NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.1
Volume:	278.965
LogP:	3.432
LogD:	3.261
LogS:	-4.751
# Rotatable Bonds:	0
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.737
Synthetic Accessibility Score:	3.583
Fsp3:	0.375
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.728
MDCK Permeability:	2.6091676772921346e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.192

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	95.5093002319336%
Volume Distribution (VD):	0.52
Pgp-substrate:	2.068897247314453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.624
CYP2C19-inhibitor:	0.89
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.834
CYP2C9-substrate:	0.675
CYP2D6-inhibitor:	0.958
CYP2D6-substrate:	0.202
CYP3A4-inhibitor:	0.797
CYP3A4-substrate:	0.167

ADMET: Excretion

Clearance (CL):	8.36
Half-life (T1/2):	0.09

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.617
AMES Toxicity:	0.24
Rat Oral Acute Toxicity:	0.473
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.471
Carcinogencity:	0.645
Eye Corrosion:	0.03
Eye Irritation:	0.922
Respiratory Toxicity:	0.583

Download Data

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

Natural Product: NPC119542

Natural Product ID:	NPC119542
*Common Name:**	(-)-Trypethelone
IUPAC Name:	(2S)-7-hydroxy-2,3,3,9-tetramethyl-2H-benzo[g][1]benzofuran-4,5-dione
Synonyms:	(-)-Trypethelone
Standard InCHIKey:	MKAVSGZPSXLJKL-QMMMGPOBSA-N
Standard InCHI:	InChI=1S/C16H16O4/c1-7-5-9(17)6-10-11(7)15-12(14(19)13(10)18)16(3,4)8(2)20-15/h5-6,8,17H,1-4H3/t8-/m0/s1
SMILES:	Oc1cc(C)c2c(c1)C(=O)C(=O)C1=C2O[C@H](C1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1835011
PubChem CID:	56598333
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO6989	Coniothyrium cereale	Species	Coniothyriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21923104]
NPO6989	Coniothyrium cereale	Species	Coniothyriaceae	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	8
Others	3

Activity Type	# Activity
Cell Line	1
Individual Protein	4
Organism	3
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	IC50	>	20000.0	nM	PMID[513048]
NPT1460	Cell Line	L929	Mus musculus	IC50	=	7500.0	nM	PMID[513048]
NPT201	Individual Protein	Papain	Carica papaya	IC50	>	50000.0	nM	PMID[513048]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	>	50000.0	nM	PMID[513048]
NPT1177	Organism	Mycobacterium phlei	Mycobacterium phlei	IZ	=	18.0	mm	PMID[513048]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	14.0	mm	PMID[513048]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	12.0	mm	PMID[513048]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[513048]
NPT670	Individual Protein	Thrombin	Homo sapiens	IC50	>	50000.0	nM	PMID[513048]

☑ 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 NPC119542 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	306
0.1-0.2	1366
0.2-0.3	2871
0.3-0.4	6632
0.4-0.5	11594
0.5-0.6	4697
0.6-0.7	8721
0.7-0.8	6207
0.8-0.85	290
0.85-0.9	10
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9466	High Similarity	NPC477407
0.9185	High Similarity	NPC38158
0.875	High Similarity	NPC165612
0.8686	High Similarity	NPC310662
0.8686	High Similarity	NPC59459
0.8613	High Similarity	NPC477406
0.8551	High Similarity	NPC263817
0.8542	High Similarity	NPC471451
0.8531	High Similarity	NPC201297
0.8493	Intermediate Similarity	NPC5568
0.8487	Intermediate Similarity	NPC323965
0.8487	Intermediate Similarity	NPC313368
0.8483	Intermediate Similarity	NPC474630
0.8444	Intermediate Similarity	NPC204579
0.8444	Intermediate Similarity	NPC110211
0.8444	Intermediate Similarity	NPC15837
0.8444	Intermediate Similarity	NPC254492
0.8425	Intermediate Similarity	NPC470570
0.8414	Intermediate Similarity	NPC260152
0.8403	Intermediate Similarity	NPC308572
0.8392	Intermediate Similarity	NPC156872
0.8382	Intermediate Similarity	NPC72667
0.8369	Intermediate Similarity	NPC471670
0.8367	Intermediate Similarity	NPC476821
0.8357	Intermediate Similarity	NPC202225
0.8356	Intermediate Similarity	NPC478160
0.8356	Intermediate Similarity	NPC34482
0.8356	Intermediate Similarity	NPC225351
0.8356	Intermediate Similarity	NPC258856
0.8356	Intermediate Similarity	NPC208293
0.8345	Intermediate Similarity	NPC100242
0.8345	Intermediate Similarity	NPC159721
0.8333	Intermediate Similarity	NPC472603
0.8322	Intermediate Similarity	NPC476477
0.8322	Intermediate Similarity	NPC470568
0.8322	Intermediate Similarity	NPC256463
0.8322	Intermediate Similarity	NPC111422
0.8322	Intermediate Similarity	NPC295339
0.8322	Intermediate Similarity	NPC306835
0.8322	Intermediate Similarity	NPC471602
0.8322	Intermediate Similarity	NPC299405
0.8322	Intermediate Similarity	NPC216312
0.8322	Intermediate Similarity	NPC29771
0.8321	Intermediate Similarity	NPC3009
0.831	Intermediate Similarity	NPC475957
0.8299	Intermediate Similarity	NPC273798
0.8298	Intermediate Similarity	NPC22644
0.8289	Intermediate Similarity	NPC478223
0.8288	Intermediate Similarity	NPC42540
0.8288	Intermediate Similarity	NPC274085
0.8288	Intermediate Similarity	NPC151607
0.8288	Intermediate Similarity	NPC471305
0.8288	Intermediate Similarity	NPC89664
0.8288	Intermediate Similarity	NPC48762
0.8286	Intermediate Similarity	NPC4170
0.8286	Intermediate Similarity	NPC78307
0.8284	Intermediate Similarity	NPC282577
0.8273	Intermediate Similarity	NPC239134
0.8273	Intermediate Similarity	NPC471851
0.8269	Intermediate Similarity	NPC316262
0.8269	Intermediate Similarity	NPC314653
0.8267	Intermediate Similarity	NPC132990
0.8267	Intermediate Similarity	NPC230848
0.8267	Intermediate Similarity	NPC470569
0.8267	Intermediate Similarity	NPC46882
0.8264	Intermediate Similarity	NPC42262
0.8264	Intermediate Similarity	NPC147542
0.8264	Intermediate Similarity	NPC241349
0.8264	Intermediate Similarity	NPC220496
0.8264	Intermediate Similarity	NPC327916
0.8264	Intermediate Similarity	NPC472601
0.8264	Intermediate Similarity	NPC32749
0.8264	Intermediate Similarity	NPC37992
0.8264	Intermediate Similarity	NPC472600
0.8261	Intermediate Similarity	NPC171460
0.8255	Intermediate Similarity	NPC87630
0.8255	Intermediate Similarity	NPC116292
0.8255	Intermediate Similarity	NPC35160
0.8255	Intermediate Similarity	NPC179128
0.8255	Intermediate Similarity	NPC478219
0.8255	Intermediate Similarity	NPC267469
0.8255	Intermediate Similarity	NPC162569
0.8252	Intermediate Similarity	NPC23870
0.8252	Intermediate Similarity	NPC221104
0.8252	Intermediate Similarity	NPC61590
0.8252	Intermediate Similarity	NPC191835
0.8248	Intermediate Similarity	NPC84672
0.8248	Intermediate Similarity	NPC69424
0.8248	Intermediate Similarity	NPC176130
0.8248	Intermediate Similarity	NPC78364
0.8243	Intermediate Similarity	NPC66991
0.8243	Intermediate Similarity	NPC477483
0.8243	Intermediate Similarity	NPC325032
0.8239	Intermediate Similarity	NPC291454
0.8231	Intermediate Similarity	NPC75295
0.8227	Intermediate Similarity	NPC311339
0.8227	Intermediate Similarity	NPC194970
0.8219	Intermediate Similarity	NPC215451
0.8219	Intermediate Similarity	NPC478164
0.8219	Intermediate Similarity	NPC472006
0.8219	Intermediate Similarity	NPC3732
0.8219	Intermediate Similarity	NPC21873
0.8219	Intermediate Similarity	NPC476473
0.8219	Intermediate Similarity	NPC277369
0.8219	Intermediate Similarity	NPC471731
0.8214	Intermediate Similarity	NPC309430
0.8212	Intermediate Similarity	NPC40356
0.8212	Intermediate Similarity	NPC470340
0.8212	Intermediate Similarity	NPC154683
0.8207	Intermediate Similarity	NPC472604
0.8207	Intermediate Similarity	NPC470842
0.8207	Intermediate Similarity	NPC472605
0.8207	Intermediate Similarity	NPC257003
0.8207	Intermediate Similarity	NPC471444
0.8207	Intermediate Similarity	NPC149533
0.8205	Intermediate Similarity	NPC476822
0.8201	Intermediate Similarity	NPC108129
0.8201	Intermediate Similarity	NPC475741
0.8201	Intermediate Similarity	NPC253488
0.82	Intermediate Similarity	NPC140133
0.82	Intermediate Similarity	NPC225854
0.82	Intermediate Similarity	NPC477914
0.8188	Intermediate Similarity	NPC279442
0.8188	Intermediate Similarity	NPC132810
0.8188	Intermediate Similarity	NPC473744
0.8188	Intermediate Similarity	NPC264229
0.8188	Intermediate Similarity	NPC46549
0.8182	Intermediate Similarity	NPC290601
0.8182	Intermediate Similarity	NPC70380
0.8176	Intermediate Similarity	NPC286038
0.817	Intermediate Similarity	NPC472050
0.8169	Intermediate Similarity	NPC27407
0.8163	Intermediate Similarity	NPC477409
0.8163	Intermediate Similarity	NPC21599
0.8163	Intermediate Similarity	NPC193703
0.8163	Intermediate Similarity	NPC475201
0.8162	Intermediate Similarity	NPC199273
0.8162	Intermediate Similarity	NPC184219
0.8158	Intermediate Similarity	NPC155686
0.8158	Intermediate Similarity	NPC470102
0.8156	Intermediate Similarity	NPC477139
0.8151	Intermediate Similarity	NPC96692
0.8151	Intermediate Similarity	NPC474300
0.8151	Intermediate Similarity	NPC49108
0.8151	Intermediate Similarity	NPC471733
0.8151	Intermediate Similarity	NPC248068
0.8146	Intermediate Similarity	NPC232645
0.8146	Intermediate Similarity	NPC72958
0.8146	Intermediate Similarity	NPC221249
0.8143	Intermediate Similarity	NPC164295
0.8143	Intermediate Similarity	NPC477412
0.8143	Intermediate Similarity	NPC279596
0.8138	Intermediate Similarity	NPC168471
0.8138	Intermediate Similarity	NPC471853
0.8133	Intermediate Similarity	NPC80370
0.8133	Intermediate Similarity	NPC142654
0.8133	Intermediate Similarity	NPC247219
0.8133	Intermediate Similarity	NPC327962
0.8129	Intermediate Similarity	NPC472618
0.8129	Intermediate Similarity	NPC194979
0.8125	Intermediate Similarity	NPC94248
0.8125	Intermediate Similarity	NPC230811
0.8125	Intermediate Similarity	NPC212693
0.8125	Intermediate Similarity	NPC33144
0.8125	Intermediate Similarity	NPC478200
0.8125	Intermediate Similarity	NPC472602
0.8121	Intermediate Similarity	NPC118027
0.8121	Intermediate Similarity	NPC126767
0.8121	Intermediate Similarity	NPC289042
0.8121	Intermediate Similarity	NPC190648
0.8121	Intermediate Similarity	NPC77903
0.8121	Intermediate Similarity	NPC119767
0.8121	Intermediate Similarity	NPC312929
0.8121	Intermediate Similarity	NPC478163
0.8121	Intermediate Similarity	NPC56433
0.8121	Intermediate Similarity	NPC245584
0.8121	Intermediate Similarity	NPC17101
0.8117	Intermediate Similarity	NPC196448
0.8112	Intermediate Similarity	NPC475111
0.8112	Intermediate Similarity	NPC326847
0.8112	Intermediate Similarity	NPC315275
0.8108	Intermediate Similarity	NPC478019
0.8108	Intermediate Similarity	NPC97188
0.8108	Intermediate Similarity	NPC28632
0.8108	Intermediate Similarity	NPC476055
0.8105	Intermediate Similarity	NPC471456
0.8102	Intermediate Similarity	NPC123506
0.8102	Intermediate Similarity	NPC49938
0.8101	Intermediate Similarity	NPC263212
0.8099	Intermediate Similarity	NPC23894
0.8095	Intermediate Similarity	NPC472610
0.8095	Intermediate Similarity	NPC50954
0.8095	Intermediate Similarity	NPC469615
0.8095	Intermediate Similarity	NPC478202
0.8095	Intermediate Similarity	NPC84266
0.8092	Intermediate Similarity	NPC180944
0.8092	Intermediate Similarity	NPC226093
0.8092	Intermediate Similarity	NPC87708
0.8089	Intermediate Similarity	NPC100849
0.8085	Intermediate Similarity	NPC246693

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 NPC119542 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	917
0.2-0.3	1474
0.3-0.4	2498
0.4-0.5	2170
0.5-0.6	1198
0.6-0.7	531
0.7-0.8	92
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
0.8082	Intermediate Similarity	NPD4628	Phase 3
0.7987	Intermediate Similarity	NPD2533	Approved
0.7987	Intermediate Similarity	NPD2534	Approved
0.7987	Intermediate Similarity	NPD2532	Approved
0.7943	Intermediate Similarity	NPD3764	Approved
0.7926	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD9545	Approved
0.7794	Intermediate Similarity	NPD2932	Approved
0.777	Intermediate Similarity	NPD2800	Approved
0.777	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD3972	Approved
0.774	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6273	Approved
0.7692	Intermediate Similarity	NPD7819	Suspended
0.7664	Intermediate Similarity	NPD3019	Approved
0.7655	Intermediate Similarity	NPD230	Phase 1
0.7625	Intermediate Similarity	NPD6959	Discontinued
0.76	Intermediate Similarity	NPD8166	Discontinued
0.7589	Intermediate Similarity	NPD1470	Approved
0.758	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD3226	Approved
0.7517	Intermediate Similarity	NPD6663	Approved
0.7516	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD1510	Phase 2
0.7483	Intermediate Similarity	NPD5736	Approved
0.7483	Intermediate Similarity	NPD6651	Approved
0.7483	Intermediate Similarity	NPD1607	Approved
0.7483	Intermediate Similarity	NPD3750	Approved
0.7483	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7003	Approved
0.7467	Intermediate Similarity	NPD1549	Phase 2
0.7466	Intermediate Similarity	NPD1240	Approved
0.7464	Intermediate Similarity	NPD1651	Approved
0.745	Intermediate Similarity	NPD2935	Discontinued
0.745	Intermediate Similarity	NPD6100	Approved
0.745	Intermediate Similarity	NPD6099	Approved
0.7436	Intermediate Similarity	NPD7458	Discontinued
0.7429	Intermediate Similarity	NPD1201	Approved
0.7421	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2344	Approved
0.74	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2346	Discontinued
0.74	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1283	Approved
0.7394	Intermediate Similarity	NPD1876	Approved
0.7388	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2799	Discontinued
0.7379	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD3882	Suspended
0.7372	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6232	Discontinued
0.7362	Intermediate Similarity	NPD5711	Approved
0.7362	Intermediate Similarity	NPD5710	Approved
0.7361	Intermediate Similarity	NPD9494	Approved
0.7349	Intermediate Similarity	NPD5844	Phase 1
0.7338	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7390	Discontinued
0.7333	Intermediate Similarity	NPD2796	Approved
0.7333	Intermediate Similarity	NPD7473	Discontinued
0.7329	Intermediate Similarity	NPD7075	Discontinued
0.7296	Intermediate Similarity	NPD1934	Approved
0.729	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD4626	Approved
0.7279	Intermediate Similarity	NPD1241	Discontinued
0.7278	Intermediate Similarity	NPD6599	Discontinued
0.7267	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1608	Approved
0.725	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5494	Approved
0.7234	Intermediate Similarity	NPD3026	Approved
0.7234	Intermediate Similarity	NPD3023	Approved
0.7233	Intermediate Similarity	NPD7411	Suspended
0.723	Intermediate Similarity	NPD2979	Phase 3
0.7225	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5408	Approved
0.7219	Intermediate Similarity	NPD5404	Approved
0.7219	Intermediate Similarity	NPD5405	Approved
0.7219	Intermediate Similarity	NPD5406	Approved
0.7215	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD3025	Approved
0.7214	Intermediate Similarity	NPD3024	Approved
0.7214	Intermediate Similarity	NPD5691	Approved
0.7208	Intermediate Similarity	NPD2309	Approved
0.7185	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1281	Approved
0.7179	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1471	Phase 3
0.7162	Intermediate Similarity	NPD8032	Phase 2
0.7161	Intermediate Similarity	NPD7236	Approved
0.7153	Intermediate Similarity	NPD6696	Suspended
0.7152	Intermediate Similarity	NPD3748	Approved
0.7143	Intermediate Similarity	NPD3091	Approved
0.7143	Intermediate Similarity	NPD5760	Phase 2
0.7143	Intermediate Similarity	NPD7008	Discontinued
0.7143	Intermediate Similarity	NPD5761	Phase 2
0.7143	Intermediate Similarity	NPD2801	Approved
0.7117	Intermediate Similarity	NPD3749	Approved
0.7114	Intermediate Similarity	NPD943	Approved
0.7114	Intermediate Similarity	NPD4140	Approved
0.711	Intermediate Similarity	NPD8434	Phase 2
0.711	Intermediate Similarity	NPD8150	Discontinued
0.7105	Intermediate Similarity	NPD2438	Suspended
0.7097	Intermediate Similarity	NPD6190	Approved
0.709	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3818	Discontinued
0.7083	Intermediate Similarity	NPD7177	Discontinued
0.7081	Intermediate Similarity	NPD6801	Discontinued
0.7081	Intermediate Similarity	NPD37	Approved
0.7073	Intermediate Similarity	NPD6234	Discontinued
0.7066	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3092	Approved
0.7059	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4965	Approved
0.7055	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4967	Phase 2
0.7055	Intermediate Similarity	NPD4966	Approved
0.7055	Intermediate Similarity	NPD7768	Phase 2
0.7052	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD17	Approved
0.7042	Intermediate Similarity	NPD1778	Approved
0.7039	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4110	Phase 3
0.7032	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6559	Discontinued
0.7012	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1511	Approved
0.7006	Intermediate Similarity	NPD6799	Approved
0.7	Intermediate Similarity	NPD3620	Phase 2
0.7	Intermediate Similarity	NPD4060	Phase 1
0.7	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2531	Phase 2
0.6988	Remote Similarity	NPD8127	Discontinued
0.6986	Remote Similarity	NPD3094	Phase 2
0.6981	Remote Similarity	NPD920	Approved
0.6981	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.698	Remote Similarity	NPD2313	Discontinued
0.698	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5951	Approved
0.6968	Remote Similarity	NPD1243	Approved
0.6966	Remote Similarity	NPD5327	Phase 3
0.6966	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6166	Phase 2
0.6964	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7028	Phase 2
0.6954	Remote Similarity	NPD5735	Approved
0.6939	Remote Similarity	NPD2798	Approved
0.6937	Remote Similarity	NPD7239	Suspended
0.6936	Remote Similarity	NPD8313	Approved
0.6936	Remote Similarity	NPD8312	Approved
0.6934	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1465	Phase 2
0.6923	Remote Similarity	NPD3095	Discontinued
0.6918	Remote Similarity	NPD1512	Approved
0.6912	Remote Similarity	NPD2182	Approved
0.6897	Remote Similarity	NPD9269	Phase 2
0.6892	Remote Similarity	NPD2861	Phase 2
0.6887	Remote Similarity	NPD3142	Approved
0.6887	Remote Similarity	NPD3140	Approved
0.6883	Remote Similarity	NPD4476	Approved
0.6883	Remote Similarity	NPD1551	Phase 2
0.6883	Remote Similarity	NPD4477	Approved
0.6882	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD9493	Approved
0.686	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5953	Discontinued
0.6855	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD9268	Approved
0.6849	Remote Similarity	NPD1755	Approved
0.6845	Remote Similarity	NPD7229	Phase 3
0.6842	Remote Similarity	NPD6355	Discontinued
0.6842	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6004	Phase 3
0.6839	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6005	Phase 3
0.6839	Remote Similarity	NPD6002	Phase 3
0.6835	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3300	Phase 2
0.6828	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4624	Approved
0.6821	Remote Similarity	NPD7685	Pre-registration
0.6821	Remote Similarity	NPD6765	Approved
0.6821	Remote Similarity	NPD6764	Approved
0.6818	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7033	Discontinued
0.681	Remote Similarity	NPD6385	Approved
0.681	Remote Similarity	NPD6386	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