NPASS Compound

Structure

NPC122106 OpenBabel07101718322D 28 33 0 0 1 0 0 0 0 0999 V2000 3.5814 0.8445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4581 -3.9053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5814 -0.1274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0204 -1.7442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1018 -0.5787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9703 -2.2563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1333 0.0746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4395 -1.0994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1318 -0.3131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3624 -1.3257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8979 -2.0714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8979 -0.1274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7397 -0.6134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7397 -1.5854 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9115 -0.7613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5751 -1.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0018 -1.6031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0832 -0.4376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0562 -1.5854 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7509 -0.8950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0108 -0.7873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2155 -2.2394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1318 -1.8857 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0562 -0.6134 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 -1.7748 -1.5557 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7463 -2.3795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8177 -3.0023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 28 1 0 0 0 0 3 13 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 24 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 2 0 0 0 0 12 24 1 0 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 25 1 0 0 0 0 19 23 1 1 0 0 0 19 24 1 0 0 0 0 20 23 1 0 0 0 0 20 25 1 0 0 0 0 21 25 1 0 0 0 0 21 26 2 0 0 0 0 22 27 2 0 0 0 0 22 28 1 0 0 0 0 23 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.16
Volume:	382.298
LogP:	2.496
LogD:	2.228
LogS:	-4.689
# Rotatable Bonds:	3
TPSA:	51.54
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.758
Synthetic Accessibility Score:	5.451
Fsp3:	0.391
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:	-4.811
MDCK Permeability:	2.7471347493701614e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.625
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.869
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.947
Plasma Protein Binding (PPB):	78.86675262451172%
Volume Distribution (VD):	0.937
Pgp-substrate:	19.737361907958984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.625
CYP2C19-inhibitor:	0.568
CYP2C19-substrate:	0.916
CYP2C9-inhibitor:	0.564
CYP2C9-substrate:	0.536
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.354
CYP3A4-inhibitor:	0.635
CYP3A4-substrate:	0.923

ADMET: Excretion

Clearance (CL):	2.106
Half-life (T1/2):	0.636

ADMET: Toxicity

hERG Blockers:	0.117
Human Hepatotoxicity (H-HT):	0.225
Drug-inuced Liver Injury (DILI):	0.093
AMES Toxicity:	0.19
Rat Oral Acute Toxicity:	0.947
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.179
Carcinogencity:	0.753
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC122106

Natural Product ID:	NPC122106
*Common Name:**	Melodinine B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OJPKTXCBMCNJHG-FKHUDQKESA-N
Standard InCHI:	InChI=1S/C23H22N2O3/c1-3-13-12-24-9-8-23-17-6-4-5-7-18(17)25-20(23)15(14(13)11-19(23)24)10-16(21(25)26)22(27)28-2/h4-7,10,12,14,19H,3,8-9,11H2,1-2H3/t14-,19-,23+/m0/s1
SMILES:	CCC1=CN2CC[C@@]34c5ccccc5-n5c4c(cc(c5=O)C(=O)OC)[C@H]1C[C@H]23
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087382
PubChem CID:	44626772
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]

☑ 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

Activity Type	# Activity
Cell Line	5
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[504046]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[504047]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[504047]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[504047]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	40000.0	nM	PMID[504047]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[504046]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4.62	ug.mL-1	PMID[504046]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	12350.0	nM	PMID[504046]

☑ 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 NPC122106 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	402
0.1-0.2	1910
0.2-0.3	8363
0.3-0.4	15585
0.4-0.5	11266
0.5-0.6	2940
0.6-0.7	1953
0.7-0.8	268
0.8-0.85	5
0.85-0.9	0
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.965	High Similarity	NPC243756
0.9448	High Similarity	NPC285381
0.9128	High Similarity	NPC469536
0.9116	High Similarity	NPC154602
0.9021	High Similarity	NPC301760
0.869	High Similarity	NPC130251
0.8267	Intermediate Similarity	NPC469537
0.7895	Intermediate Similarity	NPC22082
0.7895	Intermediate Similarity	NPC186284
0.7875	Intermediate Similarity	NPC123241
0.784	Intermediate Similarity	NPC293458
0.7826	Intermediate Similarity	NPC193410
0.7778	Intermediate Similarity	NPC248117
0.7654	Intermediate Similarity	NPC61013
0.7651	Intermediate Similarity	NPC167724
0.7651	Intermediate Similarity	NPC223595
0.7651	Intermediate Similarity	NPC224970
0.7561	Intermediate Similarity	NPC225319
0.7545	Intermediate Similarity	NPC475248
0.7545	Intermediate Similarity	NPC63047
0.75	Intermediate Similarity	NPC286994
0.7427	Intermediate Similarity	NPC264482
0.7427	Intermediate Similarity	NPC203202
0.7412	Intermediate Similarity	NPC214626
0.7412	Intermediate Similarity	NPC139085
0.7412	Intermediate Similarity	NPC251212
0.7394	Intermediate Similarity	NPC36495
0.7384	Intermediate Similarity	NPC186669
0.7341	Intermediate Similarity	NPC6974
0.7341	Intermediate Similarity	NPC99043
0.7341	Intermediate Similarity	NPC218594
0.7305	Intermediate Similarity	NPC99632
0.7305	Intermediate Similarity	NPC282339
0.7284	Intermediate Similarity	NPC473329
0.7283	Intermediate Similarity	NPC260075
0.7273	Intermediate Similarity	NPC97584
0.7267	Intermediate Similarity	NPC329338
0.7267	Intermediate Similarity	NPC469726
0.7202	Intermediate Similarity	NPC472117
0.7184	Intermediate Similarity	NPC28848
0.7184	Intermediate Similarity	NPC14325
0.7076	Intermediate Similarity	NPC214960
0.7076	Intermediate Similarity	NPC279527
0.707	Intermediate Similarity	NPC471123
0.7041	Intermediate Similarity	NPC201424
0.7039	Intermediate Similarity	NPC52262
0.703	Intermediate Similarity	NPC66936
0.7027	Intermediate Similarity	NPC162440
0.7024	Intermediate Similarity	NPC113946
0.7022	Intermediate Similarity	NPC159963
0.7011	Intermediate Similarity	NPC473743
0.6961	Remote Similarity	NPC14994
0.6951	Remote Similarity	NPC469740
0.6947	Remote Similarity	NPC329833
0.6946	Remote Similarity	NPC478076
0.694	Remote Similarity	NPC22476
0.694	Remote Similarity	NPC203628
0.694	Remote Similarity	NPC25401
0.6923	Remote Similarity	NPC53044
0.6919	Remote Similarity	NPC472106
0.6914	Remote Similarity	NPC96901
0.6901	Remote Similarity	NPC472101
0.6901	Remote Similarity	NPC469741
0.6901	Remote Similarity	NPC472120
0.6885	Remote Similarity	NPC22689
0.6885	Remote Similarity	NPC105055
0.6885	Remote Similarity	NPC5630
0.6875	Remote Similarity	NPC469560
0.6859	Remote Similarity	NPC231382
0.6851	Remote Similarity	NPC322621
0.6842	Remote Similarity	NPC474058
0.6824	Remote Similarity	NPC104345
0.6818	Remote Similarity	NPC250476
0.6813	Remote Similarity	NPC311858
0.6791	Remote Similarity	NPC303214
0.6791	Remote Similarity	NPC97100
0.6791	Remote Similarity	NPC473375
0.6788	Remote Similarity	NPC264589
0.6765	Remote Similarity	NPC29285
0.6744	Remote Similarity	NPC472102
0.6744	Remote Similarity	NPC309531
0.6728	Remote Similarity	NPC315051
0.6726	Remote Similarity	NPC475763
0.6725	Remote Similarity	NPC222029
0.6707	Remote Similarity	NPC308197
0.6707	Remote Similarity	NPC109787
0.6707	Remote Similarity	NPC242000
0.6706	Remote Similarity	NPC161827
0.6705	Remote Similarity	NPC286871
0.6687	Remote Similarity	NPC471164
0.6687	Remote Similarity	NPC469735
0.6667	Remote Similarity	NPC321211
0.6667	Remote Similarity	NPC129909
0.6649	Remote Similarity	NPC67904
0.6649	Remote Similarity	NPC221687
0.6649	Remote Similarity	NPC138830
0.6647	Remote Similarity	NPC212799
0.6646	Remote Similarity	NPC267508
0.6629	Remote Similarity	NPC476425
0.6629	Remote Similarity	NPC471124
0.6615	Remote Similarity	NPC232600
0.661	Remote Similarity	NPC65080
0.659	Remote Similarity	NPC471122
0.659	Remote Similarity	NPC263709
0.659	Remote Similarity	NPC310403
0.659	Remote Similarity	NPC243673
0.659	Remote Similarity	NPC97380
0.659	Remote Similarity	NPC63210
0.659	Remote Similarity	NPC148468
0.6579	Remote Similarity	NPC177684
0.6579	Remote Similarity	NPC291962
0.6556	Remote Similarity	NPC476441
0.6556	Remote Similarity	NPC320147
0.6552	Remote Similarity	NPC68650
0.6545	Remote Similarity	NPC138615
0.6545	Remote Similarity	NPC100863
0.6545	Remote Similarity	NPC132874
0.6545	Remote Similarity	NPC218733
0.6545	Remote Similarity	NPC265642
0.6538	Remote Similarity	NPC470343
0.6538	Remote Similarity	NPC472244
0.6536	Remote Similarity	NPC161956
0.6536	Remote Similarity	NPC285622
0.6536	Remote Similarity	NPC112373
0.6536	Remote Similarity	NPC258531
0.6536	Remote Similarity	NPC307640
0.6534	Remote Similarity	NPC470069
0.6534	Remote Similarity	NPC52059
0.6522	Remote Similarity	NPC316104
0.6522	Remote Similarity	NPC162417
0.6514	Remote Similarity	NPC176983
0.6513	Remote Similarity	NPC475147
0.6513	Remote Similarity	NPC87714
0.6512	Remote Similarity	NPC473297
0.651	Remote Similarity	NPC192674
0.65	Remote Similarity	NPC475097
0.65	Remote Similarity	NPC470548
0.6494	Remote Similarity	NPC257490
0.648	Remote Similarity	NPC318183
0.648	Remote Similarity	NPC355
0.6471	Remote Similarity	NPC318086
0.6471	Remote Similarity	NPC61435
0.6457	Remote Similarity	NPC143457
0.6453	Remote Similarity	NPC281094
0.6446	Remote Similarity	NPC238499
0.6444	Remote Similarity	NPC210415
0.6444	Remote Similarity	NPC298851
0.6444	Remote Similarity	NPC276993
0.6444	Remote Similarity	NPC181138
0.6444	Remote Similarity	NPC21752
0.6444	Remote Similarity	NPC293255
0.6443	Remote Similarity	NPC471512
0.6441	Remote Similarity	NPC475420
0.6437	Remote Similarity	NPC211525
0.6437	Remote Similarity	NPC153694
0.6432	Remote Similarity	NPC470003
0.6429	Remote Similarity	NPC476326
0.6425	Remote Similarity	NPC472118
0.641	Remote Similarity	NPC1464
0.6409	Remote Similarity	NPC13367
0.6404	Remote Similarity	NPC472115
0.6404	Remote Similarity	NPC472114
0.6404	Remote Similarity	NPC126556
0.64	Remote Similarity	NPC276085
0.6392	Remote Similarity	NPC127178
0.6387	Remote Similarity	NPC475915
0.6386	Remote Similarity	NPC471574
0.6384	Remote Similarity	NPC313757
0.6382	Remote Similarity	NPC475133
0.638	Remote Similarity	NPC300299
0.6375	Remote Similarity	NPC187231
0.6373	Remote Similarity	NPC77777
0.6369	Remote Similarity	NPC33507
0.6364	Remote Similarity	NPC315368
0.6364	Remote Similarity	NPC473615
0.6364	Remote Similarity	NPC83214
0.6358	Remote Similarity	NPC295021
0.6354	Remote Similarity	NPC177261
0.6354	Remote Similarity	NPC473880
0.6352	Remote Similarity	NPC478079
0.6349	Remote Similarity	NPC473569
0.6346	Remote Similarity	NPC115588
0.6339	Remote Similarity	NPC474081
0.6332	Remote Similarity	NPC285192
0.633	Remote Similarity	NPC21425
0.633	Remote Similarity	NPC229484
0.633	Remote Similarity	NPC473815
0.6328	Remote Similarity	NPC476231
0.6327	Remote Similarity	NPC52801
0.6325	Remote Similarity	NPC207554
0.6324	Remote Similarity	NPC476428
0.6323	Remote Similarity	NPC316582
0.6321	Remote Similarity	NPC472542
0.6321	Remote Similarity	NPC472541
0.6313	Remote Similarity	NPC195787
0.6313	Remote Similarity	NPC246140
0.6313	Remote Similarity	NPC470509
0.6312	Remote Similarity	NPC209389
0.631	Remote Similarity	NPC307396
0.631	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 NPC122106 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	599
0.2-0.3	668
0.3-0.4	1608
0.4-0.5	2884
0.5-0.6	2322
0.6-0.7	742
0.7-0.8	84
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
0.7125	Intermediate Similarity	NPD5527	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5526	Phase 2
0.7019	Intermediate Similarity	NPD4430	Phase 2
0.6899	Remote Similarity	NPD2791	Discontinued
0.6879	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6395	Phase 2
0.6864	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5181	Approved
0.6849	Remote Similarity	NPD5180	Approved
0.6849	Remote Similarity	NPD5179	Approved
0.6848	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD1065	Approved
0.6831	Remote Similarity	NPD1064	Approved
0.6829	Remote Similarity	NPD6017	Discontinued
0.6829	Remote Similarity	NPD6622	Phase 1
0.6813	Remote Similarity	NPD5444	Phase 1
0.681	Remote Similarity	NPD2820	Phase 3
0.68	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5993	Phase 1
0.6752	Remote Similarity	NPD6489	Phase 3
0.6748	Remote Similarity	NPD2365	Approved
0.6742	Remote Similarity	NPD5104	Approved
0.6725	Remote Similarity	NPD8630	Approved
0.6724	Remote Similarity	NPD2915	Discontinued
0.6705	Remote Similarity	NPD7220	Approved
0.6689	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2093	Discontinued
0.6686	Remote Similarity	NPD8400	Approved
0.6686	Remote Similarity	NPD8401	Approved
0.6686	Remote Similarity	NPD8402	Approved
0.6667	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2790	Discontinued
0.6646	Remote Similarity	NPD6768	Approved
0.6597	Remote Similarity	NPD6248	Phase 2
0.6597	Remote Similarity	NPD6249	Phase 2
0.6587	Remote Similarity	NPD3278	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6206	Phase 1
0.6575	Remote Similarity	NPD4116	Approved
0.6566	Remote Similarity	NPD7487	Discontinued
0.6559	Remote Similarity	NPD4334	Discontinued
0.6558	Remote Similarity	NPD4176	Approved
0.6558	Remote Similarity	NPD4178	Approved
0.6549	Remote Similarity	NPD708	Approved
0.6545	Remote Similarity	NPD6261	Phase 3
0.6545	Remote Similarity	NPD6566	Discontinued
0.6538	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD5932	Phase 3
0.6527	Remote Similarity	NPD5933	Phase 3
0.6527	Remote Similarity	NPD5931	Phase 3
0.651	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.649	Remote Similarity	NPD6070	Approved
0.649	Remote Similarity	NPD6069	Approved
0.6486	Remote Similarity	NPD3865	Approved
0.6486	Remote Similarity	NPD5075	Discontinued
0.6477	Remote Similarity	NPD6805	Discontinued
0.6477	Remote Similarity	NPD5427	Suspended
0.6463	Remote Similarity	NPD7633	Discontinued
0.6457	Remote Similarity	NPD2506	Approved
0.645	Remote Similarity	NPD7478	Approved
0.6448	Remote Similarity	NPD6879	Phase 2
0.6448	Remote Similarity	NPD6878	Phase 2
0.6441	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD3277	Phase 3
0.6433	Remote Similarity	NPD7606	Phase 3
0.6409	Remote Similarity	NPD3423	Phase 2
0.6409	Remote Similarity	NPD3422	Phase 3
0.64	Remote Similarity	NPD3387	Approved
0.64	Remote Similarity	NPD7599	Phase 2
0.6395	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5487	Phase 1
0.6378	Remote Similarity	NPD7205	Discontinued
0.6374	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD4315	Phase 2
0.6359	Remote Similarity	NPD4330	Approved
0.6359	Remote Similarity	NPD4329	Approved
0.6358	Remote Similarity	NPD2949	Approved
0.6358	Remote Similarity	NPD2950	Approved
0.6343	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5600	Discontinued
0.6327	Remote Similarity	NPD4114	Approved
0.6327	Remote Similarity	NPD4115	Approved
0.6327	Remote Similarity	NPD5253	Approved
0.6316	Remote Similarity	NPD5504	Discontinued
0.6316	Remote Similarity	NPD5042	Phase 1
0.631	Remote Similarity	NPD2129	Approved
0.6307	Remote Similarity	NPD2427	Approved
0.6304	Remote Similarity	NPD3782	Discontinued
0.6303	Remote Similarity	NPD2670	Approved
0.63	Remote Similarity	NPD5835	Phase 3
0.63	Remote Similarity	NPD5834	Phase 3
0.6298	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD1920	Approved
0.6296	Remote Similarity	NPD1919	Approved
0.6294	Remote Similarity	NPD3777	Phase 3
0.6292	Remote Similarity	NPD3789	Approved
0.6291	Remote Similarity	NPD2914	Approved
0.6291	Remote Similarity	NPD2913	Approved
0.6289	Remote Similarity	NPD2840	Approved
0.6286	Remote Similarity	NPD1663	Discontinued
0.6286	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.628	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD2037	Approved
0.6278	Remote Similarity	NPD2404	Discontinued
0.6273	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD4347	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD5918	Discontinued
0.6271	Remote Similarity	NPD7244	Discontinued
0.6271	Remote Similarity	NPD7600	Phase 2
0.6264	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD7854	Phase 2
0.6264	Remote Similarity	NPD3377	Discontinued
0.6259	Remote Similarity	NPD3545	Approved
0.6259	Remote Similarity	NPD3546	Approved
0.6258	Remote Similarity	NPD1527	Phase 2
0.625	Remote Similarity	NPD3792	Approved
0.6243	Remote Similarity	NPD7795	Phase 2
0.6237	Remote Similarity	NPD3470	Approved
0.6237	Remote Similarity	NPD3471	Approved
0.6236	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD486	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD5060	Phase 1
0.6235	Remote Similarity	NPD2754	Discontinued
0.6235	Remote Similarity	NPD7295	Approved
0.6234	Remote Similarity	NPD7480	Approved
0.6234	Remote Similarity	NPD7481	Approved
0.6231	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD5423	Phase 2
0.6221	Remote Similarity	NPD4942	Approved
0.622	Remote Similarity	NPD5185	Approved
0.622	Remote Similarity	NPD5182	Approved
0.622	Remote Similarity	NPD5184	Approved
0.6215	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD3388	Phase 1
0.6213	Remote Similarity	NPD5020	Approved
0.6213	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6213	Remote Similarity	NPD7082	Approved
0.6211	Remote Similarity	NPD4549	Discontinued
0.6209	Remote Similarity	NPD2431	Approved
0.6209	Remote Similarity	NPD2432	Approved
0.6207	Remote Similarity	NPD3248	Phase 1
0.6207	Remote Similarity	NPD7573	Discontinued
0.6203	Remote Similarity	NPD519	Approved
0.6196	Remote Similarity	NPD4075	Phase 2
0.6196	Remote Similarity	NPD3978	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD6570	Approved
0.6193	Remote Similarity	NPD6571	Approved
0.619	Remote Similarity	NPD3625	Discontinued
0.6188	Remote Similarity	NPD2455	Approved
0.6188	Remote Similarity	NPD2454	Approved
0.6188	Remote Similarity	NPD3240	Phase 2
0.6188	Remote Similarity	NPD6457	Approved
0.6184	Remote Similarity	NPD1175	Approved
0.6176	Remote Similarity	NPD7259	Approved
0.6175	Remote Similarity	NPD5997	Discontinued
0.6174	Remote Similarity	NPD1342	Approved
0.6173	Remote Similarity	NPD4365	Phase 2
0.6173	Remote Similarity	NPD5131	Approved
0.6171	Remote Similarity	NPD4121	Phase 3
0.6171	Remote Similarity	NPD5086	Approved
0.6171	Remote Similarity	NPD4120	Approved
0.617	Remote Similarity	NPD4412	Phase 2
0.6169	Remote Similarity	NPD1344	Phase 2
0.6168	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD3170	Approved
0.6164	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD3793	Phase 3
0.6159	Remote Similarity	NPD2039	Approved
0.6159	Remote Similarity	NPD2038	Approved
0.6158	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5186	Approved
0.6154	Remote Similarity	NPD5183	Approved
0.6154	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD5631	Phase 3
0.6144	Remote Similarity	NPD5629	Discontinued
0.614	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD5742	Approved
0.6136	Remote Similarity	NPD7072	Phase 2
0.6136	Remote Similarity	NPD5743	Approved
0.6136	Remote Similarity	NPD5741	Approved
0.6135	Remote Similarity	NPD3118	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD3548	Approved
0.6133	Remote Similarity	NPD4063	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7881	Approved
0.6129	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD5941	Approved
0.6127	Remote Similarity	NPD5942	Approved
0.6127	Remote Similarity	NPD4888	Discontinued
0.6127	Remote Similarity	NPD979	Approved
0.6117	Remote Similarity	NPD8281	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