NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	236.14
Volume:	246.129
LogP:	2.728
LogD:	2.651
LogS:	-3.911
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.516
Synthetic Accessibility Score:	4.704
Fsp3:	0.786
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:	-4.686
MDCK Permeability:	2.6335772417951375e-05
Pgp-inhibitor:	0.066
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.18
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.953
Plasma Protein Binding (PPB):	73.98780059814453%
Volume Distribution (VD):	0.971
Pgp-substrate:	23.755979537963867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.638
CYP1A2-substrate:	0.609
CYP2C19-inhibitor:	0.837
CYP2C19-substrate:	0.851
CYP2C9-inhibitor:	0.137
CYP2C9-substrate:	0.231
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.175
CYP3A4-inhibitor:	0.724
CYP3A4-substrate:	0.466

ADMET: Excretion

Clearance (CL):	5.365
Half-life (T1/2):	0.604

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.186
Drug-inuced Liver Injury (DILI):	0.324
AMES Toxicity:	0.303
Rat Oral Acute Toxicity:	0.171
Maximum Recommended Daily Dose:	0.136
Skin Sensitization:	0.747
Carcinogencity:	0.716
Eye Corrosion:	0.417
Eye Irritation:	0.872
Respiratory Toxicity:	0.524

Download Data

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

Natural Product: NPC15059

Natural Product ID:	NPC15059
*Common Name:**	Oblongolide C
IUPAC Name:	(3aR,5aR,7S,9aS,9bR)-3a-hydroxy-7,9b-dimethyl-5a,6,7,8,9,9a-hexahydro-3H-benzo[g][2]benzofuran-1-one
Synonyms:	Oblongolide C
Standard InCHIKey:	QSSKWTDLXGNHNM-GRLWGSQLSA-N
Standard InCHI:	InChI=1S/C14H20O3/c1-9-3-4-11-10(7-9)5-6-14(16)8-17-12(15)13(11,14)2/h5-6,9-11,16H,3-4,7-8H2,1-2H3/t9-,10-,11-,13-,14-/m0/s1
SMILES:	C[C@H]1CC[C@H]2[C@@H](C=C[C@@]3(COC(=O)[C@]23C)O)C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087687
PubChem CID:	11601128
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
NPO33230	Phomopsis sp. BCC 9789	Species	Valsaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20038128]

☑ 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	4
MIC	2

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	212000.0	nM	PMID[479107]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	85000.0	nM	PMID[479107]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	>	85000.0	nM	PMID[479107]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	212000.0	nM	PMID[479107]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	MIC	>	212000.0	nM	PMID[479107]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	85000.0	nM	PMID[479107]

☑ 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 NPC15059 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	161
0.1-0.2	940
0.2-0.3	4125
0.3-0.4	10376
0.4-0.5	12291
0.5-0.6	6914
0.6-0.7	6598
0.7-0.8	1261
0.8-0.85	28
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8667	High Similarity	NPC214844
0.837	Intermediate Similarity	NPC252433
0.8367	Intermediate Similarity	NPC296950
0.8367	Intermediate Similarity	NPC146731
0.8333	Intermediate Similarity	NPC41017
0.8333	Intermediate Similarity	NPC171722
0.8315	Intermediate Similarity	NPC52628
0.8229	Intermediate Similarity	NPC278008
0.8211	Intermediate Similarity	NPC469528
0.8211	Intermediate Similarity	NPC469369
0.8182	Intermediate Similarity	NPC258532
0.8172	Intermediate Similarity	NPC230623
0.8172	Intermediate Similarity	NPC303697
0.8161	Intermediate Similarity	NPC195424
0.8152	Intermediate Similarity	NPC471222
0.81	Intermediate Similarity	NPC477125
0.809	Intermediate Similarity	NPC470948
0.8085	Intermediate Similarity	NPC115021
0.8022	Intermediate Similarity	NPC6979
0.8	Intermediate Similarity	NPC295799
0.798	Intermediate Similarity	NPC183571
0.7961	Intermediate Similarity	NPC29133
0.7961	Intermediate Similarity	NPC5103
0.7961	Intermediate Similarity	NPC235014
0.7957	Intermediate Similarity	NPC168131
0.7935	Intermediate Similarity	NPC128644
0.7931	Intermediate Similarity	NPC35574
0.7931	Intermediate Similarity	NPC179028
0.79	Intermediate Similarity	NPC69171
0.79	Intermediate Similarity	NPC474165
0.7889	Intermediate Similarity	NPC22611
0.7885	Intermediate Similarity	NPC304180
0.7885	Intermediate Similarity	NPC179798
0.7885	Intermediate Similarity	NPC470961
0.7879	Intermediate Similarity	NPC244456
0.7879	Intermediate Similarity	NPC469657
0.7872	Intermediate Similarity	NPC472307
0.7865	Intermediate Similarity	NPC327002
0.7857	Intermediate Similarity	NPC159763
0.7857	Intermediate Similarity	NPC278386
0.7857	Intermediate Similarity	NPC124512
0.7849	Intermediate Similarity	NPC477128
0.7843	Intermediate Similarity	NPC473284
0.7843	Intermediate Similarity	NPC301666
0.783	Intermediate Similarity	NPC117712
0.7826	Intermediate Similarity	NPC82979
0.7826	Intermediate Similarity	NPC476982
0.7822	Intermediate Similarity	NPC220964
0.7822	Intermediate Similarity	NPC475676
0.7812	Intermediate Similarity	NPC250075
0.781	Intermediate Similarity	NPC269530
0.781	Intermediate Similarity	NPC191620
0.7789	Intermediate Similarity	NPC472814
0.7789	Intermediate Similarity	NPC177037
0.7789	Intermediate Similarity	NPC186363
0.7789	Intermediate Similarity	NPC233345
0.7767	Intermediate Similarity	NPC475418
0.7767	Intermediate Similarity	NPC473482
0.7767	Intermediate Similarity	NPC318363
0.7766	Intermediate Similarity	NPC36668
0.7766	Intermediate Similarity	NPC79027
0.7766	Intermediate Similarity	NPC118011
0.7757	Intermediate Similarity	NPC270929
0.7742	Intermediate Similarity	NPC312561
0.7742	Intermediate Similarity	NPC167877
0.7736	Intermediate Similarity	NPC469454
0.7736	Intermediate Similarity	NPC469463
0.7736	Intermediate Similarity	NPC56448
0.7736	Intermediate Similarity	NPC469496
0.7732	Intermediate Similarity	NPC53565
0.7732	Intermediate Similarity	NPC183012
0.7732	Intermediate Similarity	NPC248574
0.7727	Intermediate Similarity	NPC321514
0.7727	Intermediate Similarity	NPC218817
0.7727	Intermediate Similarity	NPC11796
0.7723	Intermediate Similarity	NPC4620
0.7723	Intermediate Similarity	NPC159533
0.7723	Intermediate Similarity	NPC475050
0.7717	Intermediate Similarity	NPC269638
0.7717	Intermediate Similarity	NPC329738
0.7717	Intermediate Similarity	NPC147921
0.7717	Intermediate Similarity	NPC76333
0.7714	Intermediate Similarity	NPC324683
0.7708	Intermediate Similarity	NPC166346
0.77	Intermediate Similarity	NPC235142
0.7692	Intermediate Similarity	NPC475065
0.7692	Intermediate Similarity	NPC49208
0.7685	Intermediate Similarity	NPC470493
0.7685	Intermediate Similarity	NPC470492
0.7685	Intermediate Similarity	NPC470775
0.7685	Intermediate Similarity	NPC469684
0.7685	Intermediate Similarity	NPC176513
0.7685	Intermediate Similarity	NPC167606
0.7685	Intermediate Similarity	NPC140055
0.7685	Intermediate Similarity	NPC183580
0.7685	Intermediate Similarity	NPC312824
0.7685	Intermediate Similarity	NPC286528
0.7685	Intermediate Similarity	NPC20302
0.7677	Intermediate Similarity	NPC234617
0.7677	Intermediate Similarity	NPC316598
0.7677	Intermediate Similarity	NPC124703
0.7677	Intermediate Similarity	NPC23364
0.767	Intermediate Similarity	NPC230541
0.767	Intermediate Similarity	NPC67321
0.767	Intermediate Similarity	NPC187435
0.767	Intermediate Similarity	NPC91034
0.767	Intermediate Similarity	NPC330011
0.767	Intermediate Similarity	NPC329048
0.7664	Intermediate Similarity	NPC67259
0.7664	Intermediate Similarity	NPC147912
0.766	Intermediate Similarity	NPC215831
0.7653	Intermediate Similarity	NPC472733
0.7653	Intermediate Similarity	NPC472734
0.7647	Intermediate Similarity	NPC473175
0.764	Intermediate Similarity	NPC327674
0.7634	Intermediate Similarity	NPC476104
0.7634	Intermediate Similarity	NPC329692
0.7634	Intermediate Similarity	NPC478112
0.7634	Intermediate Similarity	NPC262085
0.7634	Intermediate Similarity	NPC198761
0.7634	Intermediate Similarity	NPC473226
0.7634	Intermediate Similarity	NPC278283
0.7634	Intermediate Similarity	NPC9231
0.7634	Intermediate Similarity	NPC194417
0.7634	Intermediate Similarity	NPC324063
0.7634	Intermediate Similarity	NPC250981
0.7629	Intermediate Similarity	NPC167219
0.7629	Intermediate Similarity	NPC53685
0.7619	Intermediate Similarity	NPC161816
0.7619	Intermediate Similarity	NPC115257
0.7619	Intermediate Similarity	NPC37116
0.7615	Intermediate Similarity	NPC329736
0.7615	Intermediate Similarity	NPC470776
0.7615	Intermediate Similarity	NPC186525
0.7615	Intermediate Similarity	NPC709
0.7615	Intermediate Similarity	NPC50774
0.7609	Intermediate Similarity	NPC32676
0.7609	Intermediate Similarity	NPC165064
0.7604	Intermediate Similarity	NPC49420
0.76	Intermediate Similarity	NPC474012
0.76	Intermediate Similarity	NPC476299
0.76	Intermediate Similarity	NPC477655
0.76	Intermediate Similarity	NPC477656
0.76	Intermediate Similarity	NPC54705
0.7596	Intermediate Similarity	NPC472218
0.7596	Intermediate Similarity	NPC233379
0.7596	Intermediate Similarity	NPC474664
0.7596	Intermediate Similarity	NPC151393
0.7596	Intermediate Similarity	NPC472217
0.7596	Intermediate Similarity	NPC14862
0.7596	Intermediate Similarity	NPC472219
0.7596	Intermediate Similarity	NPC306265
0.7596	Intermediate Similarity	NPC94377
0.7593	Intermediate Similarity	NPC179626
0.7593	Intermediate Similarity	NPC64318
0.7586	Intermediate Similarity	NPC476795
0.7582	Intermediate Similarity	NPC186276
0.7582	Intermediate Similarity	NPC474252
0.7582	Intermediate Similarity	NPC178676
0.7579	Intermediate Similarity	NPC474700
0.7579	Intermediate Similarity	NPC77001
0.7579	Intermediate Similarity	NPC5509
0.7579	Intermediate Similarity	NPC474570
0.7579	Intermediate Similarity	NPC73995
0.7579	Intermediate Similarity	NPC253618
0.7576	Intermediate Similarity	NPC472732
0.7576	Intermediate Similarity	NPC73911
0.7576	Intermediate Similarity	NPC27105
0.7576	Intermediate Similarity	NPC107243
0.7576	Intermediate Similarity	NPC208094
0.7576	Intermediate Similarity	NPC170131
0.7576	Intermediate Similarity	NPC53844
0.7576	Intermediate Similarity	NPC475894
0.7576	Intermediate Similarity	NPC124246
0.7576	Intermediate Similarity	NPC472731
0.7573	Intermediate Similarity	NPC16313
0.7573	Intermediate Similarity	NPC472655
0.7573	Intermediate Similarity	NPC9303
0.7573	Intermediate Similarity	NPC475802
0.7556	Intermediate Similarity	NPC104120
0.7556	Intermediate Similarity	NPC157895
0.7556	Intermediate Similarity	NPC148685
0.7553	Intermediate Similarity	NPC23622
0.7553	Intermediate Similarity	NPC245004
0.7551	Intermediate Similarity	NPC295347
0.7551	Intermediate Similarity	NPC209355
0.7549	Intermediate Similarity	NPC72151
0.7549	Intermediate Similarity	NPC475321
0.7547	Intermediate Similarity	NPC317107
0.7545	Intermediate Similarity	NPC61520
0.7545	Intermediate Similarity	NPC264954
0.7528	Intermediate Similarity	NPC239098
0.7527	Intermediate Similarity	NPC476602
0.7527	Intermediate Similarity	NPC471344
0.7526	Intermediate Similarity	NPC476416
0.7525	Intermediate Similarity	NPC476134
0.7525	Intermediate Similarity	NPC308824
0.7525	Intermediate Similarity	NPC97435
0.7525	Intermediate Similarity	NPC101067
0.7525	Intermediate Similarity	NPC303559

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 NPC15059 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	1272
0.2-0.3	3730
0.3-0.4	2627
0.4-0.5	801
0.5-0.6	333
0.6-0.7	220
0.7-0.8	26
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
0.7857	Intermediate Similarity	NPD4225	Approved
0.7685	Intermediate Similarity	NPD7115	Discovery
0.7347	Intermediate Similarity	NPD5778	Approved
0.7347	Intermediate Similarity	NPD5779	Approved
0.7347	Intermediate Similarity	NPD6399	Phase 3
0.734	Intermediate Similarity	NPD1694	Approved
0.7245	Intermediate Similarity	NPD6411	Approved
0.72	Intermediate Similarity	NPD5695	Phase 3
0.7157	Intermediate Similarity	NPD5696	Approved
0.7083	Intermediate Similarity	NPD4623	Approved
0.7083	Intermediate Similarity	NPD4519	Discontinued
0.7071	Intermediate Similarity	NPD7637	Suspended
0.7059	Intermediate Similarity	NPD6084	Phase 2
0.7059	Intermediate Similarity	NPD6083	Phase 2
0.7041	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6101	Approved
0.703	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4269	Approved
0.7021	Intermediate Similarity	NPD4270	Approved
0.7021	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3667	Approved
0.697	Remote Similarity	NPD5785	Approved
0.697	Remote Similarity	NPD5207	Approved
0.6915	Remote Similarity	NPD5369	Approved
0.6907	Remote Similarity	NPD6684	Approved
0.6907	Remote Similarity	NPD7146	Approved
0.6907	Remote Similarity	NPD7334	Approved
0.6907	Remote Similarity	NPD6409	Approved
0.6907	Remote Similarity	NPD7521	Approved
0.6907	Remote Similarity	NPD5786	Approved
0.6907	Remote Similarity	NPD5330	Approved
0.69	Remote Similarity	NPD5281	Approved
0.69	Remote Similarity	NPD5284	Approved
0.69	Remote Similarity	NPD7983	Approved
0.6875	Remote Similarity	NPD4786	Approved
0.6818	Remote Similarity	NPD6371	Approved
0.6809	Remote Similarity	NPD4252	Approved
0.6804	Remote Similarity	NPD5363	Approved
0.6789	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6686	Approved
0.6774	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7154	Phase 3
0.6768	Remote Similarity	NPD6672	Approved
0.6768	Remote Similarity	NPD6903	Approved
0.6768	Remote Similarity	NPD5737	Approved
0.6768	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5282	Discontinued
0.6765	Remote Similarity	NPD7748	Approved
0.6735	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3618	Phase 1
0.6735	Remote Similarity	NPD6098	Approved
0.6731	Remote Similarity	NPD7902	Approved
0.6727	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6319	Approved
0.6701	Remote Similarity	NPD3666	Approved
0.6701	Remote Similarity	NPD3665	Phase 1
0.6701	Remote Similarity	NPD3133	Approved
0.67	Remote Similarity	NPD4753	Phase 2
0.6699	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5210	Approved
0.6699	Remote Similarity	NPD4629	Approved
0.6697	Remote Similarity	NPD5697	Approved
0.6697	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD3573	Approved
0.6636	Remote Similarity	NPD6881	Approved
0.6636	Remote Similarity	NPD6899	Approved
0.6632	Remote Similarity	NPD4819	Approved
0.6632	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4821	Approved
0.6632	Remote Similarity	NPD4820	Approved
0.6632	Remote Similarity	NPD4822	Approved
0.663	Remote Similarity	NPD8039	Approved
0.6607	Remote Similarity	NPD6650	Approved
0.6607	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6649	Approved
0.6606	Remote Similarity	NPD6675	Approved
0.6606	Remote Similarity	NPD7128	Approved
0.6606	Remote Similarity	NPD6402	Approved
0.6606	Remote Similarity	NPD5739	Approved
0.6604	Remote Similarity	NPD7640	Approved
0.6604	Remote Similarity	NPD7639	Approved
0.6602	Remote Similarity	NPD6001	Approved
0.66	Remote Similarity	NPD5208	Approved
0.6598	Remote Similarity	NPD5362	Discontinued
0.6577	Remote Similarity	NPD6012	Approved
0.6577	Remote Similarity	NPD6014	Approved
0.6577	Remote Similarity	NPD6373	Approved
0.6577	Remote Similarity	NPD6372	Approved
0.6577	Remote Similarity	NPD6013	Approved
0.6569	Remote Similarity	NPD5693	Phase 1
0.6569	Remote Similarity	NPD7515	Phase 2
0.6569	Remote Similarity	NPD5694	Approved
0.6566	Remote Similarity	NPD5690	Phase 2
0.6545	Remote Similarity	NPD5701	Approved
0.6545	Remote Similarity	NPD6412	Phase 2
0.6535	Remote Similarity	NPD6904	Approved
0.6535	Remote Similarity	NPD6673	Approved
0.6535	Remote Similarity	NPD6080	Approved
0.6531	Remote Similarity	NPD3668	Phase 3
0.6531	Remote Similarity	NPD4197	Approved
0.6518	Remote Similarity	NPD6883	Approved
0.6518	Remote Similarity	NPD7102	Approved
0.6518	Remote Similarity	NPD7290	Approved
0.6509	Remote Similarity	NPD7638	Approved
0.65	Remote Similarity	NPD7524	Approved
0.65	Remote Similarity	NPD7492	Approved
0.6491	Remote Similarity	NPD4632	Approved
0.6486	Remote Similarity	NPD7320	Approved
0.6486	Remote Similarity	NPD6011	Approved
0.6481	Remote Similarity	NPD5211	Phase 2
0.6471	Remote Similarity	NPD5692	Phase 3
0.6471	Remote Similarity	NPD6698	Approved
0.6471	Remote Similarity	NPD46	Approved
0.6465	Remote Similarity	NPD5329	Approved
0.6465	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6869	Approved
0.646	Remote Similarity	NPD6847	Approved
0.646	Remote Similarity	NPD6617	Approved
0.646	Remote Similarity	NPD8130	Phase 1
0.6458	Remote Similarity	NPD4695	Discontinued
0.6455	Remote Similarity	NPD6008	Approved
0.6446	Remote Similarity	NPD6616	Approved
0.6442	Remote Similarity	NPD7900	Approved
0.6442	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6054	Approved
0.6421	Remote Similarity	NPD4271	Approved
0.6421	Remote Similarity	NPD4268	Approved
0.6408	Remote Similarity	NPD6079	Approved
0.6408	Remote Similarity	NPD8035	Phase 2
0.6408	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD8034	Phase 2
0.6408	Remote Similarity	NPD6050	Approved
0.6404	Remote Similarity	NPD6882	Approved
0.64	Remote Similarity	NPD4689	Approved
0.64	Remote Similarity	NPD5280	Approved
0.64	Remote Similarity	NPD4694	Approved
0.64	Remote Similarity	NPD4693	Phase 3
0.64	Remote Similarity	NPD4249	Approved
0.64	Remote Similarity	NPD5205	Approved
0.64	Remote Similarity	NPD5279	Phase 3
0.64	Remote Similarity	NPD4688	Approved
0.64	Remote Similarity	NPD4138	Approved
0.64	Remote Similarity	NPD4690	Approved
0.6396	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7078	Approved
0.6393	Remote Similarity	NPD8074	Phase 3
0.6387	Remote Similarity	NPD6015	Approved
0.6387	Remote Similarity	NPD6016	Approved
0.6373	Remote Similarity	NPD6051	Approved
0.6373	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5328	Approved
0.6372	Remote Similarity	NPD4634	Approved
0.6364	Remote Similarity	NPD5141	Approved
0.6346	Remote Similarity	NPD4202	Approved
0.6341	Remote Similarity	NPD7736	Approved
0.6337	Remote Similarity	NPD4250	Approved
0.6337	Remote Similarity	NPD4251	Approved
0.6333	Remote Similarity	NPD6370	Approved
0.6333	Remote Similarity	NPD5988	Approved
0.6327	Remote Similarity	NPD6435	Approved
0.6325	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7839	Suspended
0.6303	Remote Similarity	NPD6059	Approved
0.63	Remote Similarity	NPD1696	Phase 3
0.63	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4696	Approved
0.6296	Remote Similarity	NPD6404	Discontinued
0.6296	Remote Similarity	NPD5286	Approved
0.6296	Remote Similarity	NPD5285	Approved
0.629	Remote Similarity	NPD7319	Approved
0.6283	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD8328	Phase 3
0.6277	Remote Similarity	NPD3702	Approved
0.6263	Remote Similarity	NPD6695	Phase 3
0.6262	Remote Similarity	NPD4755	Approved
0.6261	Remote Similarity	NPD6053	Discontinued
0.626	Remote Similarity	NPD8293	Discontinued
0.625	Remote Similarity	NPD3617	Approved
0.6239	Remote Similarity	NPD5344	Discontinued
0.6239	Remote Similarity	NPD2629	Approved
0.6224	Remote Similarity	NPD4139	Approved
0.6224	Remote Similarity	NPD4692	Approved
0.6214	Remote Similarity	NPD5370	Suspended
0.6214	Remote Similarity	NPD1695	Approved
0.6211	Remote Similarity	NPD6933	Approved
0.6211	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4195	Approved
0.6186	Remote Similarity	NPD6009	Approved
0.6182	Remote Similarity	NPD5226	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