NPASS Compound

Structure

NPC208898 OpenBabel07101718182D 29 32 0 0 0 0 0 0 0 0999 V2000 -2.5296 -2.5976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0685 -4.3147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7138 -4.1723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0685 -4.3147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0447 -4.9155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5733 -3.0134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5685 -3.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4048 -3.2213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5685 -3.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9335 -4.7076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2425 -3.7565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -2.4781 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 2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5685 -3.4487 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 -0.0000 -1.0000 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 2.4752 -1.6691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 6.5685 -3.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6026 -5.4507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -4.3147 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2206 -3.5486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 29 1 0 0 0 0 2 5 1 0 0 0 0 2 9 2 0 0 0 0 3 6 2 0 0 0 0 3 9 1 0 0 0 0 4 7 2 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 8 10 2 0 0 0 0 8 13 1 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 11 24 1 0 0 0 0 12 13 2 0 0 0 0 12 25 1 0 0 0 0 13 29 1 0 0 0 0 14 15 1 0 0 0 0 14 16 2 0 0 0 0 15 18 2 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 26 2 0 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 19 23 2 0 0 0 0 19 27 1 0 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 20 28 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	393.1
Volume:	376.981
LogP:	1.718
LogD:	2.018
LogS:	-4.448
# Rotatable Bonds:	4
TPSA:	148.27
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.334
Synthetic Accessibility Score:	2.701
Fsp3:	0.05
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.7
MDCK Permeability:	6.2751223595114425e-06
Pgp-inhibitor:	0.023
Pgp-substrate:	0.028
Human Intestinal Absorption (HIA):	0.617
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.202

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	97.74655151367188%
Volume Distribution (VD):	0.437
Pgp-substrate:	3.699320077896118%

ADMET: Metabolism

CYP1A2-inhibitor:	0.948
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.385
CYP2C19-substrate:	0.041
CYP2C9-inhibitor:	0.734
CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.134
CYP2D6-substrate:	0.027
CYP3A4-inhibitor:	0.757
CYP3A4-substrate:	0.366

ADMET: Excretion

Clearance (CL):	9.453
Half-life (T1/2):	0.945

ADMET: Toxicity

hERG Blockers:	0.224
Human Hepatotoxicity (H-HT):	0.804
Drug-inuced Liver Injury (DILI):	0.993
AMES Toxicity:	0.32
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.088
Skin Sensitization:	0.039
Carcinogencity:	0.075
Eye Corrosion:	0.003
Eye Irritation:	0.052
Respiratory Toxicity:	0.859

Download Data

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

Natural Product: NPC208898

Natural Product ID:	NPC208898
*Common Name:**	6-(4-Hydroxybenzoyl)-5-(4-Hydroxy-3-Methoxyphenyl)-1Hpyrrolo[2,3-D]Pyrimidine-2,4(3H,7H)-Dione
IUPAC Name:	6-(4-hydroxybenzoyl)-5-(4-hydroxy-3-methoxyphenyl)-1,7-dihydropyrrolo[2,3-d]pyrimidine-2,4-dione
Synonyms:
Standard InCHIKey:	AVGCGIZEHNWZLG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H15N3O6/c1-29-13-8-10(4-7-12(13)25)14-15-18(22-20(28)23-19(15)27)21-16(14)17(26)9-2-5-11(24)6-3-9/h2-8,24-25H,1H3,(H3,21,22,23,27,28)
SMILES:	COc1cc(ccc1O)c1c2c([nH]c1C(=O)c1ccc(cc1)O)[nH]c(=O)nc2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2417728
PubChem CID:	11058305
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004297] Aryl-phenylketones

*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
NPO32849	eudistoma cf. rigida	Species	Polycitoridae	Eukaryota	n.a.	Okinawa; New Guinea	n.a.	PMID[23927793]

☑ 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
GI50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	GI50	>	100000.0	nM	PMID[490600]
NPT165	Cell Line	HeLa	Homo sapiens	GI50	>	100000.0	nM	PMID[490600]

☑ 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 NPC208898 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	610
0.1-0.2	3554
0.2-0.3	13051
0.3-0.4	4439
0.4-0.5	15033
0.5-0.6	4977
0.6-0.7	991
0.7-0.8	38
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9058	High Similarity	NPC9729
0.9018	High Similarity	NPC51854
0.8063	Intermediate Similarity	NPC48317
0.7637	Intermediate Similarity	NPC41501
0.7623	Intermediate Similarity	NPC303374
0.7522	Intermediate Similarity	NPC236668
0.7489	Intermediate Similarity	NPC146976
0.7466	Intermediate Similarity	NPC135887
0.7466	Intermediate Similarity	NPC199277
0.7458	Intermediate Similarity	NPC49672
0.7436	Intermediate Similarity	NPC157931
0.7404	Intermediate Similarity	NPC471762
0.7404	Intermediate Similarity	NPC194740
0.7404	Intermediate Similarity	NPC66777
0.7357	Intermediate Similarity	NPC87413
0.7333	Intermediate Similarity	NPC321428
0.7308	Intermediate Similarity	NPC94842
0.7293	Intermediate Similarity	NPC232225
0.7291	Intermediate Similarity	NPC89549
0.7254	Intermediate Similarity	NPC15406
0.7253	Intermediate Similarity	NPC150239
0.7243	Intermediate Similarity	NPC210296
0.7241	Intermediate Similarity	NPC247803
0.7225	Intermediate Similarity	NPC39679
0.7218	Intermediate Similarity	NPC473188
0.7217	Intermediate Similarity	NPC266931
0.7212	Intermediate Similarity	NPC300156
0.7212	Intermediate Similarity	NPC45190
0.721	Intermediate Similarity	NPC288987
0.7203	Intermediate Similarity	NPC179287
0.7193	Intermediate Similarity	NPC325297
0.7191	Intermediate Similarity	NPC220851
0.7191	Intermediate Similarity	NPC210434
0.719	Intermediate Similarity	NPC6786
0.7183	Intermediate Similarity	NPC129897
0.7181	Intermediate Similarity	NPC4687
0.7181	Intermediate Similarity	NPC249583
0.7179	Intermediate Similarity	NPC174760
0.7172	Intermediate Similarity	NPC475844
0.7149	Intermediate Similarity	NPC77878
0.7143	Intermediate Similarity	NPC257851
0.7137	Intermediate Similarity	NPC175602
0.7137	Intermediate Similarity	NPC22481
0.7131	Intermediate Similarity	NPC35761
0.7118	Intermediate Similarity	NPC61038
0.7113	Intermediate Similarity	NPC237978
0.7094	Intermediate Similarity	NPC46561
0.7094	Intermediate Similarity	NPC184408
0.7087	Intermediate Similarity	NPC124086
0.7083	Intermediate Similarity	NPC278525
0.7083	Intermediate Similarity	NPC24019
0.708	Intermediate Similarity	NPC183537
0.7078	Intermediate Similarity	NPC108342
0.7056	Intermediate Similarity	NPC220337
0.7051	Intermediate Similarity	NPC246658
0.7051	Intermediate Similarity	NPC169402
0.7049	Intermediate Similarity	NPC189903
0.7049	Intermediate Similarity	NPC182907
0.7042	Intermediate Similarity	NPC274640
0.7042	Intermediate Similarity	NPC246381
0.7039	Intermediate Similarity	NPC298449
0.7034	Intermediate Similarity	NPC323969
0.7031	Intermediate Similarity	NPC270918
0.7026	Intermediate Similarity	NPC310211
0.7026	Intermediate Similarity	NPC308137
0.7021	Intermediate Similarity	NPC303658
0.7009	Intermediate Similarity	NPC3207
0.7008	Intermediate Similarity	NPC473187
0.7004	Intermediate Similarity	NPC280799
0.7004	Intermediate Similarity	NPC198503
0.7	Intermediate Similarity	NPC478078
0.6996	Remote Similarity	NPC207866
0.6992	Remote Similarity	NPC208084
0.6987	Remote Similarity	NPC472287
0.6987	Remote Similarity	NPC472286
0.6983	Remote Similarity	NPC474701
0.6974	Remote Similarity	NPC223427
0.6967	Remote Similarity	NPC277351
0.6967	Remote Similarity	NPC253675
0.6966	Remote Similarity	NPC116238
0.6966	Remote Similarity	NPC118228
0.6966	Remote Similarity	NPC190401
0.6966	Remote Similarity	NPC239763
0.6957	Remote Similarity	NPC243850
0.6955	Remote Similarity	NPC233334
0.6953	Remote Similarity	NPC316981
0.6951	Remote Similarity	NPC473821
0.6951	Remote Similarity	NPC166722
0.6946	Remote Similarity	NPC51388
0.6944	Remote Similarity	NPC181081
0.6944	Remote Similarity	NPC473800
0.6944	Remote Similarity	NPC67401
0.6933	Remote Similarity	NPC121069
0.6933	Remote Similarity	NPC74153
0.6932	Remote Similarity	NPC63971
0.6932	Remote Similarity	NPC91868
0.6926	Remote Similarity	NPC172222
0.6926	Remote Similarity	NPC90185
0.6926	Remote Similarity	NPC215837
0.6923	Remote Similarity	NPC39500
0.692	Remote Similarity	NPC136924
0.692	Remote Similarity	NPC269270
0.6914	Remote Similarity	NPC474688
0.6911	Remote Similarity	NPC184680
0.691	Remote Similarity	NPC23294
0.691	Remote Similarity	NPC9894
0.691	Remote Similarity	NPC187501
0.6908	Remote Similarity	NPC160100
0.6907	Remote Similarity	NPC13599
0.6907	Remote Similarity	NPC3214
0.6907	Remote Similarity	NPC191088
0.6907	Remote Similarity	NPC303384
0.6907	Remote Similarity	NPC298840
0.6907	Remote Similarity	NPC268393
0.6905	Remote Similarity	NPC165964
0.6904	Remote Similarity	NPC46970
0.6904	Remote Similarity	NPC280272
0.6904	Remote Similarity	NPC144452
0.6902	Remote Similarity	NPC472589
0.6898	Remote Similarity	NPC90875
0.6895	Remote Similarity	NPC119134
0.6891	Remote Similarity	NPC54066
0.6891	Remote Similarity	NPC225279
0.6891	Remote Similarity	NPC469439
0.6891	Remote Similarity	NPC14686
0.689	Remote Similarity	NPC472588
0.6887	Remote Similarity	NPC191489
0.6883	Remote Similarity	NPC470785
0.6883	Remote Similarity	NPC470784
0.688	Remote Similarity	NPC124313
0.6877	Remote Similarity	NPC302807
0.6875	Remote Similarity	NPC122436
0.6867	Remote Similarity	NPC303951
0.6867	Remote Similarity	NPC207283
0.6867	Remote Similarity	NPC84164
0.6864	Remote Similarity	NPC322064
0.6858	Remote Similarity	NPC70956
0.6858	Remote Similarity	NPC243834
0.6853	Remote Similarity	NPC100573
0.6853	Remote Similarity	NPC207873
0.6853	Remote Similarity	NPC86834
0.6853	Remote Similarity	NPC210828
0.6851	Remote Similarity	NPC89508
0.6849	Remote Similarity	NPC308906
0.6848	Remote Similarity	NPC478006
0.6846	Remote Similarity	NPC88923
0.6846	Remote Similarity	NPC315634
0.6846	Remote Similarity	NPC100734
0.6844	Remote Similarity	NPC276517
0.6842	Remote Similarity	NPC235685
0.6842	Remote Similarity	NPC15801
0.684	Remote Similarity	NPC188400
0.6836	Remote Similarity	NPC318068
0.6835	Remote Similarity	NPC305984
0.6835	Remote Similarity	NPC312645
0.6828	Remote Similarity	NPC306376
0.6827	Remote Similarity	NPC148889
0.6824	Remote Similarity	NPC314882
0.682	Remote Similarity	NPC315467
0.682	Remote Similarity	NPC276657
0.6816	Remote Similarity	NPC475720
0.6816	Remote Similarity	NPC474192
0.6815	Remote Similarity	NPC82472
0.6815	Remote Similarity	NPC101350
0.6813	Remote Similarity	NPC160898
0.681	Remote Similarity	NPC193777
0.681	Remote Similarity	NPC315499
0.681	Remote Similarity	NPC16249
0.6809	Remote Similarity	NPC63109
0.6809	Remote Similarity	NPC110182
0.6808	Remote Similarity	NPC132385
0.6807	Remote Similarity	NPC467439
0.6806	Remote Similarity	NPC473639
0.6802	Remote Similarity	NPC477549
0.6795	Remote Similarity	NPC471304
0.6794	Remote Similarity	NPC478009
0.6789	Remote Similarity	NPC473182
0.6787	Remote Similarity	NPC475816
0.6784	Remote Similarity	NPC473814
0.6784	Remote Similarity	NPC78767
0.6783	Remote Similarity	NPC475112
0.6783	Remote Similarity	NPC475085
0.6783	Remote Similarity	NPC295898
0.6783	Remote Similarity	NPC291535
0.6783	Remote Similarity	NPC74619
0.6778	Remote Similarity	NPC74360
0.6777	Remote Similarity	NPC21638
0.6775	Remote Similarity	NPC116701
0.6774	Remote Similarity	NPC473183
0.6773	Remote Similarity	NPC176127
0.6772	Remote Similarity	NPC134637
0.677	Remote Similarity	NPC93390
0.6769	Remote Similarity	NPC209981
0.6766	Remote Similarity	NPC294375
0.6765	Remote Similarity	NPC27041
0.6765	Remote Similarity	NPC293151
0.6759	Remote Similarity	NPC472068
0.6754	Remote Similarity	NPC472284
0.6753	Remote Similarity	NPC134848
0.6752	Remote Similarity	NPC209769

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 NPC208898 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	660
0.2-0.3	1006
0.3-0.4	1813
0.4-0.5	2936
0.5-0.6	1830
0.6-0.7	517
0.7-0.8	35
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
0.7627	Intermediate Similarity	NPD5805	Approved
0.7459	Intermediate Similarity	NPD7588	Discontinued
0.7347	Intermediate Similarity	NPD4558	Phase 2
0.7238	Intermediate Similarity	NPD4885	Approved
0.7237	Intermediate Similarity	NPD3392	Approved
0.7203	Intermediate Similarity	NPD4132	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5866	Approved
0.7167	Intermediate Similarity	NPD1926	Approved
0.7149	Intermediate Similarity	NPD4923	Phase 1
0.7119	Intermediate Similarity	NPD1954	Phase 1
0.7106	Intermediate Similarity	NPD6242	Discontinued
0.7098	Intermediate Similarity	NPD3814	Phase 1
0.7059	Intermediate Similarity	NPD6745	Discontinued
0.7004	Intermediate Similarity	NPD7022	Phase 2
0.7	Intermediate Similarity	NPD5658	Approved
0.6996	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD7689	Approved
0.6962	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6958	Remote Similarity	NPD3263	Phase 3
0.6953	Remote Similarity	NPD6228	Discontinued
0.6951	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3920	Phase 2
0.6941	Remote Similarity	NPD8091	Phase 3
0.6936	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6517	Phase 3
0.6934	Remote Similarity	NPD7403	Phase 1
0.6926	Remote Similarity	NPD4373	Phase 2
0.6926	Remote Similarity	NPD6376	Discontinued
0.692	Remote Similarity	NPD3258	Approved
0.6914	Remote Similarity	NPD6962	Phase 2
0.6904	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5014	Discontinued
0.6887	Remote Similarity	NPD7708	Approved
0.6872	Remote Similarity	NPD5924	Discontinued
0.687	Remote Similarity	NPD5469	Phase 3
0.6867	Remote Similarity	NPD3322	Phase 1
0.6864	Remote Similarity	NPD2762	Phase 2
0.686	Remote Similarity	NPD4328	Approved
0.6849	Remote Similarity	NPD6974	Phase 3
0.6846	Remote Similarity	NPD7803	Approved
0.6834	Remote Similarity	NPD5399	Discovery
0.6824	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD3257	Approved
0.682	Remote Similarity	NPD7180	Phase 3
0.6816	Remote Similarity	NPD1961	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD3917	Approved
0.6809	Remote Similarity	NPD2794	Discontinued
0.6809	Remote Similarity	NPD3918	Approved
0.6809	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5632	Approved
0.6806	Remote Similarity	NPD5459	Phase 2
0.6803	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4952	Phase 3
0.6802	Remote Similarity	NPD5861	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6716	Phase 1
0.6798	Remote Similarity	NPD4052	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4080	Discontinued
0.6778	Remote Similarity	NPD4312	Approved
0.6776	Remote Similarity	NPD1505	Phase 2
0.6766	Remote Similarity	NPD3915	Approved
0.6751	Remote Similarity	NPD5903	Approved
0.6751	Remote Similarity	NPD5902	Approved
0.6746	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD7853	Phase 2
0.6723	Remote Similarity	NPD8149	Discontinued
0.6723	Remote Similarity	NPD4048	Approved
0.6723	Remote Similarity	NPD5612	Discontinued
0.6721	Remote Similarity	NPD4845	Discontinued
0.672	Remote Similarity	NPD5905	Phase 1
0.671	Remote Similarity	NPD2779	Approved
0.6707	Remote Similarity	NPD3442	Approved
0.6707	Remote Similarity	NPD1867	Approved
0.6707	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3441	Approved
0.6694	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD3328	Phase 2
0.6692	Remote Similarity	NPD1225	Phase 2
0.6692	Remote Similarity	NPD1224	Phase 2
0.6681	Remote Similarity	NPD3921	Approved
0.6681	Remote Similarity	NPD3922	Approved
0.6681	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD3923	Approved
0.6681	Remote Similarity	NPD3924	Approved
0.6667	Remote Similarity	NPD7278	Phase 2
0.6667	Remote Similarity	NPD7134	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7279	Phase 2
0.6654	Remote Similarity	NPD7955	Approved
0.6654	Remote Similarity	NPD7956	Approved
0.6653	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD3259	Approved
0.664	Remote Similarity	NPD3488	Phase 1
0.664	Remote Similarity	NPD4996	Approved
0.664	Remote Similarity	NPD4995	Approved
0.6638	Remote Similarity	NPD1842	Approved
0.6627	Remote Similarity	NPD2757	Phase 2
0.6625	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6282	Discontinued
0.6611	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD2917	Approved
0.6602	Remote Similarity	NPD8442	Discontinued
0.6599	Remote Similarity	NPD4925	Approved
0.6599	Remote Similarity	NPD1900	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD7225	Discontinued
0.6597	Remote Similarity	NPD6202	Discontinued
0.6584	Remote Similarity	NPD8310	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD5914	Approved
0.658	Remote Similarity	NPD2778	Approved
0.6576	Remote Similarity	NPD6244	Phase 3
0.6576	Remote Similarity	NPD6243	Phase 3
0.6571	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.657	Remote Similarity	NPD2884	Phase 1
0.6569	Remote Similarity	NPD3945	Discontinued
0.6564	Remote Similarity	NPD8463	Approved
0.6561	Remote Similarity	NPD6790	Phase 1
0.6555	Remote Similarity	NPD5416	Discontinued
0.6553	Remote Similarity	NPD3003	Approved
0.6552	Remote Similarity	NPD3290	Approved
0.6552	Remote Similarity	NPD3289	Phase 3
0.655	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6230	Discontinued
0.6542	Remote Similarity	NPD5149	Phase 2
0.6542	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6473	Phase 1
0.6535	Remote Similarity	NPD1483	Discontinued
0.6532	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5022	Discontinued
0.6532	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5479	Discontinued
0.6529	Remote Similarity	NPD7395	Discontinued
0.6524	Remote Similarity	NPD4511	Phase 1
0.6522	Remote Similarity	NPD2482	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD5482	Discontinued
0.651	Remote Similarity	NPD7620	Phase 2
0.6509	Remote Similarity	NPD3541	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD7684	Approved
0.6506	Remote Similarity	NPD7682	Approved
0.6506	Remote Similarity	NPD5139	Phase 1
0.6504	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD3925	Approved
0.6502	Remote Similarity	NPD5116	Phase 1
0.65	Remote Similarity	NPD4356	Discontinued
0.65	Remote Similarity	NPD5532	Phase 2
0.6494	Remote Similarity	NPD2951	Discontinued
0.6492	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.649	Remote Similarity	NPD6209	Approved
0.6488	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD7568	Phase 1
0.648	Remote Similarity	NPD7031	Phase 1
0.648	Remote Similarity	NPD5015	Clinical (unspecified phase)
0.648	Remote Similarity	NPD3746	Discontinued
0.6478	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD7013	Phase 3
0.6473	Remote Similarity	NPD4897	Phase 2
0.6473	Remote Similarity	NPD7012	Phase 3
0.6468	Remote Similarity	NPD3006	Discontinued
0.6462	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD4429	Discontinued
0.646	Remote Similarity	NPD3315	Phase 3
0.6459	Remote Similarity	NPD5118	Phase 2
0.6457	Remote Similarity	NPD7886	Phase 2
0.6457	Remote Similarity	NPD7885	Phase 2
0.6456	Remote Similarity	NPD7452	Approved
0.6456	Remote Similarity	NPD7222	Phase 2
0.6456	Remote Similarity	NPD7453	Approved
0.6454	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7994	Phase 2
0.645	Remote Similarity	NPD5512	Phase 3
0.6444	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD6531	Approved
0.6439	Remote Similarity	NPD6530	Approved
0.6438	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD2835	Phase 2
0.6435	Remote Similarity	NPD1038	Approved
0.6435	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6431	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.642	Remote Similarity	NPD7206	Clinical (unspecified phase)
0.642	Remote Similarity	NPD7980	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7660	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD8046	Discontinued
0.641	Remote Similarity	NPD484	Approved
0.641	Remote Similarity	NPD6612	Phase 2
0.6409	Remote Similarity	NPD8102	Discontinued
0.6407	Remote Similarity	NPD4418	Discontinued
0.6406	Remote Similarity	NPD5833	Phase 1
0.6405	Remote Similarity	NPD1638	Discovery
0.6395	Remote Similarity	NPD5071	Phase 2
0.6395	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD8364	Approved
0.6394	Remote Similarity	NPD8363	Approved

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