NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	352.13
Volume:	360.406
LogP:	5.228
LogD:	3.815
LogS:	-3.497
# Rotatable Bonds:	1
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.622
Synthetic Accessibility Score:	3.109
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.872
MDCK Permeability:	1.6490239431732334e-05
Pgp-inhibitor:	0.556
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.11
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.047

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	98.56635284423828%
Volume Distribution (VD):	0.627
Pgp-substrate:	2.5867462158203125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.903
CYP1A2-substrate:	0.7
CYP2C19-inhibitor:	0.609
CYP2C19-substrate:	0.088
CYP2C9-inhibitor:	0.843
CYP2C9-substrate:	0.825
CYP2D6-inhibitor:	0.51
CYP2D6-substrate:	0.209
CYP3A4-inhibitor:	0.317
CYP3A4-substrate:	0.153

ADMET: Excretion

Clearance (CL):	2.155
Half-life (T1/2):	0.237

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.916
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.622
Rat Oral Acute Toxicity:	0.874
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.526
Carcinogencity:	0.857
Eye Corrosion:	0.004
Eye Irritation:	0.385
Respiratory Toxicity:	0.784

Download Data

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

Natural Product: NPC329678

Natural Product ID:	NPC329678
*Common Name:**	Artonol A
IUPAC Name:	6-hydroxy-3,3-dimethyl-9-prop-1-en-2-yl-9,10-dihydro-8H-pyrano[2,3-c]xanthene-7,11-dione
Synonyms:
Standard InCHIKey:	XCESLDIMJGQRPW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H20O5/c1-10(2)11-7-13-18(24)17-14(22)9-16-12(5-6-21(3,4)26-16)20(17)25-19(13)15(23)8-11/h5-6,9,11,22H,1,7-8H2,2-4H3
SMILES:	C=C(C)C1Cc2c(=O)c3c(cc4c(C=CC(C)(C)O4)c3oc2C(=O)C1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463089
PubChem CID:	10736715
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003521] Pyranoxanthones

*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
NPO2376	Artocarpus elasticus	Species	Moraceae	Eukaryota	roots	Ping-Tung Hsien, Taiwan	2002-AUG	PMID[16309328]
NPO32569	artocarpus rigida	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384315]
NPO32569	artocarpus rigida	Species	Moraceae	Eukaryota	Stems	n.a.	n.a.	PMID[29227656]
NPO2376	Artocarpus elasticus	Species	Moraceae	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	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	1.1	ug ml-1	PMID[567193]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	3.1	ug ml-1	PMID[567193]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	2.7	ug ml-1	PMID[567193]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	21.9	ug ml-1	PMID[567193]

☑ 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 NPC329678 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	415
0.1-0.2	1716
0.2-0.3	4539
0.3-0.4	11690
0.4-0.5	6643
0.5-0.6	4528
0.6-0.7	5938
0.7-0.8	4358
0.8-0.85	1888
0.85-0.9	862
0.9-0.95	118
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC204469
0.951	High Similarity	NPC14001
0.951	High Similarity	NPC166757
0.9504	High Similarity	NPC62840
0.9504	High Similarity	NPC293852
0.9504	High Similarity	NPC59739
0.9504	High Similarity	NPC78803
0.9504	High Similarity	NPC217083
0.9504	High Similarity	NPC214236
0.9504	High Similarity	NPC299080
0.9496	High Similarity	NPC470668
0.9496	High Similarity	NPC470669
0.9444	High Similarity	NPC244407
0.9441	High Similarity	NPC220418
0.9384	High Similarity	NPC81474
0.9371	High Similarity	NPC326500
0.9366	High Similarity	NPC200694
0.931	High Similarity	NPC296869
0.9306	High Similarity	NPC476088
0.9306	High Similarity	NPC5820
0.9306	High Similarity	NPC124729
0.9306	High Similarity	NPC474161
0.9306	High Similarity	NPC178343
0.9306	High Similarity	NPC306488
0.9301	High Similarity	NPC38219
0.9301	High Similarity	NPC219915
0.9301	High Similarity	NPC293053
0.9301	High Similarity	NPC158874
0.9301	High Similarity	NPC212932
0.9301	High Similarity	NPC9117
0.9301	High Similarity	NPC24821
0.9301	High Similarity	NPC190637
0.9296	High Similarity	NPC282300
0.9296	High Similarity	NPC205006
0.9296	High Similarity	NPC156590
0.9296	High Similarity	NPC118840
0.9296	High Similarity	NPC64908
0.9296	High Similarity	NPC147688
0.9291	High Similarity	NPC301217
0.9291	High Similarity	NPC303633
0.9291	High Similarity	NPC216978
0.9291	High Similarity	NPC55018
0.9291	High Similarity	NPC220062
0.9291	High Similarity	NPC96565
0.9291	High Similarity	NPC23257
0.9262	High Similarity	NPC470354
0.9262	High Similarity	NPC470352
0.9247	High Similarity	NPC470461
0.9241	High Similarity	NPC201731
0.9241	High Similarity	NPC237635
0.9241	High Similarity	NPC79469
0.9241	High Similarity	NPC249942
0.9241	High Similarity	NPC24673
0.9241	High Similarity	NPC104406
0.9241	High Similarity	NPC97716
0.9241	High Similarity	NPC297886
0.9236	High Similarity	NPC273538
0.9236	High Similarity	NPC319752
0.9236	High Similarity	NPC216538
0.9231	High Similarity	NPC226636
0.9231	High Similarity	NPC11561
0.9231	High Similarity	NPC473042
0.9225	High Similarity	NPC235239
0.9225	High Similarity	NPC150522
0.9225	High Similarity	NPC159275
0.9225	High Similarity	NPC172986
0.9225	High Similarity	NPC261227
0.9225	High Similarity	NPC305355
0.9225	High Similarity	NPC241100
0.9225	High Similarity	NPC471587
0.9225	High Similarity	NPC475680
0.9225	High Similarity	NPC270883
0.922	High Similarity	NPC201395
0.922	High Similarity	NPC470671
0.922	High Similarity	NPC131130
0.922	High Similarity	NPC474487
0.922	High Similarity	NPC474504
0.922	High Similarity	NPC470672
0.9214	High Similarity	NPC174999
0.9189	High Similarity	NPC45934
0.9178	High Similarity	NPC469933
0.9178	High Similarity	NPC161191
0.9178	High Similarity	NPC211811
0.9178	High Similarity	NPC321623
0.9178	High Similarity	NPC161864
0.9178	High Similarity	NPC6511
0.9178	High Similarity	NPC470460
0.9178	High Similarity	NPC208303
0.9178	High Similarity	NPC189087
0.9178	High Similarity	NPC266572
0.9172	High Similarity	NPC54577
0.9172	High Similarity	NPC246948
0.9172	High Similarity	NPC142405
0.9172	High Similarity	NPC67805
0.9172	High Similarity	NPC176229
0.9172	High Similarity	NPC470647
0.9172	High Similarity	NPC20488
0.9172	High Similarity	NPC195621
0.9172	High Similarity	NPC57470
0.9172	High Similarity	NPC88964
0.9172	High Similarity	NPC470458
0.9172	High Similarity	NPC301276
0.9172	High Similarity	NPC111786
0.9172	High Similarity	NPC214774
0.9172	High Similarity	NPC475052
0.9172	High Similarity	NPC312973
0.9172	High Similarity	NPC83357
0.9172	High Similarity	NPC267375
0.9161	High Similarity	NPC103362
0.9161	High Similarity	NPC470555
0.9161	High Similarity	NPC262094
0.9161	High Similarity	NPC110969
0.9161	High Similarity	NPC14871
0.9161	High Similarity	NPC90582
0.9155	High Similarity	NPC78913
0.9155	High Similarity	NPC217186
0.9155	High Similarity	NPC18260
0.9155	High Similarity	NPC53181
0.9155	High Similarity	NPC472343
0.9155	High Similarity	NPC473076
0.9143	High Similarity	NPC46869
0.9143	High Similarity	NPC151113
0.9143	High Similarity	NPC101752
0.9137	High Similarity	NPC93756
0.9137	High Similarity	NPC108113
0.9128	High Similarity	NPC311579
0.9128	High Similarity	NPC236756
0.9116	High Similarity	NPC469932
0.9116	High Similarity	NPC5173
0.911	High Similarity	NPC180477
0.911	High Similarity	NPC296998
0.911	High Similarity	NPC110303
0.911	High Similarity	NPC23728
0.911	High Similarity	NPC283234
0.911	High Similarity	NPC473077
0.9103	High Similarity	NPC257236
0.9103	High Similarity	NPC278175
0.9103	High Similarity	NPC234629
0.9103	High Similarity	NPC131568
0.9103	High Similarity	NPC131579
0.9103	High Similarity	NPC311741
0.9097	High Similarity	NPC144499
0.9091	High Similarity	NPC477272
0.9091	High Similarity	NPC146679
0.9091	High Similarity	NPC103342
0.9091	High Similarity	NPC69769
0.9091	High Similarity	NPC59951
0.9091	High Similarity	NPC103904
0.9091	High Similarity	NPC230285
0.9091	High Similarity	NPC221173
0.9091	High Similarity	NPC184536
0.9085	High Similarity	NPC54820
0.9085	High Similarity	NPC180501
0.9085	High Similarity	NPC17848
0.9085	High Similarity	NPC268178
0.9078	High Similarity	NPC187826
0.9078	High Similarity	NPC13408
0.9078	High Similarity	NPC156910
0.9071	High Similarity	NPC125920
0.9065	High Similarity	NPC10971
0.906	High Similarity	NPC142527
0.906	High Similarity	NPC470353
0.9054	High Similarity	NPC471984
0.9054	High Similarity	NPC188403
0.9054	High Similarity	NPC29777
0.9054	High Similarity	NPC61258
0.9054	High Similarity	NPC471115
0.9048	High Similarity	NPC132592
0.9048	High Similarity	NPC160821
0.9041	High Similarity	NPC285630
0.9041	High Similarity	NPC127059
0.9041	High Similarity	NPC154217
0.9041	High Similarity	NPC477955
0.9034	High Similarity	NPC112791
0.9034	High Similarity	NPC106985
0.9034	High Similarity	NPC94794
0.9034	High Similarity	NPC223812
0.9034	High Similarity	NPC473812
0.9034	High Similarity	NPC242100
0.9034	High Similarity	NPC81697
0.9034	High Similarity	NPC87609
0.9034	High Similarity	NPC214166
0.9034	High Similarity	NPC85162
0.9034	High Similarity	NPC470296
0.9034	High Similarity	NPC316816
0.9034	High Similarity	NPC278249
0.9034	High Similarity	NPC125894
0.9034	High Similarity	NPC473813
0.9034	High Similarity	NPC107177
0.9034	High Similarity	NPC77794
0.9034	High Similarity	NPC11700
0.9034	High Similarity	NPC188632
0.9034	High Similarity	NPC255133
0.9034	High Similarity	NPC166138
0.9034	High Similarity	NPC18585
0.9034	High Similarity	NPC196459
0.9034	High Similarity	NPC478086
0.9028	High Similarity	NPC316911
0.9028	High Similarity	NPC136840
0.9028	High Similarity	NPC316560

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 NPC329678 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	372
0.1-0.2	981
0.2-0.3	1583
0.3-0.4	2775
0.4-0.5	1908
0.5-0.6	1067
0.6-0.7	325
0.7-0.8	101
0.8-0.85	32
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9236	High Similarity	NPD4378	Clinical (unspecified phase)
0.9103	High Similarity	NPD7410	Clinical (unspecified phase)
0.8621	High Similarity	NPD1552	Clinical (unspecified phase)
0.8621	High Similarity	NPD1550	Clinical (unspecified phase)
0.8581	High Similarity	NPD7075	Discontinued
0.8571	High Similarity	NPD8443	Clinical (unspecified phase)
0.8562	High Similarity	NPD6801	Discontinued
0.8562	High Similarity	NPD1549	Phase 2
0.8506	High Similarity	NPD7096	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD7411	Suspended
0.8483	Intermediate Similarity	NPD1510	Phase 2
0.8462	Intermediate Similarity	NPD1240	Approved
0.8431	Intermediate Similarity	NPD4380	Phase 2
0.8425	Intermediate Similarity	NPD2796	Approved
0.8411	Intermediate Similarity	NPD1512	Approved
0.84	Intermediate Similarity	NPD6799	Approved
0.8387	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD2800	Approved
0.8345	Intermediate Similarity	NPD1607	Approved
0.8345	Intermediate Similarity	NPD6651	Approved
0.8333	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD3750	Approved
0.8278	Intermediate Similarity	NPD1511	Approved
0.8235	Intermediate Similarity	NPD5403	Approved
0.8194	Intermediate Similarity	NPD6599	Discontinued
0.8188	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD3882	Suspended
0.8153	Intermediate Similarity	NPD7819	Suspended
0.8153	Intermediate Similarity	NPD2801	Approved
0.8113	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD5401	Approved
0.8101	Intermediate Similarity	NPD3817	Phase 2
0.8089	Intermediate Similarity	NPD1934	Approved
0.805	Intermediate Similarity	NPD7768	Phase 2
0.8037	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD6166	Phase 2
0.8013	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1243	Approved
0.8	Intermediate Similarity	NPD3749	Approved
0.7987	Intermediate Similarity	NPD3748	Approved
0.7963	Intermediate Similarity	NPD6959	Discontinued
0.7905	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD5124	Phase 1
0.7904	Intermediate Similarity	NPD6797	Phase 2
0.7875	Intermediate Similarity	NPD5402	Approved
0.7867	Intermediate Similarity	NPD2799	Discontinued
0.7857	Intermediate Similarity	NPD7251	Discontinued
0.7843	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD6100	Approved
0.7815	Intermediate Similarity	NPD6099	Approved
0.7811	Intermediate Similarity	NPD7808	Phase 3
0.7811	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD5494	Approved
0.7771	Intermediate Similarity	NPD920	Approved
0.7756	Intermediate Similarity	NPD2532	Approved
0.7756	Intermediate Similarity	NPD2534	Approved
0.7756	Intermediate Similarity	NPD2533	Approved
0.7742	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD919	Approved
0.7727	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD3268	Approved
0.7703	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD2313	Discontinued
0.7697	Intermediate Similarity	NPD2935	Discontinued
0.7697	Intermediate Similarity	NPD1551	Phase 2
0.7692	Intermediate Similarity	NPD422	Phase 1
0.7679	Intermediate Similarity	NPD7054	Approved
0.7665	Intermediate Similarity	NPD7473	Discontinued
0.7647	Intermediate Similarity	NPD2344	Approved
0.7643	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD9717	Approved
0.7636	Intermediate Similarity	NPD1247	Approved
0.7633	Intermediate Similarity	NPD7074	Phase 3
0.7633	Intermediate Similarity	NPD7472	Approved
0.7619	Intermediate Similarity	NPD3818	Discontinued
0.7603	Intermediate Similarity	NPD2797	Approved
0.7603	Intermediate Similarity	NPD1203	Approved
0.759	Intermediate Similarity	NPD6232	Discontinued
0.7588	Intermediate Similarity	NPD5953	Discontinued
0.7584	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7286	Phase 2
0.7568	Intermediate Similarity	NPD4908	Phase 1
0.7551	Intermediate Similarity	NPD2798	Approved
0.7534	Intermediate Similarity	NPD3225	Approved
0.7516	Intermediate Similarity	NPD7033	Discontinued
0.7516	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2403	Approved
0.7472	Intermediate Similarity	NPD4363	Phase 3
0.7472	Intermediate Similarity	NPD4360	Phase 2
0.7468	Intermediate Similarity	NPD7390	Discontinued
0.7466	Intermediate Similarity	NPD4749	Approved
0.7453	Intermediate Similarity	NPD3226	Approved
0.7452	Intermediate Similarity	NPD2309	Approved
0.7442	Intermediate Similarity	NPD6559	Discontinued
0.7436	Intermediate Similarity	NPD2654	Approved
0.7413	Intermediate Similarity	NPD1548	Phase 1
0.7403	Intermediate Similarity	NPD4308	Phase 3
0.7368	Intermediate Similarity	NPD943	Approved
0.7368	Intermediate Similarity	NPD5844	Phase 1
0.7365	Intermediate Similarity	NPD3267	Approved
0.7365	Intermediate Similarity	NPD3266	Approved
0.7351	Intermediate Similarity	NPD1296	Phase 2
0.7337	Intermediate Similarity	NPD3926	Phase 2
0.7333	Intermediate Similarity	NPD4288	Approved
0.7333	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6832	Phase 2
0.7333	Intermediate Similarity	NPD4361	Phase 2
0.7329	Intermediate Similarity	NPD1610	Phase 2
0.7329	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2346	Discontinued
0.7294	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4625	Phase 3
0.7283	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4628	Phase 3
0.7267	Intermediate Similarity	NPD5049	Phase 3
0.7263	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6798	Discontinued
0.7233	Intermediate Similarity	NPD2354	Approved
0.7225	Intermediate Similarity	NPD1729	Discontinued
0.7209	Intermediate Similarity	NPD3751	Discontinued
0.7197	Intermediate Similarity	NPD1471	Phase 3
0.7195	Intermediate Similarity	NPD6585	Discontinued
0.7183	Intermediate Similarity	NPD1241	Discontinued
0.7179	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5711	Approved
0.7176	Intermediate Similarity	NPD5710	Approved
0.7172	Intermediate Similarity	NPD9545	Approved
0.7169	Intermediate Similarity	NPD1465	Phase 2
0.7162	Intermediate Similarity	NPD1608	Approved
0.7153	Intermediate Similarity	NPD9493	Approved
0.7143	Intermediate Similarity	NPD4307	Phase 2
0.7134	Intermediate Similarity	NPD7458	Discontinued
0.7124	Intermediate Similarity	NPD411	Approved
0.7099	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD447	Suspended
0.7097	Intermediate Similarity	NPD6355	Discontinued
0.7089	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2353	Approved
0.7076	Intermediate Similarity	NPD3787	Discontinued
0.7063	Intermediate Similarity	NPD7003	Approved
0.7056	Intermediate Similarity	NPD4287	Approved
0.7048	Intermediate Similarity	NPD5890	Approved
0.7048	Intermediate Similarity	NPD5889	Approved
0.7047	Intermediate Similarity	NPD3972	Approved
0.7045	Intermediate Similarity	NPD6104	Discontinued
0.7039	Intermediate Similarity	NPD8434	Phase 2
0.7037	Intermediate Similarity	NPD7584	Approved
0.7035	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4060	Phase 1
0.703	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5406	Approved
0.7025	Intermediate Similarity	NPD5405	Approved
0.7025	Intermediate Similarity	NPD5408	Approved
0.7025	Intermediate Similarity	NPD5404	Approved
0.7019	Intermediate Similarity	NPD3887	Approved
0.7013	Intermediate Similarity	NPD3764	Approved
0.7012	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1933	Approved
0.6987	Remote Similarity	NPD230	Phase 1
0.698	Remote Similarity	NPD1201	Approved
0.6977	Remote Similarity	NPD7229	Phase 3
0.6975	Remote Similarity	NPD3300	Phase 2
0.6974	Remote Similarity	NPD1019	Discontinued
0.6968	Remote Similarity	NPD6233	Phase 2
0.6959	Remote Similarity	NPD17	Approved
0.6954	Remote Similarity	NPD3446	Phase 1
0.6944	Remote Similarity	NPD8150	Discontinued
0.6937	Remote Similarity	NPD2424	Discontinued
0.6928	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2296	Approved
0.6908	Remote Similarity	NPD1164	Approved
0.6908	Remote Similarity	NPD1470	Approved
0.6905	Remote Similarity	NPD7577	Discontinued
0.6898	Remote Similarity	NPD6779	Approved
0.6898	Remote Similarity	NPD6781	Approved
0.6898	Remote Similarity	NPD6782	Approved
0.6898	Remote Similarity	NPD6780	Approved
0.6898	Remote Similarity	NPD6778	Approved
0.6898	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD6777	Approved
0.6898	Remote Similarity	NPD6776	Approved
0.6894	Remote Similarity	NPD1652	Phase 2
0.6879	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7435	Discontinued
0.6875	Remote Similarity	NPD6004	Phase 3
0.6875	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6002	Phase 3
0.6875	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6003	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