NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	254.868
LogP:	2.283
LogD:	2.416
LogS:	-4.206
# Rotatable Bonds:	0
TPSA:	49.83
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.524
Synthetic Accessibility Score:	5.595
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.951
MDCK Permeability:	3.885637488565408e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.172
Plasma Protein Binding (PPB):	74.01150512695312%
Volume Distribution (VD):	1.19
Pgp-substrate:	36.54923629760742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.503
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.854
CYP2C9-inhibitor:	0.095
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.454
CYP3A4-inhibitor:	0.058
CYP3A4-substrate:	0.284

ADMET: Excretion

Clearance (CL):	7.353
Half-life (T1/2):	0.388

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.357
Drug-inuced Liver Injury (DILI):	0.263
AMES Toxicity:	0.221
Rat Oral Acute Toxicity:	0.906
Maximum Recommended Daily Dose:	0.869
Skin Sensitization:	0.695
Carcinogencity:	0.186
Eye Corrosion:	0.311
Eye Irritation:	0.143
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC475488

Natural Product ID:	NPC475488
*Common Name:**	Hypnophilin
IUPAC Name:	n.a.
Synonyms:	Hypnophilin
Standard InCHIKey:	FBSAMOXBBLSEEW-ZYHYCFKLSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-7-10(16)12-15(18-12)6-8-5-13(2,3)11(17)9(8)14(7,15)4/h8-9,11-12,17H,1,5-6H2,2-4H3/t8-,9+,11-,12-,14+,15-/m1/s1
SMILES:	O=C1[C@H]2O[C@]32[C@](C1=C)(C)[C@H]1[C@@H](C3)CC([C@@H]1O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506567
PubChem CID:	10264031
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32883	lentinus connatus bcc 8996	Species	Lentinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309322]
NPO24980	Lentinus crinitus	Species	Lentinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO24980	Lentinus crinitus	Species	Lentinaceae	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
IC50	5
MIC	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[551596]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[551596]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	50.0	ug.mL-1	PMID[551596]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	1.0	ug.mL-1	PMID[551595]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	=	1.0	ug.mL-1	PMID[551595]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	MIC	=	1.0	ug.mL-1	PMID[551595]
NPT6422	Organism	Amylomyces rouxii	Amylomyces rouxii	MIC	=	1.0	ug.mL-1	PMID[551595]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	>	20.0	ug.mL-1	PMID[551596]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20.0	ug.mL-1	PMID[551596]

☑ 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 NPC475488 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	302
0.1-0.2	2663
0.2-0.3	9810
0.3-0.4	14962
0.4-0.5	8353
0.5-0.6	5277
0.6-0.7	1242
0.7-0.8	85
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8953	High Similarity	NPC473629
0.8061	Intermediate Similarity	NPC109556
0.8021	Intermediate Similarity	NPC298919
0.8	Intermediate Similarity	NPC474699
0.7941	Intermediate Similarity	NPC474101
0.7835	Intermediate Similarity	NPC473331
0.7789	Intermediate Similarity	NPC97032
0.7732	Intermediate Similarity	NPC200237
0.7732	Intermediate Similarity	NPC153590
0.7685	Intermediate Similarity	NPC300051
0.7684	Intermediate Similarity	NPC315911
0.7677	Intermediate Similarity	NPC91771
0.7677	Intermediate Similarity	NPC142529
0.7619	Intermediate Similarity	NPC9013
0.7614	Intermediate Similarity	NPC201263
0.7576	Intermediate Similarity	NPC163228
0.7549	Intermediate Similarity	NPC477356
0.75	Intermediate Similarity	NPC310586
0.7447	Intermediate Similarity	NPC475796
0.7429	Intermediate Similarity	NPC44004
0.7426	Intermediate Similarity	NPC87090
0.7426	Intermediate Similarity	NPC311904
0.7407	Intermediate Similarity	NPC470281
0.7396	Intermediate Similarity	NPC270270
0.7387	Intermediate Similarity	NPC475305
0.7379	Intermediate Similarity	NPC171759
0.7379	Intermediate Similarity	NPC471767
0.7374	Intermediate Similarity	NPC473263
0.7374	Intermediate Similarity	NPC473234
0.7374	Intermediate Similarity	NPC60386
0.7374	Intermediate Similarity	NPC473273
0.7374	Intermediate Similarity	NPC308656
0.7374	Intermediate Similarity	NPC125180
0.7353	Intermediate Similarity	NPC477355
0.7321	Intermediate Similarity	NPC475401
0.732	Intermediate Similarity	NPC178875
0.7308	Intermediate Similarity	NPC118405
0.7308	Intermediate Similarity	NPC15396
0.7308	Intermediate Similarity	NPC250594
0.7292	Intermediate Similarity	NPC56593
0.729	Intermediate Similarity	NPC211224
0.7283	Intermediate Similarity	NPC80999
0.7282	Intermediate Similarity	NPC471381
0.7273	Intermediate Similarity	NPC469627
0.7273	Intermediate Similarity	NPC155215
0.7273	Intermediate Similarity	NPC286341
0.7273	Intermediate Similarity	NPC191339
0.7264	Intermediate Similarity	NPC314244
0.7263	Intermediate Similarity	NPC90446
0.7257	Intermediate Similarity	NPC477092
0.7255	Intermediate Similarity	NPC190080
0.7255	Intermediate Similarity	NPC111187
0.7245	Intermediate Similarity	NPC12872
0.7245	Intermediate Similarity	NPC155935
0.7245	Intermediate Similarity	NPC215556
0.7245	Intermediate Similarity	NPC168679
0.7228	Intermediate Similarity	NPC476053
0.7216	Intermediate Similarity	NPC118601
0.7204	Intermediate Similarity	NPC258965
0.7204	Intermediate Similarity	NPC156658
0.72	Intermediate Similarity	NPC258216
0.7188	Intermediate Similarity	NPC204105
0.7188	Intermediate Similarity	NPC300082
0.7188	Intermediate Similarity	NPC284534
0.7172	Intermediate Similarity	NPC65359
0.7172	Intermediate Similarity	NPC54065
0.7172	Intermediate Similarity	NPC35809
0.7172	Intermediate Similarity	NPC216284
0.7172	Intermediate Similarity	NPC297474
0.7158	Intermediate Similarity	NPC111409
0.7158	Intermediate Similarity	NPC157328
0.7158	Intermediate Similarity	NPC260852
0.7157	Intermediate Similarity	NPC477354
0.7143	Intermediate Similarity	NPC79549
0.713	Intermediate Similarity	NPC117604
0.7129	Intermediate Similarity	NPC90453
0.7115	Intermediate Similarity	NPC186861
0.7113	Intermediate Similarity	NPC470242
0.71	Intermediate Similarity	NPC57304
0.71	Intermediate Similarity	NPC293001
0.71	Intermediate Similarity	NPC133888
0.71	Intermediate Similarity	NPC29821
0.71	Intermediate Similarity	NPC184063
0.71	Intermediate Similarity	NPC63193
0.71	Intermediate Similarity	NPC35959
0.71	Intermediate Similarity	NPC171360
0.7097	Intermediate Similarity	NPC469608
0.7091	Intermediate Similarity	NPC475495
0.7091	Intermediate Similarity	NPC207689
0.7091	Intermediate Similarity	NPC214797
0.7091	Intermediate Similarity	NPC118860
0.7091	Intermediate Similarity	NPC231589
0.7087	Intermediate Similarity	NPC474313
0.7087	Intermediate Similarity	NPC213947
0.7087	Intermediate Similarity	NPC108475
0.7087	Intermediate Similarity	NPC170143
0.7071	Intermediate Similarity	NPC232747
0.7071	Intermediate Similarity	NPC41217
0.7065	Intermediate Similarity	NPC276769
0.7064	Intermediate Similarity	NPC77089
0.7048	Intermediate Similarity	NPC195192
0.7048	Intermediate Similarity	NPC201718
0.7048	Intermediate Similarity	NPC304738
0.7041	Intermediate Similarity	NPC201658
0.7037	Intermediate Similarity	NPC204884
0.703	Intermediate Similarity	NPC475788
0.703	Intermediate Similarity	NPC202824
0.703	Intermediate Similarity	NPC477361
0.7027	Intermediate Similarity	NPC477093
0.7027	Intermediate Similarity	NPC170487
0.7027	Intermediate Similarity	NPC473522
0.7027	Intermediate Similarity	NPC475277
0.7019	Intermediate Similarity	NPC470188
0.701	Intermediate Similarity	NPC36350
0.7009	Intermediate Similarity	NPC13149
0.7	Intermediate Similarity	NPC477711
0.7	Intermediate Similarity	NPC19087
0.7	Intermediate Similarity	NPC2946
0.7	Intermediate Similarity	NPC246173
0.699	Remote Similarity	NPC126156
0.699	Remote Similarity	NPC476009
0.6981	Remote Similarity	NPC105725
0.697	Remote Similarity	NPC477710
0.6964	Remote Similarity	NPC202889
0.6961	Remote Similarity	NPC191094
0.6961	Remote Similarity	NPC302008
0.6957	Remote Similarity	NPC473437
0.6957	Remote Similarity	NPC226242
0.6957	Remote Similarity	NPC142759
0.6957	Remote Similarity	NPC124289
0.6957	Remote Similarity	NPC25908
0.6957	Remote Similarity	NPC141346
0.6957	Remote Similarity	NPC115719
0.6952	Remote Similarity	NPC267921
0.6947	Remote Similarity	NPC126248
0.6944	Remote Similarity	NPC54737
0.6944	Remote Similarity	NPC265127
0.6939	Remote Similarity	NPC309757
0.6939	Remote Similarity	NPC469626
0.6939	Remote Similarity	NPC236692
0.6939	Remote Similarity	NPC475491
0.6931	Remote Similarity	NPC20713
0.6931	Remote Similarity	NPC476168
0.6923	Remote Similarity	NPC477949
0.6923	Remote Similarity	NPC471150
0.6916	Remote Similarity	NPC87927
0.6916	Remote Similarity	NPC159442
0.6916	Remote Similarity	NPC123505
0.6916	Remote Similarity	NPC266
0.6916	Remote Similarity	NPC469985
0.6909	Remote Similarity	NPC470257
0.6909	Remote Similarity	NPC241927
0.6909	Remote Similarity	NPC474901
0.6909	Remote Similarity	NPC475941
0.6909	Remote Similarity	NPC258543
0.6907	Remote Similarity	NPC194859
0.6907	Remote Similarity	NPC224386
0.69	Remote Similarity	NPC170775
0.69	Remote Similarity	NPC472872
0.69	Remote Similarity	NPC38392
0.6893	Remote Similarity	NPC475900
0.6893	Remote Similarity	NPC52044
0.6893	Remote Similarity	NPC469873
0.6893	Remote Similarity	NPC231060
0.6893	Remote Similarity	NPC472873
0.6893	Remote Similarity	NPC37408
0.6893	Remote Similarity	NPC138245
0.6893	Remote Similarity	NPC84018
0.6893	Remote Similarity	NPC470191
0.6887	Remote Similarity	NPC304624
0.6887	Remote Similarity	NPC289148
0.6887	Remote Similarity	NPC475099
0.6887	Remote Similarity	NPC52899
0.6887	Remote Similarity	NPC477950
0.6887	Remote Similarity	NPC163963
0.6887	Remote Similarity	NPC474053
0.6881	Remote Similarity	NPC201908
0.6881	Remote Similarity	NPC58370
0.6881	Remote Similarity	NPC176949
0.6881	Remote Similarity	NPC43285
0.687	Remote Similarity	NPC118638
0.6863	Remote Similarity	NPC109414
0.6863	Remote Similarity	NPC181594
0.6863	Remote Similarity	NPC144739
0.6857	Remote Similarity	NPC45125
0.6857	Remote Similarity	NPC471038
0.6857	Remote Similarity	NPC221615
0.6852	Remote Similarity	NPC96268
0.6852	Remote Similarity	NPC137657
0.6842	Remote Similarity	NPC270958
0.6842	Remote Similarity	NPC51507
0.6833	Remote Similarity	NPC473253
0.6832	Remote Similarity	NPC80401
0.6832	Remote Similarity	NPC37607
0.6832	Remote Similarity	NPC301969
0.6827	Remote Similarity	NPC158416
0.6827	Remote Similarity	NPC24956
0.6827	Remote Similarity	NPC94337
0.6827	Remote Similarity	NPC18019
0.6827	Remote Similarity	NPC470883

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 NPC475488 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	375
0.1-0.2	3384
0.2-0.3	3819
0.3-0.4	1010
0.4-0.5	326
0.5-0.6	206
0.6-0.7	29
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
0.6961	Remote Similarity	NPD5282	Discontinued
0.6752	Remote Similarity	NPD6054	Approved
0.6729	Remote Similarity	NPD1700	Approved
0.6695	Remote Similarity	NPD6015	Approved
0.6695	Remote Similarity	NPD6016	Approved
0.6694	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6639	Remote Similarity	NPD6370	Approved
0.6639	Remote Similarity	NPD5988	Approved
0.6636	Remote Similarity	NPD6008	Approved
0.661	Remote Similarity	NPD6059	Approved
0.661	Remote Similarity	NPD6319	Approved
0.6577	Remote Similarity	NPD5697	Approved
0.6571	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD1695	Approved
0.6549	Remote Similarity	NPD4634	Approved
0.6549	Remote Similarity	NPD6371	Approved
0.6545	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD7492	Approved
0.6518	Remote Similarity	NPD6881	Approved
0.6518	Remote Similarity	NPD6899	Approved
0.6518	Remote Similarity	NPD6011	Approved
0.6491	Remote Similarity	NPD6649	Approved
0.6491	Remote Similarity	NPD6650	Approved
0.6486	Remote Similarity	NPD6402	Approved
0.6486	Remote Similarity	NPD7128	Approved
0.6486	Remote Similarity	NPD5739	Approved
0.6486	Remote Similarity	NPD6675	Approved
0.6481	Remote Similarity	NPD4696	Approved
0.6481	Remote Similarity	NPD5285	Approved
0.6481	Remote Similarity	NPD5286	Approved
0.6475	Remote Similarity	NPD6616	Approved
0.6465	Remote Similarity	NPD4788	Approved
0.646	Remote Similarity	NPD6012	Approved
0.646	Remote Similarity	NPD6372	Approved
0.646	Remote Similarity	NPD6013	Approved
0.646	Remote Similarity	NPD6014	Approved
0.646	Remote Similarity	NPD6373	Approved
0.6449	Remote Similarity	NPD4755	Approved
0.6429	Remote Similarity	NPD5369	Approved
0.6429	Remote Similarity	NPD5701	Approved
0.6429	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5223	Approved
0.6404	Remote Similarity	NPD7102	Approved
0.6404	Remote Similarity	NPD6883	Approved
0.6404	Remote Similarity	NPD7290	Approved
0.6379	Remote Similarity	NPD4632	Approved
0.6371	Remote Similarity	NPD7736	Approved
0.6364	Remote Similarity	NPD4633	Approved
0.6364	Remote Similarity	NPD5211	Phase 2
0.6364	Remote Similarity	NPD5225	Approved
0.6364	Remote Similarity	NPD5224	Approved
0.6364	Remote Similarity	NPD5226	Approved
0.6356	Remote Similarity	NPD6009	Approved
0.6348	Remote Similarity	NPD6847	Approved
0.6348	Remote Similarity	NPD6869	Approved
0.6348	Remote Similarity	NPD6617	Approved
0.6348	Remote Similarity	NPD8130	Phase 1
0.6346	Remote Similarity	NPD5785	Approved
0.633	Remote Similarity	NPD4700	Approved
0.6311	Remote Similarity	NPD7604	Phase 2
0.6306	Remote Similarity	NPD5174	Approved
0.6306	Remote Similarity	NPD5175	Approved
0.6296	Remote Similarity	NPD6083	Phase 2
0.6296	Remote Similarity	NPD6084	Phase 2
0.6293	Remote Similarity	NPD6882	Approved
0.6293	Remote Similarity	NPD8297	Approved
0.629	Remote Similarity	NPD8293	Discontinued
0.6281	Remote Similarity	NPD5983	Phase 2
0.6275	Remote Similarity	NPD5786	Approved
0.6262	Remote Similarity	NPD4629	Approved
0.6262	Remote Similarity	NPD5695	Phase 3
0.6262	Remote Similarity	NPD5210	Approved
0.625	Remote Similarity	NPD5141	Approved
0.625	Remote Similarity	NPD4753	Phase 2
0.624	Remote Similarity	NPD6033	Approved
0.6239	Remote Similarity	NPD5696	Approved
0.6207	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6435	Approved
0.6176	Remote Similarity	NPD5363	Approved
0.6161	Remote Similarity	NPD4754	Approved
0.6154	Remote Similarity	NPD6053	Discontinued
0.6134	Remote Similarity	NPD6274	Approved
0.6117	Remote Similarity	NPD5279	Phase 3
0.6117	Remote Similarity	NPD5690	Phase 2
0.6087	Remote Similarity	NPD4729	Approved
0.6087	Remote Similarity	NPD5128	Approved
0.6087	Remote Similarity	NPD4730	Approved
0.6083	Remote Similarity	NPD6317	Approved
0.608	Remote Similarity	NPD6336	Discontinued
0.6078	Remote Similarity	NPD3133	Approved
0.6078	Remote Similarity	NPD4197	Approved
0.6078	Remote Similarity	NPD3665	Phase 1
0.6078	Remote Similarity	NPD3666	Approved
0.6075	Remote Similarity	NPD4202	Approved
0.6055	Remote Similarity	NPD4697	Phase 3
0.6055	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD5222	Approved
0.6055	Remote Similarity	NPD5221	Approved
0.6053	Remote Similarity	NPD4768	Approved
0.6053	Remote Similarity	NPD4767	Approved
0.604	Remote Similarity	NPD4270	Approved
0.604	Remote Similarity	NPD4269	Approved
0.6033	Remote Similarity	NPD6314	Approved
0.6033	Remote Similarity	NPD6313	Approved
0.6033	Remote Similarity	NPD6335	Approved
0.6019	Remote Similarity	NPD5329	Approved
0.6019	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD5956	Approved
0.6	Remote Similarity	NPD5368	Approved
0.6	Remote Similarity	NPD5173	Approved
0.5984	Remote Similarity	NPD7101	Approved
0.5984	Remote Similarity	NPD7100	Approved
0.5983	Remote Similarity	NPD5251	Approved
0.5983	Remote Similarity	NPD5135	Approved
0.5983	Remote Similarity	NPD5247	Approved
0.5983	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD5249	Phase 3
0.5983	Remote Similarity	NPD5169	Approved
0.5983	Remote Similarity	NPD5248	Approved
0.5983	Remote Similarity	NPD5250	Approved
0.5981	Remote Similarity	NPD6079	Approved
0.598	Remote Similarity	NPD5362	Discontinued
0.5962	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD4694	Approved
0.5962	Remote Similarity	NPD5280	Approved
0.5948	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5328	Approved
0.5941	Remote Similarity	NPD4790	Discontinued
0.5932	Remote Similarity	NPD5127	Approved
0.5932	Remote Similarity	NPD5217	Approved
0.5932	Remote Similarity	NPD5216	Approved
0.5932	Remote Similarity	NPD5215	Approved
0.5926	Remote Similarity	NPD6399	Phase 3
0.5922	Remote Similarity	NPD4786	Approved
0.5882	Remote Similarity	NPD4221	Approved
0.5882	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD3667	Approved
0.5882	Remote Similarity	NPD4223	Phase 3
0.5865	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6412	Phase 2
0.5854	Remote Similarity	NPD4522	Approved
0.5849	Remote Similarity	NPD6903	Approved
0.5842	Remote Similarity	NPD4252	Approved
0.5821	Remote Similarity	NPD6333	Approved
0.5821	Remote Similarity	NPD6334	Approved
0.582	Remote Similarity	NPD7115	Discovery
0.581	Remote Similarity	NPD4249	Approved
0.581	Remote Similarity	NPD6098	Approved
0.581	Remote Similarity	NPD3618	Phase 1
0.58	Remote Similarity	NPD4238	Approved
0.58	Remote Similarity	NPD4802	Phase 2
0.5794	Remote Similarity	NPD6080	Approved
0.5794	Remote Similarity	NPD6673	Approved
0.5794	Remote Similarity	NPD6904	Approved
0.5785	Remote Similarity	NPD5167	Approved
0.578	Remote Similarity	NPD5133	Approved
0.576	Remote Similarity	NPD6908	Approved
0.576	Remote Similarity	NPD6909	Approved
0.5755	Remote Similarity	NPD4250	Approved
0.5755	Remote Similarity	NPD4251	Approved
0.5741	Remote Similarity	NPD5692	Phase 3
0.5714	Remote Similarity	NPD1696	Phase 3
0.5701	Remote Similarity	NPD6672	Approved
0.5701	Remote Similarity	NPD4518	Approved
0.5701	Remote Similarity	NPD5737	Approved
0.5692	Remote Similarity	NPD7319	Approved
0.5688	Remote Similarity	NPD7983	Approved
0.5688	Remote Similarity	NPD5281	Approved
0.5688	Remote Similarity	NPD5693	Phase 1
0.5688	Remote Similarity	NPD5694	Approved
0.5688	Remote Similarity	NPD6411	Approved
0.5688	Remote Similarity	NPD5284	Approved
0.5688	Remote Similarity	NPD6050	Approved
0.5688	Remote Similarity	NPD8035	Phase 2
0.5688	Remote Similarity	NPD8034	Phase 2
0.5676	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD5331	Approved
0.5673	Remote Similarity	NPD5332	Approved
0.566	Remote Similarity	NPD5330	Approved
0.566	Remote Similarity	NPD4688	Approved
0.566	Remote Similarity	NPD7521	Approved
0.566	Remote Similarity	NPD7146	Approved
0.566	Remote Similarity	NPD4138	Approved
0.566	Remote Similarity	NPD4693	Phase 3
0.566	Remote Similarity	NPD4690	Approved
0.566	Remote Similarity	NPD7334	Approved
0.566	Remote Similarity	NPD6684	Approved
0.566	Remote Similarity	NPD4689	Approved
0.566	Remote Similarity	NPD5205	Approved
0.566	Remote Similarity	NPD6409	Approved
0.5657	Remote Similarity	NPD3703	Phase 2
0.5657	Remote Similarity	NPD3702	Approved
0.5644	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD3617	Approved
0.5636	Remote Similarity	NPD5779	Approved
0.5636	Remote Similarity	NPD5778	Approved
0.5631	Remote Similarity	NPD4692	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