NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	260.788
LogP:	3.278
LogD:	2.942
LogS:	-3.068
# Rotatable Bonds:	0
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.691
Synthetic Accessibility Score:	5.372
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.834
MDCK Permeability:	1.60083181981463e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.981
30% Bioavailability (F30%):	0.564

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	93.1642837524414%
Volume Distribution (VD):	2.007
Pgp-substrate:	10.353031158447266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.093
CYP1A2-substrate:	0.674
CYP2C19-inhibitor:	0.123
CYP2C19-substrate:	0.807
CYP2C9-inhibitor:	0.48
CYP2C9-substrate:	0.944
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.765
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.396

ADMET: Excretion

Clearance (CL):	12.081
Half-life (T1/2):	0.53

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.626
Drug-inuced Liver Injury (DILI):	0.331
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.654
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.096
Carcinogencity:	0.227
Eye Corrosion:	0.004
Eye Irritation:	0.031
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC472377

Natural Product ID:	NPC472377
*Common Name:**	OPFPNLNBWGYRAV-LEKOTGGOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OPFPNLNBWGYRAV-LEKOTGGOSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-8-4-9-7-15(2,3)11(8)6-12(16)10-5-13(17)18-14(9)10/h4-5,9,11-12,14,16H,6-7H2,1-3H3/t9-,11+,12-,14+/m1/s1
SMILES:	O=C1C=C2[C@@H](O1)[C@@H]1C=C([C@H](C[C@H]2O)C(C1)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3397812
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO33203	euryspongia sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23434422]
NPO33203	euryspongia sp.	Species	Dysideidae	Eukaryota	n.a.	Iriomote Island	n.a.	PMID[25600405]

☑ 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	3

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	40000.0	nM	PMID[555503]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	40000.0	nM	PMID[555503]
NPT27	Others	Unspecified		IC50	>	40000.0	nM	PMID[555503]

☑ 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 NPC472377 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	188
0.1-0.2	1310
0.2-0.3	5438
0.3-0.4	15864
0.4-0.5	10038
0.5-0.6	6883
0.6-0.7	2699
0.7-0.8	260
0.8-0.85	11
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.939	High Similarity	NPC472378
0.9012	High Similarity	NPC311070
0.881	High Similarity	NPC312561
0.878	High Similarity	NPC474809
0.8765	High Similarity	NPC475944
0.8734	High Similarity	NPC262747
0.8625	High Similarity	NPC474816
0.8625	High Similarity	NPC209135
0.8605	High Similarity	NPC470734
0.8571	High Similarity	NPC471795
0.8554	High Similarity	NPC42476
0.8506	High Similarity	NPC232426
0.8506	High Similarity	NPC281942
0.8506	High Similarity	NPC78973
0.8488	Intermediate Similarity	NPC472810
0.8488	Intermediate Similarity	NPC472809
0.8471	Intermediate Similarity	NPC131813
0.8427	Intermediate Similarity	NPC104925
0.8427	Intermediate Similarity	NPC298973
0.8409	Intermediate Similarity	NPC141831
0.8353	Intermediate Similarity	NPC42586
0.8353	Intermediate Similarity	NPC473251
0.8333	Intermediate Similarity	NPC474193
0.8333	Intermediate Similarity	NPC12283
0.8315	Intermediate Similarity	NPC115021
0.8315	Intermediate Similarity	NPC472954
0.8315	Intermediate Similarity	NPC472812
0.8295	Intermediate Similarity	NPC280149
0.8295	Intermediate Similarity	NPC221111
0.8295	Intermediate Similarity	NPC182136
0.8293	Intermediate Similarity	NPC242767
0.8256	Intermediate Similarity	NPC471219
0.8242	Intermediate Similarity	NPC165632
0.8222	Intermediate Similarity	NPC469697
0.8214	Intermediate Similarity	NPC323251
0.8214	Intermediate Similarity	NPC471298
0.8202	Intermediate Similarity	NPC177037
0.8202	Intermediate Similarity	NPC472811
0.8202	Intermediate Similarity	NPC472814
0.8182	Intermediate Similarity	NPC50488
0.8182	Intermediate Similarity	NPC474396
0.8171	Intermediate Similarity	NPC184737
0.8161	Intermediate Similarity	NPC471796
0.8118	Intermediate Similarity	NPC193198
0.8118	Intermediate Similarity	NPC471297
0.8111	Intermediate Similarity	NPC53555
0.8111	Intermediate Similarity	NPC205034
0.8111	Intermediate Similarity	NPC162615
0.8111	Intermediate Similarity	NPC152778
0.809	Intermediate Similarity	NPC310479
0.8068	Intermediate Similarity	NPC474629
0.8046	Intermediate Similarity	NPC329692
0.8043	Intermediate Similarity	NPC162346
0.8023	Intermediate Similarity	NPC471301
0.8023	Intermediate Similarity	NPC126518
0.8023	Intermediate Similarity	NPC474865
0.8023	Intermediate Similarity	NPC82297
0.8023	Intermediate Similarity	NPC31086
0.8022	Intermediate Similarity	NPC53685
0.8022	Intermediate Similarity	NPC470255
0.8	Intermediate Similarity	NPC471218
0.8	Intermediate Similarity	NPC16349
0.8	Intermediate Similarity	NPC72845
0.8	Intermediate Similarity	NPC2882
0.8	Intermediate Similarity	NPC222244
0.7978	Intermediate Similarity	NPC5509
0.7957	Intermediate Similarity	NPC205143
0.7957	Intermediate Similarity	NPC53844
0.7955	Intermediate Similarity	NPC476600
0.7955	Intermediate Similarity	NPC473891
0.7935	Intermediate Similarity	NPC276110
0.7931	Intermediate Similarity	NPC86316
0.7931	Intermediate Similarity	NPC106416
0.7931	Intermediate Similarity	NPC163606
0.7912	Intermediate Similarity	NPC139692
0.7907	Intermediate Similarity	NPC321385
0.7907	Intermediate Similarity	NPC23748
0.7889	Intermediate Similarity	NPC220216
0.7882	Intermediate Similarity	NPC159148
0.7857	Intermediate Similarity	NPC80471
0.7857	Intermediate Similarity	NPC5908
0.7857	Intermediate Similarity	NPC110373
0.7849	Intermediate Similarity	NPC242848
0.7849	Intermediate Similarity	NPC16967
0.7849	Intermediate Similarity	NPC473153
0.7849	Intermediate Similarity	NPC134072
0.7849	Intermediate Similarity	NPC234993
0.7831	Intermediate Similarity	NPC473756
0.7831	Intermediate Similarity	NPC189206
0.7831	Intermediate Similarity	NPC283619
0.7826	Intermediate Similarity	NPC57117
0.7826	Intermediate Similarity	NPC191521
0.7816	Intermediate Similarity	NPC471302
0.7816	Intermediate Similarity	NPC96055
0.7802	Intermediate Similarity	NPC477122
0.7802	Intermediate Similarity	NPC124374
0.7802	Intermediate Similarity	NPC329842
0.7791	Intermediate Similarity	NPC256112
0.7789	Intermediate Similarity	NPC38855
0.7789	Intermediate Similarity	NPC474012
0.7789	Intermediate Similarity	NPC476299
0.7789	Intermediate Similarity	NPC472644
0.7778	Intermediate Similarity	NPC261320
0.7778	Intermediate Similarity	NPC168131
0.7778	Intermediate Similarity	NPC174342
0.7766	Intermediate Similarity	NPC475709
0.7766	Intermediate Similarity	NPC208094
0.7766	Intermediate Similarity	NPC477719
0.7766	Intermediate Similarity	NPC477718
0.7765	Intermediate Similarity	NPC10636
0.7765	Intermediate Similarity	NPC268827
0.7765	Intermediate Similarity	NPC281880
0.7753	Intermediate Similarity	NPC166857
0.775	Intermediate Similarity	NPC4299
0.7742	Intermediate Similarity	NPC472441
0.7742	Intermediate Similarity	NPC183012
0.7738	Intermediate Similarity	NPC172066
0.7727	Intermediate Similarity	NPC52628
0.7727	Intermediate Similarity	NPC65661
0.7727	Intermediate Similarity	NPC30984
0.7727	Intermediate Similarity	NPC35933
0.7717	Intermediate Similarity	NPC156553
0.7717	Intermediate Similarity	NPC99653
0.7701	Intermediate Similarity	NPC49208
0.7701	Intermediate Similarity	NPC79945
0.7701	Intermediate Similarity	NPC477124
0.7692	Intermediate Similarity	NPC472642
0.7692	Intermediate Similarity	NPC51486
0.7692	Intermediate Similarity	NPC477782
0.7684	Intermediate Similarity	NPC124512
0.7684	Intermediate Similarity	NPC278386
0.7684	Intermediate Similarity	NPC222303
0.7684	Intermediate Similarity	NPC474440
0.7684	Intermediate Similarity	NPC159763
0.7684	Intermediate Similarity	NPC23364
0.7684	Intermediate Similarity	NPC275086
0.7684	Intermediate Similarity	NPC325229
0.7674	Intermediate Similarity	NPC170303
0.7674	Intermediate Similarity	NPC325031
0.7654	Intermediate Similarity	NPC472254
0.7647	Intermediate Similarity	NPC100906
0.764	Intermediate Similarity	NPC474062
0.764	Intermediate Similarity	NPC477668
0.7634	Intermediate Similarity	NPC474554
0.7634	Intermediate Similarity	NPC105490
0.7634	Intermediate Similarity	NPC474555
0.7634	Intermediate Similarity	NPC469491
0.7625	Intermediate Similarity	NPC101622
0.7619	Intermediate Similarity	NPC54996
0.7619	Intermediate Similarity	NPC315394
0.7614	Intermediate Similarity	NPC474693
0.7614	Intermediate Similarity	NPC32223
0.7614	Intermediate Similarity	NPC470800
0.7614	Intermediate Similarity	NPC474359
0.7609	Intermediate Similarity	NPC477783
0.7609	Intermediate Similarity	NPC234335
0.7609	Intermediate Similarity	NPC233345
0.7609	Intermediate Similarity	NPC186363
0.7604	Intermediate Similarity	NPC477721
0.7604	Intermediate Similarity	NPC477716
0.7604	Intermediate Similarity	NPC227865
0.7595	Intermediate Similarity	NPC472266
0.759	Intermediate Similarity	NPC329852
0.7586	Intermediate Similarity	NPC324170
0.7582	Intermediate Similarity	NPC314727
0.7582	Intermediate Similarity	NPC251528
0.7582	Intermediate Similarity	NPC146554
0.7582	Intermediate Similarity	NPC473647
0.7582	Intermediate Similarity	NPC79027
0.7582	Intermediate Similarity	NPC246028
0.7582	Intermediate Similarity	NPC20946
0.7579	Intermediate Similarity	NPC73911
0.7579	Intermediate Similarity	NPC69385
0.7579	Intermediate Similarity	NPC51499
0.7579	Intermediate Similarity	NPC474343
0.7558	Intermediate Similarity	NPC271104
0.7556	Intermediate Similarity	NPC475678
0.7556	Intermediate Similarity	NPC131329
0.7556	Intermediate Similarity	NPC471779
0.7553	Intermediate Similarity	NPC295347
0.7553	Intermediate Similarity	NPC209355
0.7529	Intermediate Similarity	NPC471220
0.7529	Intermediate Similarity	NPC475994
0.7528	Intermediate Similarity	NPC474013
0.7528	Intermediate Similarity	NPC475860
0.7528	Intermediate Similarity	NPC474694
0.7528	Intermediate Similarity	NPC189311
0.7528	Intermediate Similarity	NPC119001
0.7528	Intermediate Similarity	NPC473659
0.7528	Intermediate Similarity	NPC472442
0.7528	Intermediate Similarity	NPC109528
0.7527	Intermediate Similarity	NPC476598
0.7527	Intermediate Similarity	NPC166346
0.7527	Intermediate Similarity	NPC472640
0.7527	Intermediate Similarity	NPC7349
0.7527	Intermediate Similarity	NPC476597
0.7527	Intermediate Similarity	NPC472641
0.7526	Intermediate Similarity	NPC477717
0.7526	Intermediate Similarity	NPC469657
0.7526	Intermediate Similarity	NPC244456

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 NPC472377 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1821
0.2-0.3	3986
0.3-0.4	2288
0.4-0.5	591
0.5-0.6	256
0.6-0.7	39
0.7-0.8	1
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
0.8023	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD4225	Approved
0.7386	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7640	Approved
0.7245	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD7638	Approved
0.701	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1694	Approved
0.6947	Remote Similarity	NPD5785	Approved
0.6923	Remote Similarity	NPD6686	Approved
0.6914	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7637	Suspended
0.6842	Remote Similarity	NPD6051	Approved
0.6832	Remote Similarity	NPD5344	Discontinued
0.6804	Remote Similarity	NPD5779	Approved
0.6804	Remote Similarity	NPD5778	Approved
0.6782	Remote Similarity	NPD8264	Approved
0.6778	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD46	Approved
0.6771	Remote Similarity	NPD6698	Approved
0.6771	Remote Similarity	NPD7838	Discovery
0.6739	Remote Similarity	NPD6695	Phase 3
0.6739	Remote Similarity	NPD7154	Phase 3
0.6727	Remote Similarity	NPD7115	Discovery
0.6705	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7146	Approved
0.6702	Remote Similarity	NPD7521	Approved
0.6702	Remote Similarity	NPD7334	Approved
0.6702	Remote Similarity	NPD6409	Approved
0.6702	Remote Similarity	NPD6684	Approved
0.6702	Remote Similarity	NPD5330	Approved
0.6701	Remote Similarity	NPD6411	Approved
0.67	Remote Similarity	NPD6083	Phase 2
0.67	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6929	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.6633	Remote Similarity	NPD6399	Phase 3
0.663	Remote Similarity	NPD3667	Approved
0.6602	Remote Similarity	NPD7632	Discontinued
0.6596	Remote Similarity	NPD1696	Phase 3
0.6596	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6931	Approved
0.6593	Remote Similarity	NPD4822	Approved
0.6593	Remote Similarity	NPD6930	Phase 2
0.6593	Remote Similarity	NPD4819	Approved
0.6593	Remote Similarity	NPD4821	Approved
0.6593	Remote Similarity	NPD4820	Approved
0.6591	Remote Similarity	NPD7339	Approved
0.6591	Remote Similarity	NPD8039	Approved
0.6591	Remote Similarity	NPD6942	Approved
0.6585	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6648	Approved
0.6566	Remote Similarity	NPD7748	Approved
0.6562	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6903	Approved
0.6559	Remote Similarity	NPD5362	Discontinued
0.6556	Remote Similarity	NPD4271	Approved
0.6556	Remote Similarity	NPD4268	Approved
0.6556	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD4191	Approved
0.6543	Remote Similarity	NPD368	Approved
0.6543	Remote Similarity	NPD4194	Approved
0.6543	Remote Similarity	NPD4193	Approved
0.6543	Remote Similarity	NPD4192	Approved
0.6542	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7515	Phase 2
0.6526	Remote Similarity	NPD5279	Phase 3
0.6526	Remote Similarity	NPD3618	Phase 1
0.6514	Remote Similarity	NPD6053	Discontinued
0.6495	Remote Similarity	NPD6101	Approved
0.6495	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4786	Approved
0.6484	Remote Similarity	NPD7645	Phase 2
0.6481	Remote Similarity	NPD6371	Approved
0.6477	Remote Similarity	NPD6926	Approved
0.6477	Remote Similarity	NPD6924	Approved
0.6471	Remote Similarity	NPD5696	Approved
0.6458	Remote Similarity	NPD7750	Discontinued
0.6458	Remote Similarity	NPD7524	Approved
0.6458	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5209	Approved
0.6444	Remote Similarity	NPD6925	Approved
0.6444	Remote Similarity	NPD5776	Phase 2
0.6421	Remote Similarity	NPD5363	Approved
0.6415	Remote Similarity	NPD5739	Approved
0.6415	Remote Similarity	NPD6402	Approved
0.6415	Remote Similarity	NPD7128	Approved
0.6415	Remote Similarity	NPD6675	Approved
0.6413	Remote Similarity	NPD7332	Phase 2
0.6413	Remote Similarity	NPD7514	Phase 3
0.641	Remote Similarity	NPD342	Phase 1
0.6392	Remote Similarity	NPD5737	Approved
0.6392	Remote Similarity	NPD6672	Approved
0.6383	Remote Similarity	NPD5331	Approved
0.6383	Remote Similarity	NPD5332	Approved
0.6374	Remote Similarity	NPD7145	Approved
0.6374	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7902	Approved
0.6372	Remote Similarity	NPD7327	Approved
0.6372	Remote Similarity	NPD7328	Approved
0.6364	Remote Similarity	NPD5693	Phase 1
0.6355	Remote Similarity	NPD5697	Approved
0.6355	Remote Similarity	NPD5701	Approved
0.6354	Remote Similarity	NPD4623	Approved
0.6354	Remote Similarity	NPD4249	Approved
0.6354	Remote Similarity	NPD4519	Discontinued
0.6348	Remote Similarity	NPD8033	Approved
0.6344	Remote Similarity	NPD6902	Approved
0.6344	Remote Similarity	NPD4790	Discontinued
0.6333	Remote Similarity	NPD6933	Approved
0.633	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5328	Approved
0.6327	Remote Similarity	NPD4753	Phase 2
0.6316	Remote Similarity	NPD7516	Approved
0.6311	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4195	Approved
0.6296	Remote Similarity	NPD7320	Approved
0.6296	Remote Similarity	NPD6899	Approved
0.6296	Remote Similarity	NPD6881	Approved
0.6289	Remote Similarity	NPD4251	Approved
0.6289	Remote Similarity	NPD4250	Approved
0.6277	Remote Similarity	NPD4270	Approved
0.6277	Remote Similarity	NPD4269	Approved
0.6275	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD8377	Approved
0.6261	Remote Similarity	NPD8294	Approved
0.625	Remote Similarity	NPD6893	Approved
0.6239	Remote Similarity	NPD6012	Approved
0.6239	Remote Similarity	NPD6373	Approved
0.6239	Remote Similarity	NPD6014	Approved
0.6239	Remote Similarity	NPD6372	Approved
0.6239	Remote Similarity	NPD6013	Approved
0.6237	Remote Similarity	NPD4695	Discontinued
0.6207	Remote Similarity	NPD7503	Approved
0.6207	Remote Similarity	NPD8296	Approved
0.6207	Remote Similarity	NPD8335	Approved
0.6207	Remote Similarity	NPD8379	Approved
0.6207	Remote Similarity	NPD8378	Approved
0.6207	Remote Similarity	NPD8380	Approved
0.6207	Remote Similarity	NPD6922	Approved
0.6207	Remote Similarity	NPD6923	Approved
0.62	Remote Similarity	NPD6079	Approved
0.62	Remote Similarity	NPD7087	Discontinued
0.6186	Remote Similarity	NPD5786	Approved
0.6182	Remote Similarity	NPD7290	Approved
0.6182	Remote Similarity	NPD6883	Approved
0.6182	Remote Similarity	NPD7102	Approved
0.617	Remote Similarity	NPD6898	Phase 1
0.6162	Remote Similarity	NPD1695	Approved
0.6147	Remote Similarity	NPD6011	Approved
0.6139	Remote Similarity	NPD4202	Approved
0.6136	Remote Similarity	NPD7144	Approved
0.6136	Remote Similarity	NPD7143	Approved
0.6132	Remote Similarity	NPD5211	Phase 2
0.6126	Remote Similarity	NPD6847	Approved
0.6126	Remote Similarity	NPD6649	Approved
0.6126	Remote Similarity	NPD6869	Approved
0.6126	Remote Similarity	NPD8130	Phase 1
0.6126	Remote Similarity	NPD6617	Approved
0.6126	Remote Similarity	NPD6650	Approved
0.6105	Remote Similarity	NPD6435	Approved
0.6105	Remote Similarity	NPD4221	Approved
0.6105	Remote Similarity	NPD4223	Phase 3
0.6087	Remote Similarity	NPD6932	Approved
0.6082	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD7900	Approved
0.6078	Remote Similarity	NPD5282	Discontinued
0.6071	Remote Similarity	NPD8297	Approved
0.6071	Remote Similarity	NPD6882	Approved
0.6067	Remote Similarity	NPD7151	Approved
0.6067	Remote Similarity	NPD7152	Approved
0.6067	Remote Similarity	NPD7150	Approved
0.6064	Remote Similarity	NPD7509	Discontinued
0.6064	Remote Similarity	NPD7525	Registered
0.6064	Remote Similarity	NPD4252	Approved
0.6061	Remote Similarity	NPD5208	Approved
0.6058	Remote Similarity	NPD4755	Approved
0.6055	Remote Similarity	NPD6412	Phase 2
0.6055	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.604	Remote Similarity	NPD7983	Approved
0.604	Remote Similarity	NPD5284	Approved
0.604	Remote Similarity	NPD5281	Approved
0.6019	Remote Similarity	NPD4629	Approved
0.6019	Remote Similarity	NPD5210	Approved
0.6019	Remote Similarity	NPD5141	Approved
0.6	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6673	Approved
0.6	Remote Similarity	NPD6904	Approved
0.6	Remote Similarity	NPD7505	Discontinued
0.6	Remote Similarity	NPD6080	Approved
0.6	Remote Similarity	NPD7507	Approved
0.6	Remote Similarity	NPD5369	Approved
0.5982	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD4197	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