NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	216.09
Volume:	222.751
LogP:	1.459
LogD:	1.685
LogS:	-1.42
# Rotatable Bonds:	3
TPSA:	55.24
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.847
Synthetic Accessibility Score:	2.126
Fsp3:	0.167
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:	-4.605
MDCK Permeability:	1.5267763956217095e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.099

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.573
Plasma Protein Binding (PPB):	79.09142303466797%
Volume Distribution (VD):	0.991
Pgp-substrate:	15.923055648803711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.878
CYP1A2-substrate:	0.613
CYP2C19-inhibitor:	0.06
CYP2C19-substrate:	0.258
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.642
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.855
CYP3A4-inhibitor:	0.036
CYP3A4-substrate:	0.274

ADMET: Excretion

Clearance (CL):	6.995
Half-life (T1/2):	0.789

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.169
Drug-inuced Liver Injury (DILI):	0.794
AMES Toxicity:	0.393
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.256
Skin Sensitization:	0.276
Carcinogencity:	0.048
Eye Corrosion:	0.007
Eye Irritation:	0.949
Respiratory Toxicity:	0.899

Download Data

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

Natural Product: NPC219963

Natural Product ID:	NPC219963
*Common Name:**	Caerulomycin F
IUPAC Name:	(4-methoxy-6-pyridin-2-ylpyridin-2-yl)methanol
Synonyms:	Caerulomycin F
Standard InCHIKey:	PELLYAWYWQZSJV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H12N2O2/c1-16-10-6-9(8-15)14-12(7-10)11-4-2-3-5-13-11/h2-7,15H,8H2,1H3
SMILES:	COc1cc(CO)nc(c1)c1ccccn1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1823031
PubChem CID:	25192237
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	>	50000.0	nM	PMID[517617]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[517617]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	15700.0	nM	PMID[517617]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000.0	nM	PMID[517617]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>=	100000.0	nM	PMID[517617]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>=	100000.0	nM	PMID[517617]
NPT720	Organism	Enterobacter aerogenes	Enterobacter aerogenes	MIC	>=	100000.0	nM	PMID[517617]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>=	100000.0	nM	PMID[517617]

☑ 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 NPC219963 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	448
0.1-0.2	5709
0.2-0.3	11807
0.3-0.4	12511
0.4-0.5	8126
0.5-0.6	3022
0.6-0.7	907
0.7-0.8	150
0.8-0.85	5
0.85-0.9	4
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	NPC161887
0.9415	High Similarity	NPC226202
0.9325	High Similarity	NPC14651
0.9325	High Similarity	NPC121658
0.9264	High Similarity	NPC476518
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
0.8075	Intermediate Similarity	NPC19872
0.7965	Intermediate Similarity	NPC177404
0.7946	Intermediate Similarity	NPC84853
0.7906	Intermediate Similarity	NPC264166
0.7906	Intermediate Similarity	NPC274291
0.7906	Intermediate Similarity	NPC329708
0.7906	Intermediate Similarity	NPC165349
0.7906	Intermediate Similarity	NPC47059
0.7906	Intermediate Similarity	NPC118832
0.7876	Intermediate Similarity	NPC287208
0.7844	Intermediate Similarity	NPC220523
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
0.7701	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
0.7634	Intermediate Similarity	NPC110741
0.7626	Intermediate Similarity	NPC26679
0.7604	Intermediate Similarity	NPC315957
0.7604	Intermediate Similarity	NPC176538
0.7563	Intermediate Similarity	NPC174672
0.7563	Intermediate Similarity	NPC469589
0.756	Intermediate Similarity	NPC470404
0.756	Intermediate Similarity	NPC470403
0.756	Intermediate Similarity	NPC470394
0.7538	Intermediate Similarity	NPC470500
0.7525	Intermediate Similarity	NPC123976
0.7525	Intermediate Similarity	NPC167860
0.7514	Intermediate Similarity	NPC26872
0.7514	Intermediate Similarity	NPC263439
0.75	Intermediate Similarity	NPC118776
0.75	Intermediate Similarity	NPC258773
0.75	Intermediate Similarity	NPC310118
0.7488	Intermediate Similarity	NPC110151
0.7475	Intermediate Similarity	NPC174758
0.7473	Intermediate Similarity	NPC42591
0.7471	Intermediate Similarity	NPC470395
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
0.7424	Intermediate Similarity	NPC82548
0.7419	Intermediate Similarity	NPC284559
0.7419	Intermediate Similarity	NPC284678
0.7415	Intermediate Similarity	NPC60621
0.7409	Intermediate Similarity	NPC239954
0.7398	Intermediate Similarity	NPC475774
0.7396	Intermediate Similarity	NPC251090
0.7386	Intermediate Similarity	NPC26850
0.7382	Intermediate Similarity	NPC198673
0.7374	Intermediate Similarity	NPC471178
0.7371	Intermediate Similarity	NPC287437
0.7371	Intermediate Similarity	NPC63562
0.7371	Intermediate Similarity	NPC18487
0.7371	Intermediate Similarity	NPC476167
0.7368	Intermediate Similarity	NPC314954
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
0.7353	Intermediate Similarity	NPC197141
0.7346	Intermediate Similarity	NPC469554
0.7337	Intermediate Similarity	NPC283152
0.7333	Intermediate Similarity	NPC121772
0.7327	Intermediate Similarity	NPC469592
0.7327	Intermediate Similarity	NPC471080
0.7327	Intermediate Similarity	NPC476287
0.7323	Intermediate Similarity	NPC472111
0.732	Intermediate Similarity	NPC192315
0.732	Intermediate Similarity	NPC212213
0.7318	Intermediate Similarity	NPC118511
0.7314	Intermediate Similarity	NPC36168
0.7308	Intermediate Similarity	NPC252590
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
0.7292	Intermediate Similarity	NPC307963
0.7288	Intermediate Similarity	NPC132680
0.7288	Intermediate Similarity	NPC269919
0.7283	Intermediate Similarity	NPC203754
0.7283	Intermediate Similarity	NPC150048
0.7273	Intermediate Similarity	NPC36229
0.7273	Intermediate Similarity	NPC174421
0.7273	Intermediate Similarity	NPC476581
0.7273	Intermediate Similarity	NPC16452
0.7268	Intermediate Similarity	NPC224928
0.7264	Intermediate Similarity	NPC101543
0.7257	Intermediate Similarity	NPC153769
0.7257	Intermediate Similarity	NPC284348
0.7255	Intermediate Similarity	NPC274982
0.7255	Intermediate Similarity	NPC288349
0.7248	Intermediate Similarity	NPC472434
0.724	Intermediate Similarity	NPC324149
0.7236	Intermediate Similarity	NPC470164
0.7236	Intermediate Similarity	NPC323345
0.7234	Intermediate Similarity	NPC62069
0.7231	Intermediate Similarity	NPC168911
0.7222	Intermediate Similarity	NPC200836
0.7211	Intermediate Similarity	NPC66083
0.7202	Intermediate Similarity	NPC289786
0.72	Intermediate Similarity	NPC193238
0.7194	Intermediate Similarity	NPC476578
0.7194	Intermediate Similarity	NPC476582
0.7194	Intermediate Similarity	NPC4071
0.7189	Intermediate Similarity	NPC288943
0.7184	Intermediate Similarity	NPC469594
0.7184	Intermediate Similarity	NPC173080
0.7173	Intermediate Similarity	NPC296527
0.7164	Intermediate Similarity	NPC308392
0.7151	Intermediate Similarity	NPC84508
0.715	Intermediate Similarity	NPC133140
0.715	Intermediate Similarity	NPC195268
0.715	Intermediate Similarity	NPC471736
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
0.7101	Intermediate Similarity	NPC314270
0.71	Intermediate Similarity	NPC285558
0.7098	Intermediate Similarity	NPC92111
0.7086	Intermediate Similarity	NPC257142
0.7085	Intermediate Similarity	NPC211813
0.7083	Intermediate Similarity	NPC295228
0.707	Intermediate Similarity	NPC141053
0.7067	Intermediate Similarity	NPC472435
0.7067	Intermediate Similarity	NPC292958
0.7056	Intermediate Similarity	NPC260434
0.705	Intermediate Similarity	NPC223427
0.7043	Intermediate Similarity	NPC95898
0.7037	Intermediate Similarity	NPC182222
0.7033	Intermediate Similarity	NPC211187
0.7032	Intermediate Similarity	NPC99891
0.7029	Intermediate Similarity	NPC161292
0.7026	Intermediate Similarity	NPC279401
0.7026	Intermediate Similarity	NPC329541
0.7026	Intermediate Similarity	NPC79293
0.7024	Intermediate Similarity	NPC202768
0.7024	Intermediate Similarity	NPC296482
0.7024	Intermediate Similarity	NPC53069
0.7015	Intermediate Similarity	NPC475070
0.7014	Intermediate Similarity	NPC122436
0.7012	Intermediate Similarity	NPC151489
0.7011	Intermediate Similarity	NPC471323
0.7005	Intermediate Similarity	NPC477110
0.7	Intermediate Similarity	NPC116573
0.6995	Remote Similarity	NPC475910
0.699	Remote Similarity	NPC162530
0.6985	Remote Similarity	NPC234197
0.6979	Remote Similarity	NPC314573
0.6974	Remote Similarity	NPC472436
0.6973	Remote Similarity	NPC256828
0.6967	Remote Similarity	NPC216612
0.6967	Remote Similarity	NPC470501
0.6963	Remote Similarity	NPC320394
0.6959	Remote Similarity	NPC3715
0.6954	Remote Similarity	NPC473053
0.6947	Remote Similarity	NPC470474
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
0.6931	Remote Similarity	NPC42979
0.6931	Remote Similarity	NPC472259
0.6927	Remote Similarity	NPC11464
0.6927	Remote Similarity	NPC290689
0.6927	Remote Similarity	NPC314002
0.6927	Remote Similarity	NPC85273
0.6919	Remote Similarity	NPC470502
0.6915	Remote Similarity	NPC194724

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 NPC219963 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	235
0.1-0.2	779
0.2-0.3	837
0.3-0.4	1620
0.4-0.5	2877
0.5-0.6	2035
0.6-0.7	662
0.7-0.8	105
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7906	Intermediate Similarity	NPD4034	Approved
0.7906	Intermediate Similarity	NPD4033	Approved
0.7906	Intermediate Similarity	NPD4036	Approved
0.7906	Intermediate Similarity	NPD4039	Approved
0.7906	Intermediate Similarity	NPD4035	Approved
0.7906	Intermediate Similarity	NPD4037	Approved
0.7906	Intermediate Similarity	NPD31	Approved
0.7906	Intermediate Similarity	NPD4122	Approved
0.7906	Intermediate Similarity	NPD4038	Approved
0.7906	Intermediate Similarity	NPD32	Approved
0.7892	Intermediate Similarity	NPD6569	Phase 2
0.7886	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD4081	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD1034	Phase 3
0.7766	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD3477	Phase 2
0.7746	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD1622	Discontinued
0.7701	Intermediate Similarity	NPD4372	Phase 1
0.7692	Intermediate Similarity	NPD4204	Approved
0.7692	Intermediate Similarity	NPD4203	Approved
0.764	Intermediate Similarity	NPD565	Phase 2
0.7635	Intermediate Similarity	NPD1856	Discontinued
0.7604	Intermediate Similarity	NPD1739	Approved
0.7604	Intermediate Similarity	NPD1740	Approved
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
0.7526	Intermediate Similarity	NPD3396	Approved
0.7526	Intermediate Similarity	NPD3395	Approved
0.7514	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD4131	Phase 3
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
0.7448	Intermediate Similarity	NPD2952	Discontinued
0.7443	Intermediate Similarity	NPD5255	Approved
0.74	Intermediate Similarity	NPD3570	Phase 2
0.7386	Intermediate Similarity	NPD2581	Approved
0.7386	Intermediate Similarity	NPD2582	Approved
0.7386	Intermediate Similarity	NPD9574	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD1392	Approved
0.733	Intermediate Similarity	NPD1274	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD863	Approved
0.7318	Intermediate Similarity	NPD861	Approved
0.7318	Intermediate Similarity	NPD862	Approved
0.7317	Intermediate Similarity	NPD6500	Approved
0.7317	Intermediate Similarity	NPD6501	Approved
0.7316	Intermediate Similarity	NPD8063	Discontinued
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
0.7303	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1038	Approved
0.7288	Intermediate Similarity	NPD9382	Approved
0.7288	Intermediate Similarity	NPD9383	Approved
0.7278	Intermediate Similarity	NPD926	Approved
0.7278	Intermediate Similarity	NPD925	Approved
0.7273	Intermediate Similarity	NPD5640	Discontinued
0.7263	Intermediate Similarity	NPD4021	Phase 2
0.7254	Intermediate Similarity	NPD1602	Discontinued
0.7249	Intermediate Similarity	NPD3039	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2314	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2772	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD5530	Phase 1
0.7228	Intermediate Similarity	NPD9690	Approved
0.7225	Intermediate Similarity	NPD3321	Discontinued
0.7213	Intermediate Similarity	NPD2123	Phase 3
0.7211	Intermediate Similarity	NPD6393	Clinical (unspecified phase)
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	NPD5999	Phase 2
0.719	Intermediate Similarity	NPD7675	Phase 3
0.719	Intermediate Similarity	NPD7426	Phase 1
0.719	Intermediate Similarity	NPD7674	Phase 3
0.719	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2334	Discontinued
0.7179	Intermediate Similarity	NPD1229	Phase 2
0.7179	Intermediate Similarity	NPD2959	Phase 3
0.7165	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4071	Approved
0.7151	Intermediate Similarity	NPD1032	Phase 2
0.7151	Intermediate Similarity	NPD4072	Approved
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	NPD5066	Phase 2
0.7135	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD1649	Discontinued
0.7122	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD9076	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1418	Phase 2
0.7108	Intermediate Similarity	NPD7069	Discontinued
0.7107	Intermediate Similarity	NPD4548	Discontinued
0.7107	Intermediate Similarity	NPD2958	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD4148	Approved
0.7089	Intermediate Similarity	NPD3302	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD2816	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD2599	Approved
0.7074	Intermediate Similarity	NPD2601	Approved
0.7074	Intermediate Similarity	NPD2600	Approved
0.7073	Intermediate Similarity	NPD5945	Phase 1
0.7073	Intermediate Similarity	NPD5944	Phase 1
0.707	Intermediate Similarity	NPD7558	Phase 2
0.7053	Intermediate Similarity	NPD1334	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7222	Phase 2
0.7027	Intermediate Similarity	NPD9548	Phase 2
0.7026	Intermediate Similarity	NPD4528	Approved
0.7026	Intermediate Similarity	NPD4526	Approved
0.7026	Intermediate Similarity	NPD9695	Approved
0.7026	Intermediate Similarity	NPD4529	Approved
0.7024	Intermediate Similarity	NPD3816	Phase 1
0.7024	Intermediate Similarity	NPD3815	Phase 1
0.702	Intermediate Similarity	NPD1768	Approved
0.7019	Intermediate Similarity	NPD6568	Discontinued
0.7016	Intermediate Similarity	NPD3082	Discontinued
0.7006	Intermediate Similarity	NPD715	Phase 3
0.7005	Intermediate Similarity	NPD8510	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5612	Discontinued
0.7	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6590	Discontinued
0.6989	Remote Similarity	NPD2076	Approved
0.6989	Remote Similarity	NPD2077	Approved
0.6986	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5256	Discontinued
0.6976	Remote Similarity	NPD3939	Suspended
0.6976	Remote Similarity	NPD4502	Phase 2
0.6974	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6856	Discontinued
0.6952	Remote Similarity	NPD158	Discontinued
0.6952	Remote Similarity	NPD8479	Phase 2
0.6949	Remote Similarity	NPD3575	Approved
0.6949	Remote Similarity	NPD3576	Approved
0.6948	Remote Similarity	NPD1273	Discontinued
0.6948	Remote Similarity	NPD1603	Discontinued
0.6943	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6361	Phase 2
0.6935	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.693	Remote Similarity	NPD8512	Phase 3
0.6919	Remote Similarity	NPD2781	Approved
0.6919	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5862	Discovery
0.6912	Remote Similarity	NPD6366	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6494	Phase 2
0.6912	Remote Similarity	NPD2739	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD2782	Approved
0.6902	Remote Similarity	NPD2780	Approved
0.6898	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5601	Phase 2
0.6897	Remote Similarity	NPD3003	Approved
0.6893	Remote Similarity	NPD2540	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD706	Phase 1
0.6891	Remote Similarity	NPD4919	Phase 3
0.6891	Remote Similarity	NPD4921	Phase 3
0.6886	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5513	Phase 2
0.6881	Remote Similarity	NPD2757	Phase 2
0.6878	Remote Similarity	NPD6159	Phase 2
0.6875	Remote Similarity	NPD3569	Discontinued
0.6872	Remote Similarity	NPD5316	Approved
0.6869	Remote Similarity	NPD1704	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1621	Discontinued
0.6864	Remote Similarity	NPD2414	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7452	Approved
0.6863	Remote Similarity	NPD2886	Approved
0.6863	Remote Similarity	NPD2885	Approved
0.6863	Remote Similarity	NPD7453	Approved
0.6861	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.686	Remote Similarity	NPD3330	Phase 1
0.685	Remote Similarity	NPD3825	Phase 3
0.6847	Remote Similarity	NPD3397	Phase 2
0.6844	Remote Similarity	NPD5644	Phase 1
0.6842	Remote Similarity	NPD8247	Approved
0.6842	Remote Similarity	NPD8246	Approved
0.6833	Remote Similarity	NPD1927	Discontinued
0.6832	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5529	Phase 1

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