NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.05
Volume:	254.143
LogP:	1.592
LogD:	1.06
LogS:	-3.02
# Rotatable Bonds:	3
TPSA:	62.5
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.797
Synthetic Accessibility Score:	3.652
Fsp3:	0.154
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:	-4.628
MDCK Permeability:	2.2669380996376276e-05
Pgp-inhibitor:	0.226
Pgp-substrate:	0.397
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	80.18265533447266%
Volume Distribution (VD):	1.055
Pgp-substrate:	20.599382400512695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.961
CYP1A2-substrate:	0.937
CYP2C19-inhibitor:	0.098
CYP2C19-substrate:	0.788
CYP2C9-inhibitor:	0.059
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.077
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.294

ADMET: Excretion

Clearance (CL):	4.349
Half-life (T1/2):	0.699

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.661
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.954
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.829
Skin Sensitization:	0.404
Carcinogencity:	0.938
Eye Corrosion:	0.007
Eye Irritation:	0.76
Respiratory Toxicity:	0.457

Download Data

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

Natural Product: NPC472882

Natural Product ID:	NPC472882
*Common Name:**	OGHRWNHXJDCWDO-AATRIKPKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OGHRWNHXJDCWDO-AATRIKPKSA-N
Standard InCHI:	InChI=1S/C13H12O4S/c1-16-9-3-4-13-11(7-9)12(14)8-10(17-13)5-6-18(2)15/h3-8H,1-2H3/b6-5+
SMILES:	COc1ccc2c(c1)c(=O)cc(o2)/C=C/S(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3593557
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579873]
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26225905]
NPO23424	Dirca palustris	Species	Thymelaeaceae	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
IC50	3
Others	3

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	9000.0	nM	PMID[456510]
NPT81	Cell Line	A549	Homo sapiens	Ratio IC50	=	5.0	n.a.	PMID[456510]
NPT579	Cell Line	DLD-1	Homo sapiens	Ratio IC50	=	5.0	n.a.	PMID[456510]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1100.0	nM	PMID[456510]
NPT27	Others	Unspecified		IC50	=	6000.0	nM	PMID[456510]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC90	=	4.1	ug.mL-1	PMID[456510]

☑ 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 NPC472882 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	398
0.1-0.2	2414
0.2-0.3	6140
0.3-0.4	12606
0.4-0.5	4521
0.5-0.6	7019
0.6-0.7	7174
0.7-0.8	2392
0.8-0.85	24
0.85-0.9	6
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9538	High Similarity	NPC472881
0.928	High Similarity	NPC472888
0.8992	High Similarity	NPC298884
0.8984	High Similarity	NPC224657
0.8741	High Similarity	NPC472884
0.8613	High Similarity	NPC472883
0.8561	High Similarity	NPC45537
0.8531	High Similarity	NPC472885
0.8507	High Similarity	NPC7569
0.8444	Intermediate Similarity	NPC141549
0.8382	Intermediate Similarity	NPC474340
0.837	Intermediate Similarity	NPC278787
0.8359	Intermediate Similarity	NPC171023
0.8359	Intermediate Similarity	NPC32298
0.8333	Intermediate Similarity	NPC472886
0.8295	Intermediate Similarity	NPC54243
0.8258	Intermediate Similarity	NPC182646
0.8254	Intermediate Similarity	NPC279916
0.8248	Intermediate Similarity	NPC118253
0.8195	Intermediate Similarity	NPC4012
0.8195	Intermediate Similarity	NPC56332
0.8175	Intermediate Similarity	NPC301717
0.8154	Intermediate Similarity	NPC201284
0.8154	Intermediate Similarity	NPC35744
0.8148	Intermediate Similarity	NPC71525
0.8143	Intermediate Similarity	NPC77955
0.8134	Intermediate Similarity	NPC2771
0.8133	Intermediate Similarity	NPC472887
0.812	Intermediate Similarity	NPC93730
0.8112	Intermediate Similarity	NPC145673
0.8106	Intermediate Similarity	NPC314329
0.8092	Intermediate Similarity	NPC230951
0.8074	Intermediate Similarity	NPC474264
0.8071	Intermediate Similarity	NPC22222
0.8071	Intermediate Similarity	NPC281513
0.8056	Intermediate Similarity	NPC214919
0.8056	Intermediate Similarity	NPC124467
0.8043	Intermediate Similarity	NPC205360
0.8043	Intermediate Similarity	NPC477412
0.8028	Intermediate Similarity	NPC98395
0.8015	Intermediate Similarity	NPC470841
0.7972	Intermediate Similarity	NPC18457
0.7969	Intermediate Similarity	NPC53953
0.7958	Intermediate Similarity	NPC301341
0.7958	Intermediate Similarity	NPC471542
0.7958	Intermediate Similarity	NPC284184
0.7956	Intermediate Similarity	NPC125887
0.7955	Intermediate Similarity	NPC470092
0.7945	Intermediate Similarity	NPC23955
0.7941	Intermediate Similarity	NPC237868
0.7926	Intermediate Similarity	NPC193805
0.7923	Intermediate Similarity	NPC316062
0.7914	Intermediate Similarity	NPC324488
0.7907	Intermediate Similarity	NPC87563
0.7905	Intermediate Similarity	NPC205522
0.7899	Intermediate Similarity	NPC473019
0.7887	Intermediate Similarity	NPC232996
0.7883	Intermediate Similarity	NPC41721
0.7883	Intermediate Similarity	NPC49852
0.7883	Intermediate Similarity	NPC475496
0.7872	Intermediate Similarity	NPC477210
0.7863	Intermediate Similarity	NPC217423
0.7846	Intermediate Similarity	NPC240163
0.7846	Intermediate Similarity	NPC188907
0.7838	Intermediate Similarity	NPC231013
0.7838	Intermediate Similarity	NPC215932
0.7838	Intermediate Similarity	NPC106461
0.7838	Intermediate Similarity	NPC40818
0.7838	Intermediate Similarity	NPC14958
0.7838	Intermediate Similarity	NPC110639
0.7832	Intermediate Similarity	NPC472516
0.7826	Intermediate Similarity	NPC473907
0.7826	Intermediate Similarity	NPC201419
0.7817	Intermediate Similarity	NPC217914
0.7817	Intermediate Similarity	NPC298900
0.7812	Intermediate Similarity	NPC54626
0.7808	Intermediate Similarity	NPC329493
0.7803	Intermediate Similarity	NPC152159
0.7785	Intermediate Similarity	NPC46941
0.7785	Intermediate Similarity	NPC85233
0.7778	Intermediate Similarity	NPC311219
0.777	Intermediate Similarity	NPC57552
0.777	Intermediate Similarity	NPC136278
0.777	Intermediate Similarity	NPC473894
0.7755	Intermediate Similarity	NPC169479
0.7755	Intermediate Similarity	NPC159855
0.7754	Intermediate Similarity	NPC22783
0.7746	Intermediate Similarity	NPC1249
0.7746	Intermediate Similarity	NPC292998
0.774	Intermediate Similarity	NPC124365
0.7733	Intermediate Similarity	NPC63256
0.7733	Intermediate Similarity	NPC10304
0.773	Intermediate Similarity	NPC278556
0.773	Intermediate Similarity	NPC284424
0.7727	Intermediate Similarity	NPC269414
0.7727	Intermediate Similarity	NPC240664
0.7724	Intermediate Similarity	NPC268691
0.7721	Intermediate Similarity	NPC141252
0.7721	Intermediate Similarity	NPC11799
0.7718	Intermediate Similarity	NPC308799
0.7718	Intermediate Similarity	NPC302408
0.7718	Intermediate Similarity	NPC283002
0.7708	Intermediate Similarity	NPC254741
0.7708	Intermediate Similarity	NPC477534
0.7708	Intermediate Similarity	NPC130976
0.7703	Intermediate Similarity	NPC89664
0.7703	Intermediate Similarity	NPC113089
0.7703	Intermediate Similarity	NPC274085
0.7698	Intermediate Similarity	NPC196034
0.7692	Intermediate Similarity	NPC143649
0.7682	Intermediate Similarity	NPC294502
0.7682	Intermediate Similarity	NPC200221
0.7682	Intermediate Similarity	NPC266499
0.7682	Intermediate Similarity	NPC69752
0.7676	Intermediate Similarity	NPC229646
0.7676	Intermediate Similarity	NPC477536
0.7676	Intermediate Similarity	NPC473655
0.7676	Intermediate Similarity	NPC101294
0.7674	Intermediate Similarity	NPC23332
0.7671	Intermediate Similarity	NPC477537
0.7669	Intermediate Similarity	NPC166591
0.7667	Intermediate Similarity	NPC61284
0.7667	Intermediate Similarity	NPC55557
0.7667	Intermediate Similarity	NPC61871
0.7667	Intermediate Similarity	NPC113428
0.7667	Intermediate Similarity	NPC30647
0.7664	Intermediate Similarity	NPC470163
0.7664	Intermediate Similarity	NPC470162
0.7651	Intermediate Similarity	NPC473951
0.7651	Intermediate Similarity	NPC165512
0.7651	Intermediate Similarity	NPC98926
0.7647	Intermediate Similarity	NPC46634
0.7643	Intermediate Similarity	NPC187907
0.7639	Intermediate Similarity	NPC141934
0.7639	Intermediate Similarity	NPC194847
0.7639	Intermediate Similarity	NPC278832
0.7639	Intermediate Similarity	NPC21797
0.7639	Intermediate Similarity	NPC64157
0.7635	Intermediate Similarity	NPC70853
0.7635	Intermediate Similarity	NPC9966
0.7632	Intermediate Similarity	NPC101957
0.7632	Intermediate Similarity	NPC259058
0.7632	Intermediate Similarity	NPC306821
0.7632	Intermediate Similarity	NPC120105
0.7632	Intermediate Similarity	NPC201547
0.7632	Intermediate Similarity	NPC184136
0.763	Intermediate Similarity	NPC225245
0.7622	Intermediate Similarity	NPC265793
0.7619	Intermediate Similarity	NPC171094
0.7619	Intermediate Similarity	NPC149780
0.7619	Intermediate Similarity	NPC58229
0.7616	Intermediate Similarity	NPC118726
0.7616	Intermediate Similarity	NPC5537
0.7616	Intermediate Similarity	NPC186397
0.7616	Intermediate Similarity	NPC37135
0.7616	Intermediate Similarity	NPC12367
0.7616	Intermediate Similarity	NPC474107
0.7612	Intermediate Similarity	NPC43435
0.7609	Intermediate Similarity	NPC65041
0.7609	Intermediate Similarity	NPC4164
0.7609	Intermediate Similarity	NPC470858
0.7606	Intermediate Similarity	NPC477406
0.7606	Intermediate Similarity	NPC475589
0.7606	Intermediate Similarity	NPC31872
0.7606	Intermediate Similarity	NPC473584
0.7603	Intermediate Similarity	NPC36414
0.7603	Intermediate Similarity	NPC477408
0.76	Intermediate Similarity	NPC216314
0.76	Intermediate Similarity	NPC60389
0.76	Intermediate Similarity	NPC195919
0.76	Intermediate Similarity	NPC120924
0.7597	Intermediate Similarity	NPC186507
0.7597	Intermediate Similarity	NPC476289
0.7597	Intermediate Similarity	NPC183648
0.7597	Intermediate Similarity	NPC472408
0.7594	Intermediate Similarity	NPC45104
0.7589	Intermediate Similarity	NPC228184
0.7589	Intermediate Similarity	NPC473271
0.7586	Intermediate Similarity	NPC72452
0.7586	Intermediate Similarity	NPC61546
0.7582	Intermediate Similarity	NPC226973
0.7582	Intermediate Similarity	NPC149614
0.7582	Intermediate Similarity	NPC308451
0.7582	Intermediate Similarity	NPC475076
0.7582	Intermediate Similarity	NPC208043
0.7574	Intermediate Similarity	NPC476165
0.7569	Intermediate Similarity	NPC125269
0.7569	Intermediate Similarity	NPC66705
0.7568	Intermediate Similarity	NPC24075
0.7568	Intermediate Similarity	NPC29536
0.7566	Intermediate Similarity	NPC181250
0.7566	Intermediate Similarity	NPC238366
0.7566	Intermediate Similarity	NPC223988
0.7556	Intermediate Similarity	NPC246214
0.7554	Intermediate Similarity	NPC51037
0.7552	Intermediate Similarity	NPC25937
0.7552	Intermediate Similarity	NPC182428
0.7552	Intermediate Similarity	NPC128216
0.7551	Intermediate Similarity	NPC109007
0.7551	Intermediate Similarity	NPC472515

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 NPC472882 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	1055
0.2-0.3	1482
0.3-0.4	2801
0.4-0.5	1967
0.5-0.6	1107
0.6-0.7	306
0.7-0.8	65
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8106	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD2313	Discontinued
0.7929	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1241	Discontinued
0.7826	Intermediate Similarity	NPD6832	Phase 2
0.781	Intermediate Similarity	NPD1019	Discontinued
0.7801	Intermediate Similarity	NPD447	Suspended
0.7778	Intermediate Similarity	NPD2346	Discontinued
0.7778	Intermediate Similarity	NPD9717	Approved
0.7708	Intermediate Similarity	NPD2935	Discontinued
0.7681	Intermediate Similarity	NPD2798	Approved
0.7647	Intermediate Similarity	NPD6844	Discontinued
0.7639	Intermediate Similarity	NPD2799	Discontinued
0.7609	Intermediate Similarity	NPD1203	Approved
0.7589	Intermediate Similarity	NPD411	Approved
0.7586	Intermediate Similarity	NPD2796	Approved
0.7484	Intermediate Similarity	NPD2801	Approved
0.7436	Intermediate Similarity	NPD5402	Approved
0.7431	Intermediate Similarity	NPD1933	Approved
0.7415	Intermediate Similarity	NPD2344	Approved
0.7415	Intermediate Similarity	NPD1471	Phase 3
0.7372	Intermediate Similarity	NPD3496	Discontinued
0.7361	Intermediate Similarity	NPD4307	Phase 2
0.7351	Intermediate Similarity	NPD1511	Approved
0.7338	Intermediate Similarity	NPD3226	Approved
0.7324	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD920	Approved
0.7312	Intermediate Similarity	NPD1247	Approved
0.7303	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1510	Phase 2
0.7267	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD9493	Approved
0.7259	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1512	Approved
0.725	Intermediate Similarity	NPD5494	Approved
0.7248	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1549	Phase 2
0.7241	Intermediate Similarity	NPD1240	Approved
0.7234	Intermediate Similarity	NPD3267	Approved
0.7234	Intermediate Similarity	NPD3266	Approved
0.723	Intermediate Similarity	NPD2531	Phase 2
0.723	Intermediate Similarity	NPD1551	Phase 2
0.7219	Intermediate Similarity	NPD2309	Approved
0.7209	Intermediate Similarity	NPD9697	Approved
0.72	Intermediate Similarity	NPD1243	Approved
0.719	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD17	Approved
0.7171	Intermediate Similarity	NPD7440	Discontinued
0.7169	Intermediate Similarity	NPD5953	Discontinued
0.7163	Intermediate Similarity	NPD1876	Approved
0.7162	Intermediate Similarity	NPD4308	Phase 3
0.7162	Intermediate Similarity	NPD3748	Approved
0.7143	Intermediate Similarity	NPD3972	Approved
0.7143	Intermediate Similarity	NPD1607	Approved
0.7124	Intermediate Similarity	NPD6799	Approved
0.7107	Intermediate Similarity	NPD3817	Phase 2
0.7089	Intermediate Similarity	NPD1934	Approved
0.7078	Intermediate Similarity	NPD5401	Approved
0.7071	Intermediate Similarity	NPD1611	Approved
0.7063	Intermediate Similarity	NPD3882	Suspended
0.7059	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6671	Approved
0.705	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7819	Suspended
0.7044	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD5049	Phase 3
0.7021	Intermediate Similarity	NPD1608	Approved
0.7021	Intermediate Similarity	NPD1481	Phase 2
0.7007	Intermediate Similarity	NPD3142	Approved
0.7007	Intermediate Similarity	NPD3140	Approved
0.6993	Remote Similarity	NPD1470	Approved
0.6993	Remote Similarity	NPD2797	Approved
0.6987	Remote Similarity	NPD5403	Approved
0.6986	Remote Similarity	NPD3268	Approved
0.6978	Remote Similarity	NPD1651	Approved
0.6978	Remote Similarity	NPD5585	Approved
0.6975	Remote Similarity	NPD919	Approved
0.6974	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4661	Approved
0.6968	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4662	Approved
0.6957	Remote Similarity	NPD5536	Phase 2
0.695	Remote Similarity	NPD1535	Discovery
0.6946	Remote Similarity	NPD7286	Phase 2
0.6939	Remote Similarity	NPD4062	Phase 3
0.6929	Remote Similarity	NPD1778	Approved
0.6928	Remote Similarity	NPD3750	Approved
0.6923	Remote Similarity	NPD9261	Approved
0.6899	Remote Similarity	NPD2651	Approved
0.6899	Remote Similarity	NPD2649	Approved
0.6897	Remote Similarity	NPD9494	Approved
0.6889	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6279	Approved
0.6875	Remote Similarity	NPD6280	Approved
0.6871	Remote Similarity	NPD1296	Phase 2
0.6863	Remote Similarity	NPD2800	Approved
0.6855	Remote Similarity	NPD6599	Discontinued
0.6855	Remote Similarity	NPD4380	Phase 2
0.6832	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD1201	Approved
0.6831	Remote Similarity	NPD1281	Approved
0.6829	Remote Similarity	NPD1559	Discontinued
0.6813	Remote Similarity	NPD7411	Suspended
0.6813	Remote Similarity	NPD5890	Approved
0.6813	Remote Similarity	NPD5889	Approved
0.681	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD3926	Phase 2
0.6786	Remote Similarity	NPD3818	Discontinued
0.6783	Remote Similarity	NPD1244	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD2339	Phase 3
0.6774	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6801	Discontinued
0.6767	Remote Similarity	NPD968	Approved
0.6753	Remote Similarity	NPD1652	Phase 2
0.675	Remote Similarity	NPD6585	Discontinued
0.6747	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7229	Phase 3
0.6742	Remote Similarity	NPD164	Approved
0.6738	Remote Similarity	NPD5691	Approved
0.6736	Remote Similarity	NPD4359	Approved
0.6733	Remote Similarity	NPD4622	Approved
0.6733	Remote Similarity	NPD4618	Approved
0.6732	Remote Similarity	NPD2353	Approved
0.6732	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD9267	Approved
0.6716	Remote Similarity	NPD9264	Approved
0.6716	Remote Similarity	NPD1358	Approved
0.6716	Remote Similarity	NPD9263	Approved
0.6711	Remote Similarity	NPD6233	Phase 2
0.671	Remote Similarity	NPD4628	Phase 3
0.6707	Remote Similarity	NPD7075	Discontinued
0.6707	Remote Similarity	NPD6971	Discontinued
0.669	Remote Similarity	NPD3225	Approved
0.669	Remote Similarity	NPD1283	Approved
0.6687	Remote Similarity	NPD2296	Approved
0.6687	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5712	Approved
0.6667	Remote Similarity	NPD2182	Approved
0.6667	Remote Similarity	NPD943	Approved
0.6667	Remote Similarity	NPD1894	Discontinued
0.6667	Remote Similarity	NPD6166	Phase 2
0.6667	Remote Similarity	NPD74	Approved
0.6667	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9266	Approved
0.6667	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3887	Approved
0.6667	Remote Similarity	NPD7317	Phase 3
0.6667	Remote Similarity	NPD2979	Phase 3
0.6667	Remote Similarity	NPD9545	Approved
0.6647	Remote Similarity	NPD6808	Phase 2
0.6647	Remote Similarity	NPD7054	Approved
0.6646	Remote Similarity	NPD7768	Phase 2
0.6646	Remote Similarity	NPD2534	Approved
0.6646	Remote Similarity	NPD2532	Approved
0.6646	Remote Similarity	NPD2533	Approved
0.6645	Remote Similarity	NPD5689	Approved
0.6645	Remote Similarity	NPD5688	Approved
0.6645	Remote Similarity	NPD2654	Approved
0.6644	Remote Similarity	NPD6798	Discontinued
0.6644	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD3134	Approved
0.6626	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4340	Discontinued
0.6623	Remote Similarity	NPD6355	Discontinued
0.6621	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD7472	Approved
0.6606	Remote Similarity	NPD3749	Approved
0.6604	Remote Similarity	NPD6273	Approved
0.6603	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD7033	Discontinued
0.66	Remote Similarity	NPD8032	Phase 2
0.6599	Remote Similarity	NPD5647	Approved
0.6597	Remote Similarity	NPD422	Phase 1
0.6594	Remote Similarity	NPD5535	Approved
0.6593	Remote Similarity	NPD290	Approved
0.6587	Remote Similarity	NPD6959	Discontinued
0.6587	Remote Similarity	NPD5262	Discontinued
0.6585	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7318	Phase 3
0.6581	Remote Similarity	NPD2424	Discontinued
0.6573	Remote Similarity	NPD4626	Approved
0.657	Remote Similarity	NPD6797	Phase 2
0.6565	Remote Similarity	NPD1238	Approved
0.6562	Remote Similarity	NPD8012	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD2354	Approved
0.6558	Remote Similarity	NPD6032	Approved
0.6554	Remote Similarity	NPD2237	Approved
0.6545	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6559	Discontinued
0.6532	Remote Similarity	NPD7251	Discontinued
0.6522	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD160	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