similarity	NPC243673
0.6494	Remote Similarity	NPC257490
0.6494	Remote Similarity	NPC263709
0.6494	Remote Similarity	NPC97380
0.6494	Remote Similarity	NPC63210
0.6494	Remote Similarity	NPC310403
0.6492	Remote Similarity	NPC471199
0.6488	Remote Similarity	NPC478039
0.6486	Remote Similarity	NPC322621
0.6485	Remote Similarity	NPC470301
0.648	Remote Similarity	NPC225400
0.6478	Remote Similarity	NPC280807
0.6478	Remote Similarity	NPC472245
0.6471	Remote Similarity	NPC61435
0.6457	Remote Similarity	NPC27904
0.6456	Remote Similarity	NPC476950
0.6453	Remote Similarity	NPC281094
0.6452	Remote Similarity	NPC311858
0.6448	Remote Similarity	NPC24864
0.6447	Remote Similarity	NPC471155
0.6447	Remote Similarity	NPC470786
0.6446	Remote Similarity	NPC238499
0.6444	Remote Similarity	NPC476425
0.6441	Remote Similarity	NPC52059
0.6441	Remote Similarity	NPC470069
0.6429	Remote Similarity	NPC87714
0.6425	Remote Similarity	NPC65080
0.6414	Remote Similarity	NPC270241
0.6413	Remote Similarity	NPC476428
0.6412	Remote Similarity	NPC242000
0.641	Remote Similarity	NPC1464
0.6407	Remote Similarity	NPC308197
0.6404	Remote Similarity	NPC126556
0.64	Remote Similarity	NPC276085
0.6392	Remote Similarity	NPC250476
0.6392	Remote Similarity	NPC475489
0.6387	Remote Similarity	NPC475915
0.6386	Remote Similarity	NPC471574
0.638	Remote Similarity	NPC300299
0.6379	Remote Similarity	NPC84317
0.6375	Remote Similarity	NPC194562
0.6364	Remote Similarity	NPC83214
0.6358	Remote Similarity	NPC295021
0.6354	Remote Similarity	NPC21752
0.6354	Remote Similarity	NPC285622
0.6354	Remote Similarity	NPC293255
0.6354	Remote Similarity	NPC181138
0.6354	Remote Similarity	NPC473880
0.6354	Remote Similarity	NPC210415
0.6354	Remote Similarity	NPC298851
0.6354	Remote Similarity	NPC276993
0.6349	Remote Similarity	NPC471195
0.6349	Remote Similarity	NPC471196
0.6348	Remote Similarity	NPC471130
0.6346	Remote Similarity	NPC39818
0.6339	Remote Similarity	NPC14849
0.6328	Remote Similarity	NPC176983

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 NPC285381 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	564
0.2-0.3	658
0.3-0.4	1676
0.4-0.5	2805
0.5-0.6	2316
0.6-0.7	794
0.7-0.8	106
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
0.7452	Intermediate Similarity	NPD4430	Phase 2
0.7338	Intermediate Similarity	NPD2791	Discontinued
0.7193	Intermediate Similarity	NPD3376	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6395	Phase 2
0.7169	Intermediate Similarity	NPD6396	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6017	Discontinued
0.7125	Intermediate Similarity	NPD5526	Phase 2
0.7125	Intermediate Similarity	NPD5527	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2820	Phase 3
0.7067	Intermediate Similarity	NPD3623	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3622	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2365	Approved
0.6951	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD8402	Approved
0.6886	Remote Similarity	NPD8401	Approved
0.6886	Remote Similarity	NPD8400	Approved
0.6879	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5181	Approved
0.6849	Remote Similarity	NPD5180	Approved
0.6849	Remote Similarity	NPD5179	Approved
0.6846	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2506	Approved
0.6831	Remote Similarity	NPD1065	Approved
0.6831	Remote Similarity	NPD1064	Approved
0.6826	Remote Similarity	NPD3277	Phase 3
0.6725	Remote Similarity	NPD8630	Approved
0.6722	Remote Similarity	NPD4330	Approved
0.6722	Remote Similarity	NPD4329	Approved
0.6707	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2093	Discontinued
0.6686	Remote Similarity	NPD2427	Approved
0.6685	Remote Similarity	NPD3422	Phase 3
0.6685	Remote Similarity	NPD3423	Phase 2
0.6667	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5504	Discontinued
0.6667	Remote Similarity	NPD3782	Discontinued
0.6648	Remote Similarity	NPD2037	Approved
0.6648	Remote Similarity	NPD2404	Discontinued
0.6647	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2790	Discontinued
0.6646	Remote Similarity	NPD6768	Approved
0.6629	Remote Similarity	NPD3377	Discontinued
0.6611	Remote Similarity	NPD3792	Approved
0.6597	Remote Similarity	NPD6248	Phase 2
0.6597	Remote Similarity	NPD6249	Phase 2
0.6593	Remote Similarity	NPD3470	Approved
0.6593	Remote Similarity	NPD3471	Approved
0.6587	Remote Similarity	NPD3278	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6206	Phase 1
0.6575	Remote Similarity	NPD4116	Approved
0.6573	Remote Similarity	NPD2431	Approved
0.6573	Remote Similarity	NPD2432	Approved
0.6573	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD5993	Phase 1
0.6559	Remote Similarity	NPD4334	Discontinued
0.6556	Remote Similarity	NPD3978	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD2455	Approved
0.6554	Remote Similarity	NPD2454	Approved
0.655	Remote Similarity	NPD5086	Approved
0.6549	Remote Similarity	NPD708	Approved
0.6545	Remote Similarity	NPD6261	Phase 3
0.6545	Remote Similarity	NPD6566	Discontinued
0.6541	Remote Similarity	NPD6489	Phase 3
0.6527	Remote Similarity	NPD5932	Phase 3
0.6527	Remote Similarity	NPD5933	Phase 3
0.6527	Remote Similarity	NPD5931	Phase 3
0.6522	Remote Similarity	NPD4412	Phase 2
0.6517	Remote Similarity	NPD7795	Phase 2
0.6514	Remote Similarity	NPD7220	Approved
0.651	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD4888	Discontinued
0.6506	Remote Similarity	NPD7082	Approved
0.6506	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD5020	Approved
0.6494	Remote Similarity	NPD7599	Phase 2
0.6489	Remote Similarity	NPD5042	Phase 1
0.6486	Remote Similarity	NPD3865	Approved
0.6485	Remote Similarity	NPD3625	Discontinued
0.6474	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7259	Approved
0.6467	Remote Similarity	NPD5631	Phase 3
0.6464	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD7633	Discontinued
0.6463	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.646	Remote Similarity	NPD1527	Phase 2
0.6452	Remote Similarity	NPD5444	Phase 1
0.6437	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6622	Phase 1
0.6429	Remote Similarity	NPD7295	Approved
0.642	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD3990	Phase 3
0.6412	Remote Similarity	NPD5423	Phase 2
0.6412	Remote Similarity	NPD979	Approved
0.6412	Remote Similarity	NPD4942	Approved
0.64	Remote Similarity	NPD3387	Approved
0.6395	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6805	Discontinued
0.6391	Remote Similarity	NPD3141	Discontinued
0.6389	Remote Similarity	NPD1165	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD1344	Phase 2
0.6379	Remote Similarity	NPD1663	Discontinued
0.6378	Remote Similarity	NPD5487	Phase 1
0.6378	Remote Similarity	NPD7205	Discontinued
0.6375	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5104	Approved
0.6369	Remote Similarity	NPD7487	Discontinued
0.6368	Remote Similarity	NPD4315	Phase 2
0.6364	Remote Similarity	NPD7600	Phase 2
0.6359	Remote Similarity	NPD6878	Phase 2
0.6359	Remote Similarity	NPD3989	Phase 3
0.6359	Remote Similarity	NPD6879	Phase 2
0.6358	Remote Similarity	NPD2360	Approved
0.6358	Remote Similarity	NPD4121	Phase 3
0.6358	Remote Similarity	NPD2949	Approved
0.6358	Remote Similarity	NPD4120	Approved
0.6358	Remote Similarity	NPD2950	Approved
0.6353	Remote Similarity	NPD7478	Approved
0.6348	Remote Similarity	NPD2915	Discontinued
0.6346	Remote Similarity	NPD4176	Approved
0.6346	Remote Similarity	NPD4178	Approved
0.6341	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD4092	Approved
0.6333	Remote Similarity	NPD734	Approved
0.6329	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4114	Approved
0.6327	Remote Similarity	NPD4115	Approved
0.6327	Remote Similarity	NPD5253	Approved
0.6322	Remote Similarity	NPD5743	Approved
0.6322	Remote Similarity	NPD5741	Approved
0.6322	Remote Similarity	NPD5742	Approved
0.6316	Remote Similarity	NPD2622	Approved
0.631	Remote Similarity	NPD6557	Phase 2
0.631	Remote Similarity	NPD2129	Approved
0.631	Remote Similarity	NPD1625	Approved
0.631	Remote Similarity	NPD5024	Approved
0.6306	Remote Similarity	NPD519	Approved
0.6303	Remote Similarity	NPD6636	Phase 3
0.63	Remote Similarity	NPD5835	Phase 3
0.63	Remote Similarity	NPD5834	Phase 3
0.6296	Remote Similarity	NPD1920	Approved
0.6296	Remote Similarity	NPD1919	Approved
0.6294	Remote Similarity	NPD3777	Phase 3
0.6292	Remote Similarity	NPD3790	Phase 2
0.6291	Remote Similarity	NPD2913	Approved
0.6291	Remote Similarity	NPD2914	Approved
0.6289	Remote Similarity	NPD2840	Approved
0.6289	Remote Similarity	NPD6900	Discontinued
0.6287	Remote Similarity	NPD6789	Approved
0.6286	Remote Similarity	NPD951	Approved
0.6284	Remote Similarity	NPD4091	Approved
0.628	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD3468	Approved
0.6275	Remote Similarity	NPD6069	Approved
0.6275	Remote Similarity	NPD6070	Approved
0.6272	Remote Similarity	NPD5918	Discontinued
0.6272	Remote Similarity	NPD4347	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD3546	Approved
0.6259	Remote Similarity	NPD3545	Approved
0.6257	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD7606	Phase 3
0.6235	Remote Similarity	NPD486	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD5060	Phase 1
0.6235	Remote Similarity	NPD2754	Discontinued
0.6234	Remote Similarity	NPD7480	Approved
0.6234	Remote Similarity	NPD7481	Approved
0.6231	Remote Similarity	NPD6260	Discontinued
0.6231	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.623	Remote Similarity	NPD8240	Discontinued
0.623	Remote Similarity	NPD3522	Approved
0.623	Remote Similarity	NPD3304	Phase 2
0.623	Remote Similarity	NPD3884	Discontinued
0.6229	Remote Similarity	NPD5606	Discontinued
0.6228	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6320	Approved
0.6223	Remote Similarity	NPD2397	Discontinued
0.6216	Remote Similarity	NPD3997	Approved
0.6216	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD3998	Approved
0.6216	Remote Similarity	NPD3999	Approved
0.6211	Remote Similarity	NPD4549	Discontinued
0.6207	Remote Similarity	NPD3248	Phase 1
0.6205	Remote Similarity	NPD4411	Phase 1
0.6205	Remote Similarity	NPD4410	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD1360	Approved
0.6198	Remote Similarity	NPD8146	Phase 2
0.6196	Remote Similarity	NPD4075	Phase 2
0.6196	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD3240	Phase 2
0.6185	Remote Similarity	NPD6144	Discontinued
0.6184	Remote Similarity	NPD1175	Approved
0.6184	Remote Similarity	NPD23	Approved
0.6183	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD1342	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