NPASS Compound

Structure

NPC474975 OpenBabel07101719242D 23 26 0 0 1 0 0 0 0 0999 V2000 -4.5468 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2202 4.2544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5962 3.4263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7872 2.0250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 1.2024 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1180 2.7681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1399 2.5602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 3.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5292 3.3034 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7007 2.4317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 3.6342 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 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 5 1 0 0 0 0 3 9 2 0 0 0 0 4 6 2 0 0 0 0 4 9 1 0 0 0 0 5 10 2 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 21 1 0 0 0 0 8 22 1 0 0 0 0 9 13 1 0 0 0 0 10 19 1 0 0 0 0 11 14 1 0 0 0 0 11 23 1 0 0 0 0 12 15 2 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 17 1 0 0 0 0 14 16 2 0 0 0 0 15 16 1 0 0 0 0 15 22 1 0 0 0 0 16 20 1 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.08
Volume:	302.649
LogP:	3.8
LogD:	3.375
LogS:	-4.668
# Rotatable Bonds:	3
TPSA:	70.29
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.797
Synthetic Accessibility Score:	2.574
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.677
MDCK Permeability:	2.6985022486769594e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	95.34923553466797%
Volume Distribution (VD):	0.602
Pgp-substrate:	6.322908401489258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.963
CYP1A2-substrate:	0.63
CYP2C19-inhibitor:	0.928
CYP2C19-substrate:	0.132
CYP2C9-inhibitor:	0.834
CYP2C9-substrate:	0.925
CYP2D6-inhibitor:	0.677
CYP2D6-substrate:	0.924
CYP3A4-inhibitor:	0.694
CYP3A4-substrate:	0.245

ADMET: Excretion

Clearance (CL):	13.498
Half-life (T1/2):	0.191

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.171
Drug-inuced Liver Injury (DILI):	0.913
AMES Toxicity:	0.165
Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.153
Skin Sensitization:	0.089
Carcinogencity:	0.828
Eye Corrosion:	0.004
Eye Irritation:	0.135
Respiratory Toxicity:	0.483

Download Data

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

Natural Product: NPC474975

Natural Product ID:	NPC474975
*Common Name:**	Aglalactone
IUPAC Name:	8-methoxy-7-(4-methoxyphenyl)-7H-furo[2,3-f][1,3]benzodioxol-6-one
Synonyms:	Aglalactone
Standard InCHIKey:	NLCAMZUTWGFUSW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O6/c1-19-10-5-3-9(4-6-10)13-14-11(23-17(13)18)7-12-15(16(14)20-2)22-8-21-12/h3-7,13H,8H2,1-2H3
SMILES:	COC1=CC=C(C=C1)C2C3=C(C4=C(C=C3OC2=O)OCO4)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490541
PubChem CID:	10591326
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004189] Coumarans [CHEMONTID:0004190] 1-phenylcoumarans

*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
NPO32616	aglaia sp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10775404]
NPO32616	aglaia sp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8496701]
NPO32616	aglaia sp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868148]

☑ 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
EC50	2
ED50	4
MIC	1
Others	2

Activity Type	# Activity
Cell Line	4
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[454575]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[454575]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[454575]
NPT737	Cell Line	HUVEC	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[454575]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	LC50	>	100.0	ug/g	PMID[454574]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	EC50	>	100.0	ug/g	PMID[454574]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	MIC	>	200.0	ug.mL-1	PMID[454576]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC90	>	200.0	ug ml-1	PMID[454576]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC50	>	200.0	ug.mL-1	PMID[454576]

☑ 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 NPC474975 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	431
0.1-0.2	1799
0.2-0.3	4574
0.3-0.4	10831
0.4-0.5	7303
0.5-0.6	4132
0.6-0.7	6540
0.7-0.8	6589
0.8-0.85	439
0.85-0.9	57
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9103	High Similarity	NPC176586
0.9103	High Similarity	NPC210354
0.9041	High Similarity	NPC474288
0.898	High Similarity	NPC191158
0.898	High Similarity	NPC177644
0.8973	High Similarity	NPC151423
0.8973	High Similarity	NPC40237
0.8889	High Similarity	NPC273578
0.8859	High Similarity	NPC87295
0.8851	High Similarity	NPC92693
0.8851	High Similarity	NPC218841
0.8851	High Similarity	NPC475000
0.8839	High Similarity	NPC258644
0.8839	High Similarity	NPC474990
0.8831	High Similarity	NPC202249
0.8831	High Similarity	NPC42871
0.8831	High Similarity	NPC188962
0.8824	High Similarity	NPC292460
0.8824	High Similarity	NPC144162
0.882	High Similarity	NPC475964
0.8816	High Similarity	NPC303519
0.8792	High Similarity	NPC474158
0.8776	High Similarity	NPC300798
0.8776	High Similarity	NPC58137
0.8766	High Similarity	NPC244371
0.8758	High Similarity	NPC104353
0.875	High Similarity	NPC149505
0.8742	High Similarity	NPC187923
0.8734	High Similarity	NPC478199
0.8733	High Similarity	NPC193779
0.8726	High Similarity	NPC131557
0.8716	High Similarity	NPC80326
0.8716	High Similarity	NPC472562
0.8701	High Similarity	NPC474514
0.8693	High Similarity	NPC210642
0.8693	High Similarity	NPC13985
0.869	High Similarity	NPC211386
0.8684	High Similarity	NPC216223
0.8684	High Similarity	NPC145569
0.8684	High Similarity	NPC477698
0.8675	High Similarity	NPC304687
0.8675	High Similarity	NPC80230
0.8675	High Similarity	NPC101755
0.8675	High Similarity	NPC104024
0.8675	High Similarity	NPC65574
0.8654	High Similarity	NPC301897
0.865	High Similarity	NPC72455
0.8645	High Similarity	NPC348849
0.8645	High Similarity	NPC178195
0.8636	High Similarity	NPC56184
0.863	High Similarity	NPC11453
0.8616	High Similarity	NPC469575
0.8608	High Similarity	NPC119910
0.86	High Similarity	NPC18211
0.8599	High Similarity	NPC220462
0.8591	High Similarity	NPC174522
0.8581	High Similarity	NPC148497
0.8581	High Similarity	NPC153008
0.8571	High Similarity	NPC164082
0.8562	High Similarity	NPC477695
0.8562	High Similarity	NPC474965
0.8562	High Similarity	NPC72796
0.8562	High Similarity	NPC262455
0.8562	High Similarity	NPC44245
0.8562	High Similarity	NPC177476
0.8562	High Similarity	NPC73071
0.8562	High Similarity	NPC174512
0.8562	High Similarity	NPC668
0.8562	High Similarity	NPC293757
0.8552	High Similarity	NPC205915
0.8544	High Similarity	NPC104459
0.8544	High Similarity	NPC325122
0.8544	High Similarity	NPC257914
0.8544	High Similarity	NPC238405
0.8537	High Similarity	NPC474568
0.8535	High Similarity	NPC477380
0.8535	High Similarity	NPC261484
0.8526	High Similarity	NPC478213
0.8526	High Similarity	NPC186507
0.8516	High Similarity	NPC477699
0.8516	High Similarity	NPC220577
0.8503	High Similarity	NPC143895
0.85	High Similarity	NPC61141
0.8494	Intermediate Similarity	NPC29587
0.8491	Intermediate Similarity	NPC474770
0.8491	Intermediate Similarity	NPC96593
0.8487	Intermediate Similarity	NPC224687
0.8485	Intermediate Similarity	NPC66804
0.8481	Intermediate Similarity	NPC207584
0.8481	Intermediate Similarity	NPC19947
0.8481	Intermediate Similarity	NPC477885
0.8477	Intermediate Similarity	NPC143092
0.8462	Intermediate Similarity	NPC308555
0.8462	Intermediate Similarity	NPC68882
0.8452	Intermediate Similarity	NPC477700
0.8447	Intermediate Similarity	NPC110257
0.8446	Intermediate Similarity	NPC20796
0.8443	Intermediate Similarity	NPC236089
0.8438	Intermediate Similarity	NPC258322
0.8438	Intermediate Similarity	NPC288149
0.8438	Intermediate Similarity	NPC191352
0.8435	Intermediate Similarity	NPC240915
0.8435	Intermediate Similarity	NPC234865
0.8428	Intermediate Similarity	NPC125713
0.8425	Intermediate Similarity	NPC266848
0.8425	Intermediate Similarity	NPC136750
0.8421	Intermediate Similarity	NPC474749
0.8421	Intermediate Similarity	NPC205316
0.8421	Intermediate Similarity	NPC11422
0.8421	Intermediate Similarity	NPC178014
0.8421	Intermediate Similarity	NPC42716
0.8418	Intermediate Similarity	NPC237946
0.8418	Intermediate Similarity	NPC32373
0.8418	Intermediate Similarity	NPC155063
0.8414	Intermediate Similarity	NPC192255
0.8408	Intermediate Similarity	NPC279930
0.8408	Intermediate Similarity	NPC136757
0.8408	Intermediate Similarity	NPC57211
0.8405	Intermediate Similarity	NPC42230
0.8405	Intermediate Similarity	NPC474948
0.8403	Intermediate Similarity	NPC153547
0.8397	Intermediate Similarity	NPC198615
0.8397	Intermediate Similarity	NPC474663
0.8397	Intermediate Similarity	NPC279061
0.8397	Intermediate Similarity	NPC473732
0.8395	Intermediate Similarity	NPC222531
0.8395	Intermediate Similarity	NPC474647
0.8395	Intermediate Similarity	NPC475953
0.8389	Intermediate Similarity	NPC9068
0.8387	Intermediate Similarity	NPC475170
0.8387	Intermediate Similarity	NPC238366
0.8385	Intermediate Similarity	NPC18284
0.8385	Intermediate Similarity	NPC273021
0.8378	Intermediate Similarity	NPC209229
0.8378	Intermediate Similarity	NPC286843
0.8377	Intermediate Similarity	NPC301961
0.8377	Intermediate Similarity	NPC262804
0.8377	Intermediate Similarity	NPC166584
0.8377	Intermediate Similarity	NPC40654
0.8375	Intermediate Similarity	NPC470637
0.8375	Intermediate Similarity	NPC139876
0.8373	Intermediate Similarity	NPC107739
0.8373	Intermediate Similarity	NPC290304
0.8373	Intermediate Similarity	NPC236327
0.8367	Intermediate Similarity	NPC110958
0.8367	Intermediate Similarity	NPC19890
0.8367	Intermediate Similarity	NPC474600
0.8367	Intermediate Similarity	NPC7163
0.8366	Intermediate Similarity	NPC3982
0.8366	Intermediate Similarity	NPC296575
0.8366	Intermediate Similarity	NPC321958
0.8366	Intermediate Similarity	NPC162193
0.8366	Intermediate Similarity	NPC287275
0.8366	Intermediate Similarity	NPC321696
0.8365	Intermediate Similarity	NPC310206
0.8365	Intermediate Similarity	NPC82733
0.8365	Intermediate Similarity	NPC181168
0.8365	Intermediate Similarity	NPC115281
0.8365	Intermediate Similarity	NPC76458
0.8365	Intermediate Similarity	NPC163527
0.8364	Intermediate Similarity	NPC475825
0.8364	Intermediate Similarity	NPC223375
0.8356	Intermediate Similarity	NPC65183
0.8356	Intermediate Similarity	NPC7744
0.8356	Intermediate Similarity	NPC261812
0.8356	Intermediate Similarity	NPC72046
0.8354	Intermediate Similarity	NPC241774
0.8354	Intermediate Similarity	NPC34725
0.8354	Intermediate Similarity	NPC254163
0.8354	Intermediate Similarity	NPC284353
0.8354	Intermediate Similarity	NPC276059
0.8354	Intermediate Similarity	NPC211309
0.8354	Intermediate Similarity	NPC122623
0.8354	Intermediate Similarity	NPC478238
0.8344	Intermediate Similarity	NPC287124
0.8344	Intermediate Similarity	NPC311057
0.8344	Intermediate Similarity	NPC473236
0.8344	Intermediate Similarity	NPC52623
0.8344	Intermediate Similarity	NPC475116
0.8344	Intermediate Similarity	NPC113093
0.8333	Intermediate Similarity	NPC32079
0.8333	Intermediate Similarity	NPC470178
0.8333	Intermediate Similarity	NPC29056
0.8323	Intermediate Similarity	NPC23593
0.8323	Intermediate Similarity	NPC10304
0.8323	Intermediate Similarity	NPC263955
0.8323	Intermediate Similarity	NPC239890
0.8323	Intermediate Similarity	NPC209411
0.8323	Intermediate Similarity	NPC162668
0.8323	Intermediate Similarity	NPC63256
0.8323	Intermediate Similarity	NPC196771
0.8323	Intermediate Similarity	NPC85141
0.8323	Intermediate Similarity	NPC115624
0.8322	Intermediate Similarity	NPC14022
0.8313	Intermediate Similarity	NPC15764
0.8313	Intermediate Similarity	NPC474043
0.8313	Intermediate Similarity	NPC215375
0.8313	Intermediate Similarity	NPC62518
0.8313	Intermediate Similarity	NPC50430
0.8312	Intermediate Similarity	NPC106461

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 NPC474975 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	377
0.1-0.2	931
0.2-0.3	1882
0.3-0.4	2770
0.4-0.5	1696
0.5-0.6	959
0.6-0.7	416
0.7-0.8	110
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8553	High Similarity	NPD7199	Phase 2
0.8447	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD4965	Approved
0.8418	Intermediate Similarity	NPD4966	Approved
0.8418	Intermediate Similarity	NPD4967	Phase 2
0.8377	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD6234	Discontinued
0.8261	Intermediate Similarity	NPD5494	Approved
0.8228	Intermediate Similarity	NPD37	Approved
0.8182	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD3818	Discontinued
0.7964	Intermediate Similarity	NPD7228	Approved
0.795	Intermediate Similarity	NPD2801	Approved
0.7917	Intermediate Similarity	NPD5844	Phase 1
0.7901	Intermediate Similarity	NPD3817	Phase 2
0.7866	Intermediate Similarity	NPD919	Approved
0.7852	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD17	Approved
0.7778	Intermediate Similarity	NPD1934	Approved
0.7778	Intermediate Similarity	NPD7240	Approved
0.7771	Intermediate Similarity	NPD1247	Approved
0.7744	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD3882	Suspended
0.7736	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1465	Phase 2
0.7679	Intermediate Similarity	NPD3926	Phase 2
0.7671	Intermediate Similarity	NPD1608	Approved
0.7661	Intermediate Similarity	NPD7074	Phase 3
0.7619	Intermediate Similarity	NPD6232	Discontinued
0.7602	Intermediate Similarity	NPD7054	Approved
0.76	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7473	Discontinued
0.7582	Intermediate Similarity	NPD1933	Approved
0.7578	Intermediate Similarity	NPD920	Approved
0.7558	Intermediate Similarity	NPD7472	Approved
0.7548	Intermediate Similarity	NPD3748	Approved
0.7531	Intermediate Similarity	NPD1653	Approved
0.7515	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7229	Phase 3
0.75	Intermediate Similarity	NPD6799	Approved
0.75	Intermediate Similarity	NPD1511	Approved
0.7483	Intermediate Similarity	NPD3705	Approved
0.7471	Intermediate Similarity	NPD5242	Approved
0.7468	Intermediate Similarity	NPD1243	Approved
0.7453	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6599	Discontinued
0.7429	Intermediate Similarity	NPD7808	Phase 3
0.7414	Intermediate Similarity	NPD6797	Phase 2
0.741	Intermediate Similarity	NPD7819	Suspended
0.7407	Intermediate Similarity	NPD1512	Approved
0.7405	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD3266	Approved
0.74	Intermediate Similarity	NPD3267	Approved
0.7389	Intermediate Similarity	NPD2796	Approved
0.7381	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7251	Discontinued
0.7368	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6355	Discontinued
0.7355	Intermediate Similarity	NPD447	Suspended
0.7346	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6166	Phase 2
0.7326	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3750	Approved
0.7312	Intermediate Similarity	NPD4110	Phase 3
0.7312	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3787	Discontinued
0.7305	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1613	Approved
0.729	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3749	Approved
0.7273	Intermediate Similarity	NPD6559	Discontinued
0.7273	Intermediate Similarity	NPD1296	Phase 2
0.7262	Intermediate Similarity	NPD5402	Approved
0.7262	Intermediate Similarity	NPD5353	Approved
0.7244	Intermediate Similarity	NPD230	Phase 1
0.7239	Intermediate Similarity	NPD2532	Approved
0.7239	Intermediate Similarity	NPD2534	Approved
0.7239	Intermediate Similarity	NPD2533	Approved
0.7239	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5283	Phase 1
0.7219	Intermediate Similarity	NPD5006	Approved
0.7219	Intermediate Similarity	NPD5005	Approved
0.7216	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3027	Phase 3
0.7205	Intermediate Similarity	NPD4628	Phase 3
0.7202	Intermediate Similarity	NPD8455	Phase 2
0.719	Intermediate Similarity	NPD3018	Phase 2
0.7186	Intermediate Similarity	NPD6385	Approved
0.7186	Intermediate Similarity	NPD6386	Approved
0.7176	Intermediate Similarity	NPD7075	Discontinued
0.7175	Intermediate Similarity	NPD7685	Pre-registration
0.7171	Intermediate Similarity	NPD2797	Approved
0.717	Intermediate Similarity	NPD6099	Approved
0.717	Intermediate Similarity	NPD6100	Approved
0.717	Intermediate Similarity	NPD2935	Discontinued
0.7161	Intermediate Similarity	NPD3268	Approved
0.7151	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3751	Discontinued
0.7143	Intermediate Similarity	NPD6801	Discontinued
0.7134	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3146	Approved
0.7134	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1281	Approved
0.7133	Intermediate Similarity	NPD1611	Approved
0.7125	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6233	Phase 2
0.7102	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4420	Approved
0.709	Intermediate Similarity	NPD7680	Approved
0.7088	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2981	Phase 2
0.7083	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7411	Suspended
0.7081	Intermediate Similarity	NPD1549	Phase 2
0.707	Intermediate Similarity	NPD1240	Approved
0.707	Intermediate Similarity	NPD2979	Phase 3
0.7063	Intermediate Similarity	NPD2438	Suspended
0.7052	Intermediate Similarity	NPD8127	Discontinued
0.7051	Intermediate Similarity	NPD6798	Discontinued
0.7047	Intermediate Similarity	NPD5585	Approved
0.7039	Intermediate Similarity	NPD7549	Discontinued
0.7039	Intermediate Similarity	NPD2983	Phase 2
0.7039	Intermediate Similarity	NPD2982	Phase 2
0.7037	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2800	Approved
0.7032	Intermediate Similarity	NPD6832	Phase 2
0.7032	Intermediate Similarity	NPD4908	Phase 1
0.7024	Intermediate Similarity	NPD7028	Phase 2
0.702	Intermediate Similarity	NPD422	Phase 1
0.702	Intermediate Similarity	NPD1610	Phase 2
0.7019	Intermediate Similarity	NPD6005	Phase 3
0.7019	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6004	Phase 3
0.7019	Intermediate Similarity	NPD6002	Phase 3
0.7006	Intermediate Similarity	NPD8032	Phase 2
0.7	Intermediate Similarity	NPD1510	Phase 2
0.7	Intermediate Similarity	NPD2799	Discontinued
0.7	Intermediate Similarity	NPD7033	Discontinued
0.6994	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1283	Approved
0.6981	Remote Similarity	NPD1607	Approved
0.6974	Remote Similarity	NPD1481	Phase 2
0.6968	Remote Similarity	NPD2861	Phase 2
0.6964	Remote Similarity	NPD7458	Discontinued
0.6964	Remote Similarity	NPD3226	Approved
0.6962	Remote Similarity	NPD4307	Phase 2
0.6962	Remote Similarity	NPD4060	Phase 1
0.6959	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1551	Phase 2
0.6951	Remote Similarity	NPD6190	Approved
0.6943	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3384	Approved
0.6941	Remote Similarity	NPD3383	Approved
0.6941	Remote Similarity	NPD3382	Approved
0.6933	Remote Similarity	NPD6674	Discontinued
0.6932	Remote Similarity	NPD2403	Approved
0.6928	Remote Similarity	NPD5401	Approved
0.6923	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4380	Phase 2
0.6919	Remote Similarity	NPD7768	Phase 2
0.6919	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5535	Approved
0.6918	Remote Similarity	NPD4622	Approved
0.6918	Remote Similarity	NPD4618	Approved
0.6914	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD5536	Phase 2
0.6908	Remote Similarity	NPD1535	Discovery
0.6905	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD3225	Approved
0.6879	Remote Similarity	NPD7095	Approved
0.6855	Remote Similarity	NPD943	Approved
0.6848	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5403	Approved
0.6836	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5688	Approved
0.6832	Remote Similarity	NPD7097	Phase 1
0.6832	Remote Similarity	NPD5689	Approved
0.6826	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4359	Approved
0.6811	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.681	Remote Similarity	NPD2346	Discontinued
0.681	Remote Similarity	NPD2344	Approved
0.68	Remote Similarity	NPD5677	Discontinued
0.6793	Remote Similarity	NPD8434	Phase 2
0.679	Remote Similarity	NPD4308	Phase 3
0.6782	Remote Similarity	NPD6971	Discontinued
0.6776	Remote Similarity	NPD1778	Approved
0.6766	Remote Similarity	NPD4357	Discontinued
0.6766	Remote Similarity	NPD7837	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