NPASS Compound

Structure

NPC186068 OpenBabel07101718302D 26 30 0 0 1 0 0 0 0 0999 V2000 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 3.1278 -0.7651 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 1.4248 0.7667 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 4.8598 -1.7651 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 0.7228 -0.6911 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 4.8598 -0.7651 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 0.4339 0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1278 -1.7651 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.9938 0.7349 0.0000 Br 0 0 0 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 -0.0400 1.7816 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 1 3 1 0 0 0 0 1 7 1 0 0 0 0 2 4 1 0 0 0 0 2 18 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 8 2 0 0 0 0 5 18 1 0 0 0 0 6 9 2 0 0 0 0 6 18 1 0 0 0 0 7 10 1 0 0 0 0 7 17 2 0 0 0 0 8 15 1 0 0 0 0 8 19 1 0 0 0 0 9 15 1 0 0 0 0 9 20 1 0 0 0 0 10 12 1 0 0 0 0 10 13 2 0 0 0 0 11 12 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 22 2 0 0 0 0 13 16 1 0 0 0 0 13 24 1 0 0 0 0 14 16 1 0 0 0 0 14 23 1 0 0 0 0 15 25 2 0 0 0 0 16 26 2 0 0 0 0 17 21 1 0 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	538.85
Volume:	364.432
LogP:	4.409
LogD:	3.209
LogS:	-3.93
# Rotatable Bonds:	0
TPSA:	77.48
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.407
Synthetic Accessibility Score:	4.85
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.241
MDCK Permeability:	1.3892587958252989e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.296
20% Bioavailability (F20%):	0.893
30% Bioavailability (F30%):	0.822

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055
Plasma Protein Binding (PPB):	99.09626007080078%
Volume Distribution (VD):	0.56
Pgp-substrate:	1.2609717845916748%

ADMET: Metabolism

CYP1A2-inhibitor:	0.878
CYP1A2-substrate:	0.292
CYP2C19-inhibitor:	0.909
CYP2C19-substrate:	0.159
CYP2C9-inhibitor:	0.913
CYP2C9-substrate:	0.907
CYP2D6-inhibitor:	0.947
CYP2D6-substrate:	0.786
CYP3A4-inhibitor:	0.397
CYP3A4-substrate:	0.135

ADMET: Excretion

Clearance (CL):	1.437
Half-life (T1/2):	0.503

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.493
Drug-inuced Liver Injury (DILI):	0.834
AMES Toxicity:	0.957
Rat Oral Acute Toxicity:	0.989
Maximum Recommended Daily Dose:	0.602
Skin Sensitization:	0.58
Carcinogencity:	0.977
Eye Corrosion:	0.003
Eye Irritation:	0.034
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC186068

Natural Product ID:	NPC186068
*Common Name:**	BLFMBWWFYPUMNR-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:	14-Bromodiscorhabdin C
Standard InCHIKey:	BLFMBWWFYPUMNR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H12Br3N3O2/c19-8-5-18(6-9(20)15(8)25)2-4-23-14-11(18)12-10-7(1-3-22-12)17(21)24-13(10)16(14)26/h5-6,23-24H,1-4H2
SMILES:	C1CN=C2c3c1c(Br)[nH]c3C(=O)C1=C2C2(CCN1)C=C(C(=O)C(=C2)Br)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450115
PubChem CID:	10530524
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
NPO32524	latrunculid sponges	Species	n.a.	n.a.	n.a.	South African	n.a.	PMID[15332840]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	77.0	nM	PMID[479265]

☑ 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 NPC186068 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	506
0.1-0.2	4254
0.2-0.3	21335
0.3-0.4	11329
0.4-0.5	2937
0.5-0.6	1839
0.6-0.7	445
0.7-0.8	38
0.8-0.85	7
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9277	High Similarity	NPC474258
0.9152	High Similarity	NPC234403
0.9053	High Similarity	NPC473946
0.9036	High Similarity	NPC79777
0.881	High Similarity	NPC182940
0.8675	High Similarity	NPC262338
0.8563	High Similarity	NPC473628
0.8475	Intermediate Similarity	NPC221726
0.8475	Intermediate Similarity	NPC225622
0.8475	Intermediate Similarity	NPC477414
0.8409	Intermediate Similarity	NPC475874
0.8202	Intermediate Similarity	NPC268966
0.809	Intermediate Similarity	NPC23476
0.809	Intermediate Similarity	NPC477415
0.809	Intermediate Similarity	NPC474259
0.7941	Intermediate Similarity	NPC274981
0.7824	Intermediate Similarity	NPC477413
0.7725	Intermediate Similarity	NPC471655
0.7708	Intermediate Similarity	NPC143075
0.7661	Intermediate Similarity	NPC474492
0.7552	Intermediate Similarity	NPC88115
0.7539	Intermediate Similarity	NPC106757
0.7514	Intermediate Similarity	NPC100104
0.7514	Intermediate Similarity	NPC470680
0.7386	Intermediate Similarity	NPC71132
0.7386	Intermediate Similarity	NPC2414
0.7363	Intermediate Similarity	NPC477042
0.7351	Intermediate Similarity	NPC469359
0.7294	Intermediate Similarity	NPC100726
0.7151	Intermediate Similarity	NPC474696
0.7127	Intermediate Similarity	NPC469976
0.7113	Intermediate Similarity	NPC477004
0.711	Intermediate Similarity	NPC473878
0.7095	Intermediate Similarity	NPC115232
0.7076	Intermediate Similarity	NPC260041
0.7069	Intermediate Similarity	NPC217021
0.7069	Intermediate Similarity	NPC470679
0.7052	Intermediate Similarity	NPC102664
0.7039	Intermediate Similarity	NPC73687
0.6995	Remote Similarity	NPC271927
0.6988	Remote Similarity	NPC150592
0.6974	Remote Similarity	NPC476143
0.6957	Remote Similarity	NPC37268
0.6923	Remote Similarity	NPC167710
0.6856	Remote Similarity	NPC19342
0.6853	Remote Similarity	NPC237414
0.6842	Remote Similarity	NPC133003
0.6837	Remote Similarity	NPC74153
0.6826	Remote Similarity	NPC20021
0.6804	Remote Similarity	NPC47190
0.6802	Remote Similarity	NPC477044
0.6802	Remote Similarity	NPC477041
0.6793	Remote Similarity	NPC471943
0.6791	Remote Similarity	NPC284775
0.6789	Remote Similarity	NPC477003
0.6788	Remote Similarity	NPC324091
0.6772	Remote Similarity	NPC184932
0.6772	Remote Similarity	NPC472861
0.6769	Remote Similarity	NPC473821
0.6766	Remote Similarity	NPC469563
0.6761	Remote Similarity	NPC123906
0.676	Remote Similarity	NPC74357
0.6757	Remote Similarity	NPC6982
0.672	Remote Similarity	NPC252572
0.6716	Remote Similarity	NPC476252
0.6705	Remote Similarity	NPC114033
0.6705	Remote Similarity	NPC129412
0.6705	Remote Similarity	NPC101130
0.6705	Remote Similarity	NPC58268
0.6702	Remote Similarity	NPC110158
0.67	Remote Similarity	NPC469577
0.67	Remote Similarity	NPC475410
0.6683	Remote Similarity	NPC136957
0.6683	Remote Similarity	NPC19696
0.6683	Remote Similarity	NPC477045
0.6667	Remote Similarity	NPC470703
0.6667	Remote Similarity	NPC469578
0.6667	Remote Similarity	NPC476423
0.6667	Remote Similarity	NPC206148
0.665	Remote Similarity	NPC269203
0.665	Remote Similarity	NPC166209
0.665	Remote Similarity	NPC175602
0.665	Remote Similarity	NPC77241
0.665	Remote Similarity	NPC13456
0.6649	Remote Similarity	NPC151635
0.6648	Remote Similarity	NPC251391
0.6633	Remote Similarity	NPC472292
0.6631	Remote Similarity	NPC80528
0.663	Remote Similarity	NPC76982
0.663	Remote Similarity	NPC233380
0.663	Remote Similarity	NPC27296
0.6618	Remote Similarity	NPC470702
0.6618	Remote Similarity	NPC473218
0.6616	Remote Similarity	NPC472293
0.6615	Remote Similarity	NPC21429
0.6612	Remote Similarity	NPC214106
0.6611	Remote Similarity	NPC474236
0.6602	Remote Similarity	NPC220594
0.6602	Remote Similarity	NPC469562
0.6601	Remote Similarity	NPC477043
0.66	Remote Similarity	NPC201266
0.66	Remote Similarity	NPC153123
0.66	Remote Similarity	NPC474318
0.66	Remote Similarity	NPC268744
0.66	Remote Similarity	NPC475914
0.66	Remote Similarity	NPC220797
0.6599	Remote Similarity	NPC304203
0.6583	Remote Similarity	NPC78767
0.6583	Remote Similarity	NPC473814
0.6583	Remote Similarity	NPC174281
0.6583	Remote Similarity	NPC475286
0.6582	Remote Similarity	NPC476460
0.6573	Remote Similarity	NPC2272
0.6562	Remote Similarity	NPC117027
0.6553	Remote Similarity	NPC61038
0.6548	Remote Similarity	NPC216550
0.6546	Remote Similarity	NPC63571
0.6546	Remote Similarity	NPC111566
0.6541	Remote Similarity	NPC474383
0.6533	Remote Similarity	NPC102592
0.6533	Remote Similarity	NPC79356
0.6517	Remote Similarity	NPC472296
0.6517	Remote Similarity	NPC472297
0.6515	Remote Similarity	NPC326422
0.6513	Remote Similarity	NPC310633
0.6512	Remote Similarity	NPC138596
0.6512	Remote Similarity	NPC195704
0.6512	Remote Similarity	NPC64661
0.6512	Remote Similarity	NPC200397
0.6512	Remote Similarity	NPC292434
0.6512	Remote Similarity	NPC14448
0.6512	Remote Similarity	NPC98156
0.6512	Remote Similarity	NPC167200
0.651	Remote Similarity	NPC191415
0.65	Remote Similarity	NPC70406
0.65	Remote Similarity	NPC475635
0.6497	Remote Similarity	NPC467188
0.6486	Remote Similarity	NPC476418
0.6486	Remote Similarity	NPC271797
0.6486	Remote Similarity	NPC21174
0.6486	Remote Similarity	NPC306160
0.6482	Remote Similarity	NPC93390
0.6477	Remote Similarity	NPC470205
0.646	Remote Similarity	NPC291389
0.6459	Remote Similarity	NPC469715
0.6458	Remote Similarity	NPC88110
0.6457	Remote Similarity	NPC302717
0.6457	Remote Similarity	NPC12831
0.6457	Remote Similarity	NPC244087
0.6457	Remote Similarity	NPC74928
0.6457	Remote Similarity	NPC48171
0.6457	Remote Similarity	NPC169308
0.6457	Remote Similarity	NPC3698
0.6457	Remote Similarity	NPC205604
0.6457	Remote Similarity	NPC77582
0.6457	Remote Similarity	NPC129753
0.6457	Remote Similarity	NPC286529
0.6457	Remote Similarity	NPC209281
0.6457	Remote Similarity	NPC97230
0.6457	Remote Similarity	NPC59839
0.6453	Remote Similarity	NPC291517
0.644	Remote Similarity	NPC157583
0.6432	Remote Similarity	NPC269886
0.6432	Remote Similarity	NPC81802
0.6432	Remote Similarity	NPC472210
0.6432	Remote Similarity	NPC247735
0.6432	Remote Similarity	NPC472295
0.6429	Remote Similarity	NPC207866
0.6425	Remote Similarity	NPC105811
0.6421	Remote Similarity	NPC97106
0.6417	Remote Similarity	NPC109447
0.6415	Remote Similarity	NPC477416
0.6402	Remote Similarity	NPC302647
0.6398	Remote Similarity	NPC50562
0.6396	Remote Similarity	NPC473666
0.6396	Remote Similarity	NPC103119
0.639	Remote Similarity	NPC317701
0.6383	Remote Similarity	NPC70949
0.6378	Remote Similarity	NPC17273
0.6378	Remote Similarity	NPC135601
0.6378	Remote Similarity	NPC141612
0.6374	Remote Similarity	NPC281094
0.6373	Remote Similarity	NPC471944
0.6368	Remote Similarity	NPC48117
0.6368	Remote Similarity	NPC476526
0.6368	Remote Similarity	NPC292361
0.6368	Remote Similarity	NPC67658
0.6368	Remote Similarity	NPC329765
0.6368	Remote Similarity	NPC179701
0.6368	Remote Similarity	NPC161861
0.6364	Remote Similarity	NPC314333
0.6364	Remote Similarity	NPC42372
0.6354	Remote Similarity	NPC52110
0.6354	Remote Similarity	NPC237188
0.6354	Remote Similarity	NPC313889
0.6339	Remote Similarity	NPC209362
0.6337	Remote Similarity	NPC262898
0.6324	Remote Similarity	NPC80681
0.6321	Remote Similarity	NPC233050
0.6321	Remote Similarity	NPC276540

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 NPC186068 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	260
0.1-0.2	628
0.2-0.3	1374
0.3-0.4	2776
0.4-0.5	3025
0.5-0.6	1010
0.6-0.7	76
0.7-0.8	1
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
0.7062	Intermediate Similarity	NPD2214	Approved
0.7062	Intermediate Similarity	NPD2213	Approved
0.6989	Remote Similarity	NPD5473	Discontinued
0.6702	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4524	Discontinued
0.6425	Remote Similarity	NPD3178	Discontinued
0.6421	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD3319	Phase 1
0.6392	Remote Similarity	NPD3318	Approved
0.6392	Remote Similarity	NPD3320	Approved
0.6364	Remote Similarity	NPD4499	Approved
0.6346	Remote Similarity	NPD6376	Discontinued
0.6326	Remote Similarity	NPD1996	Discontinued
0.6324	Remote Similarity	NPD1630	Approved
0.6303	Remote Similarity	NPD7455	Approved
0.6303	Remote Similarity	NPD7454	Approved
0.6294	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD4848	Phase 1
0.628	Remote Similarity	NPD5901	Discontinued
0.6269	Remote Similarity	NPD2753	Discontinued
0.6263	Remote Similarity	NPD4988	Discontinued
0.6263	Remote Similarity	NPD3961	Discontinued
0.6223	Remote Similarity	NPD1631	Approved
0.6219	Remote Similarity	NPD4922	Phase 2
0.6218	Remote Similarity	NPD3238	Discontinued
0.6205	Remote Similarity	NPD2479	Phase 3
0.6205	Remote Similarity	NPD2481	Approved
0.6178	Remote Similarity	NPD1573	Approved
0.6178	Remote Similarity	NPD1575	Approved
0.6134	Remote Similarity	NPD4075	Phase 2
0.6131	Remote Similarity	NPD5809	Phase 3
0.6129	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD2290	Phase 3
0.6127	Remote Similarity	NPD2289	Phase 3
0.6111	Remote Similarity	NPD7564	Discontinued
0.61	Remote Similarity	NPD3246	Discontinued
0.6089	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD482	Approved
0.6078	Remote Similarity	NPD7619	Phase 3
0.6078	Remote Similarity	NPD7618	Phase 3
0.6075	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.607	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD1270	Approved
0.6059	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6057	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD3100	Discontinued
0.6029	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD7716	Approved
0.6018	Remote Similarity	NPD7717	Approved
0.601	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6176	Phase 1
0.6	Remote Similarity	NPD4462	Approved
0.6	Remote Similarity	NPD1586	Approved
0.6	Remote Similarity	NPD4463	Approved
0.5991	Remote Similarity	NPD3393	Approved
0.5991	Remote Similarity	NPD3389	Approved
0.5991	Remote Similarity	NPD3394	Approved
0.599	Remote Similarity	NPD6446	Discontinued
0.598	Remote Similarity	NPD2095	Phase 2
0.598	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.598	Remote Similarity	NPD2092	Phase 2
0.598	Remote Similarity	NPD2094	Phase 2
0.598	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.597	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.596	Remote Similarity	NPD1643	Phase 3
0.5951	Remote Similarity	NPD460	Discontinued
0.595	Remote Similarity	NPD2096	Phase 2
0.595	Remote Similarity	NPD2091	Phase 2
0.5946	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.5944	Remote Similarity	NPD569	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD6664	Approved
0.5938	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD4520	Approved
0.5933	Remote Similarity	NPD4501	Approved
0.5933	Remote Similarity	NPD4500	Approved
0.5931	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.5916	Remote Similarity	NPD5400	Approved
0.5914	Remote Similarity	NPD2172	Phase 1
0.5909	Remote Similarity	NPD1587	Approved
0.5902	Remote Similarity	NPD1896	Approved
0.5891	Remote Similarity	NPD4940	Approved
0.5888	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD5104	Approved
0.5885	Remote Similarity	NPD3425	Discontinued
0.5879	Remote Similarity	NPD5020	Approved
0.5876	Remote Similarity	NPD1343	Approved
0.5874	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.5869	Remote Similarity	NPD2008	Discontinued
0.5866	Remote Similarity	NPD198	Clinical (unspecified phase)
0.5864	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD4948	Discontinued
0.586	Remote Similarity	NPD1600	Suspended
0.5859	Remote Similarity	NPD3506	Approved
0.5859	Remote Similarity	NPD3505	Approved
0.5855	Remote Similarity	NPD2915	Discontinued
0.5855	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.5853	Remote Similarity	NPD2411	Approved
0.5853	Remote Similarity	NPD7657	Approved
0.5853	Remote Similarity	NPD7656	Approved
0.585	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.5845	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4051	Discontinued
0.5829	Remote Similarity	NPD3076	Approved
0.5829	Remote Similarity	NPD3078	Approved
0.5829	Remote Similarity	NPD4076	Approved
0.5829	Remote Similarity	NPD3079	Approved
0.5829	Remote Similarity	NPD3077	Approved
0.5829	Remote Similarity	NPD4079	Approved
0.5824	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.5822	Remote Similarity	NPD8115	Approved
0.5822	Remote Similarity	NPD8114	Approved
0.5817	Remote Similarity	NPD1871	Approved
0.5815	Remote Similarity	NPD6017	Discontinued
0.5815	Remote Similarity	NPD5254	Discontinued
0.5814	Remote Similarity	NPD2510	Approved
0.5814	Remote Similarity	NPD2509	Approved
0.5811	Remote Similarity	NPD6242	Discontinued
0.581	Remote Similarity	NPD4880	Discontinued
0.581	Remote Similarity	NPD7308	Discontinued
0.5806	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.5805	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.5803	Remote Similarity	NPD3583	Phase 2
0.5802	Remote Similarity	NPD7187	Phase 2
0.5801	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.5799	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD2004	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD2844	Phase 3
0.5792	Remote Similarity	NPD1722	Approved
0.5787	Remote Similarity	NPD750	Phase 2
0.5782	Remote Similarity	NPD4601	Approved
0.5782	Remote Similarity	NPD4600	Approved
0.5779	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7406	Phase 2
0.5769	Remote Similarity	NPD2070	Approved
0.5769	Remote Similarity	NPD786	Approved
0.5769	Remote Similarity	NPD5853	Phase 3
0.5769	Remote Similarity	NPD2068	Approved
0.5769	Remote Similarity	NPD5855	Phase 3
0.5769	Remote Similarity	NPD2071	Approved
0.5769	Remote Similarity	NPD2069	Approved
0.5767	Remote Similarity	NPD2790	Discontinued
0.5762	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.5762	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.5762	Remote Similarity	NPD1982	Phase 1
0.5761	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD4128	Approved
0.5755	Remote Similarity	NPD7817	Phase 1
0.5755	Remote Similarity	NPD7727	Phase 2
0.575	Remote Similarity	NPD8386	Phase 2
0.575	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD3379	Phase 2
0.5748	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD6987	Phase 1
0.5748	Remote Similarity	NPD3380	Phase 3
0.5748	Remote Similarity	NPD4299	Phase 1
0.5748	Remote Similarity	NPD3947	Discontinued
0.5741	Remote Similarity	NPD2443	Approved
0.5741	Remote Similarity	NPD2442	Approved
0.5741	Remote Similarity	NPD6459	Phase 2
0.5736	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD6248	Phase 2
0.5735	Remote Similarity	NPD6249	Phase 2
0.5735	Remote Similarity	NPD3315	Phase 3
0.5734	Remote Similarity	NPD3915	Approved
0.5734	Remote Similarity	NPD6152	Phase 1
0.5728	Remote Similarity	NPD3773	Approved
0.5728	Remote Similarity	NPD3775	Approved
0.5728	Remote Similarity	NPD3774	Approved
0.5722	Remote Similarity	NPD3323	Discontinued
0.5721	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD7568	Phase 1
0.5714	Remote Similarity	NPD2408	Discontinued
0.5714	Remote Similarity	NPD7482	Phase 2
0.5714	Remote Similarity	NPD7483	Phase 2
0.5714	Remote Similarity	NPD7287	Clinical (unspecified phase)
0.5708	Remote Similarity	NPD3917	Approved
0.5708	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.5708	Remote Similarity	NPD3918	Approved
0.5708	Remote Similarity	NPD2911	Approved
0.5708	Remote Similarity	NPD2912	Approved
0.5707	Remote Similarity	NPD2770	Discontinued
0.5707	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD4304	Discovery
0.57	Remote Similarity	NPD7865	Approved
0.5695	Remote Similarity	NPD5198	Approved
0.5695	Remote Similarity	NPD5199	Approved
0.5694	Remote Similarity	NPD1506	Discontinued
0.5686	Remote Similarity	NPD5075	Discontinued
0.5684	Remote Similarity	NPD2837	Discontinued
0.5682	Remote Similarity	NPD5888	Phase 2
0.568	Remote Similarity	NPD7175	Phase 1
0.568	Remote Similarity	NPD6068	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