NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	292.05
Volume:	276.88
LogP:	2.495
LogD:	2.183
LogS:	-4.19
# Rotatable Bonds:	3
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.786
Synthetic Accessibility Score:	3.617
Fsp3:	0.333
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:	-4.699
MDCK Permeability:	2.6390247512608767e-05
Pgp-inhibitor:	0.278
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.326
Plasma Protein Binding (PPB):	95.27111053466797%
Volume Distribution (VD):	1.437
Pgp-substrate:	2.4084317684173584%

ADMET: Metabolism

CYP1A2-inhibitor:	0.538
CYP1A2-substrate:	0.2
CYP2C19-inhibitor:	0.75
CYP2C19-substrate:	0.188
CYP2C9-inhibitor:	0.468
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.445
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.57
CYP3A4-substrate:	0.422

ADMET: Excretion

Clearance (CL):	9.255
Half-life (T1/2):	0.69

ADMET: Toxicity

hERG Blockers:	0.509
Human Hepatotoxicity (H-HT):	0.305
Drug-inuced Liver Injury (DILI):	0.35
AMES Toxicity:	0.833
Rat Oral Acute Toxicity:	0.688
Maximum Recommended Daily Dose:	0.885
Skin Sensitization:	0.949
Carcinogencity:	0.745
Eye Corrosion:	0.004
Eye Irritation:	0.17
Respiratory Toxicity:	0.656

Download Data

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

Natural Product: NPC474283

Natural Product ID:	NPC474283
*Common Name:**	(3Ar,7Ar)-6-Oxo-2,3,3A,6,7,7A-Hexahydrobenzofuran-3A-Yl 4-Chlorobenzoate
IUPAC Name:	[(3aR,7aR)-6-oxo-2,3,7,7a-tetrahydro-1-benzofuran-3a-yl] 4-chlorobenzoate
Synonyms:
Standard InCHIKey:	IQCXJPAEPCYZKD-HIFRSBDPSA-N
Standard InCHI:	InChI=1S/C15H13ClO4/c16-11-3-1-10(2-4-11)14(18)20-15-6-5-12(17)9-13(15)19-8-7-15/h1-6,13H,7-9H2/t13-,15+/m1/s1
SMILES:	O=C1C=C[C@]2([C@@H](C1)OCC2)OC(=O)c1ccc(cc1)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464694
PubChem CID:	44567077
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters

*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
NPO33459	cornus controversa	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3236014]

☑ 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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.7	ug.mL-1	PMID[506399]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.9	ug.mL-1	PMID[506399]

☑ 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 NPC474283 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	312
0.1-0.2	1411
0.2-0.3	3914
0.3-0.4	10376
0.4-0.5	12219
0.5-0.6	12089
0.6-0.7	2163
0.7-0.8	204
0.8-0.85	5
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9658	High Similarity	NPC475692
0.9576	High Similarity	NPC475691
0.9043	High Similarity	NPC474176
0.8197	Intermediate Similarity	NPC149691
0.8033	Intermediate Similarity	NPC474363
0.7955	Intermediate Similarity	NPC473247
0.7917	Intermediate Similarity	NPC474364
0.7815	Intermediate Similarity	NPC269457
0.7797	Intermediate Similarity	NPC301943
0.7797	Intermediate Similarity	NPC474365
0.7769	Intermediate Similarity	NPC265407
0.7769	Intermediate Similarity	NPC83628
0.7724	Intermediate Similarity	NPC474314
0.7692	Intermediate Similarity	NPC118343
0.7672	Intermediate Similarity	NPC276775
0.7672	Intermediate Similarity	NPC249912
0.7672	Intermediate Similarity	NPC92754
0.7661	Intermediate Similarity	NPC161611
0.7647	Intermediate Similarity	NPC89886
0.7627	Intermediate Similarity	NPC42211
0.7607	Intermediate Similarity	NPC225060
0.7607	Intermediate Similarity	NPC35448
0.7607	Intermediate Similarity	NPC78701
0.76	Intermediate Similarity	NPC307651
0.76	Intermediate Similarity	NPC308744
0.7581	Intermediate Similarity	NPC158282
0.7561	Intermediate Similarity	NPC174099
0.7559	Intermediate Similarity	NPC190298
0.7542	Intermediate Similarity	NPC325497
0.7542	Intermediate Similarity	NPC146351
0.75	Intermediate Similarity	NPC469574
0.75	Intermediate Similarity	NPC130398
0.75	Intermediate Similarity	NPC474157
0.75	Intermediate Similarity	NPC234305
0.748	Intermediate Similarity	NPC469636
0.748	Intermediate Similarity	NPC100353
0.7479	Intermediate Similarity	NPC70624
0.7459	Intermediate Similarity	NPC119271
0.7459	Intermediate Similarity	NPC30594
0.7459	Intermediate Similarity	NPC37622
0.7445	Intermediate Similarity	NPC11173
0.7417	Intermediate Similarity	NPC45613
0.7398	Intermediate Similarity	NPC56493
0.7395	Intermediate Similarity	NPC203925
0.736	Intermediate Similarity	NPC210089
0.7355	Intermediate Similarity	NPC291426
0.7344	Intermediate Similarity	NPC216387
0.7339	Intermediate Similarity	NPC17417
0.7339	Intermediate Similarity	NPC10251
0.7323	Intermediate Similarity	NPC477411
0.7323	Intermediate Similarity	NPC87069
0.7313	Intermediate Similarity	NPC246166
0.7295	Intermediate Similarity	NPC31786
0.7295	Intermediate Similarity	NPC114594
0.7295	Intermediate Similarity	NPC324786
0.728	Intermediate Similarity	NPC93084
0.728	Intermediate Similarity	NPC196246
0.728	Intermediate Similarity	NPC251854
0.728	Intermediate Similarity	NPC216122
0.728	Intermediate Similarity	NPC214067
0.7279	Intermediate Similarity	NPC472707
0.7273	Intermediate Similarity	NPC188895
0.7273	Intermediate Similarity	NPC187566
0.7273	Intermediate Similarity	NPC50872
0.7259	Intermediate Similarity	NPC476599
0.7259	Intermediate Similarity	NPC476033
0.7258	Intermediate Similarity	NPC277788
0.725	Intermediate Similarity	NPC472318
0.725	Intermediate Similarity	NPC98911
0.7244	Intermediate Similarity	NPC272524
0.7244	Intermediate Similarity	NPC128368
0.7239	Intermediate Similarity	NPC472704
0.7236	Intermediate Similarity	NPC209632
0.7222	Intermediate Similarity	NPC305912
0.7222	Intermediate Similarity	NPC1082
0.7222	Intermediate Similarity	NPC260818
0.7222	Intermediate Similarity	NPC476003
0.7222	Intermediate Similarity	NPC243355
0.7214	Intermediate Similarity	NPC153617
0.7213	Intermediate Similarity	NPC60679
0.7209	Intermediate Similarity	NPC226093
0.7203	Intermediate Similarity	NPC183270
0.7203	Intermediate Similarity	NPC477904
0.72	Intermediate Similarity	NPC40178
0.7188	Intermediate Similarity	NPC172525
0.7185	Intermediate Similarity	NPC125053
0.7177	Intermediate Similarity	NPC51174
0.7165	Intermediate Similarity	NPC270699
0.7165	Intermediate Similarity	NPC321852
0.7165	Intermediate Similarity	NPC82899
0.7164	Intermediate Similarity	NPC472703
0.7164	Intermediate Similarity	NPC223351
0.7154	Intermediate Similarity	NPC85977
0.7132	Intermediate Similarity	NPC79608
0.7132	Intermediate Similarity	NPC474685
0.7132	Intermediate Similarity	NPC210092
0.7122	Intermediate Similarity	NPC291419
0.7122	Intermediate Similarity	NPC60825
0.712	Intermediate Similarity	NPC20485
0.712	Intermediate Similarity	NPC47536
0.7119	Intermediate Similarity	NPC261181
0.7113	Intermediate Similarity	NPC217673
0.7113	Intermediate Similarity	NPC52523
0.7099	Intermediate Similarity	NPC217423
0.7092	Intermediate Similarity	NPC134937
0.7092	Intermediate Similarity	NPC298547
0.7092	Intermediate Similarity	NPC324898
0.7087	Intermediate Similarity	NPC167504
0.7083	Intermediate Similarity	NPC325499
0.7083	Intermediate Similarity	NPC270654
0.708	Intermediate Similarity	NPC472706
0.7069	Intermediate Similarity	NPC173443
0.7068	Intermediate Similarity	NPC473243
0.7068	Intermediate Similarity	NPC233282
0.7063	Intermediate Similarity	NPC99846
0.7063	Intermediate Similarity	NPC86772
0.7063	Intermediate Similarity	NPC269023
0.7063	Intermediate Similarity	NPC85493
0.7054	Intermediate Similarity	NPC196075
0.7054	Intermediate Similarity	NPC153053
0.7054	Intermediate Similarity	NPC237366
0.705	Intermediate Similarity	NPC475508
0.7045	Intermediate Similarity	NPC94637
0.7042	Intermediate Similarity	NPC149401
0.7042	Intermediate Similarity	NPC79699
0.7042	Intermediate Similarity	NPC279637
0.704	Intermediate Similarity	NPC472316
0.704	Intermediate Similarity	NPC475203
0.704	Intermediate Similarity	NPC474376
0.704	Intermediate Similarity	NPC472315
0.7034	Intermediate Similarity	NPC77493
0.7031	Intermediate Similarity	NPC79496
0.7031	Intermediate Similarity	NPC212415
0.7016	Intermediate Similarity	NPC269644
0.7016	Intermediate Similarity	NPC280616
0.7016	Intermediate Similarity	NPC171831
0.7016	Intermediate Similarity	NPC242913
0.7014	Intermediate Similarity	NPC325805
0.7014	Intermediate Similarity	NPC272523
0.7	Intermediate Similarity	NPC469509
0.6992	Remote Similarity	NPC90522
0.6992	Remote Similarity	NPC328459
0.6985	Remote Similarity	NPC471466
0.6984	Remote Similarity	NPC475465
0.6984	Remote Similarity	NPC472314
0.6972	Remote Similarity	NPC136994
0.6972	Remote Similarity	NPC88255
0.6972	Remote Similarity	NPC474608
0.6972	Remote Similarity	NPC473359
0.697	Remote Similarity	NPC45104
0.6963	Remote Similarity	NPC26285
0.6959	Remote Similarity	NPC471107
0.6959	Remote Similarity	NPC471100
0.6957	Remote Similarity	NPC51292
0.6957	Remote Similarity	NPC318107
0.6957	Remote Similarity	NPC114096
0.695	Remote Similarity	NPC472394
0.6949	Remote Similarity	NPC119631
0.6948	Remote Similarity	NPC473367
0.6947	Remote Similarity	NPC188907
0.6947	Remote Similarity	NPC471616
0.6947	Remote Similarity	NPC210531
0.6944	Remote Similarity	NPC205305
0.6944	Remote Similarity	NPC327511
0.694	Remote Similarity	NPC72977
0.694	Remote Similarity	NPC230951
0.6939	Remote Similarity	NPC82467
0.6929	Remote Similarity	NPC147561
0.6929	Remote Similarity	NPC272946
0.6929	Remote Similarity	NPC42234
0.6929	Remote Similarity	NPC281604
0.6923	Remote Similarity	NPC17877
0.6923	Remote Similarity	NPC472247
0.6923	Remote Similarity	NPC472577
0.6923	Remote Similarity	NPC475262
0.6923	Remote Similarity	NPC291638
0.6923	Remote Similarity	NPC195647
0.6923	Remote Similarity	NPC290833
0.6923	Remote Similarity	NPC66761
0.6923	Remote Similarity	NPC265459
0.6918	Remote Similarity	NPC473497
0.6918	Remote Similarity	NPC242355
0.6913	Remote Similarity	NPC477737
0.6911	Remote Similarity	NPC473325
0.6906	Remote Similarity	NPC148026
0.6905	Remote Similarity	NPC37115
0.6905	Remote Similarity	NPC329705
0.6905	Remote Similarity	NPC474111
0.6905	Remote Similarity	NPC136962
0.6901	Remote Similarity	NPC273984
0.6899	Remote Similarity	NPC185840
0.6897	Remote Similarity	NPC53361
0.6897	Remote Similarity	NPC89377
0.6897	Remote Similarity	NPC121268
0.6894	Remote Similarity	NPC128825
0.6891	Remote Similarity	NPC77273
0.6884	Remote Similarity	NPC4164
0.6884	Remote Similarity	NPC236405
0.6875	Remote Similarity	NPC472551
0.6875	Remote Similarity	NPC194769

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 NPC474283 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	868
0.2-0.3	1487
0.3-0.4	3122
0.4-0.5	2441
0.5-0.6	849
0.6-0.7	140
0.7-0.8	9
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
0.7692	Intermediate Similarity	NPD1238	Approved
0.7642	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD3887	Approved
0.7447	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD2353	Approved
0.7422	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD2182	Approved
0.7295	Intermediate Similarity	NPD164	Approved
0.7286	Intermediate Similarity	NPD1654	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2354	Approved
0.7143	Intermediate Similarity	NPD1889	Phase 1
0.7132	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD1202	Approved
0.7083	Intermediate Similarity	NPD7611	Approved
0.7037	Intermediate Similarity	NPD4878	Approved
0.7031	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD2067	Discontinued
0.6957	Remote Similarity	NPD9257	Approved
0.6957	Remote Similarity	NPD9259	Approved
0.6934	Remote Similarity	NPD1888	Phase 1
0.6929	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD9493	Approved
0.6809	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5958	Discontinued
0.6769	Remote Similarity	NPD969	Suspended
0.6759	Remote Similarity	NPD2569	Approved
0.6759	Remote Similarity	NPD2567	Approved
0.6746	Remote Similarity	NPD1237	Approved
0.6738	Remote Similarity	NPD6832	Phase 2
0.6723	Remote Similarity	NPD9258	Approved
0.6723	Remote Similarity	NPD9256	Approved
0.6715	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD6287	Discontinued
0.6714	Remote Similarity	NPD1019	Discontinued
0.6689	Remote Similarity	NPD4534	Discontinued
0.6667	Remote Similarity	NPD9717	Approved
0.6667	Remote Similarity	NPD9261	Approved
0.6667	Remote Similarity	NPD454	Approved
0.6667	Remote Similarity	NPD1241	Discontinued
0.6667	Remote Similarity	NPD9545	Approved
0.6643	Remote Similarity	NPD1203	Approved
0.6623	Remote Similarity	NPD957	Approved
0.6621	Remote Similarity	NPD1933	Approved
0.6613	Remote Similarity	NPD9495	Approved
0.6596	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD1340	Discontinued
0.6571	Remote Similarity	NPD2199	Approved
0.6571	Remote Similarity	NPD2198	Approved
0.6569	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD2313	Discontinued
0.6528	Remote Similarity	NPD3764	Approved
0.6522	Remote Similarity	NPD4879	Approved
0.6507	Remote Similarity	NPD447	Suspended
0.6507	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD9260	Approved
0.6497	Remote Similarity	NPD958	Approved
0.6471	Remote Similarity	NPD1282	Approved
0.6462	Remote Similarity	NPD9267	Approved
0.6462	Remote Similarity	NPD9264	Approved
0.6462	Remote Similarity	NPD1358	Approved
0.6462	Remote Similarity	NPD9263	Approved
0.6456	Remote Similarity	NPD7029	Discontinued
0.6438	Remote Similarity	NPD4453	Approved
0.6438	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD4452	Approved
0.6429	Remote Similarity	NPD5401	Approved
0.6429	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7798	Approved
0.6418	Remote Similarity	NPD2988	Approved
0.6418	Remote Similarity	NPD2991	Approved
0.6415	Remote Similarity	NPD7460	Discontinued
0.6412	Remote Similarity	NPD74	Approved
0.6412	Remote Similarity	NPD9266	Approved
0.6406	Remote Similarity	NPD6647	Phase 2
0.6405	Remote Similarity	NPD7236	Approved
0.6395	Remote Similarity	NPD1184	Approved
0.6392	Remote Similarity	NPD3274	Phase 2
0.637	Remote Similarity	NPD2629	Approved
0.6364	Remote Similarity	NPD9249	Phase 1
0.6364	Remote Similarity	NPD6799	Approved
0.6346	Remote Similarity	NPD5403	Approved
0.6343	Remote Similarity	NPD769	Approved
0.6338	Remote Similarity	NPD5667	Approved
0.6336	Remote Similarity	NPD9532	Phase 3
0.6333	Remote Similarity	NPD1551	Phase 2
0.6331	Remote Similarity	NPD4593	Approved
0.6331	Remote Similarity	NPD4594	Approved
0.6309	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD4911	Discontinued
0.6291	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD230	Phase 1
0.6279	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD1929	Approved
0.6279	Remote Similarity	NPD1930	Approved
0.6275	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD2799	Discontinued
0.6265	Remote Similarity	NPD2403	Approved
0.6259	Remote Similarity	NPD520	Approved
0.625	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6085	Phase 2
0.625	Remote Similarity	NPD5647	Approved
0.625	Remote Similarity	NPD9281	Approved
0.6242	Remote Similarity	NPD920	Approved
0.6241	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD7008	Discontinued
0.6232	Remote Similarity	NPD2347	Approved
0.6226	Remote Similarity	NPD4972	Discontinued
0.6218	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD1578	Phase 2
0.6216	Remote Similarity	NPD4307	Phase 2
0.6207	Remote Similarity	NPD9490	Approved
0.6204	Remote Similarity	NPD4198	Discontinued
0.6203	Remote Similarity	NPD7239	Suspended
0.6202	Remote Similarity	NPD1932	Approved
0.6194	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.619	Remote Similarity	NPD1989	Approved
0.619	Remote Similarity	NPD411	Approved
0.6187	Remote Similarity	NPD4016	Approved
0.6184	Remote Similarity	NPD2346	Discontinued
0.6184	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD2034	Discontinued
0.6181	Remote Similarity	NPD9567	Approved
0.6181	Remote Similarity	NPD552	Approved
0.6181	Remote Similarity	NPD553	Approved
0.6173	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD5402	Approved
0.6172	Remote Similarity	NPD2066	Phase 3
0.6169	Remote Similarity	NPD4628	Phase 3
0.616	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD3748	Approved
0.6159	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD5588	Approved
0.6144	Remote Similarity	NPD1549	Phase 2
0.6138	Remote Similarity	NPD2798	Approved
0.6136	Remote Similarity	NPD3134	Approved
0.6134	Remote Similarity	NPD9491	Approved
0.6131	Remote Similarity	NPD3366	Approved
0.6125	Remote Similarity	NPD1092	Approved
0.6125	Remote Similarity	NPD6599	Discontinued
0.6125	Remote Similarity	NPD1093	Approved
0.6122	Remote Similarity	NPD6039	Approved
0.6118	Remote Similarity	NPD2796	Approved
0.6118	Remote Similarity	NPD2935	Discontinued
0.6111	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD1876	Approved
0.6107	Remote Similarity	NPD5909	Discontinued
0.6104	Remote Similarity	NPD1243	Approved
0.6099	Remote Similarity	NPD5305	Approved
0.6099	Remote Similarity	NPD5306	Approved
0.6096	Remote Similarity	NPD5204	Approved
0.6095	Remote Similarity	NPD7799	Discontinued
0.609	Remote Similarity	NPD5058	Phase 3
0.609	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD3972	Approved
0.608	Remote Similarity	NPD9251	Approved
0.6078	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD1471	Phase 3
0.6071	Remote Similarity	NPD1894	Discontinued
0.6071	Remote Similarity	NPD2617	Discontinued
0.6069	Remote Similarity	NPD2626	Approved
0.6069	Remote Similarity	NPD2628	Approved
0.6069	Remote Similarity	NPD3267	Approved
0.6069	Remote Similarity	NPD2625	Approved
0.6069	Remote Similarity	NPD2159	Approved
0.6069	Remote Similarity	NPD2627	Approved
0.6069	Remote Similarity	NPD3266	Approved
0.6069	Remote Similarity	NPD2160	Approved
0.6067	Remote Similarity	NPD4069	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD2863	Approved
0.6067	Remote Similarity	NPD4066	Approved
0.6067	Remote Similarity	NPD4065	Approved
0.6067	Remote Similarity	NPD4068	Approved
0.6067	Remote Similarity	NPD4067	Approved
0.6061	Remote Similarity	NPD9697	Approved
0.6061	Remote Similarity	NPD5048	Discontinued
0.6061	Remote Similarity	NPD919	Approved
0.6058	Remote Similarity	NPD2650	Approved
0.6058	Remote Similarity	NPD2652	Approved
0.6058	Remote Similarity	NPD6010	Discontinued
0.6056	Remote Similarity	NPD4135	Approved
0.6056	Remote Similarity	NPD4136	Approved
0.6056	Remote Similarity	NPD4106	Approved
0.6053	Remote Similarity	NPD1510	Phase 2
0.6053	Remote Similarity	NPD4308	Phase 3
0.6049	Remote Similarity	NPD6801	Discontinued
0.604	Remote Similarity	NPD6233	Phase 2
0.604	Remote Similarity	NPD7713	Phase 3
0.6038	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD9508	Approved
0.6028	Remote Similarity	NPD1855	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD6190	Approved
0.6026	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD4806	Approved
0.6014	Remote Similarity	NPD4807	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