NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.1
Volume:	248.837
LogP:	0.996
LogD:	1.243
LogS:	-1.133
# Rotatable Bonds:	4
TPSA:	64.47
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.888
Synthetic Accessibility Score:	2.292
Fsp3:	0.231
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:	-4.728
MDCK Permeability:	2.2020531105226837e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.851
Plasma Protein Binding (PPB):	82.67373657226562%
Volume Distribution (VD):	0.81
Pgp-substrate:	13.933445930480957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.821
CYP1A2-substrate:	0.683
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.794
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.645
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.637
CYP3A4-inhibitor:	0.037
CYP3A4-substrate:	0.446

ADMET: Excretion

Clearance (CL):	6.541
Half-life (T1/2):	0.86

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.179
Drug-inuced Liver Injury (DILI):	0.773
AMES Toxicity:	0.32
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.041
Skin Sensitization:	0.315
Carcinogencity:	0.108
Eye Corrosion:	0.004
Eye Irritation:	0.609
Respiratory Toxicity:	0.716

Download Data

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

Natural Product: NPC226202

Natural Product ID:	NPC226202
*Common Name:**	Caerulomycin G
IUPAC Name:	(4,5-dimethoxy-6-pyridin-2-ylpyridin-2-yl)methanol
Synonyms:	Caerulomycin G
Standard InCHIKey:	NOWSJBQEOYCSBC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H14N2O3/c1-17-11-7-9(8-16)15-12(13(11)18-2)10-5-3-4-6-14-10/h3-7,16H,8H2,1-2H3
SMILES:	COc1c(OC)cc(nc1c1ccccn1)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1823032
PubChem CID:	53493586
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	n.a.	n.a.	n.a.	PMID[21770434]
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.	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	>	50000.0	nM	PMID[515395]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000.0	nM	PMID[515395]

☑ 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 NPC226202 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	500
0.1-0.2	5528
0.2-0.3	11997
0.3-0.4	10505
0.4-0.5	10212
0.5-0.6	3106
0.6-0.7	689
0.7-0.8	148
0.8-0.85	5
0.85-0.9	2
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9415	High Similarity	NPC219963
0.9364	High Similarity	NPC20249
0.9191	High Similarity	NPC161887
0.9191	High Similarity	NPC266551
0.8786	High Similarity	NPC14651
0.8786	High Similarity	NPC121658
0.8728	High Similarity	NPC476518
0.8523	High Similarity	NPC111624
0.8488	Intermediate Similarity	NPC25899
0.8333	Intermediate Similarity	NPC48192
0.8216	Intermediate Similarity	NPC74382
0.8216	Intermediate Similarity	NPC206251
0.8158	Intermediate Similarity	NPC267928
0.7979	Intermediate Similarity	NPC224327
0.7938	Intermediate Similarity	NPC19872
0.7937	Intermediate Similarity	NPC134079
0.7921	Intermediate Similarity	NPC470799
0.7921	Intermediate Similarity	NPC8022
0.7812	Intermediate Similarity	NPC84853
0.7803	Intermediate Similarity	NPC220523
0.78	Intermediate Similarity	NPC185782
0.7778	Intermediate Similarity	NPC329708
0.7778	Intermediate Similarity	NPC264166
0.7778	Intermediate Similarity	NPC274291
0.7778	Intermediate Similarity	NPC47059
0.7778	Intermediate Similarity	NPC118832
0.7778	Intermediate Similarity	NPC165349
0.7772	Intermediate Similarity	NPC26679
0.775	Intermediate Similarity	NPC287208
0.7704	Intermediate Similarity	NPC187558
0.7573	Intermediate Similarity	NPC288349
0.7554	Intermediate Similarity	NPC1527
0.755	Intermediate Similarity	NPC476138
0.755	Intermediate Similarity	NPC245816
0.7545	Intermediate Similarity	NPC472434
0.7527	Intermediate Similarity	NPC177404
0.7513	Intermediate Similarity	NPC110741
0.7488	Intermediate Similarity	NPC469554
0.7488	Intermediate Similarity	NPC308392
0.7473	Intermediate Similarity	NPC258773
0.7443	Intermediate Similarity	NPC470395
0.7416	Intermediate Similarity	NPC197141
0.7407	Intermediate Similarity	NPC101543
0.7389	Intermediate Similarity	NPC471736
0.7383	Intermediate Similarity	NPC110151
0.7382	Intermediate Similarity	NPC118776
0.7381	Intermediate Similarity	NPC193267
0.7381	Intermediate Similarity	NPC213530
0.7358	Intermediate Similarity	NPC42591
0.7357	Intermediate Similarity	NPC472435
0.7343	Intermediate Similarity	NPC112206
0.7343	Intermediate Similarity	NPC202605
0.734	Intermediate Similarity	NPC470500
0.733	Intermediate Similarity	NPC470394
0.733	Intermediate Similarity	NPC470404
0.733	Intermediate Similarity	NPC470403
0.7311	Intermediate Similarity	NPC310118
0.7306	Intermediate Similarity	NPC284559
0.7297	Intermediate Similarity	NPC263439
0.7291	Intermediate Similarity	NPC475774
0.7287	Intermediate Similarity	NPC252590
0.7283	Intermediate Similarity	NPC285635
0.7282	Intermediate Similarity	NPC469589
0.7277	Intermediate Similarity	NPC232727
0.7269	Intermediate Similarity	NPC314954
0.7264	Intermediate Similarity	NPC18487
0.7261	Intermediate Similarity	NPC472436
0.7255	Intermediate Similarity	NPC476581
0.7255	Intermediate Similarity	NPC36229
0.7255	Intermediate Similarity	NPC16452
0.7251	Intermediate Similarity	NPC173080
0.7234	Intermediate Similarity	NPC473764
0.7234	Intermediate Similarity	NPC314940
0.7228	Intermediate Similarity	NPC176538
0.7228	Intermediate Similarity	NPC315957
0.7225	Intermediate Similarity	NPC476287
0.7204	Intermediate Similarity	NPC118511
0.7198	Intermediate Similarity	NPC174672
0.7182	Intermediate Similarity	NPC182222
0.7178	Intermediate Similarity	NPC4071
0.7178	Intermediate Similarity	NPC476578
0.7178	Intermediate Similarity	NPC476582
0.7178	Intermediate Similarity	NPC476167
0.7173	Intermediate Similarity	NPC194724
0.717	Intermediate Similarity	NPC314270
0.7164	Intermediate Similarity	NPC224928
0.7163	Intermediate Similarity	NPC167860
0.7163	Intermediate Similarity	NPC123976
0.7158	Intermediate Similarity	NPC63562
0.7157	Intermediate Similarity	NPC66815
0.7151	Intermediate Similarity	NPC79911
0.7143	Intermediate Similarity	NPC162530
0.7136	Intermediate Similarity	NPC472111
0.7136	Intermediate Similarity	NPC133140
0.7136	Intermediate Similarity	NPC195268
0.7129	Intermediate Similarity	NPC239954
0.7129	Intermediate Similarity	NPC192315
0.7128	Intermediate Similarity	NPC62069
0.7128	Intermediate Similarity	NPC284678
0.7119	Intermediate Similarity	NPC318935
0.7115	Intermediate Similarity	NPC174758
0.7108	Intermediate Similarity	NPC31930
0.7104	Intermediate Similarity	NPC26872
0.7101	Intermediate Similarity	NPC193238
0.71	Intermediate Similarity	NPC79293
0.71	Intermediate Similarity	NPC198673
0.71	Intermediate Similarity	NPC289786
0.71	Intermediate Similarity	NPC279401
0.7098	Intermediate Similarity	NPC99891
0.7097	Intermediate Similarity	NPC322976
0.7097	Intermediate Similarity	NPC120798
0.7097	Intermediate Similarity	NPC63338
0.7097	Intermediate Similarity	NPC324203
0.7089	Intermediate Similarity	NPC469594
0.7089	Intermediate Similarity	NPC473822
0.7081	Intermediate Similarity	NPC132680
0.7081	Intermediate Similarity	NPC269919
0.7081	Intermediate Similarity	NPC5145
0.7077	Intermediate Similarity	NPC48938
0.7072	Intermediate Similarity	NPC295228
0.707	Intermediate Similarity	NPC60621
0.7067	Intermediate Similarity	NPC82548
0.7062	Intermediate Similarity	NPC168486
0.7062	Intermediate Similarity	NPC222592
0.7062	Intermediate Similarity	NPC471080
0.7062	Intermediate Similarity	NPC469592
0.7052	Intermediate Similarity	NPC174421
0.7049	Intermediate Similarity	NPC284348
0.7049	Intermediate Similarity	NPC153769
0.7044	Intermediate Similarity	NPC212213
0.7035	Intermediate Similarity	NPC316224
0.703	Intermediate Similarity	NPC251090
0.7023	Intermediate Similarity	NPC174049
0.7014	Intermediate Similarity	NPC53069
0.7014	Intermediate Similarity	NPC203168
0.7014	Intermediate Similarity	NPC202768
0.7014	Intermediate Similarity	NPC296482
0.701	Intermediate Similarity	NPC472168
0.701	Intermediate Similarity	NPC287437
0.6996	Remote Similarity	NPC258048
0.6989	Remote Similarity	NPC26850
0.6984	Remote Similarity	NPC471178
0.6982	Remote Similarity	NPC141053
0.6977	Remote Similarity	NPC292958
0.6976	Remote Similarity	NPC121772
0.6976	Remote Similarity	NPC234197
0.6968	Remote Similarity	NPC124542
0.6968	Remote Similarity	NPC471177
0.6968	Remote Similarity	NPC201508
0.6968	Remote Similarity	NPC59779
0.6963	Remote Similarity	NPC473513
0.6961	Remote Similarity	NPC168911
0.6959	Remote Similarity	NPC283152
0.6938	Remote Similarity	NPC313189
0.6934	Remote Similarity	NPC96405
0.6934	Remote Similarity	NPC316981
0.6934	Remote Similarity	NPC171409
0.6931	Remote Similarity	NPC307963
0.6919	Remote Similarity	NPC219664
0.6919	Remote Similarity	NPC36168
0.6919	Remote Similarity	NPC290689
0.6916	Remote Similarity	NPC274982
0.6907	Remote Similarity	NPC203754
0.6907	Remote Similarity	NPC150048
0.6906	Remote Similarity	NPC96584
0.6906	Remote Similarity	NPC255800
0.6901	Remote Similarity	NPC266931
0.6893	Remote Similarity	NPC328029
0.6893	Remote Similarity	NPC477019
0.689	Remote Similarity	NPC470164
0.689	Remote Similarity	NPC323345
0.6885	Remote Similarity	NPC257142
0.6881	Remote Similarity	NPC216612
0.6881	Remote Similarity	NPC324149
0.6875	Remote Similarity	NPC200836
0.6863	Remote Similarity	NPC473053
0.6857	Remote Similarity	NPC135549
0.6856	Remote Similarity	NPC95898
0.6856	Remote Similarity	NPC312872
0.685	Remote Similarity	NPC66083
0.6842	Remote Similarity	NPC211187
0.6837	Remote Similarity	NPC477110
0.6831	Remote Similarity	NPC161292
0.6821	Remote Similarity	NPC288943
0.6816	Remote Similarity	NPC296527
0.6816	Remote Similarity	NPC260434
0.6812	Remote Similarity	NPC291609
0.6812	Remote Similarity	NPC316756
0.681	Remote Similarity	NPC26543
0.681	Remote Similarity	NPC304183
0.6809	Remote Similarity	NPC116573
0.6809	Remote Similarity	NPC53534
0.6804	Remote Similarity	NPC122463
0.6804	Remote Similarity	NPC470501
0.68	Remote Similarity	NPC314573
0.6798	Remote Similarity	NPC148889
0.6794	Remote Similarity	NPC53144
0.6789	Remote Similarity	NPC54066
0.6788	Remote Similarity	NPC256828
0.6782	Remote Similarity	NPC3715

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 NPC226202 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	845
0.2-0.3	880
0.3-0.4	1833
0.4-0.5	2898
0.5-0.6	1852
0.6-0.7	522
0.7-0.8	65
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
0.7778	Intermediate Similarity	NPD4037	Approved
0.7778	Intermediate Similarity	NPD4038	Approved
0.7778	Intermediate Similarity	NPD31	Approved
0.7778	Intermediate Similarity	NPD4036	Approved
0.7778	Intermediate Similarity	NPD1856	Discontinued
0.7778	Intermediate Similarity	NPD32	Approved
0.7778	Intermediate Similarity	NPD4034	Approved
0.7778	Intermediate Similarity	NPD4039	Approved
0.7778	Intermediate Similarity	NPD4122	Approved
0.7778	Intermediate Similarity	NPD4035	Approved
0.7778	Intermediate Similarity	NPD4033	Approved
0.7751	Intermediate Similarity	NPD5640	Discontinued
0.7723	Intermediate Similarity	NPD4131	Phase 3
0.7644	Intermediate Similarity	NPD1034	Phase 3
0.7644	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD3477	Phase 2
0.7577	Intermediate Similarity	NPD6569	Phase 2
0.7514	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD565	Phase 2
0.7487	Intermediate Similarity	NPD4372	Phase 1
0.7459	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5320	Approved
0.7419	Intermediate Similarity	NPD5319	Approved
0.7409	Intermediate Similarity	NPD4375	Approved
0.7385	Intermediate Similarity	NPD4081	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD1622	Discontinued
0.7333	Intermediate Similarity	NPD9596	Approved
0.7333	Intermediate Similarity	NPD9595	Approved
0.7308	Intermediate Similarity	NPD2314	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2772	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD862	Approved
0.7297	Intermediate Similarity	NPD861	Approved
0.7297	Intermediate Similarity	NPD863	Approved
0.7292	Intermediate Similarity	NPD4203	Approved
0.7292	Intermediate Similarity	NPD4204	Approved
0.7268	Intermediate Similarity	NPD9574	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD1602	Discontinued
0.7233	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD1739	Approved
0.7228	Intermediate Similarity	NPD1740	Approved
0.7219	Intermediate Similarity	NPD425	Approved
0.7219	Intermediate Similarity	NPD424	Approved
0.7216	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6494	Phase 2
0.7202	Intermediate Similarity	NPD3386	Phase 2
0.7184	Intermediate Similarity	NPD1392	Approved
0.715	Intermediate Similarity	NPD3395	Approved
0.715	Intermediate Similarity	NPD3396	Approved
0.7143	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD3922	Approved
0.7136	Intermediate Similarity	NPD3923	Approved
0.7136	Intermediate Similarity	NPD3921	Approved
0.7136	Intermediate Similarity	NPD3924	Approved
0.712	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD112	Approved
0.7097	Intermediate Similarity	NPD9705	Discontinued
0.7097	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4795	Phase 2
0.7081	Intermediate Similarity	NPD9382	Approved
0.7081	Intermediate Similarity	NPD2581	Approved
0.7081	Intermediate Similarity	NPD2582	Approved
0.7081	Intermediate Similarity	NPD9383	Approved
0.7079	Intermediate Similarity	NPD2952	Discontinued
0.7071	Intermediate Similarity	NPD4021	Phase 2
0.707	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7558	Phase 2
0.7056	Intermediate Similarity	NPD6500	Approved
0.7056	Intermediate Similarity	NPD6501	Approved
0.7048	Intermediate Similarity	NPD3570	Phase 2
0.7043	Intermediate Similarity	NPD5255	Approved
0.7035	Intermediate Similarity	NPD8063	Discontinued
0.7031	Intermediate Similarity	NPD9690	Approved
0.7027	Intermediate Similarity	NPD3074	Discontinued
0.702	Intermediate Similarity	NPD6393	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7675	Phase 3
0.7018	Intermediate Similarity	NPD7426	Phase 1
0.7018	Intermediate Similarity	NPD7674	Phase 3
0.7016	Intermediate Similarity	NPD2123	Phase 3
0.7015	Intermediate Similarity	NPD4551	Phase 2
0.7014	Intermediate Similarity	NPD3816	Phase 1
0.7014	Intermediate Similarity	NPD3815	Phase 1
0.7013	Intermediate Similarity	NPD8370	Discontinued
0.701	Intermediate Similarity	NPD5999	Phase 2
0.7005	Intermediate Similarity	NPD1418	Phase 2
0.7	Intermediate Similarity	NPD4148	Approved
0.6995	Remote Similarity	NPD1229	Phase 2
0.6995	Remote Similarity	NPD8510	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD4502	Phase 2
0.6967	Remote Similarity	NPD5066	Phase 2
0.6967	Remote Similarity	NPD5067	Phase 2
0.6963	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4071	Approved
0.6959	Remote Similarity	NPD4072	Approved
0.6957	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD1274	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD1038	Approved
0.6927	Remote Similarity	NPD9548	Phase 2
0.6927	Remote Similarity	NPD4548	Discontinued
0.6923	Remote Similarity	NPD3302	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8512	Phase 3
0.6906	Remote Similarity	NPD4080	Discontinued
0.6897	Remote Similarity	NPD7859	Phase 2
0.6897	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD926	Approved
0.6895	Remote Similarity	NPD925	Approved
0.689	Remote Similarity	NPD5530	Phase 1
0.6887	Remote Similarity	NPD3939	Suspended
0.6884	Remote Similarity	NPD5256	Discontinued
0.6884	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD1032	Phase 2
0.6869	Remote Similarity	NPD1334	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD6856	Discontinued
0.6866	Remote Similarity	NPD3321	Discontinued
0.6866	Remote Similarity	NPD5316	Approved
0.6847	Remote Similarity	NPD6361	Phase 2
0.6847	Remote Similarity	NPD9695	Approved
0.6847	Remote Similarity	NPD5022	Discontinued
0.6845	Remote Similarity	NPD1768	Approved
0.6845	Remote Similarity	NPD2958	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5612	Discontinued
0.6834	Remote Similarity	NPD4889	Approved
0.6832	Remote Similarity	NPD2334	Discontinued
0.6829	Remote Similarity	NPD2959	Phase 3
0.6822	Remote Similarity	NPD5944	Phase 1
0.6822	Remote Similarity	NPD5945	Phase 1
0.682	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD1941	Approved
0.681	Remote Similarity	NPD5482	Discontinued
0.6806	Remote Similarity	NPD4989	Phase 2
0.6798	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD8479	Phase 2
0.6787	Remote Similarity	NPD1907	Phase 3
0.6787	Remote Similarity	NPD1273	Discontinued
0.6787	Remote Similarity	NPD1603	Discontinued
0.6784	Remote Similarity	NPD6750	Phase 2
0.6784	Remote Similarity	NPD2414	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD1095	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7222	Phase 2
0.6776	Remote Similarity	NPD7069	Discontinued
0.6774	Remote Similarity	NPD6568	Discontinued
0.6769	Remote Similarity	NPD158	Discontinued
0.6765	Remote Similarity	NPD4529	Approved
0.6765	Remote Similarity	NPD4526	Approved
0.6765	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4528	Approved
0.6758	Remote Similarity	NPD6298	Discontinued
0.6757	Remote Similarity	NPD1906	Approved
0.6754	Remote Similarity	NPD1927	Discontinued
0.6754	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5908	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3343	Phase 3
0.6745	Remote Similarity	NPD6366	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD2816	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.674	Remote Similarity	NPD1649	Discontinued
0.6738	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6590	Discontinued
0.673	Remote Similarity	NPD3003	Approved
0.6729	Remote Similarity	NPD949	Phase 1
0.6722	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD2077	Approved
0.6718	Remote Similarity	NPD2076	Approved
0.6717	Remote Similarity	NPD2599	Approved
0.6717	Remote Similarity	NPD2601	Approved
0.6717	Remote Similarity	NPD2600	Approved
0.6714	Remote Similarity	NPD4437	Phase 3
0.6713	Remote Similarity	NPD5903	Approved
0.6713	Remote Similarity	NPD5902	Approved
0.6712	Remote Similarity	NPD5930	Phase 3
0.6701	Remote Similarity	NPD6159	Phase 2
0.6699	Remote Similarity	NPD1621	Discontinued
0.6699	Remote Similarity	NPD6550	Discontinued
0.6697	Remote Similarity	NPD4429	Discontinued
0.6697	Remote Similarity	NPD5948	Phase 2
0.6697	Remote Similarity	NPD6306	Phase 2
0.6695	Remote Similarity	NPD5644	Phase 1
0.6686	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD2175	Phase 3
0.6683	Remote Similarity	NPD2177	Approved
0.6683	Remote Similarity	NPD2176	Approved
0.6682	Remote Similarity	NPD4086	Phase 1
0.6681	Remote Similarity	NPD4858	Phase 2
0.6667	Remote Similarity	NPD3082	Discontinued
0.6667	Remote Similarity	NPD3920	Phase 2
0.6667	Remote Similarity	NPD5911	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5658	Approved
0.6667	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD8356	Approved
0.6652	Remote Similarity	NPD6964	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