NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.09
Volume:	232.35
LogP:	1.623
LogD:	1.475
LogS:	-2.308
# Rotatable Bonds:	1
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.742
Synthetic Accessibility Score:	4.385
Fsp3:	0.462
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.903
MDCK Permeability:	2.724635851336643e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.614

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.477
Plasma Protein Binding (PPB):	60.28759002685547%
Volume Distribution (VD):	1.242
Pgp-substrate:	24.35931968688965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.113
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.27
CYP2C9-inhibitor:	0.099
CYP2C9-substrate:	0.158
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.135
CYP3A4-inhibitor:	0.051
CYP3A4-substrate:	0.362

ADMET: Excretion

Clearance (CL):	11.937
Half-life (T1/2):	0.656

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.731
Drug-inuced Liver Injury (DILI):	0.926
AMES Toxicity:	0.555
Rat Oral Acute Toxicity:	0.081
Maximum Recommended Daily Dose:	0.368
Skin Sensitization:	0.435
Carcinogencity:	0.517
Eye Corrosion:	0.028
Eye Irritation:	0.644
Respiratory Toxicity:	0.035

Download Data

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

Natural Product: NPC172525

Natural Product ID:	NPC172525
*Common Name:**	9-Deoxygoniopypyrone
IUPAC Name:	(1R,3S,4S,5R)-4-hydroxy-3-phenyl-2,6-dioxabicyclo[3.3.1]nonan-7-one
Synonyms:	9-Deoxygoniopypyrone
Standard InCHIKey:	ZPVLUTBGTWEMGV-AAXDQBDMSA-N
Standard InCHI:	InChI=1S/C13H14O4/c14-11-7-9-6-10(17-11)12(15)13(16-9)8-4-2-1-3-5-8/h1-5,9-10,12-13,15H,6-7H2/t9-,10-,12+,13+/m1/s1
SMILES:	O=C1C[C@H]2C[C@@H](O1)[C@@H]([C@@H](O2)c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505003
PubChem CID:	126233
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002204] C-glycosyl compounds

*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
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713398]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	bark	n.a.	PMID[1479382]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[1479382]
NPO21404	Anagallis monelli	Species	Primulaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17329877]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791471]
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791473]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614426]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9322367]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917277]
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21404	Anagallis monelli	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20329	Gymnacranthera paniculata	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27877	Eliokarmos thyrsoides	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15866	Goniothalamus amuyon	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	3
Others	1

Activity Type	# Activity
Cell Line	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	27.2	ug ml-1	PMID[490498]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	25.35	ug ml-1	PMID[490498]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	7.38	ug ml-1	PMID[490498]
NPT140	Organism	Artemia	Artemia	LC50	>	500.0	ug.mL-1	PMID[490498]

☑ 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 NPC172525 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	247
0.1-0.2	918
0.2-0.3	2135
0.3-0.4	5855
0.4-0.5	11757
0.5-0.6	12336
0.6-0.7	8746
0.7-0.8	688
0.8-0.85	12
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8729	High Similarity	NPC138798
0.8596	High Similarity	NPC210531
0.843	Intermediate Similarity	NPC476033
0.8288	Intermediate Similarity	NPC474376
0.8288	Intermediate Similarity	NPC472315
0.8288	Intermediate Similarity	NPC37115
0.8288	Intermediate Similarity	NPC475203
0.8288	Intermediate Similarity	NPC472316
0.8279	Intermediate Similarity	NPC79608
0.8273	Intermediate Similarity	NPC242913
0.8273	Intermediate Similarity	NPC280616
0.8273	Intermediate Similarity	NPC171831
0.8261	Intermediate Similarity	NPC474363
0.8246	Intermediate Similarity	NPC158282
0.8214	Intermediate Similarity	NPC20485
0.8214	Intermediate Similarity	NPC277788
0.8197	Intermediate Similarity	NPC57607
0.8182	Intermediate Similarity	NPC160382
0.8174	Intermediate Similarity	NPC265002
0.8125	Intermediate Similarity	NPC136962
0.812	Intermediate Similarity	NPC471616
0.8103	Intermediate Similarity	NPC87069
0.8087	Intermediate Similarity	NPC234376
0.8047	Intermediate Similarity	NPC88255
0.8047	Intermediate Similarity	NPC136994
0.8033	Intermediate Similarity	NPC223351
0.7982	Intermediate Similarity	NPC210529
0.7982	Intermediate Similarity	NPC175852
0.7982	Intermediate Similarity	NPC160548
0.7931	Intermediate Similarity	NPC185840
0.7931	Intermediate Similarity	NPC474314
0.792	Intermediate Similarity	NPC114096
0.7863	Intermediate Similarity	NPC474176
0.7857	Intermediate Similarity	NPC148026
0.7826	Intermediate Similarity	NPC40178
0.7823	Intermediate Similarity	NPC471466
0.7812	Intermediate Similarity	NPC289415
0.7812	Intermediate Similarity	NPC319995
0.7795	Intermediate Similarity	NPC301857
0.7788	Intermediate Similarity	NPC85977
0.7788	Intermediate Similarity	NPC19136
0.7759	Intermediate Similarity	NPC276061
0.7759	Intermediate Similarity	NPC474148
0.7757	Intermediate Similarity	NPC317645
0.775	Intermediate Similarity	NPC190298
0.7748	Intermediate Similarity	NPC98911
0.7748	Intermediate Similarity	NPC472318
0.7744	Intermediate Similarity	NPC62800
0.7744	Intermediate Similarity	NPC324262
0.7742	Intermediate Similarity	NPC469927
0.7739	Intermediate Similarity	NPC47536
0.7731	Intermediate Similarity	NPC306740
0.7731	Intermediate Similarity	NPC29607
0.7719	Intermediate Similarity	NPC152384
0.7719	Intermediate Similarity	NPC37714
0.7717	Intermediate Similarity	NPC472707
0.7699	Intermediate Similarity	NPC82426
0.7699	Intermediate Similarity	NPC91820
0.7699	Intermediate Similarity	NPC234305
0.7698	Intermediate Similarity	NPC123704
0.7692	Intermediate Similarity	NPC30563
0.7692	Intermediate Similarity	NPC269421
0.768	Intermediate Similarity	NPC236981
0.7674	Intermediate Similarity	NPC17567
0.7658	Intermediate Similarity	NPC271475
0.7642	Intermediate Similarity	NPC304760
0.7623	Intermediate Similarity	NPC104514
0.7619	Intermediate Similarity	NPC246166
0.7619	Intermediate Similarity	NPC244454
0.7619	Intermediate Similarity	NPC317163
0.7612	Intermediate Similarity	NPC197666
0.7612	Intermediate Similarity	NPC126739
0.76	Intermediate Similarity	NPC141970
0.76	Intermediate Similarity	NPC140561
0.7597	Intermediate Similarity	NPC262819
0.7586	Intermediate Similarity	NPC156648
0.7578	Intermediate Similarity	NPC231627
0.7576	Intermediate Similarity	NPC477896
0.7576	Intermediate Similarity	NPC34456
0.7565	Intermediate Similarity	NPC269457
0.7565	Intermediate Similarity	NPC472919
0.7563	Intermediate Similarity	NPC272524
0.7547	Intermediate Similarity	NPC89377
0.7542	Intermediate Similarity	NPC210089
0.7542	Intermediate Similarity	NPC260818
0.7542	Intermediate Similarity	NPC476003
0.7541	Intermediate Similarity	NPC469574
0.754	Intermediate Similarity	NPC228739
0.7538	Intermediate Similarity	NPC291419
0.7538	Intermediate Similarity	NPC60825
0.7536	Intermediate Similarity	NPC477737
0.7522	Intermediate Similarity	NPC42211
0.7521	Intermediate Similarity	NPC469636
0.7521	Intermediate Similarity	NPC474364
0.7521	Intermediate Similarity	NPC281604
0.7521	Intermediate Similarity	NPC149691
0.7519	Intermediate Similarity	NPC158673
0.7519	Intermediate Similarity	NPC237182
0.7519	Intermediate Similarity	NPC226101
0.75	Intermediate Similarity	NPC329705
0.75	Intermediate Similarity	NPC474111
0.75	Intermediate Similarity	NPC475827
0.75	Intermediate Similarity	NPC308744
0.75	Intermediate Similarity	NPC474223
0.75	Intermediate Similarity	NPC472706
0.75	Intermediate Similarity	NPC114116
0.7482	Intermediate Similarity	NPC212808
0.7481	Intermediate Similarity	NPC108553
0.748	Intermediate Similarity	NPC87153
0.748	Intermediate Similarity	NPC162925
0.7479	Intermediate Similarity	NPC321852
0.7479	Intermediate Similarity	NPC79496
0.7478	Intermediate Similarity	NPC148060
0.7462	Intermediate Similarity	NPC27712
0.746	Intermediate Similarity	NPC472703
0.7458	Intermediate Similarity	NPC174099
0.7458	Intermediate Similarity	NPC326187
0.7444	Intermediate Similarity	NPC477893
0.744	Intermediate Similarity	NPC229600
0.7438	Intermediate Similarity	NPC474685
0.7436	Intermediate Similarity	NPC475465
0.7436	Intermediate Similarity	NPC472314
0.7434	Intermediate Similarity	NPC118343
0.7426	Intermediate Similarity	NPC77493
0.7422	Intermediate Similarity	NPC275576
0.7422	Intermediate Similarity	NPC77651
0.7422	Intermediate Similarity	NPC28069
0.7417	Intermediate Similarity	NPC48525
0.7411	Intermediate Similarity	NPC92754
0.7411	Intermediate Similarity	NPC249912
0.7411	Intermediate Similarity	NPC477767
0.7411	Intermediate Similarity	NPC276775
0.7407	Intermediate Similarity	NPC220893
0.7405	Intermediate Similarity	NPC469705
0.7405	Intermediate Similarity	NPC17968
0.7405	Intermediate Similarity	NPC470122
0.7402	Intermediate Similarity	NPC472704
0.7398	Intermediate Similarity	NPC45794
0.7398	Intermediate Similarity	NPC122245
0.7398	Intermediate Similarity	NPC216605
0.7398	Intermediate Similarity	NPC266389
0.7395	Intermediate Similarity	NPC264784
0.7395	Intermediate Similarity	NPC474157
0.7395	Intermediate Similarity	NPC167504
0.7391	Intermediate Similarity	NPC474365
0.7391	Intermediate Similarity	NPC301943
0.7388	Intermediate Similarity	NPC142027
0.7387	Intermediate Similarity	NPC206764
0.7377	Intermediate Similarity	NPC100353
0.7373	Intermediate Similarity	NPC265407
0.7373	Intermediate Similarity	NPC83628
0.7373	Intermediate Similarity	NPC85493
0.7372	Intermediate Similarity	NPC80098
0.7372	Intermediate Similarity	NPC64664
0.7368	Intermediate Similarity	NPC158623
0.7364	Intermediate Similarity	NPC124878
0.7364	Intermediate Similarity	NPC169913
0.7364	Intermediate Similarity	NPC253681
0.7364	Intermediate Similarity	NPC231888
0.7364	Intermediate Similarity	NPC63404
0.7364	Intermediate Similarity	NPC204214
0.7364	Intermediate Similarity	NPC92283
0.7364	Intermediate Similarity	NPC198918
0.7364	Intermediate Similarity	NPC290276
0.7364	Intermediate Similarity	NPC10883
0.7364	Intermediate Similarity	NPC35338
0.7364	Intermediate Similarity	NPC10121
0.736	Intermediate Similarity	NPC474222
0.736	Intermediate Similarity	NPC475804
0.7358	Intermediate Similarity	NPC58616
0.7355	Intermediate Similarity	NPC120217
0.7355	Intermediate Similarity	NPC307651
0.7355	Intermediate Similarity	NPC153053
0.735	Intermediate Similarity	NPC475905
0.735	Intermediate Similarity	NPC193640
0.735	Intermediate Similarity	NPC25385
0.735	Intermediate Similarity	NPC119271
0.7348	Intermediate Similarity	NPC233692
0.7348	Intermediate Similarity	NPC476407
0.7348	Intermediate Similarity	NPC239358
0.7345	Intermediate Similarity	NPC78701
0.7345	Intermediate Similarity	NPC35448
0.7345	Intermediate Similarity	NPC225060
0.7338	Intermediate Similarity	NPC127857
0.7333	Intermediate Similarity	NPC470825
0.7333	Intermediate Similarity	NPC471345
0.7328	Intermediate Similarity	NPC214246
0.7328	Intermediate Similarity	NPC82712
0.7328	Intermediate Similarity	NPC469549
0.7328	Intermediate Similarity	NPC11025
0.7323	Intermediate Similarity	NPC474159
0.7323	Intermediate Similarity	NPC474254
0.7317	Intermediate Similarity	NPC212891
0.7317	Intermediate Similarity	NPC473556
0.7317	Intermediate Similarity	NPC301651
0.7313	Intermediate Similarity	NPC472247
0.7313	Intermediate Similarity	NPC471029
0.7308	Intermediate Similarity	NPC471025
0.7305	Intermediate Similarity	NPC250046
0.7305	Intermediate Similarity	NPC60509

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 NPC172525 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	663
0.2-0.3	1295
0.3-0.4	2731
0.4-0.5	2455
0.5-0.6	1307
0.6-0.7	460
0.7-0.8	33
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
0.7982	Intermediate Similarity	NPD9495	Approved
0.7797	Intermediate Similarity	NPD6010	Discontinued
0.7731	Intermediate Similarity	NPD2629	Approved
0.7719	Intermediate Similarity	NPD5048	Discontinued
0.7609	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD4198	Discontinued
0.7479	Intermediate Similarity	NPD969	Suspended
0.7458	Intermediate Similarity	NPD2067	Discontinued
0.7438	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1238	Approved
0.7424	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD6233	Phase 2
0.7281	Intermediate Similarity	NPD7798	Approved
0.7273	Intermediate Similarity	NPD6798	Discontinued
0.725	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD2182	Approved
0.7222	Intermediate Similarity	NPD5126	Approved
0.7222	Intermediate Similarity	NPD5125	Phase 3
0.7206	Intermediate Similarity	NPD7033	Discontinued
0.7179	Intermediate Similarity	NPD1237	Approved
0.7179	Intermediate Similarity	NPD164	Approved
0.7177	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD9491	Approved
0.7099	Intermediate Similarity	NPD6085	Phase 2
0.7099	Intermediate Similarity	NPD5647	Approved
0.7099	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5305	Approved
0.7087	Intermediate Similarity	NPD5306	Approved
0.7077	Intermediate Similarity	NPD5667	Approved
0.7068	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1894	Discontinued
0.7063	Intermediate Similarity	NPD9545	Approved
0.704	Intermediate Similarity	NPD9493	Approved
0.7034	Intermediate Similarity	NPD5909	Discontinued
0.7031	Intermediate Similarity	NPD4106	Approved
0.7031	Intermediate Similarity	NPD4136	Approved
0.7031	Intermediate Similarity	NPD4135	Approved
0.7023	Intermediate Similarity	NPD2160	Approved
0.7023	Intermediate Similarity	NPD2628	Approved
0.7023	Intermediate Similarity	NPD2627	Approved
0.7023	Intermediate Similarity	NPD2159	Approved
0.7023	Intermediate Similarity	NPD2625	Approved
0.7023	Intermediate Similarity	NPD2626	Approved
0.6992	Remote Similarity	NPD4620	Approved
0.6992	Remote Similarity	NPD5201	Approved
0.6992	Remote Similarity	NPD4617	Approved
0.6992	Remote Similarity	NPD5203	Approved
0.6985	Remote Similarity	NPD6355	Discontinued
0.6981	Remote Similarity	NPD226	Approved
0.6977	Remote Similarity	NPD4807	Approved
0.6977	Remote Similarity	NPD4806	Approved
0.697	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD1239	Approved
0.6963	Remote Similarity	NPD4062	Phase 3
0.695	Remote Similarity	NPD2575	Approved
0.695	Remote Similarity	NPD4628	Phase 3
0.6949	Remote Similarity	NPD6647	Phase 2
0.6937	Remote Similarity	NPD800	Approved
0.6923	Remote Similarity	NPD1608	Approved
0.6917	Remote Similarity	NPD6685	Approved
0.6912	Remote Similarity	NPD5120	Approved
0.6912	Remote Similarity	NPD5119	Approved
0.6912	Remote Similarity	NPD5121	Approved
0.6911	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6190	Approved
0.6889	Remote Similarity	NPD2313	Discontinued
0.6889	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1089	Approved
0.6875	Remote Similarity	NPD4105	Approved
0.6875	Remote Similarity	NPD1090	Approved
0.6875	Remote Similarity	NPD1086	Approved
0.6875	Remote Similarity	NPD9258	Approved
0.6875	Remote Similarity	NPD9256	Approved
0.6875	Remote Similarity	NPD4102	Approved
0.6871	Remote Similarity	NPD4380	Phase 2
0.687	Remote Similarity	NPD1989	Approved
0.6866	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.686	Remote Similarity	NPD290	Approved
0.6857	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7236	Approved
0.6846	Remote Similarity	NPD2611	Approved
0.6846	Remote Similarity	NPD1535	Discovery
0.6846	Remote Similarity	NPD2608	Approved
0.6846	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4215	Approved
0.6846	Remote Similarity	NPD4218	Approved
0.6846	Remote Similarity	NPD3131	Approved
0.6846	Remote Similarity	NPD4216	Approved
0.6846	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4217	Approved
0.6846	Remote Similarity	NPD2609	Approved
0.6846	Remote Similarity	NPD2610	Approved
0.6846	Remote Similarity	NPD2612	Approved
0.6846	Remote Similarity	NPD3132	Approved
0.6842	Remote Similarity	NPD1202	Approved
0.6842	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6653	Approved
0.6809	Remote Similarity	NPD1549	Phase 2
0.6807	Remote Similarity	NPD5765	Approved
0.6803	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2650	Approved
0.68	Remote Similarity	NPD2652	Approved
0.6794	Remote Similarity	NPD1481	Phase 2
0.6794	Remote Similarity	NPD9717	Approved
0.6792	Remote Similarity	NPD9490	Approved
0.6791	Remote Similarity	NPD5204	Approved
0.6788	Remote Similarity	NPD6309	Approved
0.6788	Remote Similarity	NPD6311	Approved
0.6788	Remote Similarity	NPD6310	Approved
0.6783	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD1693	Approved
0.6777	Remote Similarity	NPD467	Phase 1
0.6772	Remote Similarity	NPD5291	Approved
0.6772	Remote Similarity	NPD5292	Approved
0.6767	Remote Similarity	NPD2797	Approved
0.6767	Remote Similarity	NPD1203	Approved
0.6765	Remote Similarity	NPD3268	Approved
0.6763	Remote Similarity	NPD7097	Phase 1
0.6759	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5401	Approved
0.6757	Remote Similarity	NPD1282	Approved
0.6757	Remote Similarity	NPD4793	Discontinued
0.6754	Remote Similarity	NPD1088	Approved
0.6742	Remote Similarity	NPD7876	Discontinued
0.6741	Remote Similarity	NPD2613	Approved
0.6739	Remote Similarity	NPD230	Phase 1
0.6733	Remote Similarity	NPD8455	Phase 2
0.6726	Remote Similarity	NPD3673	Approved
0.6726	Remote Similarity	NPD3672	Approved
0.6718	Remote Similarity	NPD1091	Approved
0.6711	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7075	Discontinued
0.6698	Remote Similarity	NPD225	Approved
0.6698	Remote Similarity	NPD227	Approved
0.6695	Remote Similarity	NPD2066	Phase 3
0.6692	Remote Similarity	NPD17	Approved
0.6691	Remote Similarity	NPD7008	Discontinued
0.669	Remote Similarity	NPD6799	Approved
0.6667	Remote Similarity	NPD3661	Approved
0.6667	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD1564	Approved
0.6667	Remote Similarity	NPD1934	Approved
0.6667	Remote Similarity	NPD1565	Approved
0.6667	Remote Similarity	NPD2684	Approved
0.6667	Remote Similarity	NPD9257	Approved
0.6667	Remote Similarity	NPD3662	Phase 3
0.6667	Remote Similarity	NPD6801	Discontinued
0.6667	Remote Similarity	NPD3663	Approved
0.6667	Remote Similarity	NPD9259	Approved
0.6667	Remote Similarity	NPD1566	Phase 3
0.6667	Remote Similarity	NPD3664	Approved
0.6643	Remote Similarity	NPD2569	Approved
0.6643	Remote Similarity	NPD2567	Approved
0.6642	Remote Similarity	NPD3267	Approved
0.6642	Remote Similarity	NPD6362	Approved
0.6642	Remote Similarity	NPD3266	Approved
0.6641	Remote Similarity	NPD3847	Discontinued
0.664	Remote Similarity	NPD6912	Phase 3
0.6637	Remote Similarity	NPD5346	Phase 2
0.6637	Remote Similarity	NPD5347	Phase 2
0.6622	Remote Similarity	NPD7239	Suspended
0.662	Remote Similarity	NPD7266	Discontinued
0.662	Remote Similarity	NPD6002	Phase 3
0.662	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.662	Remote Similarity	NPD6004	Phase 3
0.662	Remote Similarity	NPD6005	Phase 3
0.662	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.662	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.662	Remote Similarity	NPD2346	Discontinued
0.6619	Remote Similarity	NPD447	Suspended
0.6619	Remote Similarity	NPD1933	Approved
0.6618	Remote Similarity	NPD6832	Phase 2
0.6607	Remote Similarity	NPD1087	Approved
0.6604	Remote Similarity	NPD9294	Approved
0.6596	Remote Similarity	NPD7305	Phase 1
0.6596	Remote Similarity	NPD1510	Phase 2
0.6594	Remote Similarity	NPD3089	Approved
0.6594	Remote Similarity	NPD2570	Approved
0.6594	Remote Similarity	NPD2573	Approved
0.6594	Remote Similarity	NPD2566	Approved
0.6594	Remote Similarity	NPD3616	Approved
0.6594	Remote Similarity	NPD4745	Approved
0.6594	Remote Similarity	NPD3087	Approved
0.6594	Remote Similarity	NPD3088	Approved
0.6594	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD4746	Phase 3
0.6594	Remote Similarity	NPD3614	Approved
0.6594	Remote Similarity	NPD3090	Approved
0.6594	Remote Similarity	NPD2571	Approved
0.6594	Remote Similarity	NPD3615	Approved
0.6594	Remote Similarity	NPD2574	Discontinued
0.6593	Remote Similarity	NPD1019	Discontinued
0.6591	Remote Similarity	NPD6287	Discontinued
0.6587	Remote Similarity	NPD7843	Approved
0.6585	Remote Similarity	NPD9264	Approved
0.6585	Remote Similarity	NPD1358	Approved
0.6585	Remote Similarity	NPD9267	Approved
0.6585	Remote Similarity	NPD9263	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