NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	197.11
Volume:	202.418
LogP:	0.359
LogD:	0.934
LogS:	-2.192
# Rotatable Bonds:	4
TPSA:	73.32
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.665
Synthetic Accessibility Score:	3.194
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.922
MDCK Permeability:	6.7350010795053095e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.758
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.524
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.381
Plasma Protein Binding (PPB):	5.876448631286621%
Volume Distribution (VD):	0.733
Pgp-substrate:	74.0209732055664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.812
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.202
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.407
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.234

ADMET: Excretion

Clearance (CL):	7.487
Half-life (T1/2):	0.878

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.17
Drug-inuced Liver Injury (DILI):	0.522
AMES Toxicity:	0.161
Rat Oral Acute Toxicity:	0.523
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.279
Carcinogencity:	0.569
Eye Corrosion:	0.004
Eye Irritation:	0.189
Respiratory Toxicity:	0.888

Download Data

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

Natural Product: NPC153769

Natural Product ID:	NPC153769
*Common Name:**	Chrysogedone B
IUPAC Name:	5-[(1S)-1-hydroxybutyl]-6-(hydroxymethyl)-1H-pyridin-2-one
Synonyms:	Chrysogedone B
Standard InCHIKey:	FNQPTDUMOGZQBY-VIFPVBQESA-N
Standard InCHI:	InChI=1S/C10H15NO3/c1-2-3-9(13)7-4-5-10(14)11-8(7)6-12/h4-5,9,12-13H,2-3,6H2,1H3,(H,11,14)/t9-/m0/s1
SMILES:	CCC[C@@H](c1ccc(nc1CO)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1802295
PubChem CID:	53355908
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0002224] Hydropyridines [CHEMONTID:0001160] Pyridinones

*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
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1367520]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974609]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21381678]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22118684]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26692349]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33089690]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8626236]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	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	2
MIC	6

Activity Type	# Activity
Cell Line	2
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000.0	nM	PMID[536077]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[536077]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	150000.0	nM	PMID[536077]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	150000.0	nM	PMID[536077]
NPT720	Organism	Enterobacter aerogenes	Enterobacter aerogenes	MIC	>	150000.0	nM	PMID[536077]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	150000.0	nM	PMID[536077]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	150000.0	nM	PMID[536077]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	150000.0	nM	PMID[536077]

☑ 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 NPC153769 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	299
0.1-0.2	2746
0.2-0.3	13115
0.3-0.4	8856
0.4-0.5	12288
0.5-0.6	4090
0.6-0.7	1137
0.7-0.8	148
0.8-0.85	11
0.85-0.9	5
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9716	High Similarity	NPC161292
0.8716	High Similarity	NPC470395
0.8581	High Similarity	NPC470394
0.8581	High Similarity	NPC470404
0.8581	High Similarity	NPC470403
0.8523	High Similarity	NPC471598
0.8389	Intermediate Similarity	NPC60553
0.828	Intermediate Similarity	NPC84508
0.8255	Intermediate Similarity	NPC280853
0.82	Intermediate Similarity	NPC245657
0.82	Intermediate Similarity	NPC285016
0.8188	Intermediate Similarity	NPC471596
0.8133	Intermediate Similarity	NPC478032
0.8095	Intermediate Similarity	NPC320394
0.8089	Intermediate Similarity	NPC63562
0.8077	Intermediate Similarity	NPC284348
0.7988	Intermediate Similarity	NPC62069
0.7987	Intermediate Similarity	NPC116573
0.7987	Intermediate Similarity	NPC132680
0.7987	Intermediate Similarity	NPC269919
0.7947	Intermediate Similarity	NPC471594
0.7941	Intermediate Similarity	NPC42591
0.7927	Intermediate Similarity	NPC126481
0.7888	Intermediate Similarity	NPC63338
0.7888	Intermediate Similarity	NPC322976
0.7888	Intermediate Similarity	NPC324203
0.7885	Intermediate Similarity	NPC257142
0.784	Intermediate Similarity	NPC47298
0.784	Intermediate Similarity	NPC315214
0.7821	Intermediate Similarity	NPC220523
0.7798	Intermediate Similarity	NPC283152
0.7791	Intermediate Similarity	NPC263439
0.7791	Intermediate Similarity	NPC32028
0.7791	Intermediate Similarity	NPC159319
0.7758	Intermediate Similarity	NPC44161
0.7697	Intermediate Similarity	NPC108469
0.7683	Intermediate Similarity	NPC211187
0.7633	Intermediate Similarity	NPC194724
0.7633	Intermediate Similarity	NPC288943
0.7619	Intermediate Similarity	NPC471294
0.7619	Intermediate Similarity	NPC259545
0.7586	Intermediate Similarity	NPC314573
0.7578	Intermediate Similarity	NPC26872
0.7576	Intermediate Similarity	NPC473057
0.756	Intermediate Similarity	NPC158129
0.7543	Intermediate Similarity	NPC66083
0.753	Intermediate Similarity	NPC471178
0.7529	Intermediate Similarity	NPC241025
0.7528	Intermediate Similarity	NPC79293
0.7528	Intermediate Similarity	NPC279401
0.7515	Intermediate Similarity	NPC177404
0.7514	Intermediate Similarity	NPC469390
0.75	Intermediate Similarity	NPC256828
0.75	Intermediate Similarity	NPC473764
0.75	Intermediate Similarity	NPC314940
0.7486	Intermediate Similarity	NPC194040
0.7471	Intermediate Similarity	NPC303225
0.747	Intermediate Similarity	NPC118511
0.7457	Intermediate Similarity	NPC314394
0.7456	Intermediate Similarity	NPC252590
0.7446	Intermediate Similarity	NPC317572
0.7442	Intermediate Similarity	NPC232340
0.7439	Intermediate Similarity	NPC26850
0.7412	Intermediate Similarity	NPC474409
0.741	Intermediate Similarity	NPC79911
0.7405	Intermediate Similarity	NPC164374
0.7405	Intermediate Similarity	NPC137929
0.74	Intermediate Similarity	NPC278451
0.7386	Intermediate Similarity	NPC61350
0.7371	Intermediate Similarity	NPC207851
0.7363	Intermediate Similarity	NPC472284
0.7349	Intermediate Similarity	NPC120798
0.7341	Intermediate Similarity	NPC72980
0.7314	Intermediate Similarity	NPC133306
0.7305	Intermediate Similarity	NPC124542
0.7305	Intermediate Similarity	NPC471177
0.7305	Intermediate Similarity	NPC59779
0.7299	Intermediate Similarity	NPC325705
0.7299	Intermediate Similarity	NPC52831
0.7297	Intermediate Similarity	NPC66815
0.7285	Intermediate Similarity	NPC165370
0.7263	Intermediate Similarity	NPC3715
0.7262	Intermediate Similarity	NPC97367
0.7257	Intermediate Similarity	NPC219963
0.7256	Intermediate Similarity	NPC36168
0.7246	Intermediate Similarity	NPC25899
0.7241	Intermediate Similarity	NPC88363
0.7235	Intermediate Similarity	NPC278874
0.7234	Intermediate Similarity	NPC474595
0.7228	Intermediate Similarity	NPC280714
0.7228	Intermediate Similarity	NPC128823
0.7225	Intermediate Similarity	NPC134586
0.7219	Intermediate Similarity	NPC470500
0.7216	Intermediate Similarity	NPC212535
0.7207	Intermediate Similarity	NPC183805
0.7202	Intermediate Similarity	NPC224632
0.72	Intermediate Similarity	NPC249662
0.7189	Intermediate Similarity	NPC249040
0.7184	Intermediate Similarity	NPC211997
0.7182	Intermediate Similarity	NPC141915
0.7182	Intermediate Similarity	NPC114335
0.7182	Intermediate Similarity	NPC280964
0.7181	Intermediate Similarity	NPC472286
0.7181	Intermediate Similarity	NPC472287
0.7171	Intermediate Similarity	NPC212125
0.7169	Intermediate Similarity	NPC141353
0.7167	Intermediate Similarity	NPC144381
0.7159	Intermediate Similarity	NPC144114
0.7152	Intermediate Similarity	NPC151489
0.7151	Intermediate Similarity	NPC476686
0.7151	Intermediate Similarity	NPC105758
0.7151	Intermediate Similarity	NPC206186
0.7151	Intermediate Similarity	NPC476688
0.7143	Intermediate Similarity	NPC230403
0.7143	Intermediate Similarity	NPC289786
0.7135	Intermediate Similarity	NPC94943
0.7126	Intermediate Similarity	NPC138018
0.712	Intermediate Similarity	NPC224928
0.712	Intermediate Similarity	NPC5145
0.7111	Intermediate Similarity	NPC230805
0.7111	Intermediate Similarity	NPC110741
0.711	Intermediate Similarity	NPC208060
0.7101	Intermediate Similarity	NPC48192
0.7097	Intermediate Similarity	NPC256893
0.7086	Intermediate Similarity	NPC96890
0.7086	Intermediate Similarity	NPC326575
0.7079	Intermediate Similarity	NPC190007
0.7076	Intermediate Similarity	NPC41717
0.7073	Intermediate Similarity	NPC288445
0.7069	Intermediate Similarity	NPC95898
0.7068	Intermediate Similarity	NPC469589
0.7063	Intermediate Similarity	NPC318935
0.7062	Intermediate Similarity	NPC161887
0.7062	Intermediate Similarity	NPC266551
0.7056	Intermediate Similarity	NPC46580
0.7049	Intermediate Similarity	NPC45850
0.7049	Intermediate Similarity	NPC226202
0.7041	Intermediate Similarity	NPC322644
0.7039	Intermediate Similarity	NPC314002
0.7039	Intermediate Similarity	NPC62510
0.7039	Intermediate Similarity	NPC295158
0.7037	Intermediate Similarity	NPC165349
0.7037	Intermediate Similarity	NPC471323
0.7037	Intermediate Similarity	NPC264166
0.7037	Intermediate Similarity	NPC274291
0.7037	Intermediate Similarity	NPC329708
0.7037	Intermediate Similarity	NPC47059
0.7037	Intermediate Similarity	NPC118832
0.7029	Intermediate Similarity	NPC150048
0.7029	Intermediate Similarity	NPC203754
0.7026	Intermediate Similarity	NPC477110
0.7025	Intermediate Similarity	NPC328029
0.7025	Intermediate Similarity	NPC29702
0.7006	Intermediate Similarity	NPC168486
0.7006	Intermediate Similarity	NPC222592
0.7	Intermediate Similarity	NPC71079
0.7	Intermediate Similarity	NPC472111
0.6989	Remote Similarity	NPC184964
0.6987	Remote Similarity	NPC174421
0.6983	Remote Similarity	NPC204717
0.6971	Remote Similarity	NPC312872
0.6966	Remote Similarity	NPC477891
0.6961	Remote Similarity	NPC36498
0.6959	Remote Similarity	NPC203168
0.6959	Remote Similarity	NPC474217
0.6954	Remote Similarity	NPC469594
0.6952	Remote Similarity	NPC476167
0.6948	Remote Similarity	NPC306397
0.6935	Remote Similarity	NPC243834
0.6935	Remote Similarity	NPC70956
0.6935	Remote Similarity	NPC474188
0.6927	Remote Similarity	NPC220765
0.6923	Remote Similarity	NPC469592
0.6923	Remote Similarity	NPC246700
0.6923	Remote Similarity	NPC471080
0.6923	Remote Similarity	NPC474594
0.6923	Remote Similarity	NPC128751
0.6919	Remote Similarity	NPC85918
0.6919	Remote Similarity	NPC276517
0.6911	Remote Similarity	NPC474145
0.6911	Remote Similarity	NPC475841
0.6906	Remote Similarity	NPC171171
0.6898	Remote Similarity	NPC192315
0.6898	Remote Similarity	NPC306376
0.6897	Remote Similarity	NPC164664
0.6895	Remote Similarity	NPC476098
0.6894	Remote Similarity	NPC85443
0.6885	Remote Similarity	NPC469497
0.6885	Remote Similarity	NPC106833
0.6882	Remote Similarity	NPC113812
0.6882	Remote Similarity	NPC251090
0.6879	Remote Similarity	NPC127730
0.6879	Remote Similarity	NPC278366
0.6872	Remote Similarity	NPC118776
0.6865	Remote Similarity	NPC329541
0.6862	Remote Similarity	NPC18487
0.686	Remote Similarity	NPC102423
0.6856	Remote Similarity	NPC219664
0.6854	Remote Similarity	NPC133261
0.6854	Remote Similarity	NPC42979

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 NPC153769 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	656
0.2-0.3	844
0.3-0.4	1231
0.4-0.5	3275
0.5-0.6	2382
0.6-0.7	493
0.7-0.8	55
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8194	Intermediate Similarity	NPD5352	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD861	Approved
0.8125	Intermediate Similarity	NPD862	Approved
0.8125	Intermediate Similarity	NPD863	Approved
0.8092	Intermediate Similarity	NPD3525	Discontinued
0.7987	Intermediate Similarity	NPD9383	Approved
0.7987	Intermediate Similarity	NPD9382	Approved
0.7953	Intermediate Similarity	NPD2383	Phase 1
0.7888	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1685	Approved
0.784	Intermediate Similarity	NPD1684	Approved
0.7778	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD2176	Approved
0.7709	Intermediate Similarity	NPD2175	Phase 3
0.7709	Intermediate Similarity	NPD2177	Approved
0.753	Intermediate Similarity	NPD925	Approved
0.753	Intermediate Similarity	NPD926	Approved
0.7485	Intermediate Similarity	NPD6159	Phase 2
0.7459	Intermediate Similarity	NPD2727	Phase 2
0.7458	Intermediate Similarity	NPD5316	Approved
0.7457	Intermediate Similarity	NPD4204	Approved
0.7457	Intermediate Similarity	NPD4203	Approved
0.7442	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6290	Phase 2
0.7308	Intermediate Similarity	NPD1229	Phase 2
0.7301	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD9510	Approved
0.7294	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD5255	Approved
0.7283	Intermediate Similarity	NPD6642	Approved
0.7283	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6641	Approved
0.7267	Intermediate Similarity	NPD9690	Approved
0.7263	Intermediate Similarity	NPD5936	Approved
0.7263	Intermediate Similarity	NPD5939	Approved
0.7263	Intermediate Similarity	NPD4502	Phase 2
0.7246	Intermediate Similarity	NPD9705	Discontinued
0.7246	Intermediate Similarity	NPD112	Approved
0.7197	Intermediate Similarity	NPD9506	Approved
0.7195	Intermediate Similarity	NPD2882	Phase 1
0.7193	Intermediate Similarity	NPD7474	Suspended
0.7176	Intermediate Similarity	NPD425	Approved
0.7176	Intermediate Similarity	NPD424	Approved
0.7174	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD9284	Approved
0.7143	Intermediate Similarity	NPD3920	Phase 2
0.7135	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2582	Approved
0.7126	Intermediate Similarity	NPD2581	Approved
0.7111	Intermediate Similarity	NPD9714	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7418	Discontinued
0.7095	Intermediate Similarity	NPD5256	Discontinued
0.7091	Intermediate Similarity	NPD6158	Phase 2
0.7091	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD8063	Discontinued
0.7059	Intermediate Similarity	NPD444	Approved
0.7043	Intermediate Similarity	NPD1768	Approved
0.7041	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6227	Discontinued
0.7037	Intermediate Similarity	NPD4037	Approved
0.7037	Intermediate Similarity	NPD3813	Approved
0.7037	Intermediate Similarity	NPD32	Approved
0.7037	Intermediate Similarity	NPD4035	Approved
0.7037	Intermediate Similarity	NPD4034	Approved
0.7037	Intermediate Similarity	NPD31	Approved
0.7037	Intermediate Similarity	NPD4122	Approved
0.7037	Intermediate Similarity	NPD4039	Approved
0.7037	Intermediate Similarity	NPD4033	Approved
0.7037	Intermediate Similarity	NPD4036	Approved
0.7037	Intermediate Similarity	NPD4038	Approved
0.7035	Intermediate Similarity	NPD2781	Approved
0.7029	Intermediate Similarity	NPD2382	Approved
0.7029	Intermediate Similarity	NPD2381	Approved
0.7029	Intermediate Similarity	NPD2380	Approved
0.7022	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD5596	Phase 2
0.7019	Intermediate Similarity	NPD1592	Phase 3
0.7018	Intermediate Similarity	NPD2782	Approved
0.7018	Intermediate Similarity	NPD2780	Approved
0.7011	Intermediate Similarity	NPD6590	Discontinued
0.7005	Intermediate Similarity	NPD5497	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6569	Phase 2
0.6973	Remote Similarity	NPD6550	Discontinued
0.6963	Remote Similarity	NPD7222	Phase 2
0.6961	Remote Similarity	NPD1034	Phase 3
0.6961	Remote Similarity	NPD9364	Phase 2
0.6961	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD9363	Approved
0.6957	Remote Similarity	NPD1649	Discontinued
0.6954	Remote Similarity	NPD2123	Phase 3
0.6949	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD9080	Approved
0.6944	Remote Similarity	NPD3082	Discontinued
0.6944	Remote Similarity	NPD2762	Phase 2
0.694	Remote Similarity	NPD4699	Discontinued
0.6937	Remote Similarity	NPD852	Discontinued
0.6937	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1352	Discontinued
0.6932	Remote Similarity	NPD5100	Phase 3
0.6923	Remote Similarity	NPD408	Approved
0.6919	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD3321	Discontinued
0.6882	Remote Similarity	NPD5512	Phase 3
0.6865	Remote Similarity	NPD9695	Approved
0.6832	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3396	Approved
0.6828	Remote Similarity	NPD3395	Approved
0.6823	Remote Similarity	NPD3003	Approved
0.6818	Remote Similarity	NPD2077	Approved
0.6818	Remote Similarity	NPD5164	Discontinued
0.6818	Remote Similarity	NPD3224	Phase 2
0.6818	Remote Similarity	NPD2076	Approved
0.6811	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4703	Approved
0.6807	Remote Similarity	NPD4702	Approved
0.6793	Remote Similarity	NPD1213	Phase 3
0.6788	Remote Similarity	NPD7452	Approved
0.6788	Remote Similarity	NPD7453	Approved
0.6788	Remote Similarity	NPD1392	Approved
0.6782	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3386	Phase 2
0.6778	Remote Similarity	NPD9362	Approved
0.6778	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4551	Phase 2
0.6768	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD3717	Discontinued
0.6766	Remote Similarity	NPD7726	Phase 1
0.6765	Remote Similarity	NPD4086	Phase 1
0.6755	Remote Similarity	NPD2952	Discontinued
0.6755	Remote Similarity	NPD1622	Discontinued
0.6755	Remote Similarity	NPD6988	Phase 1
0.6739	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4021	Phase 2
0.6737	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD5530	Phase 1
0.6728	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6182	Approved
0.6723	Remote Similarity	NPD43	Approved
0.6723	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD6452	Discontinued
0.6721	Remote Similarity	NPD4375	Approved
0.672	Remote Similarity	NPD3921	Approved
0.672	Remote Similarity	NPD712	Clinical (unspecified phase)
0.672	Remote Similarity	NPD3923	Approved
0.672	Remote Similarity	NPD3924	Approved
0.672	Remote Similarity	NPD9689	Approved
0.672	Remote Similarity	NPD3922	Approved
0.6719	Remote Similarity	NPD6991	Approved
0.6717	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1325	Approved
0.6705	Remote Similarity	NPD1326	Approved
0.6702	Remote Similarity	NPD3477	Phase 2
0.6702	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3037	Phase 1
0.6685	Remote Similarity	NPD158	Discontinued
0.6685	Remote Similarity	NPD6492	Phase 2
0.6684	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5140	Approved
0.6667	Remote Similarity	NPD3875	Discontinued
0.6667	Remote Similarity	NPD7948	Phase 1
0.6667	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5138	Approved
0.6649	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD5862	Discovery
0.6632	Remote Similarity	NPD7777	Approved
0.6632	Remote Similarity	NPD53	Approved
0.6632	Remote Similarity	NPD7778	Approved
0.6624	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5429	Discontinued
0.6606	Remote Similarity	NPD5020	Approved
0.6602	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD8395	Approved
0.6597	Remote Similarity	NPD8396	Approved
0.6597	Remote Similarity	NPD3814	Phase 1
0.6596	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4528	Approved
0.6596	Remote Similarity	NPD4529	Approved
0.6596	Remote Similarity	NPD6361	Phase 2
0.6596	Remote Similarity	NPD802	Phase 2
0.6596	Remote Similarity	NPD1038	Approved
0.6596	Remote Similarity	NPD4526	Approved
0.6582	Remote Similarity	NPD2916	Discontinued
0.6582	Remote Similarity	NPD7671	Approved
0.6582	Remote Similarity	NPD7672	Approved
0.6579	Remote Similarity	NPD5003	Discontinued
0.6576	Remote Similarity	NPD4889	Approved
0.6573	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.657	Remote Similarity	NPD1274	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD3575	Approved
0.6568	Remote Similarity	NPD3576	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