NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.09
Volume:	261.669
LogP:	1.668
LogD:	1.392
LogS:	-2.778
# Rotatable Bonds:	2
TPSA:	70.67
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.865
Synthetic Accessibility Score:	3.326
Fsp3:	0.267
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:	-5.05
MDCK Permeability:	1.884601078927517e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.943
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.181
Plasma Protein Binding (PPB):	84.27242279052734%
Volume Distribution (VD):	0.555
Pgp-substrate:	10.914311408996582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.211
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.787
CYP2C9-inhibitor:	0.097
CYP2C9-substrate:	0.947
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.413
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.629

ADMET: Excretion

Clearance (CL):	3.925
Half-life (T1/2):	0.873

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.521
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.321
Rat Oral Acute Toxicity:	0.857
Maximum Recommended Daily Dose:	0.809
Skin Sensitization:	0.344
Carcinogencity:	0.126
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.906

Download Data

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

Natural Product: NPC87069

Natural Product ID:	NPC87069
*Common Name:**	Cochinolide
IUPAC Name:	(6S)-6-hydroxy-3-[hydroxy(phenyl)methyl]-5,6-dihydro-4H-1-benzofuran-2-one
Synonyms:	Cochinolide
Standard InCHIKey:	BSEKYAJQRZECLG-XLLULAGJSA-N
Standard InCHI:	InChI=1S/C15H14O4/c16-10-6-7-11-12(8-10)19-15(18)13(11)14(17)9-4-2-1-3-5-9/h1-5,8,10,14,16-17H,6-7H2/t10-,14?/m0/s1
SMILES:	O[C@H]1CCC2=C(C(=O)OC2=C1)C(c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448078
PubChem CID:	10332730
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO30966	Homalium cochinchinensis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104498]
NPO30966	Homalium cochinchinensis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584406]
NPO30966	Homalium cochinchinensis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26516	Homalium cochinchinense	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26516	Homalium cochinchinense	Species	Salicaceae	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
EC50	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	EC50	=	31000.0	nM	PMID[545544]
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	EC50	=	86000.0	nM	PMID[545544]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	EC50	=	8.0	ug.mL-1	PMID[545545]
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	EC50	=	22.2	ug.mL-1	PMID[545545]

☑ 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 NPC87069 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	223
0.1-0.2	875
0.2-0.3	2648
0.3-0.4	6482
0.4-0.5	11005
0.5-0.6	11546
0.6-0.7	9066
0.7-0.8	809
0.8-0.85	40
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8519	High Similarity	NPC82426
0.8519	High Similarity	NPC91820
0.8407	Intermediate Similarity	NPC474314
0.8279	Intermediate Similarity	NPC79608
0.8214	Intermediate Similarity	NPC20485
0.8214	Intermediate Similarity	NPC156648
0.8182	Intermediate Similarity	NPC223351
0.8174	Intermediate Similarity	NPC272524
0.8142	Intermediate Similarity	NPC281604
0.813	Intermediate Similarity	NPC476033
0.812	Intermediate Similarity	NPC210531
0.812	Intermediate Similarity	NPC471616
0.8108	Intermediate Similarity	NPC171831
0.8108	Intermediate Similarity	NPC242913
0.8108	Intermediate Similarity	NPC280616
0.8103	Intermediate Similarity	NPC172525
0.8087	Intermediate Similarity	NPC158282
0.8051	Intermediate Similarity	NPC190298
0.8051	Intermediate Similarity	NPC128249
0.8017	Intermediate Similarity	NPC474176
0.8016	Intermediate Similarity	NPC214246
0.7982	Intermediate Similarity	NPC40178
0.7982	Intermediate Similarity	NPC474364
0.7965	Intermediate Similarity	NPC37115
0.7965	Intermediate Similarity	NPC136962
0.7949	Intermediate Similarity	NPC474363
0.7907	Intermediate Similarity	NPC136994
0.7907	Intermediate Similarity	NPC88255
0.7895	Intermediate Similarity	NPC47536
0.7895	Intermediate Similarity	NPC277788
0.789	Intermediate Similarity	NPC270654
0.7881	Intermediate Similarity	NPC306740
0.7881	Intermediate Similarity	NPC474685
0.7863	Intermediate Similarity	NPC17693
0.7857	Intermediate Similarity	NPC160382
0.7845	Intermediate Similarity	NPC474157
0.7845	Intermediate Similarity	NPC476003
0.7823	Intermediate Similarity	NPC138798
0.7818	Intermediate Similarity	NPC160548
0.7818	Intermediate Similarity	NPC210529
0.7818	Intermediate Similarity	NPC175852
0.7815	Intermediate Similarity	NPC149691
0.7812	Intermediate Similarity	NPC17567
0.7807	Intermediate Similarity	NPC477251
0.7807	Intermediate Similarity	NPC472315
0.7807	Intermediate Similarity	NPC472316
0.7807	Intermediate Similarity	NPC475203
0.7807	Intermediate Similarity	NPC51174
0.7807	Intermediate Similarity	NPC474376
0.7795	Intermediate Similarity	NPC79332
0.7788	Intermediate Similarity	NPC269644
0.7787	Intermediate Similarity	NPC474223
0.7787	Intermediate Similarity	NPC475827
0.7778	Intermediate Similarity	NPC472706
0.7769	Intermediate Similarity	NPC311091
0.7769	Intermediate Similarity	NPC471033
0.776	Intermediate Similarity	NPC244454
0.7742	Intermediate Similarity	NPC472703
0.7692	Intermediate Similarity	NPC260818
0.768	Intermediate Similarity	NPC472704
0.768	Intermediate Similarity	NPC228739
0.7679	Intermediate Similarity	NPC42211
0.7674	Intermediate Similarity	NPC60825
0.7674	Intermediate Similarity	NPC12694
0.7674	Intermediate Similarity	NPC291419
0.7672	Intermediate Similarity	NPC469511
0.7652	Intermediate Similarity	NPC142027
0.7647	Intermediate Similarity	NPC308744
0.7642	Intermediate Similarity	NPC243059
0.7642	Intermediate Similarity	NPC280827
0.7642	Intermediate Similarity	NPC233282
0.7638	Intermediate Similarity	NPC110211
0.7636	Intermediate Similarity	NPC30361
0.7632	Intermediate Similarity	NPC114594
0.7627	Intermediate Similarity	NPC234376
0.7627	Intermediate Similarity	NPC185840
0.7627	Intermediate Similarity	NPC321852
0.7623	Intermediate Similarity	NPC27633
0.7623	Intermediate Similarity	NPC94298
0.7623	Intermediate Similarity	NPC94637
0.7619	Intermediate Similarity	NPC246166
0.7619	Intermediate Similarity	NPC6888
0.7615	Intermediate Similarity	NPC214702
0.7615	Intermediate Similarity	NPC470831
0.7615	Intermediate Similarity	NPC23453
0.7607	Intermediate Similarity	NPC79543
0.76	Intermediate Similarity	NPC474159
0.76	Intermediate Similarity	NPC474254
0.7589	Intermediate Similarity	NPC118343
0.7576	Intermediate Similarity	NPC106406
0.7568	Intermediate Similarity	NPC92754
0.7568	Intermediate Similarity	NPC249912
0.7568	Intermediate Similarity	NPC289201
0.7568	Intermediate Similarity	NPC276775
0.7565	Intermediate Similarity	NPC209632
0.7565	Intermediate Similarity	NPC321670
0.7563	Intermediate Similarity	NPC161611
0.7563	Intermediate Similarity	NPC477245
0.7563	Intermediate Similarity	NPC477246
0.7563	Intermediate Similarity	NPC265002
0.7561	Intermediate Similarity	NPC90522
0.7561	Intermediate Similarity	NPC328459
0.7559	Intermediate Similarity	NPC236405
0.7559	Intermediate Similarity	NPC4164
0.7544	Intermediate Similarity	NPC234305
0.7544	Intermediate Similarity	NPC60679
0.7544	Intermediate Similarity	NPC301943
0.7544	Intermediate Similarity	NPC474365
0.7538	Intermediate Similarity	NPC289415
0.7538	Intermediate Similarity	NPC319995
0.7536	Intermediate Similarity	NPC475528
0.7521	Intermediate Similarity	NPC85493
0.7521	Intermediate Similarity	NPC265407
0.7521	Intermediate Similarity	NPC469636
0.7521	Intermediate Similarity	NPC83628
0.7519	Intermediate Similarity	NPC2596
0.7519	Intermediate Similarity	NPC27407
0.7519	Intermediate Similarity	NPC301857
0.7519	Intermediate Similarity	NPC469930
0.7519	Intermediate Similarity	NPC202729
0.75	Intermediate Similarity	NPC136608
0.75	Intermediate Similarity	NPC237366
0.75	Intermediate Similarity	NPC38420
0.75	Intermediate Similarity	NPC72977
0.75	Intermediate Similarity	NPC474222
0.75	Intermediate Similarity	NPC78701
0.75	Intermediate Similarity	NPC204579
0.75	Intermediate Similarity	NPC474476
0.75	Intermediate Similarity	NPC475804
0.75	Intermediate Similarity	NPC153053
0.75	Intermediate Similarity	NPC30594
0.75	Intermediate Similarity	NPC37622
0.75	Intermediate Similarity	NPC35448
0.75	Intermediate Similarity	NPC477411
0.75	Intermediate Similarity	NPC114096
0.75	Intermediate Similarity	NPC225060
0.7482	Intermediate Similarity	NPC475539
0.7482	Intermediate Similarity	NPC119773
0.7482	Intermediate Similarity	NPC143246
0.7482	Intermediate Similarity	NPC474268
0.7481	Intermediate Similarity	NPC61590
0.7481	Intermediate Similarity	NPC233692
0.7481	Intermediate Similarity	NPC318799
0.7481	Intermediate Similarity	NPC126739
0.7481	Intermediate Similarity	NPC197666
0.7481	Intermediate Similarity	NPC281798
0.748	Intermediate Similarity	NPC64340
0.748	Intermediate Similarity	NPC57607
0.748	Intermediate Similarity	NPC288945
0.7478	Intermediate Similarity	NPC249067
0.7477	Intermediate Similarity	NPC304760
0.7463	Intermediate Similarity	NPC27721
0.7463	Intermediate Similarity	NPC39549
0.7462	Intermediate Similarity	NPC82712
0.7462	Intermediate Similarity	NPC11025
0.746	Intermediate Similarity	NPC69403
0.746	Intermediate Similarity	NPC477151
0.746	Intermediate Similarity	NPC132518
0.746	Intermediate Similarity	NPC291189
0.746	Intermediate Similarity	NPC469927
0.7459	Intermediate Similarity	NPC131192
0.7459	Intermediate Similarity	NPC128825
0.7458	Intermediate Similarity	NPC326187
0.7456	Intermediate Similarity	NPC284477
0.7445	Intermediate Similarity	NPC158634
0.7444	Intermediate Similarity	NPC248150
0.7442	Intermediate Similarity	NPC148026
0.7442	Intermediate Similarity	NPC472707
0.744	Intermediate Similarity	NPC50872
0.7438	Intermediate Similarity	NPC469509
0.7438	Intermediate Similarity	NPC285350
0.7438	Intermediate Similarity	NPC210092
0.7438	Intermediate Similarity	NPC235250
0.7434	Intermediate Similarity	NPC98911
0.7434	Intermediate Similarity	NPC472318
0.7434	Intermediate Similarity	NPC146351
0.7431	Intermediate Similarity	NPC317645
0.7426	Intermediate Similarity	NPC268052
0.7426	Intermediate Similarity	NPC295339
0.7426	Intermediate Similarity	NPC32360
0.7426	Intermediate Similarity	NPC242355
0.7424	Intermediate Similarity	NPC477407
0.7422	Intermediate Similarity	NPC123704
0.7419	Intermediate Similarity	NPC61779
0.7414	Intermediate Similarity	NPC269457
0.7414	Intermediate Similarity	NPC127676
0.7414	Intermediate Similarity	NPC472919
0.7407	Intermediate Similarity	NPC475195
0.7407	Intermediate Similarity	NPC173443
0.7407	Intermediate Similarity	NPC301915
0.7407	Intermediate Similarity	NPC261292
0.7402	Intermediate Similarity	NPC471466
0.7402	Intermediate Similarity	NPC236981
0.7402	Intermediate Similarity	NPC14141
0.7398	Intermediate Similarity	NPC122117
0.7395	Intermediate Similarity	NPC477247
0.7395	Intermediate Similarity	NPC183700
0.7391	Intermediate Similarity	NPC89886
0.7388	Intermediate Similarity	NPC472551
0.7388	Intermediate Similarity	NPC472545

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 NPC87069 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	665
0.2-0.3	1453
0.3-0.4	2703
0.4-0.5	2294
0.5-0.6	1384
0.6-0.7	423
0.7-0.8	40
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
0.792	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7876	Intermediate Similarity	NPD5048	Discontinued
0.7818	Intermediate Similarity	NPD9495	Approved
0.7759	Intermediate Similarity	NPD2067	Discontinued
0.775	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD9545	Approved
0.7589	Intermediate Similarity	NPD1238	Approved
0.7544	Intermediate Similarity	NPD6647	Phase 2
0.7479	Intermediate Similarity	NPD969	Suspended
0.7478	Intermediate Similarity	NPD5909	Discontinued
0.7478	Intermediate Similarity	NPD1237	Approved
0.7463	Intermediate Similarity	NPD7033	Discontinued
0.7459	Intermediate Similarity	NPD9493	Approved
0.7395	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1282	Approved
0.7339	Intermediate Similarity	NPD9256	Approved
0.7339	Intermediate Similarity	NPD9258	Approved
0.7323	Intermediate Similarity	NPD9717	Approved
0.7295	Intermediate Similarity	NPD2629	Approved
0.7287	Intermediate Similarity	NPD1203	Approved
0.7279	Intermediate Similarity	NPD1551	Phase 2
0.7248	Intermediate Similarity	NPD689	Discontinued
0.7241	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD2182	Approved
0.7213	Intermediate Similarity	NPD6010	Discontinued
0.72	Intermediate Similarity	NPD1894	Discontinued
0.7194	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD164	Approved
0.717	Intermediate Similarity	NPD9491	Approved
0.7164	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1202	Approved
0.7143	Intermediate Similarity	NPD9267	Approved
0.7143	Intermediate Similarity	NPD3764	Approved
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9264	Approved
0.7143	Intermediate Similarity	NPD9263	Approved
0.7101	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6005	Phase 3
0.7101	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6004	Phase 3
0.7101	Intermediate Similarity	NPD6002	Phase 3
0.7099	Intermediate Similarity	NPD6085	Phase 2
0.7099	Intermediate Similarity	NPD5647	Approved
0.7099	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD9266	Approved
0.7083	Intermediate Similarity	NPD74	Approved
0.7077	Intermediate Similarity	NPD3225	Approved
0.7073	Intermediate Similarity	NPD1241	Discontinued
0.7071	Intermediate Similarity	NPD4628	Phase 3
0.7059	Intermediate Similarity	NPD6685	Approved
0.7054	Intermediate Similarity	NPD1608	Approved
0.705	Intermediate Similarity	NPD1549	Phase 2
0.705	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD2797	Approved
0.7014	Intermediate Similarity	NPD5403	Approved
0.7	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD5401	Approved
0.6992	Remote Similarity	NPD6832	Phase 2
0.6981	Remote Similarity	NPD226	Approved
0.6977	Remote Similarity	NPD1535	Discovery
0.6977	Remote Similarity	NPD422	Phase 1
0.6972	Remote Similarity	NPD9259	Approved
0.6972	Remote Similarity	NPD9257	Approved
0.6957	Remote Similarity	NPD1510	Phase 2
0.6949	Remote Similarity	NPD5765	Approved
0.694	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1481	Phase 2
0.6917	Remote Similarity	NPD467	Phase 1
0.6912	Remote Similarity	NPD1240	Approved
0.6911	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6190	Approved
0.6889	Remote Similarity	NPD2313	Discontinued
0.6889	Remote Similarity	NPD3268	Approved
0.688	Remote Similarity	NPD9281	Approved
0.6879	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD2613	Approved
0.6861	Remote Similarity	NPD230	Phase 1
0.685	Remote Similarity	NPD2347	Approved
0.6846	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1019	Discontinued
0.6838	Remote Similarity	NPD7798	Approved
0.6838	Remote Similarity	NPD2066	Phase 3
0.6838	Remote Similarity	NPD6233	Phase 2
0.6838	Remote Similarity	NPD520	Approved
0.6831	Remote Similarity	NPD3750	Approved
0.6831	Remote Similarity	NPD2575	Approved
0.6822	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1778	Approved
0.6822	Remote Similarity	NPD17	Approved
0.6814	Remote Similarity	NPD1239	Approved
0.6812	Remote Similarity	NPD1607	Approved
0.6807	Remote Similarity	NPD9261	Approved
0.6806	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6799	Approved
0.68	Remote Similarity	NPD2650	Approved
0.68	Remote Similarity	NPD2652	Approved
0.6797	Remote Similarity	NPD7741	Discontinued
0.6792	Remote Similarity	NPD9490	Approved
0.6786	Remote Similarity	NPD800	Approved
0.6786	Remote Similarity	NPD2935	Discontinued
0.6783	Remote Similarity	NPD1693	Approved
0.6774	Remote Similarity	NPD6912	Phase 3
0.6767	Remote Similarity	NPD2160	Approved
0.6767	Remote Similarity	NPD2627	Approved
0.6767	Remote Similarity	NPD2159	Approved
0.6767	Remote Similarity	NPD2626	Approved
0.6767	Remote Similarity	NPD2628	Approved
0.6767	Remote Similarity	NPD6362	Approved
0.6767	Remote Similarity	NPD2625	Approved
0.6765	Remote Similarity	NPD6798	Discontinued
0.6765	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD411	Approved
0.6765	Remote Similarity	NPD1296	Phase 2
0.6762	Remote Similarity	NPD9294	Approved
0.6739	Remote Similarity	NPD447	Suspended
0.6739	Remote Similarity	NPD6355	Discontinued
0.6739	Remote Similarity	NPD5124	Phase 1
0.6739	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD1089	Approved
0.6726	Remote Similarity	NPD1086	Approved
0.6726	Remote Similarity	NPD1090	Approved
0.6724	Remote Similarity	NPD1989	Approved
0.6721	Remote Similarity	NPD1358	Approved
0.6718	Remote Similarity	NPD1091	Approved
0.6718	Remote Similarity	NPD4217	Approved
0.6718	Remote Similarity	NPD2608	Approved
0.6718	Remote Similarity	NPD2611	Approved
0.6718	Remote Similarity	NPD4216	Approved
0.6718	Remote Similarity	NPD4215	Approved
0.6718	Remote Similarity	NPD3132	Approved
0.6718	Remote Similarity	NPD2610	Approved
0.6718	Remote Similarity	NPD4218	Approved
0.6718	Remote Similarity	NPD3131	Approved
0.6718	Remote Similarity	NPD2612	Approved
0.6718	Remote Similarity	NPD2609	Approved
0.6715	Remote Similarity	NPD3614	Approved
0.6715	Remote Similarity	NPD3088	Approved
0.6715	Remote Similarity	NPD2571	Approved
0.6715	Remote Similarity	NPD2570	Approved
0.6715	Remote Similarity	NPD2573	Approved
0.6715	Remote Similarity	NPD3615	Approved
0.6715	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD3089	Approved
0.6715	Remote Similarity	NPD2574	Discontinued
0.6715	Remote Similarity	NPD4745	Approved
0.6715	Remote Similarity	NPD4062	Phase 3
0.6715	Remote Similarity	NPD4746	Phase 3
0.6715	Remote Similarity	NPD2566	Approved
0.6715	Remote Similarity	NPD3087	Approved
0.6715	Remote Similarity	NPD3090	Approved
0.6715	Remote Similarity	NPD3616	Approved
0.6713	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7411	Suspended
0.6698	Remote Similarity	NPD225	Approved
0.6698	Remote Similarity	NPD227	Approved
0.6693	Remote Similarity	NPD4198	Discontinued
0.6692	Remote Similarity	NPD5126	Approved
0.6692	Remote Similarity	NPD5125	Phase 3
0.6692	Remote Similarity	NPD5305	Approved
0.6692	Remote Similarity	NPD5306	Approved
0.6691	Remote Similarity	NPD7008	Discontinued
0.6691	Remote Similarity	NPD6653	Approved
0.6689	Remote Similarity	NPD5402	Approved
0.6667	Remote Similarity	NPD1929	Approved
0.6667	Remote Similarity	NPD1930	Approved
0.6667	Remote Similarity	NPD6801	Discontinued
0.6667	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD4380	Phase 2
0.6644	Remote Similarity	NPD2533	Approved
0.6644	Remote Similarity	NPD2534	Approved
0.6644	Remote Similarity	NPD2532	Approved
0.6644	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2567	Approved
0.6643	Remote Similarity	NPD2569	Approved
0.6643	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD3266	Approved
0.6642	Remote Similarity	NPD3267	Approved
0.6642	Remote Similarity	NPD1164	Approved
0.6641	Remote Similarity	NPD4106	Approved
0.6641	Remote Similarity	NPD5291	Approved
0.6641	Remote Similarity	NPD4136	Approved
0.6641	Remote Similarity	NPD4135	Approved
0.6641	Remote Similarity	NPD5292	Approved
0.6641	Remote Similarity	NPD3496	Discontinued
0.6641	Remote Similarity	NPD3847	Discontinued
0.6641	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD3134	Approved
0.6638	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD7236	Approved
0.662	Remote Similarity	NPD7266	Discontinued
0.6619	Remote Similarity	NPD4684	Phase 3
0.6619	Remote Similarity	NPD4685	Phase 3
0.6619	Remote Similarity	NPD1899	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