NPASS Compound

Structure

NPC474919 OpenBabel07101719252D 29 33 0 0 1 0 0 0 0 0999 V2000 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9817 1.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7861 1.7019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4353 1.3711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7570 0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4300 0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1456 0.3602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0158 1.6730 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.6888 1.2247 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.2889 1.1176 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 4 2 0 0 0 0 2 16 1 0 0 0 0 3 5 2 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 13 1 0 0 0 0 6 14 1 0 0 0 0 7 13 1 0 0 0 0 7 15 1 0 0 0 0 8 14 1 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 22 1 0 0 0 0 10 14 1 0 0 0 0 10 22 1 0 0 0 0 11 15 1 0 0 0 0 11 22 1 0 0 0 0 12 19 1 0 0 0 0 12 24 2 0 0 0 0 16 20 2 0 0 0 0 17 19 2 0 0 0 0 17 26 1 0 0 0 0 18 27 2 0 0 0 0 18 28 1 0 0 0 0 19 20 1 0 0 0 0 20 28 1 0 0 0 0 21 23 2 3 0 0 0 21 25 1 0 0 0 0 21 29 1 0 0 0 0 22 23 1 0 0 0 0 24 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	411.16
Volume:	405.701
LogP:	4.76
LogD:	4.185
LogS:	-5.534
# Rotatable Bonds:	5
TPSA:	86.86
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.309
Synthetic Accessibility Score:	4.098
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.71
MDCK Permeability:	2.6748621166916564e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.053
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.109

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.355
Plasma Protein Binding (PPB):	98.29956817626953%
Volume Distribution (VD):	0.923
Pgp-substrate:	0.9469305276870728%

ADMET: Metabolism

CYP1A2-inhibitor:	0.831
CYP1A2-substrate:	0.359
CYP2C19-inhibitor:	0.794
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.781
CYP2C9-substrate:	0.923
CYP2D6-inhibitor:	0.199
CYP2D6-substrate:	0.186
CYP3A4-inhibitor:	0.15
CYP3A4-substrate:	0.079

ADMET: Excretion

Clearance (CL):	3.244
Half-life (T1/2):	0.355

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.889
Drug-inuced Liver Injury (DILI):	0.87
AMES Toxicity:	0.12
Rat Oral Acute Toxicity:	0.68
Maximum Recommended Daily Dose:	0.281
Skin Sensitization:	0.12
Carcinogencity:	0.902
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC474919

Natural Product ID:	NPC474919
*Common Name:**	JCGIOQDIGGMRMO-WYMPLXKRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JCGIOQDIGGMRMO-WYMPLXKRSA-N
Standard InCHI:	InChI=1S/C22H25N3O3S/c1-12(19-17(26)4-2-16-3-5-18(27)28-20(16)19)24-25-21(29)23-22-9-13-6-14(10-22)8-15(7-13)11-22/h2-5,13-15,26H,6-11H2,1H3,(H2,23,25,29)/b24-12+
SMILES:	SC(=NC12CC3CC(C2)CC(C1)C3)N/N=C(/c1c(O)ccc2c1oc(=O)cc2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487712
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0002908] Hydroxycoumarins [CHEMONTID:0002909] 7-hydroxycoumarins

*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
NPO33433	adina cordifolia	Species	Rubiaceae	Eukaryota	root bark	n.a.	n.a.	PMID[18675491]

☑ 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
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1635	Cell Line	H9c2	Rattus norvegicus	Activity	>	80.0	%	PMID[514268]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	1490000.0	nM	PMID[514268]

☑ 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 NPC474919 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	358
0.1-0.2	1877
0.2-0.3	6301
0.3-0.4	11898
0.4-0.5	7421
0.5-0.6	8559
0.6-0.7	6015
0.7-0.8	264
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9152	High Similarity	NPC474902
0.8812	High Similarity	NPC473778
0.8521	High Similarity	NPC474881
0.7869	Intermediate Similarity	NPC475411
0.7595	Intermediate Similarity	NPC243688
0.7562	Intermediate Similarity	NPC32463
0.7485	Intermediate Similarity	NPC131950
0.7468	Intermediate Similarity	NPC93219
0.7468	Intermediate Similarity	NPC244495
0.7456	Intermediate Similarity	NPC43716
0.7456	Intermediate Similarity	NPC475719
0.7456	Intermediate Similarity	NPC101255
0.7337	Intermediate Similarity	NPC314025
0.7305	Intermediate Similarity	NPC47040
0.7305	Intermediate Similarity	NPC144512
0.7305	Intermediate Similarity	NPC35501
0.7305	Intermediate Similarity	NPC137262
0.7305	Intermediate Similarity	NPC278600
0.7305	Intermediate Similarity	NPC37428
0.7297	Intermediate Similarity	NPC314656
0.7258	Intermediate Similarity	NPC315913
0.725	Intermediate Similarity	NPC168259
0.7222	Intermediate Similarity	NPC185066
0.7219	Intermediate Similarity	NPC138149
0.7219	Intermediate Similarity	NPC310370
0.7219	Intermediate Similarity	NPC170812
0.7219	Intermediate Similarity	NPC183642
0.7215	Intermediate Similarity	NPC52247
0.7212	Intermediate Similarity	NPC31849
0.7204	Intermediate Similarity	NPC314213
0.7188	Intermediate Similarity	NPC27671
0.7188	Intermediate Similarity	NPC201667
0.7188	Intermediate Similarity	NPC291899
0.7188	Intermediate Similarity	NPC73413
0.7178	Intermediate Similarity	NPC474289
0.717	Intermediate Similarity	NPC96286
0.717	Intermediate Similarity	NPC248429
0.716	Intermediate Similarity	NPC71903
0.7152	Intermediate Similarity	NPC194277
0.7151	Intermediate Similarity	NPC295696
0.7143	Intermediate Similarity	NPC471827
0.7143	Intermediate Similarity	NPC471828
0.7125	Intermediate Similarity	NPC109675
0.7125	Intermediate Similarity	NPC472518
0.7125	Intermediate Similarity	NPC273772
0.712	Intermediate Similarity	NPC198075
0.7119	Intermediate Similarity	NPC223720
0.7108	Intermediate Similarity	NPC291551
0.7108	Intermediate Similarity	NPC163557
0.7108	Intermediate Similarity	NPC241165
0.7108	Intermediate Similarity	NPC1220
0.7108	Intermediate Similarity	NPC142563
0.7108	Intermediate Similarity	NPC469952
0.7108	Intermediate Similarity	NPC141822
0.7108	Intermediate Similarity	NPC469955
0.7108	Intermediate Similarity	NPC205797
0.7107	Intermediate Similarity	NPC187868
0.7101	Intermediate Similarity	NPC279573
0.7093	Intermediate Similarity	NPC471824
0.7091	Intermediate Similarity	NPC37009
0.7091	Intermediate Similarity	NPC66430
0.7089	Intermediate Similarity	NPC247553
0.7083	Intermediate Similarity	NPC26954
0.7083	Intermediate Similarity	NPC38099
0.7081	Intermediate Similarity	NPC111347
0.7079	Intermediate Similarity	NPC268484
0.7076	Intermediate Similarity	NPC20631
0.7076	Intermediate Similarity	NPC93640
0.7066	Intermediate Similarity	NPC50896
0.7066	Intermediate Similarity	NPC204353
0.7066	Intermediate Similarity	NPC326600
0.7063	Intermediate Similarity	NPC13007
0.7063	Intermediate Similarity	NPC257188
0.7055	Intermediate Similarity	NPC258567
0.7055	Intermediate Similarity	NPC121740
0.7055	Intermediate Similarity	NPC224774
0.7052	Intermediate Similarity	NPC71739
0.7052	Intermediate Similarity	NPC469701
0.7048	Intermediate Similarity	NPC281558
0.7048	Intermediate Similarity	NPC469956
0.7048	Intermediate Similarity	NPC19157
0.7044	Intermediate Similarity	NPC302107
0.7041	Intermediate Similarity	NPC306365
0.7041	Intermediate Similarity	NPC131198
0.7039	Intermediate Similarity	NPC206736
0.7039	Intermediate Similarity	NPC195766
0.7037	Intermediate Similarity	NPC232692
0.7037	Intermediate Similarity	NPC202594
0.7029	Intermediate Similarity	NPC142863
0.7019	Intermediate Similarity	NPC315807
0.7018	Intermediate Similarity	NPC155552
0.7018	Intermediate Similarity	NPC152771
0.7018	Intermediate Similarity	NPC287286
0.7018	Intermediate Similarity	NPC195357
0.7012	Intermediate Similarity	NPC469453
0.7012	Intermediate Similarity	NPC157212
0.7012	Intermediate Similarity	NPC472519
0.7006	Intermediate Similarity	NPC469965
0.7006	Intermediate Similarity	NPC151973
0.7006	Intermediate Similarity	NPC83535
0.7	Intermediate Similarity	NPC211110
0.7	Intermediate Similarity	NPC151946
0.6994	Remote Similarity	NPC471826
0.6994	Remote Similarity	NPC36732
0.6971	Remote Similarity	NPC154217
0.697	Remote Similarity	NPC168710
0.6964	Remote Similarity	NPC213173
0.6964	Remote Similarity	NPC180716
0.6964	Remote Similarity	NPC224475
0.6964	Remote Similarity	NPC62366
0.6959	Remote Similarity	NPC312881
0.6954	Remote Similarity	NPC470296
0.6954	Remote Similarity	NPC87609
0.6954	Remote Similarity	NPC188632
0.6954	Remote Similarity	NPC106126
0.6954	Remote Similarity	NPC94794
0.6954	Remote Similarity	NPC196459
0.6954	Remote Similarity	NPC108994
0.6954	Remote Similarity	NPC112791
0.6951	Remote Similarity	NPC149796
0.6949	Remote Similarity	NPC103116
0.6941	Remote Similarity	NPC153818
0.6941	Remote Similarity	NPC281014
0.6941	Remote Similarity	NPC212124
0.6941	Remote Similarity	NPC225106
0.6941	Remote Similarity	NPC155963
0.6941	Remote Similarity	NPC294456
0.6941	Remote Similarity	NPC184861
0.6941	Remote Similarity	NPC474886
0.6941	Remote Similarity	NPC232246
0.6937	Remote Similarity	NPC235190
0.6937	Remote Similarity	NPC180006
0.6932	Remote Similarity	NPC180477
0.6932	Remote Similarity	NPC249942
0.6932	Remote Similarity	NPC297886
0.6928	Remote Similarity	NPC113098
0.6923	Remote Similarity	NPC86892
0.6923	Remote Similarity	NPC281241
0.6923	Remote Similarity	NPC61499
0.6923	Remote Similarity	NPC472424
0.6923	Remote Similarity	NPC471625
0.6923	Remote Similarity	NPC472525
0.6923	Remote Similarity	NPC471909
0.6914	Remote Similarity	NPC469935
0.6914	Remote Similarity	NPC1886
0.6914	Remote Similarity	NPC154176
0.6914	Remote Similarity	NPC196137
0.6914	Remote Similarity	NPC178627
0.6914	Remote Similarity	NPC143725
0.6914	Remote Similarity	NPC290605
0.6914	Remote Similarity	NPC173350
0.6914	Remote Similarity	NPC50720
0.6909	Remote Similarity	NPC139595
0.6909	Remote Similarity	NPC293642
0.6909	Remote Similarity	NPC60704
0.6905	Remote Similarity	NPC133956
0.6905	Remote Similarity	NPC185777
0.6905	Remote Similarity	NPC471910
0.6905	Remote Similarity	NPC207002
0.6905	Remote Similarity	NPC296624
0.6905	Remote Similarity	NPC318400
0.6905	Remote Similarity	NPC167111
0.6905	Remote Similarity	NPC77196
0.6901	Remote Similarity	NPC73078
0.6901	Remote Similarity	NPC148738
0.6901	Remote Similarity	NPC319870
0.6901	Remote Similarity	NPC327612
0.6901	Remote Similarity	NPC221046
0.6901	Remote Similarity	NPC332594
0.6897	Remote Similarity	NPC36181
0.6894	Remote Similarity	NPC144418
0.6893	Remote Similarity	NPC161864
0.6893	Remote Similarity	NPC469933
0.6893	Remote Similarity	NPC208303
0.6893	Remote Similarity	NPC146388
0.689	Remote Similarity	NPC234109
0.689	Remote Similarity	NPC188327
0.6886	Remote Similarity	NPC293203
0.6886	Remote Similarity	NPC29734
0.6886	Remote Similarity	NPC272650
0.6886	Remote Similarity	NPC267336
0.6886	Remote Similarity	NPC118683
0.6886	Remote Similarity	NPC164804
0.6886	Remote Similarity	NPC244888
0.6886	Remote Similarity	NPC211413
0.6886	Remote Similarity	NPC68205
0.6886	Remote Similarity	NPC250727
0.6882	Remote Similarity	NPC149320
0.6882	Remote Similarity	NPC188380
0.6882	Remote Similarity	NPC224543
0.6882	Remote Similarity	NPC476455
0.6882	Remote Similarity	NPC471630
0.6882	Remote Similarity	NPC78746
0.6882	Remote Similarity	NPC55615
0.6882	Remote Similarity	NPC177281
0.6882	Remote Similarity	NPC471522
0.6882	Remote Similarity	NPC283019
0.6882	Remote Similarity	NPC160727
0.6882	Remote Similarity	NPC128529
0.6875	Remote Similarity	NPC470322

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 NPC474919 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	228
0.1-0.2	776
0.2-0.3	1223
0.3-0.4	2787
0.4-0.5	2875
0.5-0.6	1046
0.6-0.7	210
0.7-0.8	5
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
0.7215	Intermediate Similarity	NPD422	Phase 1
0.7159	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD5124	Phase 1
0.7108	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7773	Phase 2
0.6928	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6502	Phase 2
0.6868	Remote Similarity	NPD6971	Discontinued
0.6857	Remote Similarity	NPD7212	Phase 2
0.6857	Remote Similarity	NPD7213	Phase 3
0.6818	Remote Similarity	NPD7447	Phase 1
0.6807	Remote Similarity	NPD4908	Phase 1
0.68	Remote Similarity	NPD6667	Approved
0.68	Remote Similarity	NPD6666	Approved
0.6782	Remote Similarity	NPD3750	Approved
0.6765	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.676	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7549	Discontinued
0.6727	Remote Similarity	NPD2797	Approved
0.6723	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7768	Phase 2
0.6685	Remote Similarity	NPD7411	Suspended
0.6646	Remote Similarity	NPD1548	Phase 1
0.6629	Remote Similarity	NPD1652	Phase 2
0.6627	Remote Similarity	NPD1296	Phase 2
0.6613	Remote Similarity	NPD6746	Phase 2
0.6612	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD1729	Discontinued
0.6593	Remote Similarity	NPD6072	Discontinued
0.6591	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD1610	Phase 2
0.6582	Remote Similarity	NPD1898	Discontinued
0.6582	Remote Similarity	NPD3490	Discontinued
0.6576	Remote Similarity	NPD2415	Discontinued
0.6575	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.657	Remote Similarity	NPD4097	Suspended
0.6566	Remote Similarity	NPD3225	Approved
0.6561	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD3268	Approved
0.6529	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD3748	Approved
0.6492	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7477	Discontinued
0.6488	Remote Similarity	NPD3690	Phase 2
0.6488	Remote Similarity	NPD3691	Phase 2
0.6477	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4625	Phase 3
0.6444	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7585	Approved
0.6429	Remote Similarity	NPD4003	Phase 3
0.6425	Remote Similarity	NPD5557	Phase 1
0.6417	Remote Similarity	NPD7075	Discontinued
0.6412	Remote Similarity	NPD2614	Approved
0.641	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD4749	Approved
0.6406	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD7583	Approved
0.6389	Remote Similarity	NPD4357	Discontinued
0.6389	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD7861	Discontinued
0.6379	Remote Similarity	NPD2157	Approved
0.6378	Remote Similarity	NPD6801	Discontinued
0.6375	Remote Similarity	NPD5535	Approved
0.6368	Remote Similarity	NPD7608	Discontinued
0.6358	Remote Similarity	NPD468	Phase 1
0.6354	Remote Similarity	NPD7019	Approved
0.6354	Remote Similarity	NPD7020	Approved
0.6344	Remote Similarity	NPD7819	Suspended
0.6344	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD1048	Approved
0.6331	Remote Similarity	NPD1232	Clinical (unspecified phase)
0.633	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.633	Remote Similarity	NPD8070	Approved
0.633	Remote Similarity	NPD3749	Approved
0.6324	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD3909	Discontinued
0.6313	Remote Similarity	NPD7003	Approved
0.6313	Remote Similarity	NPD7466	Approved
0.6313	Remote Similarity	NPD6331	Phase 2
0.6304	Remote Similarity	NPD5811	Approved
0.6304	Remote Similarity	NPD4005	Discontinued
0.6302	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5709	Phase 3
0.6292	Remote Similarity	NPD1549	Phase 2
0.6289	Remote Similarity	NPD5844	Phase 1
0.6284	Remote Similarity	NPD7427	Discontinued
0.628	Remote Similarity	NPD6823	Phase 2
0.6277	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD2796	Approved
0.627	Remote Similarity	NPD4380	Phase 2
0.627	Remote Similarity	NPD4675	Approved
0.627	Remote Similarity	NPD4678	Approved
0.6269	Remote Similarity	NPD4443	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD5605	Phase 2
0.6264	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD4060	Phase 1
0.6264	Remote Similarity	NPD3536	Discontinued
0.6264	Remote Similarity	NPD1240	Approved
0.6263	Remote Similarity	NPD4666	Phase 3
0.6257	Remote Similarity	NPD1243	Approved
0.625	Remote Similarity	NPD3552	Approved
0.625	Remote Similarity	NPD2200	Suspended
0.625	Remote Similarity	NPD3554	Approved
0.625	Remote Similarity	NPD3555	Approved
0.625	Remote Similarity	NPD3553	Approved
0.625	Remote Similarity	NPD7097	Phase 1
0.625	Remote Similarity	NPD696	Discontinued
0.625	Remote Similarity	NPD1653	Approved
0.6243	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD3453	Discontinued
0.6238	Remote Similarity	NPD7584	Approved
0.6237	Remote Similarity	NPD5090	Approved
0.6237	Remote Similarity	NPD5089	Approved
0.6237	Remote Similarity	NPD7177	Discontinued
0.6236	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD3568	Approved
0.6235	Remote Similarity	NPD3567	Approved
0.6235	Remote Similarity	NPD3267	Approved
0.6235	Remote Similarity	NPD3266	Approved
0.623	Remote Similarity	NPD2186	Approved
0.623	Remote Similarity	NPD6390	Discontinued
0.6229	Remote Similarity	NPD4340	Discontinued
0.6229	Remote Similarity	NPD654	Phase 3
0.6225	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD1252	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD4308	Phase 3
0.6215	Remote Similarity	NPD2799	Discontinued
0.6215	Remote Similarity	NPD4377	Discontinued
0.6215	Remote Similarity	NPD1510	Phase 2
0.6213	Remote Similarity	NPD6583	Phase 3
0.6213	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6213	Remote Similarity	NPD6582	Phase 2
0.6209	Remote Similarity	NPD6799	Approved
0.6201	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD7229	Phase 3
0.6197	Remote Similarity	NPD7801	Approved
0.6196	Remote Similarity	NPD5403	Approved
0.6193	Remote Similarity	NPD6104	Discontinued
0.6193	Remote Similarity	NPD1607	Approved
0.6193	Remote Similarity	NPD3054	Approved
0.6193	Remote Similarity	NPD3052	Approved
0.6186	Remote Similarity	NPD3489	Phase 3
0.6185	Remote Similarity	NPD5163	Phase 2
0.6185	Remote Similarity	NPD3136	Phase 2
0.6181	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.618	Remote Similarity	NPD6100	Approved
0.618	Remote Similarity	NPD4476	Approved
0.618	Remote Similarity	NPD2935	Discontinued
0.618	Remote Similarity	NPD6099	Approved
0.618	Remote Similarity	NPD1551	Phase 2
0.618	Remote Similarity	NPD4477	Approved
0.6179	Remote Similarity	NPD8151	Discontinued
0.6176	Remote Similarity	NPD6312	Discontinued
0.6175	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD821	Approved
0.6171	Remote Similarity	NPD1558	Phase 1
0.617	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.617	Remote Similarity	NPD5929	Approved
0.6169	Remote Similarity	NPD6841	Approved
0.6169	Remote Similarity	NPD6843	Phase 3
0.6169	Remote Similarity	NPD6842	Approved
0.6168	Remote Similarity	NPD4626	Approved
0.6164	Remote Similarity	NPD8366	Approved
0.6163	Remote Similarity	NPD1712	Approved
0.6163	Remote Similarity	NPD4993	Discontinued
0.6163	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD5604	Discontinued
0.615	Remote Similarity	NPD3778	Approved
0.615	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.615	Remote Similarity	NPD7438	Suspended
0.615	Remote Similarity	NPD2366	Approved
0.6146	Remote Similarity	NPD6959	Discontinued
0.6146	Remote Similarity	NPD5623	Approved
0.6145	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD5953	Discontinued
0.6142	Remote Similarity	NPD6184	Discontinued
0.6141	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.614	Remote Similarity	NPD1203	Approved
0.6139	Remote Similarity	NPD9697	Approved
0.6138	Remote Similarity	NPD4288	Approved
0.6138	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD7811	Phase 3
0.6135	Remote Similarity	NPD7810	Phase 3
0.6129	Remote Similarity	NPD3111	Phase 1

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