NPASS Compound

Structure

NPC9729 OpenBabel07101718322D 29 32 0 0 0 0 0 0 0 0999 V2000 6.5685 -1.7167 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 -0.5733 -3.0134 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 0.0447 -4.9155 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 5.0685 -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 0.4048 -3.2213 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 -0.9335 -4.7076 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 5.0685 -2.5827 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 -1.6026 -5.4507 0.0000 O 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 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 5.5685 -1.7167 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 14 1 0 0 0 0 10 17 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 2 0 0 0 0 20 23 1 0 0 0 0 20 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	393.1
Volume:	376.981
LogP:	1.703
LogD:	2.016
LogS:	-4.424
# 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:	2.7
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:	-5.683
MDCK Permeability:	6.321753062366042e-06
Pgp-inhibitor:	0.026
Pgp-substrate:	0.028
Human Intestinal Absorption (HIA):	0.642
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.223

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	98.06454467773438%
Volume Distribution (VD):	0.428
Pgp-substrate:	3.5205061435699463%

ADMET: Metabolism

CYP1A2-inhibitor:	0.945
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.374
CYP2C19-substrate:	0.041
CYP2C9-inhibitor:	0.704
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.13
CYP2D6-substrate:	0.027
CYP3A4-inhibitor:	0.752
CYP3A4-substrate:	0.362

ADMET: Excretion

Clearance (CL):	9.408
Half-life (T1/2):	0.944

ADMET: Toxicity

hERG Blockers:	0.218
Human Hepatotoxicity (H-HT):	0.804
Drug-inuced Liver Injury (DILI):	0.993
AMES Toxicity:	0.338
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.083
Skin Sensitization:	0.039
Carcinogencity:	0.073
Eye Corrosion:	0.003
Eye Irritation:	0.058
Respiratory Toxicity:	0.851

Download Data

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

Natural Product: NPC9729

Natural Product ID:	NPC9729
*Common Name:**	6-(4-Hydroxy-3-Methoxybenzoyl)-5-(4-Hydroxyphenyl)-1Hpyrrolo[2,3-D]Pyrimidine-2,4(3H,7H)-Dione
IUPAC Name:	6-(4-hydroxy-3-methoxybenzoyl)-5-(4-hydroxyphenyl)-1,7-dihydropyrrolo[2,3-d]pyrimidine-2,4-dione
Synonyms:
Standard InCHIKey:	PXAKFGAZHUXFTE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H15N3O6/c1-29-13-8-10(4-7-12(13)25)17(26)16-14(9-2-5-11(24)6-3-9)15-18(21-16)22-20(28)23-19(15)27/h2-8,24-25H,1H3,(H3,21,22,23,27,28)
SMILES:	COc1cc(ccc1O)C(=O)c1[nH]c2c(c1c1ccc(cc1)O)c(O)nc(n2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2417727
PubChem CID:	637183
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[538263]
NPT165	Cell Line	HeLa	Homo sapiens	GI50	>	100000.0	nM	PMID[538263]

☑ 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 NPC9729 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	591
0.1-0.2	3458
0.2-0.3	12802
0.3-0.4	4533
0.4-0.5	14447
0.5-0.6	5814
0.6-0.7	998
0.7-0.8	50
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
0.9954	High Similarity	NPC51854
0.9058	High Similarity	NPC208898
0.8899	High Similarity	NPC48317
0.7582	Intermediate Similarity	NPC41501
0.7362	Intermediate Similarity	NPC146976
0.7362	Intermediate Similarity	NPC303374
0.7319	Intermediate Similarity	NPC236668
0.7261	Intermediate Similarity	NPC94842
0.7246	Intermediate Similarity	NPC232225
0.7237	Intermediate Similarity	NPC63109
0.72	Intermediate Similarity	NPC49672
0.7186	Intermediate Similarity	NPC135887
0.7186	Intermediate Similarity	NPC199277
0.7181	Intermediate Similarity	NPC89549
0.7143	Intermediate Similarity	NPC66777
0.7143	Intermediate Similarity	NPC471762
0.7143	Intermediate Similarity	NPC15406
0.7137	Intermediate Similarity	NPC472066
0.7137	Intermediate Similarity	NPC472031
0.7137	Intermediate Similarity	NPC472067
0.7126	Intermediate Similarity	NPC472068
0.7109	Intermediate Similarity	NPC473188
0.7102	Intermediate Similarity	NPC157931
0.7089	Intermediate Similarity	NPC87413
0.7077	Intermediate Similarity	NPC74619
0.7063	Intermediate Similarity	NPC210296
0.7043	Intermediate Similarity	NPC77878
0.7031	Intermediate Similarity	NPC63971
0.7031	Intermediate Similarity	NPC91868
0.7028	Intermediate Similarity	NPC22481
0.7023	Intermediate Similarity	NPC215837
0.702	Intermediate Similarity	NPC179287
0.7017	Intermediate Similarity	NPC220337
0.7008	Intermediate Similarity	NPC210434
0.7004	Intermediate Similarity	NPC246381
0.6996	Remote Similarity	NPC150239
0.6996	Remote Similarity	NPC475844
0.6992	Remote Similarity	NPC321428
0.6983	Remote Similarity	NPC247803
0.698	Remote Similarity	NPC130570
0.6977	Remote Similarity	NPC183537
0.6977	Remote Similarity	NPC302807
0.6976	Remote Similarity	NPC24019
0.6962	Remote Similarity	NPC39679
0.6951	Remote Similarity	NPC35761
0.6944	Remote Similarity	NPC189903
0.6944	Remote Similarity	NPC182907
0.6939	Remote Similarity	NPC220851
0.6938	Remote Similarity	NPC165964
0.6936	Remote Similarity	NPC223427
0.6935	Remote Similarity	NPC237978
0.6933	Remote Similarity	NPC325297
0.6926	Remote Similarity	NPC174760
0.692	Remote Similarity	NPC4687
0.692	Remote Similarity	NPC249583
0.6908	Remote Similarity	NPC278525
0.6905	Remote Similarity	NPC108342
0.6905	Remote Similarity	NPC473187
0.6904	Remote Similarity	NPC124086
0.6903	Remote Similarity	NPC473639
0.6895	Remote Similarity	NPC478078
0.6895	Remote Similarity	NPC257851
0.6889	Remote Similarity	NPC77101
0.6888	Remote Similarity	NPC266931
0.6885	Remote Similarity	NPC288987
0.6882	Remote Similarity	NPC129897
0.6878	Remote Similarity	NPC300156
0.6878	Remote Similarity	NPC45190
0.6877	Remote Similarity	NPC235685
0.6877	Remote Similarity	NPC6786
0.6872	Remote Similarity	NPC246658
0.6867	Remote Similarity	NPC194740
0.6863	Remote Similarity	NPC119134
0.6857	Remote Similarity	NPC323969
0.685	Remote Similarity	NPC101350
0.6844	Remote Similarity	NPC46561
0.6844	Remote Similarity	NPC184408
0.6842	Remote Similarity	NPC132385
0.6842	Remote Similarity	NPC122436
0.6816	Remote Similarity	NPC100734
0.6816	Remote Similarity	NPC315634
0.6816	Remote Similarity	NPC208084
0.6816	Remote Similarity	NPC88923
0.6816	Remote Similarity	NPC136924
0.6813	Remote Similarity	NPC474701
0.6809	Remote Similarity	NPC160100
0.6807	Remote Similarity	NPC175602
0.6803	Remote Similarity	NPC169402
0.6802	Remote Similarity	NPC46970
0.68	Remote Similarity	NPC274640
0.6798	Remote Similarity	NPC90875
0.6798	Remote Similarity	NPC277351
0.6797	Remote Similarity	NPC148889
0.6792	Remote Similarity	NPC61038
0.6792	Remote Similarity	NPC191489
0.679	Remote Similarity	NPC239763
0.679	Remote Similarity	NPC298449
0.679	Remote Similarity	NPC190401
0.6786	Remote Similarity	NPC233334
0.6784	Remote Similarity	NPC166722
0.6783	Remote Similarity	NPC124313
0.6782	Remote Similarity	NPC473800
0.6777	Remote Similarity	NPC308137
0.6777	Remote Similarity	NPC310211
0.6777	Remote Similarity	NPC471603
0.6774	Remote Similarity	NPC322482
0.677	Remote Similarity	NPC144114
0.677	Remote Similarity	NPC207283
0.677	Remote Similarity	NPC295452
0.677	Remote Similarity	NPC84164
0.677	Remote Similarity	NPC171393
0.6762	Remote Similarity	NPC3207
0.6761	Remote Similarity	NPC121069
0.6749	Remote Similarity	NPC89508
0.6748	Remote Similarity	NPC308906
0.6746	Remote Similarity	NPC474688
0.6744	Remote Similarity	NPC188400
0.6743	Remote Similarity	NPC134637
0.6735	Remote Similarity	NPC3214
0.6735	Remote Similarity	NPC303384
0.6735	Remote Similarity	NPC27041
0.6735	Remote Similarity	NPC298840
0.6735	Remote Similarity	NPC191088
0.6735	Remote Similarity	NPC312645
0.6735	Remote Similarity	NPC268393
0.6735	Remote Similarity	NPC13599
0.6734	Remote Similarity	NPC280272
0.6732	Remote Similarity	NPC253675
0.6721	Remote Similarity	NPC469439
0.6721	Remote Similarity	NPC118228
0.6721	Remote Similarity	NPC116238
0.6719	Remote Similarity	NPC474192
0.6719	Remote Similarity	NPC475720
0.6719	Remote Similarity	NPC207686
0.6718	Remote Similarity	NPC160898
0.6717	Remote Similarity	NPC258048
0.6708	Remote Similarity	NPC243850
0.6708	Remote Similarity	NPC270918
0.6708	Remote Similarity	NPC316981
0.6707	Remote Similarity	NPC51388
0.6705	Remote Similarity	NPC270515
0.6695	Remote Similarity	NPC280714
0.6694	Remote Similarity	NPC198503
0.6694	Remote Similarity	NPC471304
0.6694	Remote Similarity	NPC322064
0.6693	Remote Similarity	NPC473182
0.6693	Remote Similarity	NPC172222
0.668	Remote Similarity	NPC160666
0.668	Remote Similarity	NPC39500
0.668	Remote Similarity	NPC15801
0.668	Remote Similarity	NPC207866
0.668	Remote Similarity	NPC184680
0.668	Remote Similarity	NPC473183
0.6667	Remote Similarity	NPC187501
0.6667	Remote Similarity	NPC472287
0.6667	Remote Similarity	NPC23294
0.6667	Remote Similarity	NPC472286
0.6667	Remote Similarity	NPC315499
0.6667	Remote Similarity	NPC144452
0.6654	Remote Similarity	NPC470785
0.6654	Remote Similarity	NPC470784
0.6653	Remote Similarity	NPC276657
0.6653	Remote Similarity	NPC225279
0.664	Remote Similarity	NPC96321
0.664	Remote Similarity	NPC467439
0.664	Remote Similarity	NPC473041
0.6639	Remote Similarity	NPC112206
0.6639	Remote Similarity	NPC202605
0.6639	Remote Similarity	NPC110182
0.6629	Remote Similarity	NPC284685
0.6628	Remote Similarity	NPC178858
0.6628	Remote Similarity	NPC107123
0.6628	Remote Similarity	NPC58209
0.6627	Remote Similarity	NPC60621
0.6627	Remote Similarity	NPC280799
0.6627	Remote Similarity	NPC187145
0.6627	Remote Similarity	NPC473105
0.6626	Remote Similarity	NPC303951
0.6623	Remote Similarity	NPC477891
0.6617	Remote Similarity	NPC472589
0.6614	Remote Similarity	NPC217176
0.6614	Remote Similarity	NPC260434
0.6614	Remote Similarity	NPC21638
0.6613	Remote Similarity	NPC193267
0.6613	Remote Similarity	NPC213530
0.6613	Remote Similarity	NPC269270
0.6612	Remote Similarity	NPC210828
0.6612	Remote Similarity	NPC86834
0.661	Remote Similarity	NPC70956
0.661	Remote Similarity	NPC243834
0.6604	Remote Similarity	NPC472588
0.6602	Remote Similarity	NPC473184
0.6602	Remote Similarity	NPC39370
0.66	Remote Similarity	NPC118121
0.6599	Remote Similarity	NPC305984
0.6598	Remote Similarity	NPC9894
0.6591	Remote Similarity	NPC181081
0.6586	Remote Similarity	NPC54066
0.6586	Remote Similarity	NPC14686
0.6576	Remote Similarity	NPC295228

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 NPC9729 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	674
0.2-0.3	982
0.3-0.4	1822
0.4-0.5	2913
0.5-0.6	1871
0.6-0.7	519
0.7-0.8	31
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
0.7621	Intermediate Similarity	NPD7588	Discontinued
0.7511	Intermediate Similarity	NPD1954	Phase 1
0.7429	Intermediate Similarity	NPD5805	Approved
0.7303	Intermediate Similarity	NPD4132	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5459	Phase 2
0.7248	Intermediate Similarity	NPD6228	Discontinued
0.7235	Intermediate Similarity	NPD1225	Phase 2
0.7235	Intermediate Similarity	NPD1224	Phase 2
0.7165	Intermediate Similarity	NPD4558	Phase 2
0.7137	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD2757	Phase 2
0.7126	Intermediate Similarity	NPD1961	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5905	Phase 1
0.707	Intermediate Similarity	NPD6244	Phase 3
0.707	Intermediate Similarity	NPD6243	Phase 3
0.7025	Intermediate Similarity	NPD4312	Approved
0.7016	Intermediate Similarity	NPD4996	Approved
0.7016	Intermediate Similarity	NPD4995	Approved
0.6992	Remote Similarity	NPD1273	Discontinued
0.6983	Remote Similarity	NPD1926	Approved
0.6976	Remote Similarity	NPD1900	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD4925	Approved
0.694	Remote Similarity	NPD7689	Approved
0.6932	Remote Similarity	NPD5399	Discovery
0.6923	Remote Similarity	NPD3844	Clinical (unspecified phase)
0.692	Remote Similarity	NPD4885	Approved
0.6911	Remote Similarity	NPD983	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD8091	Phase 3
0.6897	Remote Similarity	NPD8442	Discontinued
0.6891	Remote Similarity	NPD5658	Approved
0.6885	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD5703	Discontinued
0.688	Remote Similarity	NPD5139	Phase 1
0.6877	Remote Similarity	NPD3488	Phase 1
0.686	Remote Similarity	NPD6528	Phase 1
0.6858	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3590	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4442	Phase 2
0.6846	Remote Similarity	NPD6202	Discontinued
0.6846	Remote Similarity	NPD5866	Approved
0.6838	Remote Similarity	NPD7198	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD3322	Phase 1
0.6833	Remote Similarity	NPD3392	Approved
0.6831	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD6772	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4080	Discontinued
0.6822	Remote Similarity	NPD5118	Phase 2
0.6818	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7803	Approved
0.6815	Remote Similarity	NPD5509	Phase 1
0.6792	Remote Similarity	NPD7708	Approved
0.6791	Remote Similarity	NPD6023	Discontinued
0.6786	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6745	Discontinued
0.6783	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD2794	Discontinued
0.6772	Remote Similarity	NPD5861	Clinical (unspecified phase)
0.677	Remote Similarity	NPD5833	Phase 1
0.6766	Remote Similarity	NPD3814	Phase 1
0.6763	Remote Similarity	NPD4048	Approved
0.6762	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD4923	Phase 1
0.6756	Remote Similarity	NPD3920	Phase 2
0.6746	Remote Similarity	NPD6962	Phase 2
0.6744	Remote Similarity	NPD7620	Phase 2
0.6729	Remote Similarity	NPD5116	Phase 1
0.6718	Remote Similarity	NPD2777	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD3962	Phase 2
0.6718	Remote Similarity	NPD3959	Phase 2
0.6709	Remote Similarity	NPD6594	Discontinued
0.6706	Remote Similarity	NPD5924	Discontinued
0.6705	Remote Similarity	NPD7022	Phase 2
0.6705	Remote Similarity	NPD5051	Phase 1
0.6693	Remote Similarity	NPD6326	Phase 2
0.6693	Remote Similarity	NPD6327	Phase 1
0.6693	Remote Similarity	NPD4373	Phase 2
0.6693	Remote Similarity	NPD6186	Approved
0.668	Remote Similarity	NPD4403	Phase 3
0.668	Remote Similarity	NPD4401	Phase 2
0.6667	Remote Similarity	NPD5014	Discontinued
0.6667	Remote Similarity	NPD6760	Discontinued
0.6667	Remote Similarity	NPD7403	Phase 1
0.6654	Remote Similarity	NPD1572	Phase 2
0.6654	Remote Similarity	NPD7206	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD7419	Discontinued
0.6653	Remote Similarity	NPD3263	Phase 3
0.6653	Remote Similarity	NPD6242	Discontinued
0.6643	Remote Similarity	NPD7176	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD6709	Phase 3
0.6641	Remote Similarity	NPD6473	Phase 1
0.664	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD2410	Phase 2
0.6629	Remote Similarity	NPD7955	Approved
0.6629	Remote Similarity	NPD7956	Approved
0.6616	Remote Similarity	NPD5482	Discontinued
0.6615	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6376	Discontinued
0.6609	Remote Similarity	NPD2762	Phase 2
0.6604	Remote Similarity	NPD5539	Phase 2
0.6603	Remote Similarity	NPD3328	Phase 2
0.6601	Remote Similarity	NPD1571	Phase 2
0.66	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5903	Approved
0.6585	Remote Similarity	NPD5902	Approved
0.6583	Remote Similarity	NPD6231	Phase 3
0.6578	Remote Similarity	NPD3886	Phase 1
0.6578	Remote Similarity	NPD5007	Approved
0.6577	Remote Similarity	NPD6716	Phase 1
0.6576	Remote Similarity	NPD5469	Phase 3
0.6575	Remote Similarity	NPD4952	Phase 3
0.6575	Remote Similarity	NPD5022	Discontinued
0.6574	Remote Similarity	NPD7278	Phase 2
0.6574	Remote Similarity	NPD7279	Phase 2
0.6573	Remote Similarity	NPD5632	Approved
0.6568	Remote Similarity	NPD6286	Phase 3
0.6561	Remote Similarity	NPD6164	Phase 2
0.6561	Remote Similarity	NPD6165	Phase 2
0.6557	Remote Similarity	NPD5914	Approved
0.6555	Remote Similarity	NPD4052	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7067	Approved
0.6552	Remote Similarity	NPD7068	Approved
0.6549	Remote Similarity	NPD7166	Approved
0.6549	Remote Similarity	NPD7165	Approved
0.6548	Remote Similarity	NPD2835	Phase 2
0.6546	Remote Similarity	NPD2884	Phase 1
0.6545	Remote Similarity	NPD7684	Approved
0.6545	Remote Similarity	NPD7682	Approved
0.654	Remote Similarity	NPD4953	Phase 3
0.654	Remote Similarity	NPD1842	Approved
0.6534	Remote Similarity	NPD6153	Approved
0.6533	Remote Similarity	NPD7408	Phase 2
0.6531	Remote Similarity	NPD6282	Discontinued
0.6529	Remote Similarity	NPD7568	Phase 1
0.6528	Remote Similarity	NPD5008	Approved
0.6526	Remote Similarity	NPD5812	Discontinued
0.6524	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.652	Remote Similarity	NPD7180	Phase 3
0.6518	Remote Similarity	NPD429	Approved
0.6513	Remote Similarity	NPD6517	Phase 3
0.6513	Remote Similarity	NPD6490	Phase 2
0.6513	Remote Similarity	NPD1483	Discontinued
0.6513	Remote Similarity	NPD5883	Phase 2
0.6511	Remote Similarity	NPD3923	Approved
0.6511	Remote Similarity	NPD3921	Approved
0.6511	Remote Similarity	NPD3922	Approved
0.6511	Remote Similarity	NPD3924	Approved
0.6511	Remote Similarity	NPD4950	Approved
0.651	Remote Similarity	NPD5479	Discontinued
0.6507	Remote Similarity	NPD6216	Approved
0.6506	Remote Similarity	NPD4429	Discontinued
0.6504	Remote Similarity	NPD4927	Discontinued
0.65	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD2482	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD3254	Phase 1
0.6496	Remote Similarity	NPD3255	Phase 1
0.6494	Remote Similarity	NPD5869	Phase 2
0.6494	Remote Similarity	NPD5870	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD1505	Phase 2
0.6484	Remote Similarity	NPD3442	Approved
0.6484	Remote Similarity	NPD3441	Approved
0.648	Remote Similarity	NPD6974	Phase 3
0.648	Remote Similarity	NPD3258	Approved
0.6475	Remote Similarity	NPD5529	Phase 1
0.6475	Remote Similarity	NPD5528	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD1955	Discontinued
0.6466	Remote Similarity	NPD7980	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD6230	Discontinued
0.6463	Remote Similarity	NPD5416	Discontinued
0.6462	Remote Similarity	NPD2414	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD8524	Approved
0.6458	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4438	Approved
0.6454	Remote Similarity	NPD8046	Discontinued
0.6448	Remote Similarity	NPD8310	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD7853	Phase 2
0.6445	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.644	Remote Similarity	NPD7395	Discontinued
0.6439	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD2917	Approved
0.6437	Remote Similarity	NPD7117	Phase 2
0.6432	Remote Similarity	NPD7134	Clinical (unspecified phase)
0.6431	Remote Similarity	NPD4328	Approved
0.6431	Remote Similarity	NPD3259	Approved
0.6426	Remote Similarity	NPD5612	Discontinued
0.6424	Remote Similarity	NPD6558	Phase 1
0.6423	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD5447	Phase 2
0.6423	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD3013	Phase 3
0.6421	Remote Similarity	NPD6530	Approved
0.6421	Remote Similarity	NPD6531	Approved
0.6418	Remote Similarity	NPD4353	Phase 2
0.6417	Remote Similarity	NPD3925	Approved
0.6417	Remote Similarity	NPD3541	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD1624	Phase 2

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