NPASS Compound

Structure

NPC130251 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 2 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 -0.2153 2.2375 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 -0.1317 1.8842 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7457 2.3775 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0553 0.6129 0.0000 N 0 0 3 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 -0.8170 2.9999 0.0000 O 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 1 2 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 24 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 1 0 0 0 0 11 24 1 0 0 0 0 12 2 1 1 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 25 1 0 0 0 0 18 22 1 1 0 0 0 18 24 1 0 0 0 0 19 22 1 0 0 0 0 19 25 1 0 0 0 0 20 23 1 0 0 0 0 20 26 2 0 0 0 0 21 25 1 0 0 0 0 21 27 2 0 0 0 0 22 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	361.18
Volume:	369.845
LogP:	1.843
LogD:	1.845
LogS:	-4.237
# Rotatable Bonds:	2
TPSA:	68.33
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.891
Synthetic Accessibility Score:	5.313
Fsp3:	0.455
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:	-5.047
MDCK Permeability:	2.078034231089987e-05
Pgp-inhibitor:	0.531
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.177
30% Bioavailability (F30%):	0.398

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.963
Plasma Protein Binding (PPB):	64.83551788330078%
Volume Distribution (VD):	1.849
Pgp-substrate:	40.45477294921875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.483
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.933
CYP2C9-inhibitor:	0.063
CYP2C9-substrate:	0.658
CYP2D6-inhibitor:	0.302
CYP2D6-substrate:	0.489
CYP3A4-inhibitor:	0.364
CYP3A4-substrate:	0.919

ADMET: Excretion

Clearance (CL):	2.891
Half-life (T1/2):	0.188

ADMET: Toxicity

hERG Blockers:	0.885
Human Hepatotoxicity (H-HT):	0.455
Drug-inuced Liver Injury (DILI):	0.31
AMES Toxicity:	0.917
Rat Oral Acute Toxicity:	0.829
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.206
Carcinogencity:	0.682
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.896

Download Data

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

Natural Product: NPC130251

Natural Product ID:	NPC130251
*Common Name:**	Leuconicine A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CDEKPRALPONZLA-VXRMTAITSA-N
Standard InCHI:	InChI=1S/C22H23N3O2/c1-2-12-11-24-8-7-22-16-5-3-4-6-17(16)25-19(22)14(13(12)10-18(22)24)9-15(20(23)26)21(25)27/h3-6,9,12-13,18H,2,7-8,10-11H2,1H3,(H2,23,26)/t12-,13+,18+,22-/m1/s1
SMILES:	CC[C@@H]1CN2CC[C@@]34c5ccccc5-n5c4c(cc(C(=O)N)c5=O)[C@H]1C[C@H]23
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087883
PubChem CID:	44626771
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]
NPO33278	melodinus henryi	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20041704]
NPO32945	leuconotis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20515042]
NPO40880	Melodinus khasianus	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27584856]

☑ 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	8
Kd	1
MIC	5
Others	4

Activity Type	# Activity
Cell Line	5
Individual Protein	4
NON-MOLECULAR	8
Others	1

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[553738]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[553739]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[553739]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[553739]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	40000.0	nM	PMID[553739]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[553738]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2.57	ug.mL-1	PMID[553738]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7120.0	nM	PMID[553738]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	FC	=	3.8	n.a.	PMID[553740]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	FC	=	5.0	n.a.	PMID[553740]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	FC	=	0.3	n.a.	PMID[553740]
NPT2	Others	Unspecified		Kd	=	14100.0	nM	PMID[553740]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	FC	=	0.6	n.a.	PMID[553740]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	2000.0	nM	PMID[553741]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	150000.0	nM	PMID[553741]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	69000.0	nM	PMID[553741]

☑ 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 NPC130251 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	522
0.1-0.2	2691
0.2-0.3	13859
0.3-0.4	17825
0.4-0.5	3623
0.5-0.6	2495
0.6-0.7	1501
0.7-0.8	171
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9624	High Similarity	NPC301760
0.9481	High Similarity	NPC469537
0.9014	High Similarity	NPC243756
0.9014	High Similarity	NPC154602
0.869	High Similarity	NPC285381
0.869	High Similarity	NPC122106
0.8514	High Similarity	NPC469536
0.838	Intermediate Similarity	NPC22082
0.838	Intermediate Similarity	NPC186284
0.8077	Intermediate Similarity	NPC475248
0.8077	Intermediate Similarity	NPC63047
0.7847	Intermediate Similarity	NPC471123
0.7821	Intermediate Similarity	NPC469741
0.7806	Intermediate Similarity	NPC193410
0.7806	Intermediate Similarity	NPC36495
0.7756	Intermediate Similarity	NPC248117
0.7683	Intermediate Similarity	NPC286994
0.7673	Intermediate Similarity	NPC214960
0.7673	Intermediate Similarity	NPC279527
0.7647	Intermediate Similarity	NPC66936
0.7643	Intermediate Similarity	NPC225319
0.7632	Intermediate Similarity	NPC109787
0.7628	Intermediate Similarity	NPC123241
0.7628	Intermediate Similarity	NPC61013
0.7628	Intermediate Similarity	NPC222029
0.7625	Intermediate Similarity	NPC224970
0.7625	Intermediate Similarity	NPC167724
0.7625	Intermediate Similarity	NPC223595
0.7619	Intermediate Similarity	NPC469560
0.7595	Intermediate Similarity	NPC293458
0.7595	Intermediate Similarity	NPC282339
0.7595	Intermediate Similarity	NPC99632
0.75	Intermediate Similarity	NPC264589
0.7484	Intermediate Similarity	NPC472117
0.7448	Intermediate Similarity	NPC53044
0.7421	Intermediate Similarity	NPC309531
0.7421	Intermediate Similarity	NPC472102
0.7419	Intermediate Similarity	NPC475763
0.7405	Intermediate Similarity	NPC113946
0.74	Intermediate Similarity	NPC471164
0.7386	Intermediate Similarity	NPC469735
0.7378	Intermediate Similarity	NPC473743
0.7357	Intermediate Similarity	NPC475915
0.7338	Intermediate Similarity	NPC469740
0.7289	Intermediate Similarity	NPC203202
0.7289	Intermediate Similarity	NPC264482
0.7284	Intermediate Similarity	NPC472106
0.7267	Intermediate Similarity	NPC472120
0.7267	Intermediate Similarity	NPC472101
0.725	Intermediate Similarity	NPC276085
0.7244	Intermediate Similarity	NPC473329
0.723	Intermediate Similarity	NPC316104
0.723	Intermediate Similarity	NPC162417
0.7229	Intermediate Similarity	NPC329338
0.7229	Intermediate Similarity	NPC469726
0.7219	Intermediate Similarity	NPC315051
0.7205	Intermediate Similarity	NPC68650
0.7202	Intermediate Similarity	NPC99043
0.7202	Intermediate Similarity	NPC218594
0.7202	Intermediate Similarity	NPC6974
0.7188	Intermediate Similarity	NPC104345
0.7169	Intermediate Similarity	NPC251212
0.7169	Intermediate Similarity	NPC139085
0.7169	Intermediate Similarity	NPC214626
0.7133	Intermediate Similarity	NPC267508
0.7092	Intermediate Similarity	NPC177684
0.7092	Intermediate Similarity	NPC291962
0.7089	Intermediate Similarity	NPC206592
0.7048	Intermediate Similarity	NPC472118
0.7044	Intermediate Similarity	NPC117032
0.7042	Intermediate Similarity	NPC161956
0.7042	Intermediate Similarity	NPC112373
0.7042	Intermediate Similarity	NPC258531
0.7041	Intermediate Similarity	NPC260075
0.7041	Intermediate Similarity	NPC186669
0.7025	Intermediate Similarity	NPC318086
0.7024	Intermediate Similarity	NPC475097
0.7021	Intermediate Similarity	NPC264580
0.7007	Intermediate Similarity	NPC209389
0.7006	Intermediate Similarity	NPC212799
0.7	Intermediate Similarity	NPC295021
0.7	Intermediate Similarity	NPC478076
0.6993	Remote Similarity	NPC257490
0.697	Remote Similarity	NPC291610
0.6964	Remote Similarity	NPC242269
0.6951	Remote Similarity	NPC286871
0.6939	Remote Similarity	NPC145754
0.6939	Remote Similarity	NPC478079
0.6936	Remote Similarity	NPC97584
0.6933	Remote Similarity	NPC471122
0.6923	Remote Similarity	NPC279385
0.6923	Remote Similarity	NPC179605
0.6914	Remote Similarity	NPC29285
0.6905	Remote Similarity	NPC355
0.6897	Remote Similarity	NPC52262
0.689	Remote Similarity	NPC201424
0.6879	Remote Similarity	NPC159963
0.6875	Remote Similarity	NPC103292
0.6864	Remote Similarity	NPC285622
0.6857	Remote Similarity	NPC473615
0.6848	Remote Similarity	NPC176983
0.6842	Remote Similarity	NPC300299
0.6818	Remote Similarity	NPC83214
0.6818	Remote Similarity	NPC229484
0.6818	Remote Similarity	NPC14994
0.6815	Remote Similarity	NPC136002
0.6798	Remote Similarity	NPC25401
0.6796	Remote Similarity	NPC162440
0.6786	Remote Similarity	NPC33507
0.6781	Remote Similarity	NPC254698
0.678	Remote Similarity	NPC292675
0.6774	Remote Similarity	NPC207554
0.6766	Remote Similarity	NPC475420
0.6766	Remote Similarity	NPC471124
0.6761	Remote Similarity	NPC313673
0.6757	Remote Similarity	NPC252794
0.6755	Remote Similarity	NPC473962
0.6755	Remote Similarity	NPC207428
0.6743	Remote Similarity	NPC2933
0.6736	Remote Similarity	NPC226143
0.6731	Remote Similarity	NPC471574
0.672	Remote Similarity	NPC329833
0.6713	Remote Similarity	NPC313449
0.6712	Remote Similarity	NPC39818
0.6712	Remote Similarity	NPC268534
0.6705	Remote Similarity	NPC307396
0.6705	Remote Similarity	NPC259626
0.6692	Remote Similarity	NPC75496
0.6689	Remote Similarity	NPC126458
0.6689	Remote Similarity	NPC79698
0.6688	Remote Similarity	NPC238499
0.6687	Remote Similarity	NPC315368
0.6686	Remote Similarity	NPC470205
0.6686	Remote Similarity	NPC256288
0.6667	Remote Similarity	NPC473880
0.6667	Remote Similarity	NPC243162
0.6667	Remote Similarity	NPC100863
0.6667	Remote Similarity	NPC161861
0.6667	Remote Similarity	NPC96901
0.6648	Remote Similarity	NPC22689
0.6648	Remote Similarity	NPC105055
0.6648	Remote Similarity	NPC5630
0.6647	Remote Similarity	NPC194881
0.663	Remote Similarity	NPC106118
0.6628	Remote Similarity	NPC470548
0.6624	Remote Similarity	NPC2823
0.6623	Remote Similarity	NPC187231
0.6623	Remote Similarity	NPC472245
0.662	Remote Similarity	NPC246904
0.6612	Remote Similarity	NPC472542
0.6612	Remote Similarity	NPC472541
0.6611	Remote Similarity	NPC203628
0.6611	Remote Similarity	NPC22476
0.6607	Remote Similarity	NPC478182
0.6604	Remote Similarity	NPC311330
0.6597	Remote Similarity	NPC192209
0.6587	Remote Similarity	NPC474058
0.6585	Remote Similarity	NPC281094
0.6584	Remote Similarity	NPC478186
0.6579	Remote Similarity	NPC231382
0.6575	Remote Similarity	NPC316582
0.657	Remote Similarity	NPC177261
0.6557	Remote Similarity	NPC470787
0.6557	Remote Similarity	NPC472540
0.6557	Remote Similarity	NPC472539
0.6552	Remote Similarity	NPC28848
0.6552	Remote Similarity	NPC14325
0.6552	Remote Similarity	NPC228515
0.6549	Remote Similarity	NPC187036
0.6548	Remote Similarity	NPC472121
0.6533	Remote Similarity	NPC250476
0.6522	Remote Similarity	NPC470440
0.6519	Remote Similarity	NPC470301
0.651	Remote Similarity	NPC192533
0.6509	Remote Similarity	NPC478184
0.6506	Remote Similarity	NPC84317
0.6503	Remote Similarity	NPC221687
0.65	Remote Similarity	NPC20144
0.6494	Remote Similarity	NPC320147
0.6488	Remote Similarity	NPC143457
0.6486	Remote Similarity	NPC265642
0.6486	Remote Similarity	NPC138615
0.6486	Remote Similarity	NPC132874
0.6486	Remote Similarity	NPC218733
0.6474	Remote Similarity	NPC476425
0.6467	Remote Similarity	NPC470343
0.6467	Remote Similarity	NPC472244
0.6467	Remote Similarity	NPC97100
0.6467	Remote Similarity	NPC303214
0.6467	Remote Similarity	NPC473375
0.6464	Remote Similarity	NPC473298
0.6463	Remote Similarity	NPC33421
0.6461	Remote Similarity	NPC21429
0.6447	Remote Similarity	NPC150863
0.6446	Remote Similarity	NPC473297
0.6446	Remote Similarity	NPC161827
0.6444	Remote Similarity	NPC181928
0.6442	Remote Similarity	NPC242000
0.6438	Remote Similarity	NPC308197
0.6438	Remote Similarity	NPC277157

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 NPC130251 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	576
0.2-0.3	788
0.3-0.4	2049
0.4-0.5	2487
0.5-0.6	2154
0.6-0.7	749
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
0.7721	Intermediate Similarity	NPD1306	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD5179	Approved
0.7669	Intermediate Similarity	NPD5180	Approved
0.7669	Intermediate Similarity	NPD5181	Approved
0.7651	Intermediate Similarity	NPD5527	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5526	Phase 2
0.7647	Intermediate Similarity	NPD1668	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD3622	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD3623	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1065	Approved
0.7405	Intermediate Similarity	NPD1064	Approved
0.7368	Intermediate Similarity	NPD4116	Approved
0.7351	Intermediate Similarity	NPD6768	Approved
0.7325	Intermediate Similarity	NPD2790	Discontinued
0.732	Intermediate Similarity	NPD6017	Discontinued
0.7239	Intermediate Similarity	NPD7633	Discontinued
0.7237	Intermediate Similarity	NPD6566	Discontinued
0.7208	Intermediate Similarity	NPD5933	Phase 3
0.7208	Intermediate Similarity	NPD5932	Phase 3
0.7208	Intermediate Similarity	NPD5931	Phase 3
0.719	Intermediate Similarity	NPD4430	Phase 2
0.7164	Intermediate Similarity	NPD1721	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5918	Discontinued
0.7132	Intermediate Similarity	NPD2038	Approved
0.7132	Intermediate Similarity	NPD2039	Approved
0.7123	Intermediate Similarity	NPD4549	Discontinued
0.7081	Intermediate Similarity	NPD8630	Approved
0.7067	Intermediate Similarity	NPD2791	Discontinued
0.7044	Intermediate Similarity	NPD3248	Phase 1
0.7034	Intermediate Similarity	NPD5136	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD2913	Approved
0.7029	Intermediate Similarity	NPD2914	Approved
0.7027	Intermediate Similarity	NPD6489	Phase 3
0.7007	Intermediate Similarity	NPD3865	Approved
0.6974	Remote Similarity	NPD6358	Phase 2
0.697	Remote Similarity	NPD708	Approved
0.6968	Remote Similarity	NPD2820	Phase 3
0.6962	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7220	Approved
0.6948	Remote Similarity	NPD2010	Phase 3
0.6939	Remote Similarity	NPD5993	Phase 1
0.6937	Remote Similarity	NPD8400	Approved
0.6937	Remote Similarity	NPD8402	Approved
0.6937	Remote Similarity	NPD8401	Approved
0.6923	Remote Similarity	NPD4347	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6395	Phase 2
0.6906	Remote Similarity	NPD3387	Approved
0.6903	Remote Similarity	NPD2365	Approved
0.6899	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6342	Discontinued
0.6857	Remote Similarity	NPD5629	Discontinued
0.6855	Remote Similarity	NPD4942	Approved
0.6849	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD5131	Approved
0.6838	Remote Similarity	NPD4115	Approved
0.6838	Remote Similarity	NPD4114	Approved
0.6838	Remote Similarity	NPD5253	Approved
0.6821	Remote Similarity	NPD2950	Approved
0.6821	Remote Similarity	NPD2949	Approved
0.6818	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7254	Discontinued
0.6815	Remote Similarity	NPD7487	Discontinued
0.68	Remote Similarity	NPD486	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3546	Approved
0.6765	Remote Similarity	NPD3545	Approved
0.6763	Remote Similarity	NPD3001	Approved
0.6763	Remote Similarity	NPD2999	Approved
0.6757	Remote Similarity	NPD6900	Discontinued
0.6757	Remote Similarity	NPD2840	Approved
0.6755	Remote Similarity	NPD1920	Approved
0.6755	Remote Similarity	NPD1919	Approved
0.6752	Remote Similarity	NPD2129	Approved
0.675	Remote Similarity	NPD979	Approved
0.6748	Remote Similarity	NPD7072	Phase 2
0.6747	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4063	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD2093	Discontinued
0.6731	Remote Similarity	NPD3625	Discontinued
0.673	Remote Similarity	NPD3278	Clinical (unspecified phase)
0.673	Remote Similarity	NPD1524	Phase 1
0.6713	Remote Similarity	NPD7480	Approved
0.6713	Remote Similarity	NPD7481	Approved
0.6707	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.669	Remote Similarity	NPD1720	Phase 2
0.669	Remote Similarity	NPD1723	Phase 2
0.6688	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD4075	Phase 2
0.6667	Remote Similarity	NPD1175	Approved
0.6667	Remote Similarity	NPD1342	Approved
0.6646	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7082	Approved
0.6645	Remote Similarity	NPD5318	Discontinued
0.6644	Remote Similarity	NPD3240	Phase 2
0.6644	Remote Similarity	NPD1123	Approved
0.6644	Remote Similarity	NPD1124	Approved
0.6643	Remote Similarity	NPD6069	Approved
0.6643	Remote Similarity	NPD1344	Phase 2
0.6643	Remote Similarity	NPD6070	Approved
0.6627	Remote Similarity	NPD4393	Approved
0.6627	Remote Similarity	NPD33	Approved
0.6622	Remote Similarity	NPD2940	Approved
0.6622	Remote Similarity	NPD2938	Approved
0.662	Remote Similarity	NPD5631	Phase 3
0.6619	Remote Similarity	NPD3548	Approved
0.6606	Remote Similarity	NPD951	Approved
0.6604	Remote Similarity	NPD7259	Approved
0.6601	Remote Similarity	NPD1527	Phase 2
0.6599	Remote Similarity	NPD4178	Approved
0.6599	Remote Similarity	NPD4176	Approved
0.6597	Remote Similarity	NPD2638	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4735	Approved
0.6593	Remote Similarity	NPD4734	Approved
0.6585	Remote Similarity	NPD4120	Approved
0.6585	Remote Similarity	NPD4121	Phase 3
0.6584	Remote Similarity	NPD4402	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD6466	Approved
0.6584	Remote Similarity	NPD6467	Approved
0.6581	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD2754	Discontinued
0.6579	Remote Similarity	NPD3118	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD2961	Approved
0.6577	Remote Similarity	NPD2962	Approved
0.657	Remote Similarity	NPD7854	Phase 2
0.6564	Remote Similarity	NPD3277	Phase 3
0.6562	Remote Similarity	NPD6622	Phase 1
0.6562	Remote Similarity	NPD7295	Approved
0.6561	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD5184	Approved
0.6558	Remote Similarity	NPD5185	Approved
0.6558	Remote Similarity	NPD5182	Approved
0.6552	Remote Similarity	NPD5657	Phase 3
0.6552	Remote Similarity	NPD922	Approved
0.655	Remote Similarity	NPD7795	Phase 2
0.655	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5742	Approved
0.6545	Remote Similarity	NPD5743	Approved
0.6545	Remote Similarity	NPD5741	Approved
0.6543	Remote Similarity	NPD5423	Phase 2
0.6538	Remote Similarity	NPD4410	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4411	Phase 1
0.6522	Remote Similarity	NPD993	Approved
0.6522	Remote Similarity	NPD990	Approved
0.6519	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD3790	Phase 2
0.6503	Remote Similarity	NPD5748	Phase 2
0.6503	Remote Similarity	NPD3551	Approved
0.6494	Remote Similarity	NPD5104	Approved
0.6494	Remote Similarity	NPD3137	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD2413	Phase 2
0.6488	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD7774	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7088	Discontinued
0.6481	Remote Similarity	NPD7478	Approved
0.6477	Remote Similarity	NPD4330	Approved
0.6477	Remote Similarity	NPD4329	Approved
0.6477	Remote Similarity	NPD5473	Discontinued
0.6475	Remote Similarity	NPD6299	Approved
0.6475	Remote Similarity	NPD6300	Approved
0.6471	Remote Similarity	NPD2915	Discontinued
0.6467	Remote Similarity	NPD3080	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD8128	Discontinued
0.6467	Remote Similarity	NPD8060	Phase 1
0.6467	Remote Similarity	NPD4985	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5060	Phase 1
0.6458	Remote Similarity	NPD1323	Discontinued
0.6456	Remote Similarity	NPD5068	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD2909	Phase 3
0.6447	Remote Similarity	NPD2908	Phase 3
0.6447	Remote Similarity	NPD1781	Discontinued
0.6444	Remote Similarity	NPD787	Suspended
0.6438	Remote Similarity	NPD6301	Phase 2
0.6429	Remote Similarity	NPD5504	Discontinued
0.6424	Remote Similarity	NPD797	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD1949	Approved
0.6424	Remote Similarity	NPD1950	Approved
0.642	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.642	Remote Similarity	NPD1956	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD4461	Discontinued
0.6407	Remote Similarity	NPD2351	Discontinued
0.6407	Remote Similarity	NPD1663	Discontinued
0.6405	Remote Similarity	NPD4365	Phase 2
0.6405	Remote Similarity	NPD8263	Discontinued
0.64	Remote Similarity	NPD3547	Approved
0.64	Remote Similarity	NPD3550	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3549	Approved
0.6395	Remote Similarity	NPD2037	Approved
0.6393	Remote Similarity	NPD7786	Discontinued
0.6392	Remote Similarity	NPD7142	Discontinued

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