NPASS Compound

Structure

NPC268966 OpenBabel07101719242D 27 31 0 0 1 0 0 0 0 0999 V2000 0.9839 0.1786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2618 -0.7349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1877 -1.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1278 2.5783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1290 -1.0760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4236 2.9848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9938 0.2651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9938 2.2651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4339 -0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4248 -0.7667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8598 1.7651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8598 0.7651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1278 0.7651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6034 0.2172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4236 1.3586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5448 0.5545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7194 1.7651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7228 0.6911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9625 1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1278 1.7651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7259 2.2651 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.3076 -0.0921 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7194 2.5783 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 -5.7259 0.2651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2294 2.1482 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2618 0.2651 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 27 1 0 0 0 0 3 5 1 0 0 0 0 3 10 1 0 0 0 0 4 6 2 0 0 0 0 5 22 1 0 0 0 0 6 23 1 0 0 0 0 7 12 1 0 0 0 0 7 13 2 0 0 0 0 8 11 2 0 0 0 0 8 20 1 0 0 0 0 9 10 2 0 0 0 0 9 24 1 0 0 0 0 10 14 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 25 2 0 0 0 0 13 20 1 0 0 0 0 13 27 1 0 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 15 16 1 0 0 0 0 15 17 2 0 0 0 0 15 20 1 0 0 0 0 16 22 2 0 0 0 0 17 19 1 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 19 26 2 0 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	441.01
Volume:	376.329
LogP:	3.546
LogD:	3.424
LogS:	-4.607
# Rotatable Bonds:	1
TPSA:	66.95
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.703
Synthetic Accessibility Score:	5.322
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.025
MDCK Permeability:	2.1337498765205964e-05
Pgp-inhibitor:	0.199
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.411
20% Bioavailability (F20%):	0.974
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.19
Plasma Protein Binding (PPB):	95.69623565673828%
Volume Distribution (VD):	0.756
Pgp-substrate:	2.2432258129119873%

ADMET: Metabolism

CYP1A2-inhibitor:	0.881
CYP1A2-substrate:	0.856
CYP2C19-inhibitor:	0.685
CYP2C19-substrate:	0.806
CYP2C9-inhibitor:	0.732
CYP2C9-substrate:	0.887
CYP2D6-inhibitor:	0.661
CYP2D6-substrate:	0.199
CYP3A4-inhibitor:	0.626
CYP3A4-substrate:	0.924

ADMET: Excretion

Clearance (CL):	1.782
Half-life (T1/2):	0.467

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.712
Drug-inuced Liver Injury (DILI):	0.406
AMES Toxicity:	0.826
Rat Oral Acute Toxicity:	0.804
Maximum Recommended Daily Dose:	0.91
Skin Sensitization:	0.341
Carcinogencity:	0.975
Eye Corrosion:	0.003
Eye Irritation:	0.045
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC268966

Natural Product ID:	NPC268966
*Common Name:**	Discorhabdin U
IUPAC Name:	n.a.
Synonyms:	Discorhabdin U
Standard InCHIKey:	PJXXBELCKGMRLV-HXUWFJFHSA-N
Standard InCHI:	InChI=1S/C20H16BrN3O2S/c1-24-9-10-3-5-22-16-14(10)18(24)19(26)17-15(16)20(4-6-23-17)8-11(21)12(25)7-13(20)27-2/h4,6-9,23H,3,5H2,1-2H3/t20-/m1/s1
SMILES:	CSC1=CC(=O)C(=C[C@@]21C=CNC1=C2C2=NCCc3c2c(C1=O)n(c3)C)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460973
PubChem CID:	21777406
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001626] Phenanthrolines

*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
NPO31291	Batzella	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[10.1021/jo00110a021]
NPO31291	Batzella	n.a.	n.a.	n.a.	n.a.	Caribbean	n.a.	PMID[14695808]
NPO31291	Batzella	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9917313]

☑ 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
Others	2

Activity Type	# Activity
Cell Line	4
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.089	ug.mL-1	PMID[537069]
NPT168	Cell Line	P388	Mus musculus	IC50	=	170.0	nM	PMID[537070]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	170.0	nM	PMID[537070]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	69.0	nM	PMID[537070]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	0.0	mM	PMID[537069]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	3.0	mM	PMID[537069]

☑ 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 NPC268966 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	480
0.1-0.2	3793
0.2-0.3	20158
0.3-0.4	12399
0.4-0.5	2895
0.5-0.6	2280
0.6-0.7	625
0.7-0.8	42
0.8-0.85	12
0.85-0.9	8
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9294	High Similarity	NPC182940
0.9153	High Similarity	NPC221726
0.9153	High Similarity	NPC225622
0.9153	High Similarity	NPC477414
0.9071	High Similarity	NPC88115
0.907	High Similarity	NPC79777
0.9066	High Similarity	NPC106757
0.896	High Similarity	NPC234403
0.887	High Similarity	NPC23476
0.887	High Similarity	NPC474259
0.887	High Similarity	NPC477415
0.8721	High Similarity	NPC262338
0.8564	High Similarity	NPC475874
0.8429	Intermediate Similarity	NPC143075
0.8407	Intermediate Similarity	NPC473628
0.8398	Intermediate Similarity	NPC469359
0.8256	Intermediate Similarity	NPC477413
0.8202	Intermediate Similarity	NPC186068
0.8107	Intermediate Similarity	NPC100726
0.7958	Intermediate Similarity	NPC476143
0.7957	Intermediate Similarity	NPC473946
0.791	Intermediate Similarity	NPC274981
0.7907	Intermediate Similarity	NPC471655
0.7907	Intermediate Similarity	NPC473878
0.7898	Intermediate Similarity	NPC470680
0.7898	Intermediate Similarity	NPC100104
0.7861	Intermediate Similarity	NPC470679
0.7861	Intermediate Similarity	NPC217021
0.7754	Intermediate Similarity	NPC474258
0.7746	Intermediate Similarity	NPC102664
0.774	Intermediate Similarity	NPC474492
0.7727	Intermediate Similarity	NPC469577
0.7727	Intermediate Similarity	NPC475410
0.7716	Intermediate Similarity	NPC469563
0.7665	Intermediate Similarity	NPC476252
0.7634	Intermediate Similarity	NPC477042
0.76	Intermediate Similarity	NPC469578
0.7539	Intermediate Similarity	NPC103119
0.7525	Intermediate Similarity	NPC220594
0.7525	Intermediate Similarity	NPC469562
0.7448	Intermediate Similarity	NPC255909
0.736	Intermediate Similarity	NPC78767
0.736	Intermediate Similarity	NPC473814
0.7347	Intermediate Similarity	NPC93390
0.7308	Intermediate Similarity	NPC477416
0.7247	Intermediate Similarity	NPC123906
0.7238	Intermediate Similarity	NPC74357
0.7222	Intermediate Similarity	NPC251391
0.7157	Intermediate Similarity	NPC47190
0.71	Intermediate Similarity	NPC74153
0.71	Intermediate Similarity	NPC167710
0.7097	Intermediate Similarity	NPC71132
0.7079	Intermediate Similarity	NPC467188
0.7072	Intermediate Similarity	NPC70406
0.7071	Intermediate Similarity	NPC216550
0.7068	Intermediate Similarity	NPC157583
0.7067	Intermediate Similarity	NPC477420
0.7067	Intermediate Similarity	NPC477418
0.7065	Intermediate Similarity	NPC477044
0.7065	Intermediate Similarity	NPC477041
0.7062	Intermediate Similarity	NPC477003
0.7035	Intermediate Similarity	NPC473821
0.703	Intermediate Similarity	NPC477004
0.7021	Intermediate Similarity	NPC70949
0.7	Intermediate Similarity	NPC105811
0.6995	Remote Similarity	NPC73994
0.6979	Remote Similarity	NPC83774
0.6979	Remote Similarity	NPC284775
0.6973	Remote Similarity	NPC80681
0.6971	Remote Similarity	NPC61038
0.6965	Remote Similarity	NPC292361
0.6946	Remote Similarity	NPC477045
0.6923	Remote Similarity	NPC313889
0.6915	Remote Similarity	NPC294693
0.6907	Remote Similarity	NPC61011
0.6902	Remote Similarity	NPC209362
0.6891	Remote Similarity	NPC237188
0.6875	Remote Similarity	NPC469529
0.6866	Remote Similarity	NPC304203
0.686	Remote Similarity	NPC477043
0.685	Remote Similarity	NPC476460
0.684	Remote Similarity	NPC207866
0.6827	Remote Similarity	NPC175602
0.6816	Remote Similarity	NPC475635
0.6814	Remote Similarity	NPC34837
0.6802	Remote Similarity	NPC46895
0.6786	Remote Similarity	NPC191415
0.678	Remote Similarity	NPC237414
0.6761	Remote Similarity	NPC291517
0.6737	Remote Similarity	NPC233380
0.6737	Remote Similarity	NPC115232
0.6731	Remote Similarity	NPC317701
0.672	Remote Similarity	NPC229055
0.6719	Remote Similarity	NPC91895
0.6714	Remote Similarity	NPC469544
0.6703	Remote Similarity	NPC472260
0.67	Remote Similarity	NPC326422
0.6685	Remote Similarity	NPC472288
0.6684	Remote Similarity	NPC11126
0.6683	Remote Similarity	NPC133003
0.6667	Remote Similarity	NPC157828
0.6667	Remote Similarity	NPC281094
0.6667	Remote Similarity	NPC121327
0.6667	Remote Similarity	NPC195239
0.6649	Remote Similarity	NPC213914
0.6634	Remote Similarity	NPC11445
0.6633	Remote Similarity	NPC228835
0.6618	Remote Similarity	NPC81535
0.6615	Remote Similarity	NPC114637
0.6603	Remote Similarity	NPC143977
0.6597	Remote Similarity	NPC265100
0.6587	Remote Similarity	NPC252338
0.6583	Remote Similarity	NPC159125
0.6571	Remote Similarity	NPC138562
0.6569	Remote Similarity	NPC472292
0.6562	Remote Similarity	NPC42372
0.6558	Remote Similarity	NPC6865
0.6558	Remote Similarity	NPC471194
0.6558	Remote Similarity	NPC471193
0.6558	Remote Similarity	NPC153980
0.6558	Remote Similarity	NPC110182
0.6553	Remote Similarity	NPC472293
0.6552	Remote Similarity	NPC324091
0.655	Remote Similarity	NPC467063
0.655	Remote Similarity	NPC110158
0.6548	Remote Similarity	NPC14113
0.6548	Remote Similarity	NPC84827
0.6548	Remote Similarity	NPC248454
0.6548	Remote Similarity	NPC145885
0.6545	Remote Similarity	NPC242116
0.6538	Remote Similarity	NPC474767
0.6531	Remote Similarity	NPC293216
0.6528	Remote Similarity	NPC478183
0.6524	Remote Similarity	NPC260900
0.6522	Remote Similarity	NPC227582
0.6517	Remote Similarity	NPC308931
0.6517	Remote Similarity	NPC99939
0.6515	Remote Similarity	NPC213468
0.6513	Remote Similarity	NPC302647
0.6513	Remote Similarity	NPC6982
0.6512	Remote Similarity	NPC72956
0.651	Remote Similarity	NPC478182
0.6509	Remote Similarity	NPC472065
0.6509	Remote Similarity	NPC472064
0.6502	Remote Similarity	NPC209917
0.65	Remote Similarity	NPC102755
0.65	Remote Similarity	NPC14686
0.6492	Remote Similarity	NPC473706
0.6489	Remote Similarity	NPC200214
0.6481	Remote Similarity	NPC473218
0.6481	Remote Similarity	NPC470702
0.648	Remote Similarity	NPC477976
0.6477	Remote Similarity	NPC71236
0.6476	Remote Similarity	NPC98864
0.6462	Remote Similarity	NPC473239
0.6462	Remote Similarity	NPC471943
0.6459	Remote Similarity	NPC220797
0.6459	Remote Similarity	NPC474318
0.6459	Remote Similarity	NPC153123
0.6459	Remote Similarity	NPC472296
0.6459	Remote Similarity	NPC74413
0.6459	Remote Similarity	NPC475914
0.6459	Remote Similarity	NPC201266
0.6459	Remote Similarity	NPC123395
0.6459	Remote Similarity	NPC472297
0.6459	Remote Similarity	NPC268744
0.6455	Remote Similarity	NPC269270
0.6453	Remote Similarity	NPC17059
0.6452	Remote Similarity	NPC470703
0.6448	Remote Similarity	NPC58268
0.6448	Remote Similarity	NPC114033
0.6448	Remote Similarity	NPC101130
0.6448	Remote Similarity	NPC129412
0.6445	Remote Similarity	NPC328318
0.6445	Remote Similarity	NPC328596
0.6445	Remote Similarity	NPC472069
0.6445	Remote Similarity	NPC472063
0.6445	Remote Similarity	NPC472062
0.6442	Remote Similarity	NPC174281
0.6442	Remote Similarity	NPC475286
0.6442	Remote Similarity	NPC262898
0.6436	Remote Similarity	NPC216713
0.6432	Remote Similarity	NPC248462
0.6429	Remote Similarity	NPC13456
0.6429	Remote Similarity	NPC77241
0.6429	Remote Similarity	NPC166209
0.6429	Remote Similarity	NPC269203
0.6425	Remote Similarity	NPC478184
0.6425	Remote Similarity	NPC202812
0.6418	Remote Similarity	NPC163055
0.6415	Remote Similarity	NPC98715
0.6411	Remote Similarity	NPC248782
0.6409	Remote Similarity	NPC65408
0.64	Remote Similarity	NPC471997
0.6398	Remote Similarity	NPC300183
0.6394	Remote Similarity	NPC179701
0.6394	Remote Similarity	NPC128244
0.6393	Remote Similarity	NPC471192
0.6389	Remote Similarity	NPC23215
0.6385	Remote Similarity	NPC327592

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 NPC268966 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	603
0.2-0.3	1131
0.3-0.4	2360
0.4-0.5	2918
0.5-0.6	1602
0.6-0.7	290
0.7-0.8	3
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
0.715	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD4848	Phase 1
0.7041	Intermediate Similarity	NPD4988	Discontinued
0.6995	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6044	Discontinued
0.6891	Remote Similarity	NPD2753	Discontinued
0.6878	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3238	Discontinued
0.6802	Remote Similarity	NPD7564	Discontinued
0.6766	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4524	Discontinued
0.6735	Remote Similarity	NPD5473	Discontinued
0.6734	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD1270	Approved
0.6701	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD3178	Discontinued
0.67	Remote Similarity	NPD3961	Discontinued
0.6667	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6152	Phase 1
0.665	Remote Similarity	NPD2479	Phase 3
0.665	Remote Similarity	NPD2481	Approved
0.6649	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6173	Approved
0.663	Remote Similarity	NPD1005	Phase 2
0.663	Remote Similarity	NPD1004	Phase 2
0.6619	Remote Similarity	NPD5901	Discontinued
0.6616	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6446	Discontinued
0.6614	Remote Similarity	NPD1630	Approved
0.6582	Remote Similarity	NPD4075	Phase 2
0.658	Remote Similarity	NPD1343	Approved
0.6579	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4922	Phase 2
0.6553	Remote Similarity	NPD7027	Phase 3
0.6548	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5400	Approved
0.6544	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.654	Remote Similarity	NPD6987	Phase 1
0.6538	Remote Similarity	NPD2405	Phase 3
0.6526	Remote Similarity	NPD2213	Approved
0.6526	Remote Similarity	NPD2214	Approved
0.6513	Remote Similarity	NPD3610	Approved
0.6513	Remote Similarity	NPD3609	Approved
0.651	Remote Similarity	NPD1631	Approved
0.6505	Remote Similarity	NPD7618	Phase 3
0.6505	Remote Similarity	NPD3100	Discontinued
0.6505	Remote Similarity	NPD7619	Phase 3
0.649	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.648	Remote Similarity	NPD750	Phase 2
0.6473	Remote Similarity	NPD2289	Phase 3
0.6473	Remote Similarity	NPD2290	Phase 3
0.6465	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD3947	Discontinued
0.6458	Remote Similarity	NPD5315	Discontinued
0.6443	Remote Similarity	NPD5636	Discontinued
0.6425	Remote Similarity	NPD1996	Discontinued
0.6425	Remote Similarity	NPD3583	Phase 2
0.6425	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD1545	Discontinued
0.641	Remote Similarity	NPD2640	Approved
0.641	Remote Similarity	NPD2641	Approved
0.6409	Remote Similarity	NPD200	Phase 2
0.6409	Remote Similarity	NPD201	Phase 2
0.6406	Remote Similarity	NPD1403	Approved
0.6406	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD1404	Approved
0.6404	Remote Similarity	NPD5809	Phase 3
0.64	Remote Similarity	NPD3927	Phase 2
0.6398	Remote Similarity	NPD3890	Phase 2
0.6398	Remote Similarity	NPD3891	Phase 2
0.6398	Remote Similarity	NPD5017	Discontinued
0.639	Remote Similarity	NPD5686	Approved
0.639	Remote Similarity	NPD5685	Approved
0.6385	Remote Similarity	NPD4299	Phase 1
0.6378	Remote Similarity	NPD1573	Approved
0.6378	Remote Similarity	NPD1575	Approved
0.6376	Remote Similarity	NPD6787	Phase 2
0.6373	Remote Similarity	NPD6771	Discontinued
0.6373	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD7187	Phase 2
0.6364	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6664	Approved
0.6359	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD2639	Approved
0.6359	Remote Similarity	NPD2642	Approved
0.6355	Remote Similarity	NPD2008	Discontinued
0.6349	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD1600	Suspended
0.6343	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD7175	Phase 1
0.6339	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD4304	Discovery
0.6337	Remote Similarity	NPD5106	Approved
0.6337	Remote Similarity	NPD5105	Approved
0.6332	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD7402	Clinical (unspecified phase)
0.633	Remote Similarity	NPD2411	Approved
0.6327	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD7026	Phase 2
0.6318	Remote Similarity	NPD3393	Approved
0.6318	Remote Similarity	NPD3389	Approved
0.6318	Remote Similarity	NPD3394	Approved
0.6313	Remote Similarity	NPD4051	Discontinued
0.6311	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5199	Approved
0.6306	Remote Similarity	NPD5198	Approved
0.6301	Remote Similarity	NPD5888	Phase 2
0.63	Remote Similarity	NPD3506	Approved
0.63	Remote Similarity	NPD3505	Approved
0.6298	Remote Similarity	NPD460	Discontinued
0.6296	Remote Similarity	NPD2172	Phase 1
0.6293	Remote Similarity	NPD2770	Discontinued
0.6291	Remote Similarity	NPD2881	Approved
0.6291	Remote Similarity	NPD2879	Approved
0.6281	Remote Similarity	NPD482	Approved
0.6281	Remote Similarity	NPD1586	Approved
0.628	Remote Similarity	NPD2336	Approved
0.6279	Remote Similarity	NPD6156	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD3967	Approved
0.6277	Remote Similarity	NPD4547	Phase 3
0.6269	Remote Similarity	NPD4079	Approved
0.6269	Remote Similarity	NPD4076	Approved
0.6268	Remote Similarity	NPD5853	Phase 3
0.6268	Remote Similarity	NPD5855	Phase 3
0.6264	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD3476	Approved
0.6257	Remote Similarity	NPD3475	Approved
0.6256	Remote Similarity	NPD2094	Phase 2
0.6256	Remote Similarity	NPD2092	Phase 2
0.6256	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD2095	Phase 2
0.625	Remote Similarity	NPD2070	Approved
0.625	Remote Similarity	NPD3839	Phase 2
0.625	Remote Similarity	NPD3905	Phase 3
0.625	Remote Similarity	NPD3840	Phase 2
0.625	Remote Similarity	NPD569	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2069	Approved
0.625	Remote Similarity	NPD2071	Approved
0.625	Remote Similarity	NPD2068	Approved
0.6244	Remote Similarity	NPD4638	Approved
0.6244	Remote Similarity	NPD4640	Approved
0.6244	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD4639	Approved
0.6244	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD1643	Phase 3
0.6232	Remote Similarity	NPD4499	Approved
0.623	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD2096	Phase 2
0.6225	Remote Similarity	NPD2091	Phase 2
0.6221	Remote Similarity	NPD2510	Approved
0.6221	Remote Similarity	NPD2509	Approved
0.6221	Remote Similarity	NPD7191	Phase 2
0.622	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD9583	Approved
0.621	Remote Similarity	NPD4417	Approved
0.6209	Remote Similarity	NPD272	Approved
0.6207	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD2385	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD6242	Discontinued
0.6204	Remote Similarity	NPD7010	Phase 3
0.6203	Remote Similarity	NPD751	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4883	Approved
0.62	Remote Similarity	NPD4128	Approved
0.6193	Remote Similarity	NPD3968	Approved
0.6193	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4702	Approved
0.619	Remote Similarity	NPD4703	Approved
0.6188	Remote Similarity	NPD1587	Approved
0.6186	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD6068	Discontinued
0.6184	Remote Similarity	NPD2851	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD2850	Phase 1
0.6182	Remote Similarity	NPD7454	Approved
0.6182	Remote Similarity	NPD7455	Approved
0.618	Remote Similarity	NPD2118	Approved
0.618	Remote Similarity	NPD2119	Approved
0.6179	Remote Similarity	NPD4364	Phase 1
0.6176	Remote Similarity	NPD3318	Approved
0.6176	Remote Similarity	NPD3319	Phase 1
0.6176	Remote Similarity	NPD3320	Approved
0.6175	Remote Similarity	NPD4913	Phase 3
0.6173	Remote Similarity	NPD3323	Discontinued
0.6169	Remote Similarity	NPD5104	Approved
0.6166	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6166	Remote Similarity	NPD2580	Discontinued
0.6164	Remote Similarity	NPD6204	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