NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	252.1
Volume:	249.697
LogP:	2.117
LogD:	1.354
LogS:	-3.328
# Rotatable Bonds:	2
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.78
Synthetic Accessibility Score:	3.782
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:	-4.717
MDCK Permeability:	1.2138062629674096e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.13
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.947
Plasma Protein Binding (PPB):	78.2445297241211%
Volume Distribution (VD):	1.0
Pgp-substrate:	22.47724151611328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.824
CYP1A2-substrate:	0.816
CYP2C19-inhibitor:	0.075
CYP2C19-substrate:	0.78
CYP2C9-inhibitor:	0.061
CYP2C9-substrate:	0.714
CYP2D6-inhibitor:	0.047
CYP2D6-substrate:	0.34
CYP3A4-inhibitor:	0.257
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	9.947
Half-life (T1/2):	0.748

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.141
Drug-inuced Liver Injury (DILI):	0.236
AMES Toxicity:	0.167
Rat Oral Acute Toxicity:	0.17
Maximum Recommended Daily Dose:	0.265
Skin Sensitization:	0.463
Carcinogencity:	0.037
Eye Corrosion:	0.086
Eye Irritation:	0.733
Respiratory Toxicity:	0.43

Download Data

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

Natural Product: NPC179178

Natural Product ID:	NPC179178
*Common Name:**	(3R)-7-Hydroxy-3-[(1S)-1-Hydroxyethyl]-5-Methoxy-3,4-Dimethyl-2-Benzofuran-1-One
IUPAC Name:	(3R)-7-hydroxy-3-[(1S)-1-hydroxyethyl]-5-methoxy-3,4-dimethyl-2-benzofuran-1-one
Synonyms:
Standard InCHIKey:	YKQYIQHWWYVPHK-CPFSXVBKSA-N
Standard InCHI:	InChI=1S/C13H16O5/c1-6-9(17-4)5-8(15)10-11(6)13(3,7(2)14)18-12(10)16/h5,7,14-15H,1-4H3/t7-,13-/m0/s1
SMILES:	Cc1c(cc(c2c1[C@](C)([C@H](C)O)OC2=O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1765567
PubChem CID:	52937687
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0001578] Benzofuranones

*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
NPO29951	Leptospeciesaeria	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21265556]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5014	Organism	Cochliobolus miyabeanus	Cochliobolus miyabeanus	IC50	=	500.0	ug.mL-1	PMID[510334]

☑ 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 NPC179178 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	339
0.1-0.2	1532
0.2-0.3	3729
0.3-0.4	8016
0.4-0.5	10212
0.5-0.6	3917
0.6-0.7	5579
0.7-0.8	6902
0.8-0.85	2085
0.85-0.9	323
0.9-0.95	59
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC200773
0.9524	High Similarity	NPC240768
0.9448	High Similarity	NPC260946
0.9408	High Similarity	NPC117985
0.9384	High Similarity	NPC166583
0.9384	High Similarity	NPC53362
0.932	High Similarity	NPC470359
0.9262	High Similarity	NPC70016
0.9262	High Similarity	NPC215921
0.9257	High Similarity	NPC270160
0.9257	High Similarity	NPC237440
0.9252	High Similarity	NPC8817
0.9241	High Similarity	NPC51106
0.9236	High Similarity	NPC90411
0.9231	High Similarity	NPC275356
0.9211	High Similarity	NPC473395
0.9211	High Similarity	NPC84935
0.9211	High Similarity	NPC190020
0.9211	High Similarity	NPC77679
0.9205	High Similarity	NPC199926
0.9205	High Similarity	NPC79998
0.9195	High Similarity	NPC96501
0.9195	High Similarity	NPC469619
0.9195	High Similarity	NPC469670
0.9184	High Similarity	NPC470357
0.9178	High Similarity	NPC277426
0.9178	High Similarity	NPC210425
0.9178	High Similarity	NPC280404
0.9178	High Similarity	NPC86373
0.9172	High Similarity	NPC322112
0.9172	High Similarity	NPC82913
0.915	High Similarity	NPC470339
0.9145	High Similarity	NPC150227
0.9139	High Similarity	NPC281477
0.9139	High Similarity	NPC192189
0.9128	High Similarity	NPC198927
0.9116	High Similarity	NPC75694
0.911	High Similarity	NPC472006
0.911	High Similarity	NPC469542
0.9103	High Similarity	NPC1704
0.9103	High Similarity	NPC67650
0.9091	High Similarity	NPC472055
0.9079	High Similarity	NPC82592
0.9079	High Similarity	NPC16082
0.9073	High Similarity	NPC271681
0.9073	High Similarity	NPC167903
0.9067	High Similarity	NPC119929
0.9054	High Similarity	NPC473023
0.9054	High Similarity	NPC107625
0.9041	High Similarity	NPC474385
0.902	High Similarity	NPC472050
0.8993	High Similarity	NPC210320
0.8993	High Similarity	NPC202494
0.8993	High Similarity	NPC137296
0.8986	High Similarity	NPC83272
0.8973	High Similarity	NPC472605
0.8973	High Similarity	NPC472604
0.8968	High Similarity	NPC470358
0.8968	High Similarity	NPC470810
0.8961	High Similarity	NPC246466
0.8958	High Similarity	NPC135837
0.8954	High Similarity	NPC99381
0.8933	High Similarity	NPC215711
0.8933	High Similarity	NPC73411
0.8919	High Similarity	NPC27106
0.8912	High Similarity	NPC469579
0.8904	High Similarity	NPC472601
0.8904	High Similarity	NPC64664
0.8904	High Similarity	NPC472600
0.8904	High Similarity	NPC165172
0.8904	High Similarity	NPC158472
0.8897	High Similarity	NPC94248
0.8897	High Similarity	NPC212693
0.8889	High Similarity	NPC301233
0.8874	High Similarity	NPC77325
0.8874	High Similarity	NPC4423
0.8868	High Similarity	NPC473094
0.8867	High Similarity	NPC472036
0.8859	High Similarity	NPC473692
0.8859	High Similarity	NPC316535
0.8859	High Similarity	NPC297788
0.8854	High Similarity	NPC472402
0.8844	High Similarity	NPC475730
0.8844	High Similarity	NPC472603
0.8836	High Similarity	NPC247409
0.8836	High Similarity	NPC88269
0.8836	High Similarity	NPC139634
0.8836	High Similarity	NPC105456
0.8836	High Similarity	NPC32360
0.8828	High Similarity	NPC70380
0.8824	High Similarity	NPC470340
0.8824	High Similarity	NPC470338
0.8824	High Similarity	NPC470337
0.8824	High Similarity	NPC268992
0.8824	High Similarity	NPC273483
0.8824	High Similarity	NPC51824
0.8824	High Similarity	NPC113608
0.8824	High Similarity	NPC256141
0.8819	High Similarity	NPC180905
0.8819	High Similarity	NPC182496
0.8816	High Similarity	NPC470908
0.8812	High Similarity	NPC473095
0.8812	High Similarity	NPC473096
0.8808	High Similarity	NPC153417
0.8805	High Similarity	NPC165460
0.8805	High Similarity	NPC472452
0.88	High Similarity	NPC85734
0.88	High Similarity	NPC472033
0.88	High Similarity	NPC32058
0.8792	High Similarity	NPC470932
0.8784	High Similarity	NPC171870
0.8784	High Similarity	NPC74397
0.8782	High Similarity	NPC279732
0.8776	High Similarity	NPC187690
0.8773	High Similarity	NPC324220
0.8773	High Similarity	NPC312630
0.8767	High Similarity	NPC191835
0.8766	High Similarity	NPC197188
0.8766	High Similarity	NPC291510
0.8766	High Similarity	NPC43872
0.8766	High Similarity	NPC155686
0.8766	High Similarity	NPC238672
0.8766	High Similarity	NPC116850
0.8766	High Similarity	NPC144801
0.8759	High Similarity	NPC84699
0.8759	High Similarity	NPC50455
0.8758	High Similarity	NPC474772
0.8758	High Similarity	NPC46882
0.8758	High Similarity	NPC472423
0.8758	High Similarity	NPC474744
0.8758	High Similarity	NPC132990
0.8742	High Similarity	NPC47388
0.8742	High Similarity	NPC14098
0.8742	High Similarity	NPC470670
0.8742	High Similarity	NPC85773
0.8742	High Similarity	NPC91902
0.8742	High Similarity	NPC473133
0.8734	High Similarity	NPC478229
0.8733	High Similarity	NPC472034
0.8733	High Similarity	NPC470857
0.8725	High Similarity	NPC159721
0.8725	High Similarity	NPC471731
0.8725	High Similarity	NPC258307
0.8725	High Similarity	NPC130206
0.8725	High Similarity	NPC472610
0.8716	High Similarity	NPC244923
0.8716	High Similarity	NPC158634
0.871	High Similarity	NPC108937
0.871	High Similarity	NPC68727
0.871	High Similarity	NPC279218
0.8707	High Similarity	NPC268052
0.8704	High Similarity	NPC472620
0.8704	High Similarity	NPC471181
0.8701	High Similarity	NPC115249
0.8701	High Similarity	NPC180944
0.8699	High Similarity	NPC194579
0.8693	High Similarity	NPC180351
0.8693	High Similarity	NPC472421
0.8693	High Similarity	NPC56204
0.8693	High Similarity	NPC321387
0.8693	High Similarity	NPC327059
0.8688	High Similarity	NPC53640
0.8688	High Similarity	NPC20237
0.8688	High Similarity	NPC472621
0.8688	High Similarity	NPC170245
0.8684	High Similarity	NPC471642
0.8684	High Similarity	NPC471641
0.8684	High Similarity	NPC240622
0.8684	High Similarity	NPC37139
0.8684	High Similarity	NPC240253
0.8681	High Similarity	NPC153783
0.8679	High Similarity	NPC249181
0.8675	High Similarity	NPC163846
0.8675	High Similarity	NPC225173
0.8675	High Similarity	NPC316769
0.8671	High Similarity	NPC30655
0.8671	High Similarity	NPC92589
0.8671	High Similarity	NPC74854
0.8671	High Similarity	NPC349525
0.8671	High Similarity	NPC45124
0.8667	High Similarity	NPC42540
0.8667	High Similarity	NPC151607
0.8667	High Similarity	NPC184702
0.8662	High Similarity	NPC45846
0.8658	High Similarity	NPC471733
0.8658	High Similarity	NPC250755
0.8658	High Similarity	NPC297985
0.8654	High Similarity	NPC227062
0.8654	High Similarity	NPC78554
0.8654	High Similarity	NPC469936
0.8654	High Similarity	NPC474738
0.8654	High Similarity	NPC321372
0.8654	High Similarity	NPC474609
0.8654	High Similarity	NPC478223
0.8654	High Similarity	NPC109967
0.8654	High Similarity	NPC164427
0.8654	High Similarity	NPC129053
0.8654	High Similarity	NPC475797
0.865	High Similarity	NPC98776
0.8649	High Similarity	NPC37206

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 NPC179178 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	938
0.2-0.3	1988
0.3-0.4	2568
0.4-0.5	1771
0.5-0.6	1005
0.6-0.7	389
0.7-0.8	164
0.8-0.85	18
0.85-0.9	0
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9116	High Similarity	NPD2533	Approved
0.9116	High Similarity	NPD2532	Approved
0.9116	High Similarity	NPD2534	Approved
0.8707	High Similarity	NPD970	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD4380	Phase 2
0.8291	Intermediate Similarity	NPD7819	Suspended
0.8291	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD5710	Approved
0.8272	Intermediate Similarity	NPD5711	Approved
0.825	Intermediate Similarity	NPD7075	Discontinued
0.8232	Intermediate Similarity	NPD7473	Discontinued
0.8228	Intermediate Similarity	NPD6801	Discontinued
0.8176	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD2800	Approved
0.8113	Intermediate Similarity	NPD1934	Approved
0.8098	Intermediate Similarity	NPD6959	Discontinued
0.8075	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD3882	Suspended
0.8072	Intermediate Similarity	NPD3818	Discontinued
0.8054	Intermediate Similarity	NPD230	Phase 1
0.8025	Intermediate Similarity	NPD920	Approved
0.8024	Intermediate Similarity	NPD5844	Phase 1
0.8013	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6559	Discontinued
0.7961	Intermediate Similarity	NPD2935	Discontinued
0.795	Intermediate Similarity	NPD2801	Approved
0.795	Intermediate Similarity	NPD1465	Phase 2
0.7949	Intermediate Similarity	NPD6799	Approved
0.7927	Intermediate Similarity	NPD5494	Approved
0.7914	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD3749	Approved
0.7908	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD3817	Phase 2
0.7895	Intermediate Similarity	NPD1510	Phase 2
0.7888	Intermediate Similarity	NPD37	Approved
0.7886	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD6599	Discontinued
0.7867	Intermediate Similarity	NPD1240	Approved
0.7866	Intermediate Similarity	NPD6234	Discontinued
0.7857	Intermediate Similarity	NPD1549	Phase 2
0.7853	Intermediate Similarity	NPD4967	Phase 2
0.7853	Intermediate Similarity	NPD4966	Approved
0.7853	Intermediate Similarity	NPD4965	Approved
0.7844	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD6166	Phase 2
0.7844	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1511	Approved
0.7826	Intermediate Similarity	NPD7411	Suspended
0.7811	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD1243	Approved
0.7791	Intermediate Similarity	NPD5402	Approved
0.7791	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7074	Phase 3
0.7763	Intermediate Similarity	NPD1607	Approved
0.7758	Intermediate Similarity	NPD919	Approved
0.7756	Intermediate Similarity	NPD4628	Phase 3
0.7756	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7768	Phase 2
0.7736	Intermediate Similarity	NPD1512	Approved
0.7733	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7054	Approved
0.7673	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7472	Approved
0.7658	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6651	Approved
0.7647	Intermediate Similarity	NPD7228	Approved
0.7643	Intermediate Similarity	NPD3750	Approved
0.7633	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6797	Phase 2
0.7613	Intermediate Similarity	NPD2796	Approved
0.7613	Intermediate Similarity	NPD1551	Phase 2
0.7593	Intermediate Similarity	NPD3226	Approved
0.7582	Intermediate Similarity	NPD447	Suspended
0.7578	Intermediate Similarity	NPD5403	Approved
0.7572	Intermediate Similarity	NPD7251	Discontinued
0.756	Intermediate Similarity	NPD1247	Approved
0.756	Intermediate Similarity	NPD7199	Phase 2
0.7548	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7808	Phase 3
0.7515	Intermediate Similarity	NPD7229	Phase 3
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7286	Phase 2
0.7486	Intermediate Similarity	NPD8312	Approved
0.7486	Intermediate Similarity	NPD8313	Approved
0.7472	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7435	Discontinued
0.7458	Intermediate Similarity	NPD8150	Discontinued
0.7458	Intermediate Similarity	NPD8434	Phase 2
0.7453	Intermediate Similarity	NPD5401	Approved
0.7452	Intermediate Similarity	NPD2346	Discontinued
0.7447	Intermediate Similarity	NPD8151	Discontinued
0.7436	Intermediate Similarity	NPD2799	Discontinued
0.7414	Intermediate Similarity	NPD5953	Discontinued
0.7403	Intermediate Similarity	NPD943	Approved
0.7401	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6776	Approved
0.7391	Intermediate Similarity	NPD7390	Discontinued
0.7391	Intermediate Similarity	NPD6779	Approved
0.7391	Intermediate Similarity	NPD6780	Approved
0.7391	Intermediate Similarity	NPD6777	Approved
0.7391	Intermediate Similarity	NPD6781	Approved
0.7391	Intermediate Similarity	NPD6778	Approved
0.7391	Intermediate Similarity	NPD6782	Approved
0.7386	Intermediate Similarity	NPD3764	Approved
0.7368	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6002	Phase 3
0.7342	Intermediate Similarity	NPD6005	Phase 3
0.7342	Intermediate Similarity	NPD6004	Phase 3
0.7342	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD3751	Discontinued
0.733	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD9545	Approved
0.7325	Intermediate Similarity	NPD3748	Approved
0.7325	Intermediate Similarity	NPD7033	Discontinued
0.7315	Intermediate Similarity	NPD9269	Phase 2
0.7315	Intermediate Similarity	NPD9717	Approved
0.731	Intermediate Similarity	NPD3787	Discontinued
0.729	Intermediate Similarity	NPD4060	Phase 1
0.7284	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6100	Approved
0.7278	Intermediate Similarity	NPD6099	Approved
0.7277	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7783	Phase 2
0.7273	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7240	Approved
0.7267	Intermediate Similarity	NPD3926	Phase 2
0.7267	Intermediate Similarity	NPD6190	Approved
0.725	Intermediate Similarity	NPD2654	Approved
0.7244	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5124	Phase 1
0.7239	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2344	Approved
0.723	Intermediate Similarity	NPD4626	Approved
0.7225	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD2403	Approved
0.7225	Intermediate Similarity	NPD7874	Approved
0.7208	Intermediate Similarity	NPD3027	Phase 3
0.7192	Intermediate Similarity	NPD9493	Approved
0.719	Intermediate Similarity	NPD9494	Approved
0.7188	Intermediate Similarity	NPD2424	Discontinued
0.7181	Intermediate Similarity	NPD7697	Approved
0.7181	Intermediate Similarity	NPD7696	Phase 3
0.7181	Intermediate Similarity	NPD7698	Approved
0.7179	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1613	Approved
0.7175	Intermediate Similarity	NPD7685	Pre-registration
0.7171	Intermediate Similarity	NPD1203	Approved
0.717	Intermediate Similarity	NPD5405	Approved
0.717	Intermediate Similarity	NPD5408	Approved
0.717	Intermediate Similarity	NPD5406	Approved
0.717	Intermediate Similarity	NPD5404	Approved
0.7165	Intermediate Similarity	NPD7930	Approved
0.7162	Intermediate Similarity	NPD9268	Approved
0.7162	Intermediate Similarity	NPD5691	Approved
0.7161	Intermediate Similarity	NPD411	Approved
0.7161	Intermediate Similarity	NPD2313	Discontinued
0.716	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD1652	Phase 2
0.7143	Intermediate Similarity	NPD7871	Phase 2
0.7135	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6355	Discontinued
0.7133	Intermediate Similarity	NPD422	Phase 1
0.7128	Intermediate Similarity	NPD6823	Phase 2
0.712	Intermediate Similarity	NPD7701	Phase 2
0.712	Intermediate Similarity	NPD6535	Approved
0.712	Intermediate Similarity	NPD6534	Approved
0.7108	Intermediate Similarity	NPD1653	Approved
0.7105	Intermediate Similarity	NPD1283	Approved
0.7101	Intermediate Similarity	NPD5760	Phase 2
0.7101	Intermediate Similarity	NPD5761	Phase 2
0.7091	Intermediate Similarity	NPD6273	Approved
0.7086	Intermediate Similarity	NPD1608	Approved
0.7083	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5242	Approved
0.7066	Intermediate Similarity	NPD7458	Discontinued
0.7063	Intermediate Similarity	NPD2438	Suspended
0.7062	Intermediate Similarity	NPD1729	Discontinued
0.7055	Intermediate Similarity	NPD2309	Approved
0.7053	Intermediate Similarity	NPD8320	Phase 1
0.7053	Intermediate Similarity	NPD8319	Approved
0.7035	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6832	Phase 2
0.703	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5762	Approved
0.7019	Intermediate Similarity	NPD5763	Approved
0.7019	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1019	Discontinued

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