NPASS Compound

Structure

NPC243633 OpenBabel07101719122D 25 26 0 0 0 0 0 0 0 0999 V2000 -7.7372 5.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6032 3.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8712 2.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2731 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1391 -0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5411 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5411 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8712 3.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0052 2.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4071 0.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6180 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4071 -0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2731 1.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1391 0.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8968 1.7601 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -4.2731 2.4122 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.6750 -2.0878 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 -7.7372 4.4122 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0570 -2.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0052 1.4122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 23 1 0 0 0 0 3 8 1 0 0 0 0 3 9 1 0 0 0 0 4 5 2 0 0 0 0 4 13 1 0 0 0 0 5 17 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 21 1 0 0 0 0 8 23 1 0 0 0 0 9 25 1 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 14 1 0 0 0 0 11 16 2 0 0 0 0 12 14 2 0 0 0 0 12 22 1 0 0 0 0 14 19 1 0 0 0 0 15 17 2 0 0 0 0 15 20 1 0 0 0 0 16 18 1 0 0 0 0 16 22 1 0 0 0 0 17 25 1 0 0 0 0 18 21 1 0 0 0 0 18 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	471.02
Volume:	376.09
LogP:	4.007
LogD:	3.466
LogS:	-4.431
# Rotatable Bonds:	10
TPSA:	57.36
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.545
Synthetic Accessibility Score:	2.352
Fsp3:	0.389
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.989
MDCK Permeability:	1.4735973309143446e-05
Pgp-inhibitor:	0.942
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.925
Plasma Protein Binding (PPB):	93.70183563232422%
Volume Distribution (VD):	1.999
Pgp-substrate:	9.67822265625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.871
CYP1A2-substrate:	0.936
CYP2C19-inhibitor:	0.648
CYP2C19-substrate:	0.805
CYP2C9-inhibitor:	0.097
CYP2C9-substrate:	0.634
CYP2D6-inhibitor:	0.973
CYP2D6-substrate:	0.916
CYP3A4-inhibitor:	0.509
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	3.885
Half-life (T1/2):	0.281

ADMET: Toxicity

hERG Blockers:	0.891
Human Hepatotoxicity (H-HT):	0.153
Drug-inuced Liver Injury (DILI):	0.192
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.438
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.591
Carcinogencity:	0.07
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.585

Download Data

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

Natural Product: NPC243633

Natural Product ID:	NPC243633
*Common Name:**	Dispyrin
IUPAC Name:	4-bromo-N-[2-[3-bromo-4-[3-(dimethylamino)propoxy]phenyl]ethyl]-1H-pyrrole-2-carboxamide
Synonyms:	dispyrin
Standard InCHIKey:	MOWCGUQGNSAZSR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H23Br2N3O2/c1-23(2)8-3-9-25-17-5-4-13(10-15(17)20)6-7-21-18(24)16-11-14(19)12-22-16/h4-5,10-12,22H,3,6-9H2,1-2H3,(H,21,24)
SMILES:	CN(CCCOc1ccc(cc1Br)CCNC(=O)c1[nH]cc(c1)Br)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL493091
PubChem CID:	16215415
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers

*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
NPO27799	Agelas dispar	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18800848]
NPO27799	Agelas dispar	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461661]
NPO27799	Agelas dispar	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748394]
NPO27799	Agelas dispar	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	5
Ki	5
Others	6

Activity Type	# Activity
Individual Protein	15
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT221	Individual Protein	Alpha-1d adrenergic receptor	Homo sapiens	Inhibition	=	91.0	%	PMID[484944]
NPT221	Individual Protein	Alpha-1d adrenergic receptor	Homo sapiens	Ki	=	275.0	nM	PMID[484944]
NPT221	Individual Protein	Alpha-1d adrenergic receptor	Homo sapiens	IC50	=	560.0	nM	PMID[484944]
NPT222	Individual Protein	Alpha-2a adrenergic receptor	Homo sapiens	Inhibition	=	97.0	%	PMID[484944]
NPT222	Individual Protein	Alpha-2a adrenergic receptor	Homo sapiens	Ki	=	69.0	nM	PMID[484944]
NPT222	Individual Protein	Alpha-2a adrenergic receptor	Homo sapiens	IC50	=	185.0	nM	PMID[484944]
NPT2	Others	Unspecified		Inhibition	=	50.0	%	PMID[484944]
NPT98	Individual Protein	HERG	Homo sapiens	Inhibition	=	50.0	%	PMID[484944]
NPT989	Individual Protein	Histamine H3 receptor	Cavia porcellus	Inhibition	=	91.0	%	PMID[484944]
NPT989	Individual Protein	Histamine H3 receptor	Cavia porcellus	Ki	=	1020.0	nM	PMID[484944]
NPT989	Individual Protein	Histamine H3 receptor	Cavia porcellus	IC50	=	1250.0	nM	PMID[484944]
NPT986	Individual Protein	Histamine H3 receptor	Rattus norvegicus	Inhibition	=	91.0	%	PMID[484944]
NPT986	Individual Protein	Histamine H3 receptor	Rattus norvegicus	Ki	=	1040.0	nM	PMID[484944]
NPT986	Individual Protein	Histamine H3 receptor	Rattus norvegicus	IC50	=	2350.0	nM	PMID[484944]
NPT987	Individual Protein	Histamine H3 receptor	Homo sapiens	Ki	=	1040.0	nM	PMID[484945]
NPT987	Individual Protein	Histamine H3 receptor	Homo sapiens	IC50	=	2350.0	nM	PMID[484945]

☑ 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 NPC243633 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	460
0.1-0.2	6442
0.2-0.3	10916
0.3-0.4	10967
0.4-0.5	9384
0.5-0.6	3112
0.6-0.7	1332
0.7-0.8	78
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC175150
0.9596	High Similarity	NPC67658
0.955	High Similarity	NPC168209
0.9254	High Similarity	NPC50562
0.7658	Intermediate Similarity	NPC323969
0.7632	Intermediate Similarity	NPC196718
0.7555	Intermediate Similarity	NPC102593
0.7555	Intermediate Similarity	NPC200553
0.7532	Intermediate Similarity	NPC162002
0.75	Intermediate Similarity	NPC74153
0.7489	Intermediate Similarity	NPC174489
0.7478	Intermediate Similarity	NPC122436
0.744	Intermediate Similarity	NPC295158
0.7425	Intermediate Similarity	NPC26641
0.7424	Intermediate Similarity	NPC194740
0.7418	Intermediate Similarity	NPC473814
0.7418	Intermediate Similarity	NPC78767
0.7407	Intermediate Similarity	NPC216369
0.7403	Intermediate Similarity	NPC279189
0.7393	Intermediate Similarity	NPC101350
0.7362	Intermediate Similarity	NPC37152
0.7358	Intermediate Similarity	NPC473821
0.735	Intermediate Similarity	NPC235685
0.7339	Intermediate Similarity	NPC33064
0.7324	Intermediate Similarity	NPC93390
0.7306	Intermediate Similarity	NPC82053
0.7289	Intermediate Similarity	NPC305984
0.7284	Intermediate Similarity	NPC260434
0.7265	Intermediate Similarity	NPC475635
0.7241	Intermediate Similarity	NPC115595
0.7183	Intermediate Similarity	NPC92111
0.7181	Intermediate Similarity	NPC303658
0.7136	Intermediate Similarity	NPC76748
0.713	Intermediate Similarity	NPC77061
0.7124	Intermediate Similarity	NPC471762
0.7124	Intermediate Similarity	NPC66777
0.7118	Intermediate Similarity	NPC54066
0.7116	Intermediate Similarity	NPC307963
0.7112	Intermediate Similarity	NPC24370
0.7112	Intermediate Similarity	NPC319232
0.711	Intermediate Similarity	NPC477004
0.7098	Intermediate Similarity	NPC113369
0.7093	Intermediate Similarity	NPC322064
0.7089	Intermediate Similarity	NPC296527
0.7082	Intermediate Similarity	NPC124920
0.7082	Intermediate Similarity	NPC34580
0.7082	Intermediate Similarity	NPC118559
0.7082	Intermediate Similarity	NPC304307
0.7076	Intermediate Similarity	NPC284888
0.7061	Intermediate Similarity	NPC223189
0.7056	Intermediate Similarity	NPC470501
0.7054	Intermediate Similarity	NPC174758
0.7054	Intermediate Similarity	NPC316224
0.7051	Intermediate Similarity	NPC100547
0.7048	Intermediate Similarity	NPC477979
0.7046	Intermediate Similarity	NPC245055
0.7046	Intermediate Similarity	NPC97902
0.7045	Intermediate Similarity	NPC232727
0.7023	Intermediate Similarity	NPC138370
0.7021	Intermediate Similarity	NPC322135
0.7021	Intermediate Similarity	NPC223409
0.7021	Intermediate Similarity	NPC95240
0.7014	Intermediate Similarity	NPC295898
0.7013	Intermediate Similarity	NPC60621
0.7013	Intermediate Similarity	NPC470502
0.7009	Intermediate Similarity	NPC261251
0.7	Intermediate Similarity	NPC121772
0.7	Intermediate Similarity	NPC269270
0.6992	Remote Similarity	NPC14288
0.6987	Remote Similarity	NPC27041
0.6986	Remote Similarity	NPC127085
0.6972	Remote Similarity	NPC13880
0.6972	Remote Similarity	NPC251090
0.697	Remote Similarity	NPC14686
0.6967	Remote Similarity	NPC275292
0.6967	Remote Similarity	NPC243381
0.6966	Remote Similarity	NPC214142
0.6964	Remote Similarity	NPC183777
0.6964	Remote Similarity	NPC249583
0.6962	Remote Similarity	NPC54803
0.6962	Remote Similarity	NPC321592
0.696	Remote Similarity	NPC118940
0.6953	Remote Similarity	NPC470503
0.6951	Remote Similarity	NPC285558
0.6948	Remote Similarity	NPC258048
0.6947	Remote Similarity	NPC123839
0.6946	Remote Similarity	NPC477549
0.6946	Remote Similarity	NPC272549
0.6943	Remote Similarity	NPC152768
0.6943	Remote Similarity	NPC148183
0.694	Remote Similarity	NPC198503
0.6939	Remote Similarity	NPC63971
0.6939	Remote Similarity	NPC91868
0.6936	Remote Similarity	NPC157931
0.6936	Remote Similarity	NPC257851
0.6933	Remote Similarity	NPC323752
0.6933	Remote Similarity	NPC287208
0.693	Remote Similarity	NPC236668
0.6923	Remote Similarity	NPC19872
0.692	Remote Similarity	NPC472286
0.692	Remote Similarity	NPC472287
0.6915	Remote Similarity	NPC75135
0.6903	Remote Similarity	NPC61038
0.6903	Remote Similarity	NPC174672
0.69	Remote Similarity	NPC146976
0.6897	Remote Similarity	NPC472099
0.6889	Remote Similarity	NPC4687
0.6889	Remote Similarity	NPC321428
0.6889	Remote Similarity	NPC270918
0.6886	Remote Similarity	NPC110182
0.6885	Remote Similarity	NPC78609
0.6883	Remote Similarity	NPC469717
0.6883	Remote Similarity	NPC181081
0.6881	Remote Similarity	NPC84853
0.6872	Remote Similarity	NPC167860
0.6872	Remote Similarity	NPC233050
0.6872	Remote Similarity	NPC123976
0.6872	Remote Similarity	NPC276540
0.687	Remote Similarity	NPC274982
0.6869	Remote Similarity	NPC241025
0.6858	Remote Similarity	NPC266249
0.6858	Remote Similarity	NPC82548
0.6858	Remote Similarity	NPC476525
0.6853	Remote Similarity	NPC292958
0.6853	Remote Similarity	NPC74360
0.6852	Remote Similarity	NPC209917
0.6851	Remote Similarity	NPC21638
0.6851	Remote Similarity	NPC474196
0.6847	Remote Similarity	NPC176538
0.6846	Remote Similarity	NPC184680
0.6846	Remote Similarity	NPC240384
0.6844	Remote Similarity	NPC175602
0.6842	Remote Similarity	NPC146418
0.6831	Remote Similarity	NPC148889
0.6822	Remote Similarity	NPC477003
0.6818	Remote Similarity	NPC222018
0.6818	Remote Similarity	NPC470785
0.6818	Remote Similarity	NPC470784
0.6818	Remote Similarity	NPC82472
0.6812	Remote Similarity	NPC308137
0.6812	Remote Similarity	NPC264176
0.6812	Remote Similarity	NPC310211
0.6802	Remote Similarity	NPC136957
0.6802	Remote Similarity	NPC19696
0.6797	Remote Similarity	NPC170114
0.6794	Remote Similarity	NPC54214
0.6787	Remote Similarity	NPC262898
0.6787	Remote Similarity	NPC174281
0.6787	Remote Similarity	NPC475286
0.6783	Remote Similarity	NPC207866
0.6783	Remote Similarity	NPC266931
0.6783	Remote Similarity	NPC476287
0.6781	Remote Similarity	NPC313804
0.6781	Remote Similarity	NPC315804
0.678	Remote Similarity	NPC473706
0.6777	Remote Similarity	NPC15801
0.6773	Remote Similarity	NPC53534
0.677	Remote Similarity	NPC45190
0.6769	Remote Similarity	NPC87413
0.6763	Remote Similarity	NPC182222
0.6763	Remote Similarity	NPC233380
0.6757	Remote Similarity	NPC472284
0.6753	Remote Similarity	NPC470549
0.6752	Remote Similarity	NPC150239
0.6752	Remote Similarity	NPC474195
0.6744	Remote Similarity	NPC84478
0.6742	Remote Similarity	NPC48117
0.6742	Remote Similarity	NPC329765
0.6742	Remote Similarity	NPC476526
0.6742	Remote Similarity	NPC179701
0.6741	Remote Similarity	NPC471944
0.6739	Remote Similarity	NPC316981
0.6738	Remote Similarity	NPC473041
0.6738	Remote Similarity	NPC264285
0.6736	Remote Similarity	NPC326363
0.6734	Remote Similarity	NPC260041
0.6727	Remote Similarity	NPC88315
0.6726	Remote Similarity	NPC237414
0.6726	Remote Similarity	NPC210256
0.6725	Remote Similarity	NPC470020
0.6724	Remote Similarity	NPC288349
0.6724	Remote Similarity	NPC74969
0.6724	Remote Similarity	NPC36405
0.6723	Remote Similarity	NPC478078
0.6722	Remote Similarity	NPC172222
0.6721	Remote Similarity	NPC477585
0.6721	Remote Similarity	NPC477588
0.6721	Remote Similarity	NPC477586
0.6721	Remote Similarity	NPC477590
0.6711	Remote Similarity	NPC171787
0.6711	Remote Similarity	NPC476465
0.6709	Remote Similarity	NPC193267
0.6709	Remote Similarity	NPC213530
0.6708	Remote Similarity	NPC472061
0.6705	Remote Similarity	NPC314222
0.6705	Remote Similarity	NPC196449
0.6696	Remote Similarity	NPC300156
0.6695	Remote Similarity	NPC472285
0.6695	Remote Similarity	NPC169402
0.6694	Remote Similarity	NPC253675

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 NPC243633 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	760
0.2-0.3	815
0.3-0.4	1641
0.4-0.5	2699
0.5-0.6	2358
0.6-0.7	604
0.7-0.8	34
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
0.7444	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1659	Phase 1
0.7373	Intermediate Similarity	NPD5513	Phase 2
0.7364	Intermediate Similarity	NPD4558	Phase 2
0.7345	Intermediate Similarity	NPD1996	Discontinued
0.7345	Intermediate Similarity	NPD6242	Discontinued
0.7325	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7467	Discontinued
0.7235	Intermediate Similarity	NPD4491	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5293	Phase 2
0.719	Intermediate Similarity	NPD5482	Discontinued
0.7189	Intermediate Similarity	NPD3825	Phase 3
0.7181	Intermediate Similarity	NPD6568	Discontinued
0.7181	Intermediate Similarity	NPD5632	Approved
0.7156	Intermediate Similarity	NPD3945	Discontinued
0.715	Intermediate Similarity	NPD4372	Phase 1
0.7149	Intermediate Similarity	NPD5601	Phase 2
0.7129	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5559	Phase 2
0.7118	Intermediate Similarity	NPD8479	Phase 2
0.7117	Intermediate Similarity	NPD1392	Approved
0.7116	Intermediate Similarity	NPD1038	Approved
0.7112	Intermediate Similarity	NPD5640	Discontinued
0.7111	Intermediate Similarity	NPD5866	Approved
0.7105	Intermediate Similarity	NPD5948	Phase 2
0.7104	Intermediate Similarity	NPD3947	Discontinued
0.7101	Intermediate Similarity	NPD4314	Approved
0.7101	Intermediate Similarity	NPD4313	Approved
0.7089	Intermediate Similarity	NPD7853	Phase 2
0.7085	Intermediate Similarity	NPD2509	Approved
0.7085	Intermediate Similarity	NPD2510	Approved
0.7083	Intermediate Similarity	NPD3395	Approved
0.7083	Intermediate Similarity	NPD3396	Approved
0.7067	Intermediate Similarity	NPD5067	Phase 2
0.7067	Intermediate Similarity	NPD5066	Phase 2
0.7063	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD3569	Discontinued
0.7059	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7180	Phase 3
0.7037	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD5116	Phase 1
0.7021	Intermediate Similarity	NPD5479	Discontinued
0.7009	Intermediate Similarity	NPD7994	Phase 2
0.7	Intermediate Similarity	NPD4309	Approved
0.6986	Remote Similarity	NPD4072	Approved
0.6986	Remote Similarity	NPD4071	Approved
0.6983	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1096	Discontinued
0.6971	Remote Similarity	NPD6790	Phase 1
0.6963	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4889	Approved
0.6943	Remote Similarity	NPD3394	Approved
0.6943	Remote Similarity	NPD3393	Approved
0.6943	Remote Similarity	NPD3389	Approved
0.6943	Remote Similarity	NPD5612	Discontinued
0.6941	Remote Similarity	NPD2952	Discontinued
0.693	Remote Similarity	NPD4021	Phase 2
0.6927	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6569	Phase 2
0.6894	Remote Similarity	NPD3263	Phase 3
0.6888	Remote Similarity	NPD7660	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3178	Discontinued
0.6878	Remote Similarity	NPD4548	Discontinued
0.6875	Remote Similarity	NPD3397	Phase 2
0.6875	Remote Similarity	NPD3006	Discontinued
0.6867	Remote Similarity	NPD4923	Phase 1
0.686	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD6376	Discontinued
0.6851	Remote Similarity	NPD4890	Phase 2
0.685	Remote Similarity	NPD5450	Discontinued
0.6849	Remote Similarity	NPD8106	Phase 2
0.6844	Remote Similarity	NPD8403	Phase 1
0.6827	Remote Similarity	NPD565	Phase 2
0.6827	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD5149	Phase 2
0.6822	Remote Similarity	NPD8289	Discontinued
0.682	Remote Similarity	NPD4885	Approved
0.6818	Remote Similarity	NPD2289	Phase 3
0.6818	Remote Similarity	NPD2290	Phase 3
0.681	Remote Similarity	NPD4429	Discontinued
0.6807	Remote Similarity	NPD4952	Phase 3
0.6807	Remote Similarity	NPD5022	Discontinued
0.6802	Remote Similarity	NPD1768	Approved
0.6797	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7689	Approved
0.6771	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD4989	Phase 2
0.6766	Remote Similarity	NPD6209	Approved
0.6763	Remote Similarity	NPD2951	Discontinued
0.6758	Remote Similarity	NPD4376	Phase 3
0.6753	Remote Similarity	NPD2547	Discontinued
0.6751	Remote Similarity	NPD7603	Discontinued
0.6751	Remote Similarity	NPD7426	Phase 1
0.6734	Remote Similarity	NPD4369	Phase 2
0.6734	Remote Similarity	NPD6172	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD2831	Approved
0.6724	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD4373	Phase 2
0.6722	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2187	Approved
0.6711	Remote Similarity	NPD2189	Approved
0.6709	Remote Similarity	NPD6974	Phase 3
0.6708	Remote Similarity	NPD4368	Phase 2
0.6706	Remote Similarity	NPD6961	Discontinued
0.6696	Remote Similarity	NPD3003	Approved
0.6696	Remote Similarity	NPD7470	Discontinued
0.6693	Remote Similarity	NPD6531	Approved
0.6693	Remote Similarity	NPD6530	Approved
0.6693	Remote Similarity	NPD4353	Phase 2
0.6681	Remote Similarity	NPD6176	Phase 1
0.668	Remote Similarity	NPD7408	Phase 2
0.668	Remote Similarity	NPD4847	Phase 1
0.6667	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7069	Discontinued
0.6667	Remote Similarity	NPD2011	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD3801	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD5509	Phase 1
0.6653	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD4850	Phase 1
0.6653	Remote Similarity	NPD7558	Phase 2
0.6652	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD4795	Phase 2
0.6651	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD3386	Phase 2
0.6651	Remote Similarity	NPD1034	Phase 3
0.6639	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD946	Discontinued
0.6638	Remote Similarity	NPD3402	Phase 1
0.6638	Remote Similarity	NPD5658	Approved
0.6636	Remote Similarity	NPD2334	Discontinued
0.6624	Remote Similarity	NPD8356	Approved
0.6623	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4130	Phase 3
0.6623	Remote Similarity	NPD4131	Phase 3
0.6622	Remote Similarity	NPD1739	Approved
0.6622	Remote Similarity	NPD1740	Approved
0.6622	Remote Similarity	NPD5228	Phase 3
0.6622	Remote Similarity	NPD484	Approved
0.6612	Remote Similarity	NPD5015	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7031	Phase 1
0.6606	Remote Similarity	NPD5256	Discontinued
0.6605	Remote Similarity	NPD2600	Approved
0.6605	Remote Similarity	NPD2599	Approved
0.6605	Remote Similarity	NPD2601	Approved
0.6598	Remote Similarity	NPD5891	Approved
0.6594	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD3477	Phase 2
0.6585	Remote Similarity	NPD7885	Phase 2
0.6585	Remote Similarity	NPD7886	Phase 2
0.658	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.658	Remote Similarity	NPD3392	Approved
0.6579	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD2778	Approved
0.6577	Remote Similarity	NPD802	Phase 2
0.6577	Remote Similarity	NPD4551	Phase 2
0.6569	Remote Similarity	NPD4560	Suspended
0.6568	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6963	Approved
0.6557	Remote Similarity	NPD6964	Approved
0.6556	Remote Similarity	NPD5014	Discontinued
0.6555	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD7198	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5416	Discontinued
0.6552	Remote Similarity	NPD3570	Phase 2
0.6552	Remote Similarity	NPD5475	Discontinued
0.655	Remote Similarity	NPD7010	Phase 3
0.6547	Remote Similarity	NPD4418	Discontinued
0.6547	Remote Similarity	NPD978	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1418	Phase 2
0.6532	Remote Similarity	NPD4322	Discontinued
0.6532	Remote Similarity	NPD6716	Phase 1
0.6531	Remote Similarity	NPD5469	Phase 3
0.653	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.653	Remote Similarity	NPD4919	Phase 3
0.653	Remote Similarity	NPD4921	Phase 3
0.6529	Remote Similarity	NPD8512	Phase 3
0.6529	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD8430	Approved
0.6509	Remote Similarity	NPD2081	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD5901	Discontinued
0.6504	Remote Similarity	NPD4316	Phase 3
0.6498	Remote Similarity	NPD7414	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