NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	229.09
Volume:	231.111
LogP:	1.335
LogD:	1.525
LogS:	-1.941
# Rotatable Bonds:	3
TPSA:	78.1
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.859
Synthetic Accessibility Score:	2.086
Fsp3:	0.083
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:	-4.687
MDCK Permeability:	1.2377984603517689e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.785

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.469
Plasma Protein Binding (PPB):	87.27645111083984%
Volume Distribution (VD):	0.955
Pgp-substrate:	15.759095191955566%

ADMET: Metabolism

CYP1A2-inhibitor:	0.875
CYP1A2-substrate:	0.773
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.719
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.788
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.142

ADMET: Excretion

Clearance (CL):	6.234
Half-life (T1/2):	0.205

ADMET: Toxicity

hERG Blockers:	0.135
Human Hepatotoxicity (H-HT):	0.378
Drug-inuced Liver Injury (DILI):	0.951
AMES Toxicity:	0.351
Rat Oral Acute Toxicity:	0.367
Maximum Recommended Daily Dose:	0.226
Skin Sensitization:	0.063
Carcinogencity:	0.049
Eye Corrosion:	0.004
Eye Irritation:	0.586
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC161887

Natural Product ID:	NPC161887
*Common Name:**	Caerulomycinamide
IUPAC Name:	4-methoxy-6-pyridin-2-ylpyridine-2-carboxamide
Synonyms:	Caerulomycinamide
Standard InCHIKey:	GGOIWQPOOKIKRW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H11N3O2/c1-17-8-6-10(9-4-2-3-5-14-9)15-11(7-8)12(13)16/h2-7H,1H3,(H2,13,16)
SMILES:	COc1cc(nc(c1)c1ccccn1)C(=N)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1823039
PubChem CID:	56679736
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
MIC	1

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[469621]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000.0	nM	PMID[469621]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>=	100000.0	nM	PMID[469621]

☑ 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 NPC161887 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	490
0.1-0.2	7595
0.2-0.3	9947
0.3-0.4	13868
0.4-0.5	6530
0.5-0.6	3128
0.6-0.7	975
0.7-0.8	149
0.8-0.85	4
0.85-0.9	3
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9755	High Similarity	NPC266551
0.9755	High Similarity	NPC219963
0.9325	High Similarity	NPC14651
0.9325	High Similarity	NPC121658
0.9264	High Similarity	NPC476518
0.9191	High Similarity	NPC226202
0.9118	High Similarity	NPC20249
0.9036	High Similarity	NPC111624
0.9012	High Similarity	NPC25899
0.8841	High Similarity	NPC48192
0.8686	High Similarity	NPC206251
0.8686	High Similarity	NPC74382
0.8427	Intermediate Similarity	NPC224327
0.838	Intermediate Similarity	NPC134079
0.8306	Intermediate Similarity	NPC267928
0.827	Intermediate Similarity	NPC19872
0.8142	Intermediate Similarity	NPC84853
0.8021	Intermediate Similarity	NPC187558
0.7965	Intermediate Similarity	NPC177404
0.7959	Intermediate Similarity	NPC8022
0.7959	Intermediate Similarity	NPC470799
0.7929	Intermediate Similarity	NPC213530
0.7929	Intermediate Similarity	NPC193267
0.7876	Intermediate Similarity	NPC287208
0.7853	Intermediate Similarity	NPC245816
0.7853	Intermediate Similarity	NPC476138
0.7842	Intermediate Similarity	NPC232727
0.7835	Intermediate Similarity	NPC185782
0.7789	Intermediate Similarity	NPC315957
0.7789	Intermediate Similarity	NPC176538
0.772	Intermediate Similarity	NPC165349
0.772	Intermediate Similarity	NPC274291
0.772	Intermediate Similarity	NPC118832
0.772	Intermediate Similarity	NPC264166
0.772	Intermediate Similarity	NPC47059
0.772	Intermediate Similarity	NPC329708
0.7716	Intermediate Similarity	NPC26679
0.7704	Intermediate Similarity	NPC123976
0.7704	Intermediate Similarity	NPC167860
0.7701	Intermediate Similarity	NPC285635
0.7684	Intermediate Similarity	NPC1527
0.7673	Intermediate Similarity	NPC310118
0.7633	Intermediate Similarity	NPC220523
0.7586	Intermediate Similarity	NPC60621
0.7563	Intermediate Similarity	NPC174672
0.7552	Intermediate Similarity	NPC18487
0.7552	Intermediate Similarity	NPC476167
0.754	Intermediate Similarity	NPC110741
0.7538	Intermediate Similarity	NPC470500
0.7536	Intermediate Similarity	NPC314954
0.7514	Intermediate Similarity	NPC26872
0.7514	Intermediate Similarity	NPC284678
0.7513	Intermediate Similarity	NPC121772
0.75	Intermediate Similarity	NPC258773
0.75	Intermediate Similarity	NPC476287
0.75	Intermediate Similarity	NPC192315
0.7488	Intermediate Similarity	NPC110151
0.7475	Intermediate Similarity	NPC174758
0.7474	Intermediate Similarity	NPC307963
0.7473	Intermediate Similarity	NPC42591
0.7459	Intermediate Similarity	NPC48938
0.7446	Intermediate Similarity	NPC222592
0.7446	Intermediate Similarity	NPC168486
0.7444	Intermediate Similarity	NPC314940
0.7444	Intermediate Similarity	NPC473764
0.7437	Intermediate Similarity	NPC5145
0.7429	Intermediate Similarity	NPC101543
0.7429	Intermediate Similarity	NPC469554
0.7424	Intermediate Similarity	NPC82548
0.7421	Intermediate Similarity	NPC324149
0.7419	Intermediate Similarity	NPC284559
0.7409	Intermediate Similarity	NPC239954
0.7405	Intermediate Similarity	NPC118776
0.7398	Intermediate Similarity	NPC475774
0.7396	Intermediate Similarity	NPC251090
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
0.7363	Intermediate Similarity	NPC112206
0.7363	Intermediate Similarity	NPC202605
0.736	Intermediate Similarity	NPC124542
0.736	Intermediate Similarity	NPC79911
0.736	Intermediate Similarity	NPC59779
0.736	Intermediate Similarity	NPC471177
0.7354	Intermediate Similarity	NPC296527
0.7353	Intermediate Similarity	NPC470404
0.7353	Intermediate Similarity	NPC470403
0.7353	Intermediate Similarity	NPC470394
0.7327	Intermediate Similarity	NPC469592
0.7327	Intermediate Similarity	NPC471080
0.732	Intermediate Similarity	NPC212213
0.7318	Intermediate Similarity	NPC263439
0.7318	Intermediate Similarity	NPC118511
0.7316	Intermediate Similarity	NPC76748
0.7314	Intermediate Similarity	NPC36168
0.7308	Intermediate Similarity	NPC252590
0.7306	Intermediate Similarity	NPC13880
0.7305	Intermediate Similarity	NPC328029
0.7303	Intermediate Similarity	NPC322976
0.7303	Intermediate Similarity	NPC120798
0.7303	Intermediate Similarity	NPC324203
0.7303	Intermediate Similarity	NPC63338
0.7277	Intermediate Similarity	NPC92111
0.7273	Intermediate Similarity	NPC285558
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
0.7255	Intermediate Similarity	NPC274982
0.7255	Intermediate Similarity	NPC288349
0.7243	Intermediate Similarity	NPC295228
0.7243	Intermediate Similarity	NPC283152
0.7236	Intermediate Similarity	NPC470164
0.7236	Intermediate Similarity	NPC323345
0.7233	Intermediate Similarity	NPC292958
0.7231	Intermediate Similarity	NPC168911
0.7222	Intermediate Similarity	NPC223427
0.7222	Intermediate Similarity	NPC200836
0.7217	Intermediate Similarity	NPC260434
0.7211	Intermediate Similarity	NPC66083
0.72	Intermediate Similarity	NPC193238
0.7196	Intermediate Similarity	NPC182222
0.7194	Intermediate Similarity	NPC476578
0.7194	Intermediate Similarity	NPC476582
0.7194	Intermediate Similarity	NPC4071
0.7189	Intermediate Similarity	NPC288943
0.7186	Intermediate Similarity	NPC475070
0.7184	Intermediate Similarity	NPC469594
0.7184	Intermediate Similarity	NPC173080
0.7177	Intermediate Similarity	NPC122436
0.7175	Intermediate Similarity	NPC63562
0.7157	Intermediate Similarity	NPC162530
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	NPC318935
0.7127	Intermediate Similarity	NPC473057
0.7127	Intermediate Similarity	NPC97367
0.7121	Intermediate Similarity	NPC31930
0.712	Intermediate Similarity	NPC46580
0.7113	Intermediate Similarity	NPC289786
0.7112	Intermediate Similarity	NPC42979
0.7108	Intermediate Similarity	NPC316981
0.7105	Intermediate Similarity	NPC314002
0.7097	Intermediate Similarity	NPC203754
0.7097	Intermediate Similarity	NPC224764
0.7097	Intermediate Similarity	NPC150048
0.7095	Intermediate Similarity	NPC132680
0.7095	Intermediate Similarity	NPC269919
0.7094	Intermediate Similarity	NPC11464
0.7091	Intermediate Similarity	NPC472434
0.7086	Intermediate Similarity	NPC257142
0.7085	Intermediate Similarity	NPC211813
0.7079	Intermediate Similarity	NPC477111
0.7073	Intermediate Similarity	NPC266931
0.707	Intermediate Similarity	NPC141053
0.7065	Intermediate Similarity	NPC256828
0.7062	Intermediate Similarity	NPC153769
0.7062	Intermediate Similarity	NPC284348
0.7053	Intermediate Similarity	NPC204717
0.7043	Intermediate Similarity	NPC95898
0.7026	Intermediate Similarity	NPC329541
0.7024	Intermediate Similarity	NPC202768
0.7024	Intermediate Similarity	NPC296482
0.7024	Intermediate Similarity	NPC53069
0.7012	Intermediate Similarity	NPC151489
0.7005	Intermediate Similarity	NPC477110
0.7	Intermediate Similarity	NPC220765
0.7	Intermediate Similarity	NPC116573
0.6995	Remote Similarity	NPC475910
0.6995	Remote Similarity	NPC308392
0.6985	Remote Similarity	NPC234197
0.698	Remote Similarity	NPC471736
0.698	Remote Similarity	NPC477113
0.6979	Remote Similarity	NPC314573
0.6979	Remote Similarity	NPC171171
0.6976	Remote Similarity	NPC208284
0.6971	Remote Similarity	NPC304926
0.6971	Remote Similarity	NPC476041
0.6968	Remote Similarity	NPC96890
0.6968	Remote Similarity	NPC184964
0.6967	Remote Similarity	NPC216612
0.6967	Remote Similarity	NPC470501
0.6963	Remote Similarity	NPC84478
0.6961	Remote Similarity	NPC84508
0.6949	Remote Similarity	NPC288445
0.6946	Remote Similarity	NPC313189
0.6942	Remote Similarity	NPC171409
0.6942	Remote Similarity	NPC96405
0.694	Remote Similarity	NPC211187
0.6938	Remote Similarity	NPC314270
0.6931	Remote Similarity	NPC472259
0.6927	Remote Similarity	NPC290689

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 NPC161887 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	826
0.2-0.3	743
0.3-0.4	1573
0.4-0.5	2812
0.5-0.6	2102
0.6-0.7	759
0.7-0.8	102
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
0.7953	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7796	Intermediate Similarity	NPD6569	Phase 2
0.7789	Intermediate Similarity	NPD1739	Approved
0.7789	Intermediate Similarity	NPD1740	Approved
0.774	Intermediate Similarity	NPD565	Phase 2
0.7727	Intermediate Similarity	NPD424	Approved
0.7727	Intermediate Similarity	NPD425	Approved
0.772	Intermediate Similarity	NPD4038	Approved
0.772	Intermediate Similarity	NPD32	Approved
0.772	Intermediate Similarity	NPD4033	Approved
0.772	Intermediate Similarity	NPD4122	Approved
0.772	Intermediate Similarity	NPD4039	Approved
0.772	Intermediate Similarity	NPD4036	Approved
0.772	Intermediate Similarity	NPD4035	Approved
0.772	Intermediate Similarity	NPD4037	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)
0.768	Intermediate Similarity	NPD1620	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
0.7632	Intermediate Similarity	NPD1622	Discontinued
0.7629	Intermediate Similarity	NPD4795	Phase 2
0.7596	Intermediate Similarity	NPD4204	Approved
0.7596	Intermediate Similarity	NPD4203	Approved
0.7576	Intermediate Similarity	NPD4131	Phase 3
0.7542	Intermediate Similarity	NPD5320	Approved
0.7542	Intermediate Similarity	NPD5319	Approved
0.7539	Intermediate Similarity	NPD2952	Discontinued
0.7527	Intermediate Similarity	NPD4375	Approved
0.75	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD9574	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD1038	Approved
0.7457	Intermediate Similarity	NPD9596	Approved
0.7457	Intermediate Similarity	NPD9595	Approved
0.7443	Intermediate Similarity	NPD5255	Approved
0.7435	Intermediate Similarity	NPD3396	Approved
0.7435	Intermediate Similarity	NPD3395	Approved
0.7423	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD3570	Phase 2
0.7374	Intermediate Similarity	NPD1392	Approved
0.7371	Intermediate Similarity	NPD5999	Phase 2
0.7354	Intermediate Similarity	NPD4021	Phase 2
0.7344	Intermediate Similarity	NPD1602	Discontinued
0.7326	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD862	Approved
0.7318	Intermediate Similarity	NPD863	Approved
0.7318	Intermediate Similarity	NPD861	Approved
0.7312	Intermediate Similarity	NPD3386	Phase 2
0.7303	Intermediate Similarity	NPD112	Approved
0.7303	Intermediate Similarity	NPD9705	Discontinued
0.7303	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD2582	Approved
0.7288	Intermediate Similarity	NPD2581	Approved
0.7282	Intermediate Similarity	NPD4548	Discontinued
0.7278	Intermediate Similarity	NPD926	Approved
0.7278	Intermediate Similarity	NPD925	Approved
0.725	Intermediate Similarity	NPD2816	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD3039	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD4071	Approved
0.7243	Intermediate Similarity	NPD4072	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	NPD9690	Approved
0.7207	Intermediate Similarity	NPD1418	Phase 2
0.7202	Intermediate Similarity	NPD4551	Phase 2
0.7196	Intermediate Similarity	NPD4889	Approved
0.7195	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD2958	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5640	Discontinued
0.7188	Intermediate Similarity	NPD2334	Discontinued
0.7179	Intermediate Similarity	NPD2959	Phase 3
0.717	Intermediate Similarity	NPD3302	Clinical (unspecified phase)
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
0.7143	Intermediate Similarity	NPD5067	Phase 2
0.7143	Intermediate Similarity	NPD1334	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5066	Phase 2
0.7135	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8063	Discontinued
0.7135	Intermediate Similarity	NPD1649	Discontinued
0.712	Intermediate Similarity	NPD9548	Phase 2
0.712	Intermediate Similarity	NPD6393	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD9382	Approved
0.7095	Intermediate Similarity	NPD9383	Approved
0.7092	Intermediate Similarity	NPD1229	Phase 2
0.7087	Intermediate Similarity	NPD5612	Discontinued
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
0.707	Intermediate Similarity	NPD7558	Phase 2
0.7068	Intermediate Similarity	NPD5256	Discontinued
0.7068	Intermediate Similarity	NPD706	Phase 1
0.7064	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3321	Discontinued
0.7039	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD1273	Discontinued
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
0.7026	Intermediate Similarity	NPD9695	Approved
0.7024	Intermediate Similarity	NPD3816	Phase 1
0.7024	Intermediate Similarity	NPD7069	Discontinued
0.7024	Intermediate Similarity	NPD3815	Phase 1
0.702	Intermediate Similarity	NPD1768	Approved
0.7016	Intermediate Similarity	NPD3082	Discontinued
0.701	Intermediate Similarity	NPD4148	Approved
0.7006	Intermediate Similarity	NPD715	Phase 3
0.7005	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD5644	Phase 1
0.6995	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6494	Phase 2
0.699	Remote Similarity	NPD5944	Phase 1
0.699	Remote Similarity	NPD1951	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5945	Phase 1
0.699	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4702	Approved
0.6989	Remote Similarity	NPD4703	Approved
0.6979	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4921	Phase 3
0.6979	Remote Similarity	NPD4919	Phase 3
0.6976	Remote Similarity	NPD4502	Phase 2
0.6976	Remote Similarity	NPD949	Phase 1
0.6963	Remote Similarity	NPD3569	Discontinued
0.6961	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3717	Discontinued
0.6952	Remote Similarity	NPD6856	Discontinued
0.6952	Remote Similarity	NPD158	Discontinued
0.6949	Remote Similarity	NPD3575	Approved
0.6949	Remote Similarity	NPD3576	Approved
0.6948	Remote Similarity	NPD1603	Discontinued
0.6946	Remote Similarity	NPD7222	Phase 2
0.6942	Remote Similarity	NPD3330	Phase 1
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	NPD4429	Discontinued
0.6938	Remote Similarity	NPD6568	Discontinued
0.6937	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3825	Phase 3
0.6934	Remote Similarity	NPD6306	Phase 2
0.693	Remote Similarity	NPD8512	Phase 3
0.6919	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2781	Approved
0.6916	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5529	Phase 1
0.6912	Remote Similarity	NPD6366	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5528	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3402	Phase 1
0.6905	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD6590	Discontinued
0.6904	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD2782	Approved
0.6902	Remote Similarity	NPD2780	Approved
0.6898	Remote Similarity	NPD2062	Phase 2
0.6898	Remote Similarity	NPD2076	Approved
0.6898	Remote Similarity	NPD2077	Approved
0.6897	Remote Similarity	NPD5601	Phase 2
0.6897	Remote Similarity	NPD3003	Approved
0.6895	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD3939	Suspended
0.6892	Remote Similarity	NPD7067	Approved
0.6892	Remote Similarity	NPD7068	Approved
0.6889	Remote Similarity	NPD5482	Discontinued
0.6888	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7221	Approved
0.6887	Remote Similarity	NPD7219	Approved
0.6881	Remote Similarity	NPD2757	Phase 2
0.6878	Remote Similarity	NPD6159	Phase 2
0.6878	Remote Similarity	NPD4437	Phase 3
0.6872	Remote Similarity	NPD8479	Phase 2
0.6868	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5259	Phase 3
0.6866	Remote Similarity	NPD1621	Discontinued
0.6859	Remote Similarity	NPD7867	Phase 1
0.6857	Remote Similarity	NPD5948	Phase 2
0.6856	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD3397	Phase 2

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