NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	259.1
Volume:	257.197
LogP:	1.646
LogD:	1.358
LogS:	-2.459
# Rotatable Bonds:	5
TPSA:	73.34
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.841
Synthetic Accessibility Score:	2.281
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:	-4.571
MDCK Permeability:	1.554546361148823e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.706
Plasma Protein Binding (PPB):	86.8225326538086%
Volume Distribution (VD):	1.078
Pgp-substrate:	11.093108177185059%

ADMET: Metabolism

CYP1A2-inhibitor:	0.735
CYP1A2-substrate:	0.808
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.091
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.759
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.538
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.171

ADMET: Excretion

Clearance (CL):	7.306
Half-life (T1/2):	0.394

ADMET: Toxicity

hERG Blockers:	0.073
Human Hepatotoxicity (H-HT):	0.413
Drug-inuced Liver Injury (DILI):	0.941
AMES Toxicity:	0.541
Rat Oral Acute Toxicity:	0.399
Maximum Recommended Daily Dose:	0.6
Skin Sensitization:	0.118
Carcinogencity:	0.04
Eye Corrosion:	0.004
Eye Irritation:	0.46
Respiratory Toxicity:	0.907

Download Data

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

Natural Product: NPC266551

Natural Product ID:	NPC266551
*Common Name:**	Caerulomycin I
IUPAC Name:	N,4-dimethoxy-6-pyridin-2-ylpyridine-2-carboxamide
Synonyms:	Caerulomycin I
Standard InCHIKey:	JYJANIYSNABJRT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H13N3O3/c1-18-9-7-11(10-5-3-4-6-14-10)15-12(8-9)13(17)16-19-2/h3-8H,1-2H3,(H,16,17)
SMILES:	COc1cc(c2ccccn2)nc(c1)C(=NOC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1823034
PubChem CID:	53484025
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	=	5200.0	nM	PMID[473041]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[473041]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	370.0	nM	PMID[473041]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	50000.0	nM	PMID[473041]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>=	100000.0	nM	PMID[473041]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>=	100000.0	nM	PMID[473041]
NPT720	Organism	Enterobacter aerogenes	Enterobacter aerogenes	MIC	>=	100000.0	nM	PMID[473041]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>=	100000.0	nM	PMID[473041]

☑ 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 NPC266551 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	507
0.1-0.2	7652
0.2-0.3	9922
0.3-0.4	13938
0.4-0.5	6639
0.5-0.6	3010
0.6-0.7	879
0.7-0.8	134
0.8-0.85	2
0.85-0.9	6
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9755	High Similarity	NPC219963
0.9755	High Similarity	NPC161887
0.9565	High Similarity	NPC14651
0.9565	High Similarity	NPC121658
0.9503	High Similarity	NPC476518
0.9345	High Similarity	NPC20249
0.9191	High Similarity	NPC226202
0.9074	High Similarity	NPC48192
0.9036	High Similarity	NPC111624
0.9012	High Similarity	NPC25899
0.8902	High Similarity	NPC206251
0.8902	High Similarity	NPC74382
0.8508	High Similarity	NPC267928
0.8427	Intermediate Similarity	NPC224327
0.838	Intermediate Similarity	NPC134079
0.8176	Intermediate Similarity	NPC177404
0.8075	Intermediate Similarity	NPC19872
0.7946	Intermediate Similarity	NPC84853
0.7876	Intermediate Similarity	NPC287208
0.7831	Intermediate Similarity	NPC187558
0.7778	Intermediate Similarity	NPC470799
0.7778	Intermediate Similarity	NPC8022
0.775	Intermediate Similarity	NPC213530
0.775	Intermediate Similarity	NPC193267
0.772	Intermediate Similarity	NPC165349
0.772	Intermediate Similarity	NPC274291
0.772	Intermediate Similarity	NPC47059
0.772	Intermediate Similarity	NPC264166
0.772	Intermediate Similarity	NPC118832
0.772	Intermediate Similarity	NPC329708
0.7701	Intermediate Similarity	NPC285635
0.7684	Intermediate Similarity	NPC1527
0.7668	Intermediate Similarity	NPC476138
0.7668	Intermediate Similarity	NPC245816
0.7656	Intermediate Similarity	NPC232727
0.7653	Intermediate Similarity	NPC185782
0.7637	Intermediate Similarity	NPC222592
0.7637	Intermediate Similarity	NPC168486
0.7633	Intermediate Similarity	NPC220523
0.7604	Intermediate Similarity	NPC315957
0.7604	Intermediate Similarity	NPC176538
0.7563	Intermediate Similarity	NPC174672
0.754	Intermediate Similarity	NPC110741
0.7538	Intermediate Similarity	NPC26679
0.7525	Intermediate Similarity	NPC123976
0.7525	Intermediate Similarity	NPC167860
0.7514	Intermediate Similarity	NPC26872
0.75	Intermediate Similarity	NPC310118
0.75	Intermediate Similarity	NPC258773
0.7475	Intermediate Similarity	NPC174758
0.7473	Intermediate Similarity	NPC42591
0.7444	Intermediate Similarity	NPC314940
0.7444	Intermediate Similarity	NPC473764
0.7426	Intermediate Similarity	NPC274982
0.7424	Intermediate Similarity	NPC82548
0.7419	Intermediate Similarity	NPC284559
0.7415	Intermediate Similarity	NPC60621
0.7411	Intermediate Similarity	NPC323345
0.7411	Intermediate Similarity	NPC470164
0.7409	Intermediate Similarity	NPC239954
0.7405	Intermediate Similarity	NPC118776
0.7398	Intermediate Similarity	NPC475774
0.7387	Intermediate Similarity	NPC469589
0.7386	Intermediate Similarity	NPC26850
0.7382	Intermediate Similarity	NPC198673
0.7374	Intermediate Similarity	NPC471178
0.7371	Intermediate Similarity	NPC287437
0.7371	Intermediate Similarity	NPC476167
0.7371	Intermediate Similarity	NPC18487
0.7368	Intermediate Similarity	NPC314954
0.7363	Intermediate Similarity	NPC112206
0.7363	Intermediate Similarity	NPC202605
0.736	Intermediate Similarity	NPC470500
0.736	Intermediate Similarity	NPC124542
0.736	Intermediate Similarity	NPC79911
0.736	Intermediate Similarity	NPC59779
0.736	Intermediate Similarity	NPC471177
0.7353	Intermediate Similarity	NPC470404
0.7353	Intermediate Similarity	NPC470403
0.7353	Intermediate Similarity	NPC470394
0.7333	Intermediate Similarity	NPC121772
0.7327	Intermediate Similarity	NPC476287
0.7326	Intermediate Similarity	NPC284678
0.7321	Intermediate Similarity	NPC110151
0.732	Intermediate Similarity	NPC212213
0.732	Intermediate Similarity	NPC192315
0.7318	Intermediate Similarity	NPC263439
0.7318	Intermediate Similarity	NPC118511
0.7314	Intermediate Similarity	NPC36168
0.7308	Intermediate Similarity	NPC252590
0.7305	Intermediate Similarity	NPC328029
0.7303	Intermediate Similarity	NPC120798
0.7292	Intermediate Similarity	NPC307963
0.7273	Intermediate Similarity	NPC48938
0.7273	Intermediate Similarity	NPC36229
0.7273	Intermediate Similarity	NPC16452
0.7273	Intermediate Similarity	NPC174421
0.7273	Intermediate Similarity	NPC476581
0.7268	Intermediate Similarity	NPC224928
0.7268	Intermediate Similarity	NPC197141
0.7267	Intermediate Similarity	NPC470395
0.7264	Intermediate Similarity	NPC5145
0.7264	Intermediate Similarity	NPC469554
0.7264	Intermediate Similarity	NPC101543
0.7243	Intermediate Similarity	NPC283152
0.724	Intermediate Similarity	NPC324149
0.7231	Intermediate Similarity	NPC168911
0.723	Intermediate Similarity	NPC141053
0.7228	Intermediate Similarity	NPC95898
0.7222	Intermediate Similarity	NPC200836
0.7216	Intermediate Similarity	NPC251090
0.7211	Intermediate Similarity	NPC66083
0.72	Intermediate Similarity	NPC193238
0.7194	Intermediate Similarity	NPC476582
0.7194	Intermediate Similarity	NPC4071
0.7194	Intermediate Similarity	NPC476578
0.7189	Intermediate Similarity	NPC288943
0.7184	Intermediate Similarity	NPC173080
0.7175	Intermediate Similarity	NPC63562
0.7173	Intermediate Similarity	NPC296527
0.7157	Intermediate Similarity	NPC471080
0.7157	Intermediate Similarity	NPC469592
0.715	Intermediate Similarity	NPC195268
0.715	Intermediate Similarity	NPC472111
0.715	Intermediate Similarity	NPC133140
0.7143	Intermediate Similarity	NPC62069
0.7136	Intermediate Similarity	NPC53144
0.7135	Intermediate Similarity	NPC76748
0.7135	Intermediate Similarity	NPC318935
0.7128	Intermediate Similarity	NPC13880
0.7127	Intermediate Similarity	NPC473057
0.7127	Intermediate Similarity	NPC97367
0.7121	Intermediate Similarity	NPC31930
0.7113	Intermediate Similarity	NPC289786
0.7111	Intermediate Similarity	NPC324203
0.7111	Intermediate Similarity	NPC322976
0.7111	Intermediate Similarity	NPC63338
0.71	Intermediate Similarity	NPC285558
0.7098	Intermediate Similarity	NPC92111
0.7097	Intermediate Similarity	NPC203754
0.7097	Intermediate Similarity	NPC150048
0.7095	Intermediate Similarity	NPC132680
0.7095	Intermediate Similarity	NPC269919
0.7094	Intermediate Similarity	NPC85273
0.7091	Intermediate Similarity	NPC472434
0.7087	Intermediate Similarity	NPC288349
0.7086	Intermediate Similarity	NPC257142
0.7085	Intermediate Similarity	NPC211813
0.7083	Intermediate Similarity	NPC295228
0.7067	Intermediate Similarity	NPC292958
0.7062	Intermediate Similarity	NPC153769
0.7062	Intermediate Similarity	NPC284348
0.7056	Intermediate Similarity	NPC260434
0.705	Intermediate Similarity	NPC223427
0.7037	Intermediate Similarity	NPC470474
0.7037	Intermediate Similarity	NPC182222
0.7026	Intermediate Similarity	NPC329541
0.7024	Intermediate Similarity	NPC202768
0.7024	Intermediate Similarity	NPC296482
0.7024	Intermediate Similarity	NPC53069
0.7019	Intermediate Similarity	NPC469594
0.7015	Intermediate Similarity	NPC475070
0.7014	Intermediate Similarity	NPC122436
0.7012	Intermediate Similarity	NPC151489
0.7011	Intermediate Similarity	NPC44161
0.7	Intermediate Similarity	NPC116573
0.6995	Remote Similarity	NPC308392
0.699	Remote Similarity	NPC162530
0.6985	Remote Similarity	NPC234197
0.698	Remote Similarity	NPC471736
0.6979	Remote Similarity	NPC314573
0.6967	Remote Similarity	NPC216612
0.6961	Remote Similarity	NPC84508
0.6946	Remote Similarity	NPC313189
0.6943	Remote Similarity	NPC46580
0.6942	Remote Similarity	NPC171409
0.6942	Remote Similarity	NPC96405
0.6942	Remote Similarity	NPC316981
0.694	Remote Similarity	NPC211187
0.6938	Remote Similarity	NPC314270
0.6931	Remote Similarity	NPC42979
0.6931	Remote Similarity	NPC472168
0.6931	Remote Similarity	NPC472259
0.6927	Remote Similarity	NPC290689
0.6927	Remote Similarity	NPC11464
0.6927	Remote Similarity	NPC314002
0.6916	Remote Similarity	NPC472435
0.6915	Remote Similarity	NPC224764
0.6914	Remote Similarity	NPC471323
0.6912	Remote Similarity	NPC477111
0.6908	Remote Similarity	NPC266931
0.6907	Remote Similarity	NPC472289
0.6905	Remote Similarity	NPC17565
0.69	Remote Similarity	NPC477019
0.6897	Remote Similarity	NPC476121
0.6897	Remote Similarity	NPC476124
0.689	Remote Similarity	NPC473513
0.6882	Remote Similarity	NPC256828
0.6878	Remote Similarity	NPC99891
0.6875	Remote Similarity	NPC320394

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 NPC266551 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	858
0.2-0.3	731
0.3-0.4	1665
0.4-0.5	2861
0.5-0.6	2032
0.6-0.7	663
0.7-0.8	96
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7886	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7819	Intermediate Similarity	NPD1622	Discontinued
0.7796	Intermediate Similarity	NPD6569	Phase 2
0.7746	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.772	Intermediate Similarity	NPD4038	Approved
0.772	Intermediate Similarity	NPD4033	Approved
0.772	Intermediate Similarity	NPD4122	Approved
0.772	Intermediate Similarity	NPD4039	Approved
0.772	Intermediate Similarity	NPD4037	Approved
0.772	Intermediate Similarity	NPD4036	Approved
0.772	Intermediate Similarity	NPD32	Approved
0.772	Intermediate Similarity	NPD4035	Approved
0.772	Intermediate Similarity	NPD31	Approved
0.772	Intermediate Similarity	NPD4034	Approved
0.7701	Intermediate Similarity	NPD4372	Phase 1
0.7688	Intermediate Similarity	NPD4081	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1034	Phase 3
0.7672	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD3477	Phase 2
0.7635	Intermediate Similarity	NPD1856	Discontinued
0.7604	Intermediate Similarity	NPD1739	Approved
0.7604	Intermediate Similarity	NPD1740	Approved
0.7596	Intermediate Similarity	NPD4204	Approved
0.7596	Intermediate Similarity	NPD4203	Approved
0.7542	Intermediate Similarity	NPD565	Phase 2
0.7542	Intermediate Similarity	NPD5320	Approved
0.7542	Intermediate Similarity	NPD5319	Approved
0.7528	Intermediate Similarity	NPD424	Approved
0.7528	Intermediate Similarity	NPD425	Approved
0.7527	Intermediate Similarity	NPD4375	Approved
0.75	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD9596	Approved
0.7457	Intermediate Similarity	NPD9595	Approved
0.7449	Intermediate Similarity	NPD4795	Phase 2
0.7443	Intermediate Similarity	NPD5255	Approved
0.7435	Intermediate Similarity	NPD3396	Approved
0.7435	Intermediate Similarity	NPD3395	Approved
0.7433	Intermediate Similarity	NPD3039	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4131	Phase 3
0.7368	Intermediate Similarity	NPD2334	Discontinued
0.7358	Intermediate Similarity	NPD2952	Discontinued
0.7358	Intermediate Similarity	NPD2959	Phase 3
0.7326	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3386	Phase 2
0.7304	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD112	Approved
0.7303	Intermediate Similarity	NPD9705	Discontinued
0.7292	Intermediate Similarity	NPD1038	Approved
0.7288	Intermediate Similarity	NPD2582	Approved
0.7288	Intermediate Similarity	NPD2581	Approved
0.7288	Intermediate Similarity	NPD9574	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD926	Approved
0.7278	Intermediate Similarity	NPD925	Approved
0.7236	Intermediate Similarity	NPD5530	Phase 1
0.7233	Intermediate Similarity	NPD6501	Approved
0.7233	Intermediate Similarity	NPD6500	Approved
0.7232	Intermediate Similarity	NPD1274	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD3570	Phase 2
0.7228	Intermediate Similarity	NPD9690	Approved
0.7202	Intermediate Similarity	NPD9695	Approved
0.7202	Intermediate Similarity	NPD4551	Phase 2
0.72	Intermediate Similarity	NPD1392	Approved
0.7196	Intermediate Similarity	NPD4889	Approved
0.7194	Intermediate Similarity	NPD5999	Phase 2
0.7194	Intermediate Similarity	NPD2958	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5640	Discontinued
0.7173	Intermediate Similarity	NPD4021	Phase 2
0.7165	Intermediate Similarity	NPD1602	Discontinued
0.7163	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD2772	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD2314	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1032	Phase 2
0.715	Intermediate Similarity	NPD3924	Approved
0.715	Intermediate Similarity	NPD3923	Approved
0.715	Intermediate Similarity	NPD3922	Approved
0.715	Intermediate Similarity	NPD3921	Approved
0.7135	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD1649	Discontinued
0.7135	Intermediate Similarity	NPD8063	Discontinued
0.7127	Intermediate Similarity	NPD863	Approved
0.7127	Intermediate Similarity	NPD862	Approved
0.7127	Intermediate Similarity	NPD861	Approved
0.712	Intermediate Similarity	NPD6393	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD1603	Discontinued
0.7107	Intermediate Similarity	NPD4548	Discontinued
0.7095	Intermediate Similarity	NPD9382	Approved
0.7095	Intermediate Similarity	NPD9383	Approved
0.7092	Intermediate Similarity	NPD1229	Phase 2
0.7079	Intermediate Similarity	NPD2816	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD2599	Approved
0.7074	Intermediate Similarity	NPD2601	Approved
0.7074	Intermediate Similarity	NPD2600	Approved
0.7059	Intermediate Similarity	NPD4072	Approved
0.7059	Intermediate Similarity	NPD4071	Approved
0.7047	Intermediate Similarity	NPD3321	Discontinued
0.7039	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2757	Phase 2
0.7035	Intermediate Similarity	NPD1621	Discontinued
0.7028	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD7426	Phase 1
0.7028	Intermediate Similarity	NPD7674	Phase 3
0.7028	Intermediate Similarity	NPD7675	Phase 3
0.7027	Intermediate Similarity	NPD2123	Phase 3
0.7024	Intermediate Similarity	NPD3816	Phase 1
0.7024	Intermediate Similarity	NPD7069	Discontinued
0.7024	Intermediate Similarity	NPD3815	Phase 1
0.7017	Intermediate Similarity	NPD1418	Phase 2
0.701	Intermediate Similarity	NPD4148	Approved
0.7009	Intermediate Similarity	NPD3302	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD715	Phase 3
0.6995	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5944	Phase 1
0.699	Remote Similarity	NPD5945	Phase 1
0.6976	Remote Similarity	NPD5067	Phase 2
0.6976	Remote Similarity	NPD5066	Phase 2
0.6963	Remote Similarity	NPD1334	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6856	Discontinued
0.6952	Remote Similarity	NPD158	Discontinued
0.6949	Remote Similarity	NPD3575	Approved
0.6949	Remote Similarity	NPD3576	Approved
0.6946	Remote Similarity	NPD7222	Phase 2
0.6939	Remote Similarity	NPD4528	Approved
0.6939	Remote Similarity	NPD4529	Approved
0.6939	Remote Similarity	NPD6361	Phase 2
0.6939	Remote Similarity	NPD4526	Approved
0.6938	Remote Similarity	NPD6568	Discontinued
0.6935	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD9548	Phase 2
0.6923	Remote Similarity	NPD5612	Discontinued
0.6919	Remote Similarity	NPD4899	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2781	Approved
0.6916	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6366	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7558	Phase 2
0.6909	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD6590	Discontinued
0.6902	Remote Similarity	NPD2782	Approved
0.6902	Remote Similarity	NPD2780	Approved
0.6898	Remote Similarity	NPD2076	Approved
0.6898	Remote Similarity	NPD2077	Approved
0.6897	Remote Similarity	NPD5601	Phase 2
0.6893	Remote Similarity	NPD3939	Suspended
0.6891	Remote Similarity	NPD706	Phase 1
0.6891	Remote Similarity	NPD5256	Discontinued
0.6888	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6159	Phase 2
0.6872	Remote Similarity	NPD8479	Phase 2
0.6869	Remote Similarity	NPD1273	Discontinued
0.6868	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.685	Remote Similarity	NPD1768	Approved
0.6844	Remote Similarity	NPD5644	Phase 1
0.6842	Remote Similarity	NPD8510	Clinical (unspecified phase)
0.684	Remote Similarity	NPD6298	Discontinued
0.6839	Remote Similarity	NPD3082	Discontinued
0.6835	Remote Similarity	NPD6494	Phase 2
0.6834	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD1927	Discontinued
0.6831	Remote Similarity	NPD687	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD2739	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5862	Discovery
0.682	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1951	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD949	Phase 1
0.6812	Remote Similarity	NPD2540	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4502	Phase 2
0.681	Remote Similarity	NPD4989	Phase 2
0.6804	Remote Similarity	NPD4919	Phase 3
0.6804	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4921	Phase 3
0.6798	Remote Similarity	NPD1661	Suspended
0.6798	Remote Similarity	NPD4702	Approved
0.6798	Remote Similarity	NPD6991	Approved
0.6798	Remote Similarity	NPD4703	Approved
0.6798	Remote Similarity	NPD5513	Phase 2
0.6788	Remote Similarity	NPD3569	Discontinued
0.6787	Remote Similarity	NPD2414	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5316	Approved
0.6786	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1213	Phase 3
0.6784	Remote Similarity	NPD6550	Discontinued
0.6784	Remote Similarity	NPD1704	Clinical (unspecified phase)
0.678	Remote Similarity	NPD2885	Approved
0.678	Remote Similarity	NPD7452	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