NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	243.1
Volume:	248.407
LogP:	-0.184
LogD:	0.441
LogS:	-1.926
# Rotatable Bonds:	4
TPSA:	74.85
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.846
Synthetic Accessibility Score:	2.505
Fsp3:	0.154
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:	-4.799
MDCK Permeability:	9.938724360836204e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.031
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.139

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.835
Plasma Protein Binding (PPB):	16.754810333251953%
Volume Distribution (VD):	1.234
Pgp-substrate:	77.36725616455078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.232
CYP1A2-substrate:	0.214
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.453
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.659
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.107

ADMET: Excretion

Clearance (CL):	3.294
Half-life (T1/2):	0.463

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.365
Drug-inuced Liver Injury (DILI):	0.755
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.275
Skin Sensitization:	0.199
Carcinogencity:	0.021
Eye Corrosion:	0.004
Eye Irritation:	0.031
Respiratory Toxicity:	0.597

Download Data

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

Natural Product: NPC25899

Natural Product ID:	NPC25899
*Common Name:**	Caerulomycin J
IUPAC Name:	N-[(4-oxo-6-pyridin-2-yl-1H-pyridin-2-yl)methyl]acetamide
Synonyms:	caerulomycin J
Standard InCHIKey:	IXDVQWRMMLGZLB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H13N3O2/c1-9(17)15-8-10-6-11(18)7-13(16-10)12-4-2-3-5-14-12/h2-7H,8H2,1H3,(H,15,17)(H,16,18)
SMILES:	CC(=NCc1cc(O)cc(n1)c1ccccn1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1823035
PubChem CID:	53484027
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0000326] Bipyridines and oligopyridines

*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
NPO23850	Actinoalloteichus cyanogriseus	Species	Pseudonocardiaceae	Bacteria	isolated from marine sediments	the seashore of Weihai, China	n.a.	PMID[21770434]
NPO23850	Actinoalloteichus cyanogriseus	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21770434]
NPO23850	Actinoalloteichus cyanogriseus	Species	Pseudonocardiaceae	Bacteria	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	4
MIC	4

Activity Type	# Activity
Cell Line	4
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	25700.0	nM	PMID[466179]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[466179]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	15000.0	nM	PMID[466179]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000.0	nM	PMID[466179]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>=	100000.0	nM	PMID[466179]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>=	100000.0	nM	PMID[466179]
NPT720	Organism	Enterobacter aerogenes	Enterobacter aerogenes	MIC	>=	100000.0	nM	PMID[466179]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>=	100000.0	nM	PMID[466179]

☑ 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 NPC25899 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	468
0.1-0.2	9324
0.2-0.3	9350
0.3-0.4	15384
0.4-0.5	4431
0.5-0.6	2622
0.6-0.7	998
0.7-0.8	100
0.8-0.85	11
0.85-0.9	7
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9799	High Similarity	NPC48192
0.9051	High Similarity	NPC121658
0.9051	High Similarity	NPC14651
0.9012	High Similarity	NPC219963
0.9012	High Similarity	NPC266551
0.9012	High Similarity	NPC161887
0.8987	High Similarity	NPC476518
0.8758	High Similarity	NPC111624
0.8512	High Similarity	NPC20249
0.8488	Intermediate Similarity	NPC226202
0.8412	Intermediate Similarity	NPC206251
0.8412	Intermediate Similarity	NPC74382
0.815	Intermediate Similarity	NPC224327
0.811	Intermediate Similarity	NPC471178
0.8103	Intermediate Similarity	NPC134079
0.8098	Intermediate Similarity	NPC471177
0.8098	Intermediate Similarity	NPC59779
0.8098	Intermediate Similarity	NPC124542
0.8063	Intermediate Similarity	NPC36168
0.7975	Intermediate Similarity	NPC220523
0.791	Intermediate Similarity	NPC324149
0.7869	Intermediate Similarity	NPC200836
0.7857	Intermediate Similarity	NPC314940
0.7857	Intermediate Similarity	NPC473764
0.7831	Intermediate Similarity	NPC97367
0.7831	Intermediate Similarity	NPC473057
0.7785	Intermediate Similarity	NPC151489
0.7772	Intermediate Similarity	NPC53144
0.7771	Intermediate Similarity	NPC79911
0.7747	Intermediate Similarity	NPC476167
0.7735	Intermediate Similarity	NPC267928
0.7717	Intermediate Similarity	NPC211813
0.7712	Intermediate Similarity	NPC174421
0.7711	Intermediate Similarity	NPC120798
0.7706	Intermediate Similarity	NPC252590
0.7692	Intermediate Similarity	NPC192315
0.7673	Intermediate Similarity	NPC470404
0.7673	Intermediate Similarity	NPC470403
0.7673	Intermediate Similarity	NPC470394
0.7667	Intermediate Similarity	NPC329541
0.7665	Intermediate Similarity	NPC177404
0.7634	Intermediate Similarity	NPC475070
0.7634	Intermediate Similarity	NPC470500
0.7628	Intermediate Similarity	NPC328029
0.7584	Intermediate Similarity	NPC46580
0.7578	Intermediate Similarity	NPC470395
0.7577	Intermediate Similarity	NPC213530
0.7577	Intermediate Similarity	NPC193267
0.7571	Intermediate Similarity	NPC314002
0.7547	Intermediate Similarity	NPC318935
0.7545	Intermediate Similarity	NPC84508
0.7542	Intermediate Similarity	NPC472289
0.7529	Intermediate Similarity	NPC108469
0.7526	Intermediate Similarity	NPC5145
0.7526	Intermediate Similarity	NPC85273
0.7514	Intermediate Similarity	NPC204717
0.7514	Intermediate Similarity	NPC19872
0.75	Intermediate Similarity	NPC476121
0.75	Intermediate Similarity	NPC476124
0.75	Intermediate Similarity	NPC60553
0.7485	Intermediate Similarity	NPC257142
0.7458	Intermediate Similarity	NPC48938
0.7458	Intermediate Similarity	NPC220765
0.743	Intermediate Similarity	NPC171171
0.7429	Intermediate Similarity	NPC96890
0.7429	Intermediate Similarity	NPC184964
0.7423	Intermediate Similarity	NPC161292
0.7414	Intermediate Similarity	NPC95898
0.7396	Intermediate Similarity	NPC285635
0.7385	Intermediate Similarity	NPC476041
0.7385	Intermediate Similarity	NPC304926
0.738	Intermediate Similarity	NPC232727
0.7377	Intermediate Similarity	NPC84853
0.7371	Intermediate Similarity	NPC203754
0.7371	Intermediate Similarity	NPC150048
0.7365	Intermediate Similarity	NPC63562
0.7349	Intermediate Similarity	NPC284348
0.7338	Intermediate Similarity	NPC212125
0.7333	Intermediate Similarity	NPC288445
0.7333	Intermediate Similarity	NPC314573
0.7333	Intermediate Similarity	NPC8022
0.7333	Intermediate Similarity	NPC470799
0.733	Intermediate Similarity	NPC287208
0.7326	Intermediate Similarity	NPC315957
0.7326	Intermediate Similarity	NPC176538
0.7322	Intermediate Similarity	NPC99666
0.7312	Intermediate Similarity	NPC212213
0.7297	Intermediate Similarity	NPC242209
0.7294	Intermediate Similarity	NPC63338
0.7294	Intermediate Similarity	NPC324203
0.7294	Intermediate Similarity	NPC131718
0.7294	Intermediate Similarity	NPC322976
0.7292	Intermediate Similarity	NPC174672
0.7278	Intermediate Similarity	NPC132680
0.7278	Intermediate Similarity	NPC269919
0.7273	Intermediate Similarity	NPC187558
0.7263	Intermediate Similarity	NPC264166
0.7263	Intermediate Similarity	NPC274291
0.7263	Intermediate Similarity	NPC47059
0.7263	Intermediate Similarity	NPC472259
0.7263	Intermediate Similarity	NPC118832
0.7263	Intermediate Similarity	NPC165349
0.7263	Intermediate Similarity	NPC329708
0.7258	Intermediate Similarity	NPC90229
0.7254	Intermediate Similarity	NPC167860
0.7254	Intermediate Similarity	NPC123976
0.7246	Intermediate Similarity	NPC153769
0.724	Intermediate Similarity	NPC477111
0.7202	Intermediate Similarity	NPC174758
0.7202	Intermediate Similarity	NPC26872
0.72	Intermediate Similarity	NPC253810
0.72	Intermediate Similarity	NPC258773
0.7191	Intermediate Similarity	NPC42979
0.7184	Intermediate Similarity	NPC44161
0.7179	Intermediate Similarity	NPC202605
0.7179	Intermediate Similarity	NPC112206
0.7176	Intermediate Similarity	NPC116573
0.7175	Intermediate Similarity	NPC224764
0.7166	Intermediate Similarity	NPC77555
0.716	Intermediate Similarity	NPC280853
0.7158	Intermediate Similarity	NPC32771
0.7152	Intermediate Similarity	NPC256893
0.7151	Intermediate Similarity	NPC222592
0.7151	Intermediate Similarity	NPC168486
0.7151	Intermediate Similarity	NPC326634
0.715	Intermediate Similarity	NPC310118
0.715	Intermediate Similarity	NPC60621
0.715	Intermediate Similarity	NPC82548
0.7143	Intermediate Similarity	NPC164664
0.7143	Intermediate Similarity	NPC249040
0.7135	Intermediate Similarity	NPC477113
0.7128	Intermediate Similarity	NPC239954
0.7127	Intermediate Similarity	NPC284678
0.7127	Intermediate Similarity	NPC284559
0.7121	Intermediate Similarity	NPC469727
0.7121	Intermediate Similarity	NPC27041
0.712	Intermediate Similarity	NPC476138
0.712	Intermediate Similarity	NPC245816
0.7117	Intermediate Similarity	NPC245657
0.7117	Intermediate Similarity	NPC285016
0.7115	Intermediate Similarity	NPC471313
0.7115	Intermediate Similarity	NPC471311
0.7115	Intermediate Similarity	NPC306397
0.7113	Intermediate Similarity	NPC185782
0.711	Intermediate Similarity	NPC102423
0.711	Intermediate Similarity	NPC263439
0.711	Intermediate Similarity	NPC211187
0.7107	Intermediate Similarity	NPC237740
0.7099	Intermediate Similarity	NPC471596
0.7097	Intermediate Similarity	NPC106937
0.7097	Intermediate Similarity	NPC198673
0.7095	Intermediate Similarity	NPC72980
0.7092	Intermediate Similarity	NPC471603
0.709	Intermediate Similarity	NPC287437
0.7088	Intermediate Similarity	NPC295158
0.7086	Intermediate Similarity	NPC1527
0.7081	Intermediate Similarity	NPC29702
0.7079	Intermediate Similarity	NPC288943
0.7076	Intermediate Similarity	NPC26850
0.7074	Intermediate Similarity	NPC474188
0.7074	Intermediate Similarity	NPC156704
0.7074	Intermediate Similarity	NPC224928
0.7065	Intermediate Similarity	NPC110741
0.7062	Intermediate Similarity	NPC18348
0.7059	Intermediate Similarity	NPC6215
0.7053	Intermediate Similarity	NPC121772
0.7045	Intermediate Similarity	NPC256828
0.7044	Intermediate Similarity	NPC324611
0.7039	Intermediate Similarity	NPC283152
0.7037	Intermediate Similarity	NPC474916
0.703	Intermediate Similarity	NPC470501
0.7027	Intermediate Similarity	NPC3715
0.7006	Intermediate Similarity	NPC165370
0.7005	Intermediate Similarity	NPC307963
0.7005	Intermediate Similarity	NPC26679
0.6995	Remote Similarity	NPC16452
0.6995	Remote Similarity	NPC476581
0.6995	Remote Similarity	NPC36229
0.699	Remote Similarity	NPC309845
0.6988	Remote Similarity	NPC471323
0.6988	Remote Similarity	NPC471598
0.6985	Remote Similarity	NPC274982
0.6985	Remote Similarity	NPC477110
0.698	Remote Similarity	NPC470502
0.6976	Remote Similarity	NPC110151
0.6967	Remote Similarity	NPC477861
0.6966	Remote Similarity	NPC474409
0.6966	Remote Similarity	NPC313791
0.6964	Remote Similarity	NPC470111
0.6963	Remote Similarity	NPC315491
0.6963	Remote Similarity	NPC45459
0.6961	Remote Similarity	NPC478023
0.6959	Remote Similarity	NPC323345
0.6959	Remote Similarity	NPC470164
0.6957	Remote Similarity	NPC476451
0.6947	Remote Similarity	NPC168911
0.694	Remote Similarity	NPC62069
0.6939	Remote Similarity	NPC469589
0.6938	Remote Similarity	NPC182222
0.6932	Remote Similarity	NPC41717

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 NPC25899 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	848
0.2-0.3	733
0.3-0.4	1766
0.4-0.5	2882
0.5-0.6	1993
0.6-0.7	613
0.7-0.8	70
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8199	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD424	Approved
0.8171	Intermediate Similarity	NPD425	Approved
0.8	Intermediate Similarity	NPD925	Approved
0.8	Intermediate Similarity	NPD926	Approved
0.7867	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1649	Discontinued
0.7758	Intermediate Similarity	NPD5255	Approved
0.7647	Intermediate Similarity	NPD715	Phase 3
0.7616	Intermediate Similarity	NPD9690	Approved
0.7605	Intermediate Similarity	NPD9705	Discontinued
0.7605	Intermediate Similarity	NPD112	Approved
0.7588	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2781	Approved
0.7471	Intermediate Similarity	NPD2780	Approved
0.7471	Intermediate Similarity	NPD2782	Approved
0.7412	Intermediate Similarity	NPD861	Approved
0.7412	Intermediate Similarity	NPD863	Approved
0.7412	Intermediate Similarity	NPD862	Approved
0.7378	Intermediate Similarity	NPD4703	Approved
0.7378	Intermediate Similarity	NPD1661	Suspended
0.7378	Intermediate Similarity	NPD4702	Approved
0.7377	Intermediate Similarity	NPD9695	Approved
0.7351	Intermediate Similarity	NPD1622	Discontinued
0.7349	Intermediate Similarity	NPD2882	Phase 1
0.7346	Intermediate Similarity	NPD3717	Discontinued
0.7338	Intermediate Similarity	NPD9284	Approved
0.733	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD1740	Approved
0.7326	Intermediate Similarity	NPD1739	Approved
0.7322	Intermediate Similarity	NPD6569	Phase 2
0.7314	Intermediate Similarity	NPD158	Discontinued
0.7308	Intermediate Similarity	NPD4081	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD3813	Approved
0.7299	Intermediate Similarity	NPD2123	Phase 3
0.7294	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD9382	Approved
0.7278	Intermediate Similarity	NPD9383	Approved
0.7273	Intermediate Similarity	NPD5100	Phase 3
0.7263	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD4034	Approved
0.7263	Intermediate Similarity	NPD4036	Approved
0.7263	Intermediate Similarity	NPD32	Approved
0.7263	Intermediate Similarity	NPD4035	Approved
0.7263	Intermediate Similarity	NPD4122	Approved
0.7263	Intermediate Similarity	NPD4039	Approved
0.7263	Intermediate Similarity	NPD4038	Approved
0.7263	Intermediate Similarity	NPD4037	Approved
0.7263	Intermediate Similarity	NPD4033	Approved
0.7263	Intermediate Similarity	NPD31	Approved
0.7249	Intermediate Similarity	NPD3928	Approved
0.7249	Intermediate Similarity	NPD3931	Approved
0.7238	Intermediate Similarity	NPD4375	Approved
0.7235	Intermediate Similarity	NPD3433	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6159	Phase 2
0.7229	Intermediate Similarity	NPD3575	Approved
0.7229	Intermediate Similarity	NPD3576	Approved
0.7228	Intermediate Similarity	NPD4372	Phase 1
0.7213	Intermediate Similarity	NPD3321	Discontinued
0.7212	Intermediate Similarity	NPD7469	Discontinued
0.7207	Intermediate Similarity	NPD4204	Approved
0.7207	Intermediate Similarity	NPD7867	Phase 1
0.7207	Intermediate Similarity	NPD4203	Approved
0.7207	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD8823	Approved
0.7191	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1197	Approved
0.7179	Intermediate Similarity	NPD5352	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD4795	Phase 2
0.7159	Intermediate Similarity	NPD1599	Approved
0.7157	Intermediate Similarity	NPD7112	Discontinued
0.7151	Intermediate Similarity	NPD3396	Approved
0.7151	Intermediate Similarity	NPD3395	Approved
0.7143	Intermediate Similarity	NPD706	Phase 1
0.7143	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD1213	Phase 3
0.7115	Intermediate Similarity	NPD9080	Approved
0.7114	Intermediate Similarity	NPD1856	Discontinued
0.7112	Intermediate Similarity	NPD3477	Phase 2
0.7112	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD1034	Phase 3
0.7099	Intermediate Similarity	NPD9076	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD802	Phase 2
0.7091	Intermediate Similarity	NPD1352	Discontinued
0.7088	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD3082	Discontinued
0.7076	Intermediate Similarity	NPD2581	Approved
0.7076	Intermediate Similarity	NPD2582	Approved
0.7074	Intermediate Similarity	NPD2952	Discontinued
0.7074	Intermediate Similarity	NPD7948	Phase 1
0.7045	Intermediate Similarity	NPD5320	Approved
0.7045	Intermediate Similarity	NPD5319	Approved
0.7043	Intermediate Similarity	NPD5317	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD9689	Approved
0.7041	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6158	Phase 2
0.7037	Intermediate Similarity	NPD9506	Approved
0.7027	Intermediate Similarity	NPD5316	Approved
0.7027	Intermediate Similarity	NPD3439	Approved
0.7022	Intermediate Similarity	NPD6492	Phase 2
0.7022	Intermediate Similarity	NPD5065	Approved
0.7018	Intermediate Similarity	NPD1274	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD3386	Phase 2
0.7005	Intermediate Similarity	NPD4551	Phase 2
0.7005	Intermediate Similarity	NPD3330	Phase 1
0.7005	Intermediate Similarity	NPD1038	Approved
0.6995	Remote Similarity	NPD2762	Phase 2
0.6995	Remote Similarity	NPD4889	Approved
0.6994	Remote Similarity	NPD852	Discontinued
0.6989	Remote Similarity	NPD5862	Discovery
0.6989	Remote Similarity	NPD6022	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD2334	Discontinued
0.6979	Remote Similarity	NPD6975	Discontinued
0.6977	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD484	Approved
0.6959	Remote Similarity	NPD5530	Phase 1
0.6952	Remote Similarity	NPD6887	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD565	Phase 2
0.6943	Remote Similarity	NPD4886	Phase 2
0.6941	Remote Similarity	NPD9595	Approved
0.6941	Remote Similarity	NPD9596	Approved
0.6935	Remote Similarity	NPD8063	Discontinued
0.6919	Remote Similarity	NPD2383	Phase 1
0.6906	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD1229	Phase 2
0.6888	Remote Similarity	NPD2816	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4021	Phase 2
0.6878	Remote Similarity	NPD1602	Discontinued
0.6869	Remote Similarity	NPD4131	Phase 3
0.6866	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD3924	Approved
0.6862	Remote Similarity	NPD3923	Approved
0.6862	Remote Similarity	NPD3921	Approved
0.6862	Remote Similarity	NPD3922	Approved
0.6859	Remote Similarity	NPD5885	Approved
0.6857	Remote Similarity	NPD1684	Approved
0.6857	Remote Similarity	NPD1685	Approved
0.6848	Remote Similarity	NPD6178	Phase 3
0.6845	Remote Similarity	NPD7603	Discontinued
0.6839	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD8408	Discontinued
0.6825	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6361	Phase 2
0.6823	Remote Similarity	NPD9687	Approved
0.6823	Remote Similarity	NPD9688	Approved
0.6821	Remote Similarity	NPD3500	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2959	Phase 3
0.6803	Remote Similarity	NPD9098	Phase 3
0.6803	Remote Similarity	NPD9099	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6501	Approved
0.6798	Remote Similarity	NPD6500	Approved
0.6797	Remote Similarity	NPD9396	Approved
0.6797	Remote Similarity	NPD9392	Approved
0.6796	Remote Similarity	NPD2751	Phase 1
0.6786	Remote Similarity	NPD1918	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD3570	Phase 2
0.678	Remote Similarity	NPD4945	Discontinued
0.678	Remote Similarity	NPD8356	Approved
0.678	Remote Similarity	NPD2720	Phase 1
0.678	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2600	Approved
0.6776	Remote Similarity	NPD2599	Approved
0.6776	Remote Similarity	NPD2601	Approved
0.6774	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.677	Remote Similarity	NPD9206	Approved
0.677	Remote Similarity	NPD9207	Approved
0.6769	Remote Similarity	NPD4044	Discontinued
0.6758	Remote Similarity	NPD4072	Approved
0.6758	Remote Similarity	NPD1032	Phase 2
0.6758	Remote Similarity	NPD4071	Approved
0.6751	Remote Similarity	NPD1392	Approved
0.675	Remote Similarity	NPD3816	Phase 1
0.675	Remote Similarity	NPD3815	Phase 1
0.675	Remote Similarity	NPD7069	Discontinued
0.6739	Remote Similarity	NPD1570	Approved
0.6737	Remote Similarity	NPD4526	Approved
0.6737	Remote Similarity	NPD4529	Approved
0.6737	Remote Similarity	NPD5428	Discontinued
0.6737	Remote Similarity	NPD4528	Approved
0.6736	Remote Similarity	NPD5999	Phase 2
0.6736	Remote Similarity	NPD2177	Approved
0.6736	Remote Similarity	NPD2176	Approved
0.6736	Remote Similarity	NPD4548	Discontinued
0.6736	Remote Similarity	NPD2175	Phase 3
0.6733	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD8430	Approved
0.6723	Remote Similarity	NPD5925	Phase 1
0.6723	Remote Similarity	NPD5138	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