NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	215.07
Volume:	213.815
LogP:	0.889
LogD:	0.787
LogS:	-2.135
# Rotatable Bonds:	2
TPSA:	78.34
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.449
Synthetic Accessibility Score:	2.966
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.761
MDCK Permeability:	1.3235789992904756e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.151
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.301
Plasma Protein Binding (PPB):	47.3719482421875%
Volume Distribution (VD):	0.943
Pgp-substrate:	59.5484504699707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.946
CYP1A2-substrate:	0.123
CYP2C19-inhibitor:	0.067
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.827
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.573
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.112

ADMET: Excretion

Clearance (CL):	2.03
Half-life (T1/2):	0.487

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.11
Drug-inuced Liver Injury (DILI):	0.853
AMES Toxicity:	0.758
Rat Oral Acute Toxicity:	0.74
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.339
Carcinogencity:	0.282
Eye Corrosion:	0.748
Eye Irritation:	0.988
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC48192

Natural Product ID:	NPC48192
*Common Name:**	Caerulomycin H
IUPAC Name:	2-[(E)-hydroxyiminomethyl]-6-pyridin-2-yl-1H-pyridin-4-one
Synonyms:	Caerulomycin H
Standard InCHIKey:	XLFYSDMKBLTHTJ-NTUHNPAUSA-N
Standard InCHI:	InChI=1S/C11H9N3O2/c15-9-5-8(7-13-16)14-11(6-9)10-3-1-2-4-12-10/h1-7,16H,(H,14,15)/b13-7+
SMILES:	c1ccnc(c1)c1cc(cc(/C=N/O)n1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1823033
PubChem CID:	53484026
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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	8400.0	nM	PMID[546627]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	1600.0	nM	PMID[546627]

☑ 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 NPC48192 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	655
0.1-0.2	11949
0.2-0.3	7905
0.3-0.4	14828
0.4-0.5	3967
0.5-0.6	2528
0.6-0.7	775
0.7-0.8	72
0.8-0.85	10
0.85-0.9	6
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9799	High Similarity	NPC25899
0.9114	High Similarity	NPC121658
0.9114	High Similarity	NPC14651
0.9074	High Similarity	NPC266551
0.9051	High Similarity	NPC476518
0.8841	High Similarity	NPC219963
0.8841	High Similarity	NPC161887
0.8589	High Similarity	NPC111624
0.8571	High Similarity	NPC20249
0.8471	Intermediate Similarity	NPC74382
0.8471	Intermediate Similarity	NPC206251
0.8333	Intermediate Similarity	NPC226202
0.8061	Intermediate Similarity	NPC471178
0.8049	Intermediate Similarity	NPC59779
0.8049	Intermediate Similarity	NPC124542
0.8049	Intermediate Similarity	NPC471177
0.8012	Intermediate Similarity	NPC36168
0.8	Intermediate Similarity	NPC224327
0.7955	Intermediate Similarity	NPC134079
0.7925	Intermediate Similarity	NPC220523
0.7865	Intermediate Similarity	NPC324149
0.7826	Intermediate Similarity	NPC200836
0.7811	Intermediate Similarity	NPC473764
0.7811	Intermediate Similarity	NPC314940
0.779	Intermediate Similarity	NPC267928
0.7784	Intermediate Similarity	NPC97367
0.7733	Intermediate Similarity	NPC151489
0.773	Intermediate Similarity	NPC53144
0.7725	Intermediate Similarity	NPC79911
0.7725	Intermediate Similarity	NPC177404
0.7679	Intermediate Similarity	NPC473057
0.7676	Intermediate Similarity	NPC211813
0.7672	Intermediate Similarity	NPC85273
0.7665	Intermediate Similarity	NPC120798
0.7662	Intermediate Similarity	NPC174421
0.7661	Intermediate Similarity	NPC252590
0.765	Intermediate Similarity	NPC192315
0.7624	Intermediate Similarity	NPC329541
0.7609	Intermediate Similarity	NPC476167
0.7594	Intermediate Similarity	NPC470500
0.758	Intermediate Similarity	NPC328029
0.7572	Intermediate Similarity	NPC95898
0.7542	Intermediate Similarity	NPC46580
0.7516	Intermediate Similarity	NPC470403
0.7516	Intermediate Similarity	NPC470394
0.7516	Intermediate Similarity	NPC470404
0.75	Intermediate Similarity	NPC472289
0.75	Intermediate Similarity	NPC475070
0.75	Intermediate Similarity	NPC318935
0.75	Intermediate Similarity	NPC84508
0.7487	Intermediate Similarity	NPC5145
0.7453	Intermediate Similarity	NPC60553
0.7449	Intermediate Similarity	NPC193267
0.7449	Intermediate Similarity	NPC213530
0.743	Intermediate Similarity	NPC314002
0.7423	Intermediate Similarity	NPC470395
0.7416	Intermediate Similarity	NPC220765
0.7416	Intermediate Similarity	NPC48938
0.7386	Intermediate Similarity	NPC96890
0.7386	Intermediate Similarity	NPC184964
0.7384	Intermediate Similarity	NPC108469
0.738	Intermediate Similarity	NPC19872
0.7374	Intermediate Similarity	NPC204717
0.7368	Intermediate Similarity	NPC476121
0.7368	Intermediate Similarity	NPC476124
0.7333	Intermediate Similarity	NPC257142
0.733	Intermediate Similarity	NPC150048
0.733	Intermediate Similarity	NPC203754
0.7293	Intermediate Similarity	NPC171171
0.7289	Intermediate Similarity	NPC288445
0.7283	Intermediate Similarity	NPC99666
0.7273	Intermediate Similarity	NPC161292
0.7259	Intermediate Similarity	NPC304926
0.7259	Intermediate Similarity	NPC476041
0.7258	Intermediate Similarity	NPC242209
0.7251	Intermediate Similarity	NPC285635
0.7251	Intermediate Similarity	NPC131718
0.7249	Intermediate Similarity	NPC232727
0.7243	Intermediate Similarity	NPC84853
0.7241	Intermediate Similarity	NPC44161
0.7219	Intermediate Similarity	NPC90229
0.7219	Intermediate Similarity	NPC63562
0.7213	Intermediate Similarity	NPC32771
0.7208	Intermediate Similarity	NPC470799
0.7208	Intermediate Similarity	NPC8022
0.7207	Intermediate Similarity	NPC222592
0.7207	Intermediate Similarity	NPC168486
0.7202	Intermediate Similarity	NPC284348
0.7202	Intermediate Similarity	NPC287208
0.7198	Intermediate Similarity	NPC314573
0.7196	Intermediate Similarity	NPC315957
0.7196	Intermediate Similarity	NPC176538
0.7181	Intermediate Similarity	NPC212213
0.7179	Intermediate Similarity	NPC212125
0.7165	Intermediate Similarity	NPC174672
0.7159	Intermediate Similarity	NPC253810
0.7151	Intermediate Similarity	NPC322976
0.7151	Intermediate Similarity	NPC324203
0.7151	Intermediate Similarity	NPC42979
0.7151	Intermediate Similarity	NPC63338
0.7143	Intermediate Similarity	NPC187558
0.7135	Intermediate Similarity	NPC47059
0.7135	Intermediate Similarity	NPC274291
0.7135	Intermediate Similarity	NPC224764
0.7135	Intermediate Similarity	NPC472259
0.7135	Intermediate Similarity	NPC264166
0.7135	Intermediate Similarity	NPC165349
0.7135	Intermediate Similarity	NPC269919
0.7135	Intermediate Similarity	NPC132680
0.7135	Intermediate Similarity	NPC118832
0.7135	Intermediate Similarity	NPC329708
0.7128	Intermediate Similarity	NPC77555
0.7128	Intermediate Similarity	NPC167860
0.7128	Intermediate Similarity	NPC123976
0.7113	Intermediate Similarity	NPC477111
0.7112	Intermediate Similarity	NPC326634
0.7107	Intermediate Similarity	NPC256893
0.7102	Intermediate Similarity	NPC164664
0.7101	Intermediate Similarity	NPC153769
0.7098	Intermediate Similarity	NPC477113
0.7085	Intermediate Similarity	NPC27041
0.7085	Intermediate Similarity	NPC469727
0.7077	Intermediate Similarity	NPC174758
0.7071	Intermediate Similarity	NPC237740
0.707	Intermediate Similarity	NPC306397
0.7069	Intermediate Similarity	NPC102423
0.7062	Intermediate Similarity	NPC258773
0.7059	Intermediate Similarity	NPC26872
0.7056	Intermediate Similarity	NPC112206
0.7056	Intermediate Similarity	NPC202605
0.7056	Intermediate Similarity	NPC471603
0.7049	Intermediate Similarity	NPC295158
0.7037	Intermediate Similarity	NPC29702
0.7037	Intermediate Similarity	NPC156704
0.7035	Intermediate Similarity	NPC274982
0.7035	Intermediate Similarity	NPC116573
0.703	Intermediate Similarity	NPC310118
0.703	Intermediate Similarity	NPC60621
0.7026	Intermediate Similarity	NPC82548
0.7026	Intermediate Similarity	NPC18348
0.7024	Intermediate Similarity	NPC6215
0.7024	Intermediate Similarity	NPC470111
0.7016	Intermediate Similarity	NPC249040
0.7012	Intermediate Similarity	NPC280853
0.701	Intermediate Similarity	NPC323345
0.701	Intermediate Similarity	NPC470164
0.7	Intermediate Similarity	NPC239954
0.7	Intermediate Similarity	NPC324611
0.7	Intermediate Similarity	NPC474916
0.6995	Remote Similarity	NPC476138
0.6995	Remote Similarity	NPC284678
0.6995	Remote Similarity	NPC470501
0.6995	Remote Similarity	NPC245816
0.6995	Remote Similarity	NPC284559
0.699	Remote Similarity	NPC185782
0.6971	Remote Similarity	NPC211187
0.6971	Remote Similarity	NPC263439
0.697	Remote Similarity	NPC245657
0.697	Remote Similarity	NPC285016
0.6968	Remote Similarity	NPC106937
0.6968	Remote Similarity	NPC198673
0.6963	Remote Similarity	NPC287437
0.6962	Remote Similarity	NPC471313
0.6962	Remote Similarity	NPC165370
0.6962	Remote Similarity	NPC471311
0.6961	Remote Similarity	NPC72980
0.6954	Remote Similarity	NPC309845
0.6951	Remote Similarity	NPC471596
0.695	Remote Similarity	NPC477110
0.6949	Remote Similarity	NPC1527
0.6947	Remote Similarity	NPC224928
0.6947	Remote Similarity	NPC474188
0.6946	Remote Similarity	NPC470502
0.6944	Remote Similarity	NPC288943
0.6936	Remote Similarity	NPC26850
0.6935	Remote Similarity	NPC110741
0.6927	Remote Similarity	NPC474409
0.6927	Remote Similarity	NPC315491
0.6927	Remote Similarity	NPC45459
0.6927	Remote Similarity	NPC121772
0.6923	Remote Similarity	NPC478023
0.6923	Remote Similarity	NPC476451
0.691	Remote Similarity	NPC256828
0.6906	Remote Similarity	NPC283152
0.6898	Remote Similarity	NPC3715
0.6885	Remote Similarity	NPC144114
0.6884	Remote Similarity	NPC26679
0.6878	Remote Similarity	NPC307963
0.6878	Remote Similarity	NPC470503
0.6872	Remote Similarity	NPC476581
0.6872	Remote Similarity	NPC16452
0.6872	Remote Similarity	NPC36229
0.6864	Remote Similarity	NPC302159
0.686	Remote Similarity	NPC110151
0.6854	Remote Similarity	NPC477861
0.6845	Remote Similarity	NPC471598
0.6845	Remote Similarity	NPC471323
0.6839	Remote Similarity	NPC213308
0.6837	Remote Similarity	NPC475288
0.6833	Remote Similarity	NPC313791

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 NPC48192 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	990
0.2-0.3	618
0.3-0.4	2030
0.4-0.5	2845
0.5-0.6	1850
0.6-0.7	486
0.7-0.8	43
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
0.8121	Intermediate Similarity	NPD425	Approved
0.8121	Intermediate Similarity	NPD424	Approved
0.8054	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD926	Approved
0.7844	Intermediate Similarity	NPD925	Approved
0.761	Intermediate Similarity	NPD1649	Discontinued
0.7605	Intermediate Similarity	NPD5255	Approved
0.7572	Intermediate Similarity	NPD9690	Approved
0.756	Intermediate Similarity	NPD9705	Discontinued
0.756	Intermediate Similarity	NPD112	Approved
0.7527	Intermediate Similarity	NPD9695	Approved
0.7515	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD715	Phase 3
0.7442	Intermediate Similarity	NPD2781	Approved
0.7442	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD2782	Approved
0.7427	Intermediate Similarity	NPD2780	Approved
0.7405	Intermediate Similarity	NPD1622	Discontinued
0.7333	Intermediate Similarity	NPD1661	Suspended
0.7283	Intermediate Similarity	NPD6569	Phase 2
0.7267	Intermediate Similarity	NPD863	Approved
0.7267	Intermediate Similarity	NPD861	Approved
0.7267	Intermediate Similarity	NPD862	Approved
0.7256	Intermediate Similarity	NPD3813	Approved
0.7229	Intermediate Similarity	NPD4702	Approved
0.7229	Intermediate Similarity	NPD4703	Approved
0.7202	Intermediate Similarity	NPD2882	Phase 1
0.7196	Intermediate Similarity	NPD1739	Approved
0.7196	Intermediate Similarity	NPD1740	Approved
0.7195	Intermediate Similarity	NPD3717	Discontinued
0.7193	Intermediate Similarity	NPD3433	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD9284	Approved
0.7175	Intermediate Similarity	NPD158	Discontinued
0.7174	Intermediate Similarity	NPD4081	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD2123	Phase 3
0.7152	Intermediate Similarity	NPD8823	Approved
0.7152	Intermediate Similarity	NPD1352	Discontinued
0.7151	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4036	Approved
0.7135	Intermediate Similarity	NPD4035	Approved
0.7135	Intermediate Similarity	NPD4033	Approved
0.7135	Intermediate Similarity	NPD9383	Approved
0.7135	Intermediate Similarity	NPD31	Approved
0.7135	Intermediate Similarity	NPD4037	Approved
0.7135	Intermediate Similarity	NPD4122	Approved
0.7135	Intermediate Similarity	NPD32	Approved
0.7135	Intermediate Similarity	NPD9382	Approved
0.7135	Intermediate Similarity	NPD5100	Phase 3
0.7135	Intermediate Similarity	NPD4034	Approved
0.7135	Intermediate Similarity	NPD4038	Approved
0.7135	Intermediate Similarity	NPD4039	Approved
0.7127	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD3931	Approved
0.712	Intermediate Similarity	NPD3928	Approved
0.7105	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD4375	Approved
0.7104	Intermediate Similarity	NPD706	Phase 1
0.7099	Intermediate Similarity	NPD9506	Approved
0.7097	Intermediate Similarity	NPD4372	Phase 1
0.7095	Intermediate Similarity	NPD6159	Phase 2
0.7083	Intermediate Similarity	NPD3575	Approved
0.7083	Intermediate Similarity	NPD3576	Approved
0.7081	Intermediate Similarity	NPD1213	Phase 3
0.7081	Intermediate Similarity	NPD3321	Discontinued
0.7072	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD4203	Approved
0.7072	Intermediate Similarity	NPD7867	Phase 1
0.7072	Intermediate Similarity	NPD4204	Approved
0.707	Intermediate Similarity	NPD9080	Approved
0.7066	Intermediate Similarity	NPD7469	Discontinued
0.7065	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD1034	Phase 3
0.7062	Intermediate Similarity	NPD1197	Approved
0.7056	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD9076	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4795	Phase 2
0.7043	Intermediate Similarity	NPD2334	Discontinued
0.7037	Intermediate Similarity	NPD7948	Phase 1
0.7035	Intermediate Similarity	NPD7112	Discontinued
0.7025	Intermediate Similarity	NPD5352	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD1599	Approved
0.7021	Intermediate Similarity	NPD3396	Approved
0.7021	Intermediate Similarity	NPD3395	Approved
0.701	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD9689	Approved
0.6995	Remote Similarity	NPD1856	Discontinued
0.6984	Remote Similarity	NPD3477	Phase 2
0.6984	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5065	Approved
0.6974	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3330	Phase 1
0.6968	Remote Similarity	NPD802	Phase 2
0.6957	Remote Similarity	NPD3082	Discontinued
0.6957	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2762	Phase 2
0.6949	Remote Similarity	NPD5862	Discovery
0.6947	Remote Similarity	NPD2952	Discontinued
0.6936	Remote Similarity	NPD2581	Approved
0.6936	Remote Similarity	NPD2582	Approved
0.6927	Remote Similarity	NPD484	Approved
0.6927	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5320	Approved
0.691	Remote Similarity	NPD5319	Approved
0.6901	Remote Similarity	NPD6158	Phase 2
0.6901	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD5316	Approved
0.6898	Remote Similarity	NPD3439	Approved
0.6889	Remote Similarity	NPD6492	Phase 2
0.6885	Remote Similarity	NPD3386	Phase 2
0.6879	Remote Similarity	NPD1274	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4551	Phase 2
0.6878	Remote Similarity	NPD1038	Approved
0.6875	Remote Similarity	NPD5925	Phase 1
0.6868	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD4889	Approved
0.6862	Remote Similarity	NPD6022	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2959	Phase 3
0.6857	Remote Similarity	NPD687	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD6975	Discontinued
0.6848	Remote Similarity	NPD852	Discontinued
0.6845	Remote Similarity	NPD4021	Phase 2
0.6842	Remote Similarity	NPD1602	Discontinued
0.6839	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5530	Phase 1
0.6828	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6887	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4886	Phase 2
0.6816	Remote Similarity	NPD565	Phase 2
0.6811	Remote Similarity	NPD6178	Phase 3
0.6809	Remote Similarity	NPD8063	Discontinued
0.6802	Remote Similarity	NPD9595	Approved
0.6802	Remote Similarity	NPD9596	Approved
0.68	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD2383	Phase 1
0.6788	Remote Similarity	NPD9688	Approved
0.6788	Remote Similarity	NPD9687	Approved
0.6774	Remote Similarity	NPD6227	Discontinued
0.6771	Remote Similarity	NPD1229	Phase 2
0.6768	Remote Similarity	NPD2816	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD2751	Phase 1
0.675	Remote Similarity	NPD4131	Phase 3
0.6749	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD2757	Phase 2
0.6742	Remote Similarity	NPD2720	Phase 1
0.6742	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD3924	Approved
0.6737	Remote Similarity	NPD3922	Approved
0.6737	Remote Similarity	NPD3923	Approved
0.6737	Remote Similarity	NPD3921	Approved
0.6736	Remote Similarity	NPD5885	Approved
0.6731	Remote Similarity	NPD7603	Discontinued
0.6728	Remote Similarity	NPD9207	Approved
0.6728	Remote Similarity	NPD9206	Approved
0.6723	Remote Similarity	NPD1685	Approved
0.6723	Remote Similarity	NPD1684	Approved
0.6721	Remote Similarity	NPD1032	Phase 2
0.6703	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD8408	Discontinued
0.6702	Remote Similarity	NPD4529	Approved
0.6702	Remote Similarity	NPD6361	Phase 2
0.6702	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4528	Approved
0.6702	Remote Similarity	NPD4526	Approved
0.6701	Remote Similarity	NPD1915	Phase 1
0.6701	Remote Similarity	NPD3500	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD459	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD4699	Discontinued
0.6683	Remote Similarity	NPD6500	Approved
0.6683	Remote Similarity	NPD6501	Approved
0.6667	Remote Similarity	NPD3570	Phase 2
0.6667	Remote Similarity	NPD2380	Approved
0.6667	Remote Similarity	NPD4945	Discontinued
0.6667	Remote Similarity	NPD8356	Approved
0.6667	Remote Similarity	NPD9582	Phase 3
0.6667	Remote Similarity	NPD2381	Approved
0.6667	Remote Similarity	NPD2382	Approved
0.6667	Remote Similarity	NPD2391	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5601	Phase 2
0.6651	Remote Similarity	NPD1603	Discontinued
0.665	Remote Similarity	NPD4044	Discontinued
0.6649	Remote Similarity	NPD2599	Approved
0.6649	Remote Similarity	NPD2601	Approved
0.6649	Remote Similarity	NPD2600	Approved
0.6648	Remote Similarity	NPD9574	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD966	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2896	Discontinued
0.6647	Remote Similarity	NPD1918	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD9392	Approved
0.6645	Remote Similarity	NPD9396	Approved
0.6644	Remote Similarity	NPD9099	Clinical (unspecified phase)

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