NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	153.08
Volume:	159.036
LogP:	0.291
LogD:	0.604
LogS:	-0.398
# Rotatable Bonds:	1
TPSA:	53.35
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.63
Synthetic Accessibility Score:	2.523
Fsp3:	0.375
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.52
MDCK Permeability:	1.0096944606630132e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.318
30% Bioavailability (F30%):	0.083

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.445
Plasma Protein Binding (PPB):	39.8874397277832%
Volume Distribution (VD):	1.178
Pgp-substrate:	58.44963836669922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.211
CYP1A2-substrate:	0.769
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.595
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.262
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.664
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.305

ADMET: Excretion

Clearance (CL):	12.017
Half-life (T1/2):	0.878

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.155
Drug-inuced Liver Injury (DILI):	0.228
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.065
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.818
Carcinogencity:	0.492
Eye Corrosion:	0.015
Eye Irritation:	0.572
Respiratory Toxicity:	0.07

Download Data

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

Natural Product: NPC63562

Natural Product ID:	NPC63562
*Common Name:**	5-(Hydroxymethyl)-2,4-Dimethylpyridin-3-Ol
IUPAC Name:	5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol
Synonyms:
Standard InCHIKey:	KKOWAYISKWGDBG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H11NO2/c1-5-7(4-10)3-9-6(2)8(5)11/h3,10-11H,4H2,1-2H3
SMILES:	OCc1cnc(c(c1C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3244689
PubChem CID:	6094
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0004152] Methylpyridines

*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
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(01)00320-X]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11738417]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21462031]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	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
Others	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3577	Cell Line	TA3	Mus musculus	ID50	=	6.8	10'-8M	PMID[502738]
NPT3578	Individual Protein	Pyridoxine-5'-phosphate oxidase	Mus musculus	ID50	=	6.8	10'-8M	PMID[502739]

☑ 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 NPC63562 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	362
0.1-0.2	5186
0.2-0.3	12512
0.3-0.4	15502
0.4-0.5	5501
0.5-0.6	2694
0.6-0.7	844
0.7-0.8	83
0.8-0.85	2
0.85-0.9	2
0.9-0.95	2
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9862	High Similarity	NPC269919
0.9862	High Similarity	NPC132680
0.9728	High Similarity	NPC324203
0.9728	High Similarity	NPC63338
0.9728	High Similarity	NPC322976
0.9597	High Similarity	NPC263439
0.9467	High Similarity	NPC211187
0.9221	High Similarity	NPC256828
0.8938	High Similarity	NPC52831
0.8938	High Similarity	NPC325705
0.8503	High Similarity	NPC36498
0.8421	Intermediate Similarity	NPC220523
0.8089	Intermediate Similarity	NPC153769
0.7977	Intermediate Similarity	NPC3715
0.7892	Intermediate Similarity	NPC252590
0.7834	Intermediate Similarity	NPC161292
0.7831	Intermediate Similarity	NPC473764
0.7831	Intermediate Similarity	NPC314940
0.7821	Intermediate Similarity	NPC471598
0.78	Intermediate Similarity	NPC174421
0.7756	Intermediate Similarity	NPC470403
0.7756	Intermediate Similarity	NPC470404
0.7756	Intermediate Similarity	NPC470394
0.7742	Intermediate Similarity	NPC318935
0.7727	Intermediate Similarity	NPC471596
0.7677	Intermediate Similarity	NPC280853
0.7658	Intermediate Similarity	NPC470395
0.7651	Intermediate Similarity	NPC165370
0.7628	Intermediate Similarity	NPC245657
0.7628	Intermediate Similarity	NPC285016
0.759	Intermediate Similarity	NPC473057
0.7545	Intermediate Similarity	NPC471178
0.7533	Intermediate Similarity	NPC212125
0.75	Intermediate Similarity	NPC108469
0.75	Intermediate Similarity	NPC471594
0.7442	Intermediate Similarity	NPC194724
0.7423	Intermediate Similarity	NPC284348
0.7414	Intermediate Similarity	NPC478032
0.7396	Intermediate Similarity	NPC477110
0.7372	Intermediate Similarity	NPC29702
0.7372	Intermediate Similarity	NPC328029
0.7371	Intermediate Similarity	NPC219963
0.7365	Intermediate Similarity	NPC25899
0.7353	Intermediate Similarity	NPC44161
0.7349	Intermediate Similarity	NPC116573
0.7349	Intermediate Similarity	NPC138018
0.7337	Intermediate Similarity	NPC476167
0.7321	Intermediate Similarity	NPC471177
0.7321	Intermediate Similarity	NPC59779
0.7321	Intermediate Similarity	NPC124542
0.7305	Intermediate Similarity	NPC84508
0.7303	Intermediate Similarity	NPC306397
0.7288	Intermediate Similarity	NPC207851
0.7285	Intermediate Similarity	NPC151489
0.7283	Intermediate Similarity	NPC192315
0.7278	Intermediate Similarity	NPC97367
0.7267	Intermediate Similarity	NPC253810
0.7263	Intermediate Similarity	NPC46580
0.7249	Intermediate Similarity	NPC316403
0.7247	Intermediate Similarity	NPC314002
0.7239	Intermediate Similarity	NPC257142
0.7228	Intermediate Similarity	NPC224928
0.7226	Intermediate Similarity	NPC256893
0.7225	Intermediate Similarity	NPC5145
0.7219	Intermediate Similarity	NPC48192
0.72	Intermediate Similarity	NPC96890
0.7191	Intermediate Similarity	NPC204717
0.7175	Intermediate Similarity	NPC161887
0.7175	Intermediate Similarity	NPC266551
0.716	Intermediate Similarity	NPC471323
0.7158	Intermediate Similarity	NPC226202
0.7151	Intermediate Similarity	NPC295158
0.7143	Intermediate Similarity	NPC203754
0.7143	Intermediate Similarity	NPC150048
0.7135	Intermediate Similarity	NPC220765
0.7128	Intermediate Similarity	NPC470678
0.7128	Intermediate Similarity	NPC8022
0.7128	Intermediate Similarity	NPC470799
0.712	Intermediate Similarity	NPC18348
0.712	Intermediate Similarity	NPC477111
0.7111	Intermediate Similarity	NPC171171
0.7102	Intermediate Similarity	NPC184964
0.7095	Intermediate Similarity	NPC284559
0.7093	Intermediate Similarity	NPC41717
0.7081	Intermediate Similarity	NPC251090
0.7076	Intermediate Similarity	NPC102423
0.7069	Intermediate Similarity	NPC158129
0.7069	Intermediate Similarity	NPC273532
0.7065	Intermediate Similarity	NPC329541
0.7062	Intermediate Similarity	NPC42979
0.7056	Intermediate Similarity	NPC314270
0.7056	Intermediate Similarity	NPC241025
0.7056	Intermediate Similarity	NPC42591
0.7053	Intermediate Similarity	NPC470500
0.7052	Intermediate Similarity	NPC319456
0.7045	Intermediate Similarity	NPC224764
0.7043	Intermediate Similarity	NPC267928
0.7037	Intermediate Similarity	NPC60553
0.702	Intermediate Similarity	NPC315804
0.702	Intermediate Similarity	NPC313804
0.7018	Intermediate Similarity	NPC79911
0.7017	Intermediate Similarity	NPC314573
0.7016	Intermediate Similarity	NPC477113
0.7	Intermediate Similarity	NPC320394
0.6971	Remote Similarity	NPC302647
0.6971	Remote Similarity	NPC249614
0.697	Remote Similarity	NPC173080
0.6963	Remote Similarity	NPC329708
0.6963	Remote Similarity	NPC118832
0.6963	Remote Similarity	NPC165349
0.6963	Remote Similarity	NPC264166
0.6963	Remote Similarity	NPC274291
0.6963	Remote Similarity	NPC472259
0.6963	Remote Similarity	NPC47059
0.6961	Remote Similarity	NPC62510
0.6959	Remote Similarity	NPC120798
0.6957	Remote Similarity	NPC114974
0.6944	Remote Similarity	NPC48938
0.6943	Remote Similarity	NPC315320
0.694	Remote Similarity	NPC75544
0.694	Remote Similarity	NPC32771
0.6932	Remote Similarity	NPC313791
0.6923	Remote Similarity	NPC263455
0.6919	Remote Similarity	NPC133140
0.6919	Remote Similarity	NPC195268
0.6919	Remote Similarity	NPC177404
0.6919	Remote Similarity	NPC71079
0.6919	Remote Similarity	NPC99666
0.6914	Remote Similarity	NPC126481
0.6911	Remote Similarity	NPC475774
0.6911	Remote Similarity	NPC200836
0.6901	Remote Similarity	NPC113812
0.6901	Remote Similarity	NPC230869
0.6898	Remote Similarity	NPC242209
0.6882	Remote Similarity	NPC289786
0.6879	Remote Similarity	NPC469813
0.6879	Remote Similarity	NPC78375
0.6879	Remote Similarity	NPC474217
0.6879	Remote Similarity	NPC476446
0.6868	Remote Similarity	NPC20249
0.6863	Remote Similarity	NPC244536
0.6862	Remote Similarity	NPC156704
0.686	Remote Similarity	NPC131718
0.6859	Remote Similarity	NPC211813
0.6848	Remote Similarity	NPC472289
0.6845	Remote Similarity	NPC326634
0.6842	Remote Similarity	NPC19872
0.6842	Remote Similarity	NPC212742
0.6839	Remote Similarity	NPC85918
0.6836	Remote Similarity	NPC471294
0.6825	Remote Similarity	NPC472284
0.6823	Remote Similarity	NPC53144
0.6821	Remote Similarity	NPC185782
0.6816	Remote Similarity	NPC283152
0.6809	Remote Similarity	NPC473053
0.6806	Remote Similarity	NPC155792
0.6804	Remote Similarity	NPC88008
0.6802	Remote Similarity	NPC202605
0.6802	Remote Similarity	NPC112206
0.6802	Remote Similarity	NPC26679
0.68	Remote Similarity	NPC127730
0.68	Remote Similarity	NPC278366
0.6796	Remote Similarity	NPC470474
0.6792	Remote Similarity	NPC324611
0.6791	Remote Similarity	NPC307963
0.6791	Remote Similarity	NPC106937
0.6788	Remote Similarity	NPC475070
0.678	Remote Similarity	NPC121658
0.678	Remote Similarity	NPC14651
0.6778	Remote Similarity	NPC164340
0.6772	Remote Similarity	NPC90229
0.6772	Remote Similarity	NPC77555
0.6766	Remote Similarity	NPC302159
0.676	Remote Similarity	NPC134586
0.6757	Remote Similarity	NPC44354
0.6757	Remote Similarity	NPC110741
0.6757	Remote Similarity	NPC230805
0.6754	Remote Similarity	NPC315491
0.6754	Remote Similarity	NPC45459
0.6754	Remote Similarity	NPC249040
0.6754	Remote Similarity	NPC213308
0.6752	Remote Similarity	NPC471313
0.6752	Remote Similarity	NPC471311
0.675	Remote Similarity	NPC322488
0.6744	Remote Similarity	NPC475870
0.6742	Remote Similarity	NPC259545
0.674	Remote Similarity	NPC317010
0.6738	Remote Similarity	NPC324149
0.6736	Remote Similarity	NPC476138
0.6736	Remote Similarity	NPC245816
0.6724	Remote Similarity	NPC315214
0.6724	Remote Similarity	NPC47298
0.6723	Remote Similarity	NPC476518
0.6722	Remote Similarity	NPC211997
0.6721	Remote Similarity	NPC62069
0.6707	Remote Similarity	NPC167400
0.6705	Remote Similarity	NPC98187
0.6704	Remote Similarity	NPC95898
0.6702	Remote Similarity	NPC476578
0.6702	Remote Similarity	NPC4071

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 NPC63562 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	752
0.2-0.3	867
0.3-0.4	1844
0.4-0.5	3294
0.5-0.6	1787
0.6-0.7	368
0.7-0.8	36
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9862	High Similarity	NPD9382	Approved
0.9862	High Similarity	NPD9383	Approved
0.9728	High Similarity	NPD9398	Clinical (unspecified phase)
0.8938	High Similarity	NPD9510	Approved
0.8562	High Similarity	NPD2123	Phase 3
0.8503	High Similarity	NPD9364	Phase 2
0.8503	High Similarity	NPD9363	Approved
0.8304	Intermediate Similarity	NPD5317	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD9362	Approved
0.8114	Intermediate Similarity	NPD1229	Phase 2
0.8089	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD9690	Approved
0.7651	Intermediate Similarity	NPD926	Approved
0.7651	Intermediate Similarity	NPD925	Approved
0.7548	Intermediate Similarity	NPD9506	Approved
0.7533	Intermediate Similarity	NPD9284	Approved
0.7515	Intermediate Similarity	NPD5255	Approved
0.75	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD424	Approved
0.75	Intermediate Similarity	NPD425	Approved
0.7485	Intermediate Similarity	NPD861	Approved
0.7485	Intermediate Similarity	NPD863	Approved
0.7485	Intermediate Similarity	NPD862	Approved
0.7472	Intermediate Similarity	NPD1213	Phase 3
0.747	Intermediate Similarity	NPD112	Approved
0.747	Intermediate Similarity	NPD9705	Discontinued
0.7384	Intermediate Similarity	NPD158	Discontinued
0.7374	Intermediate Similarity	NPD5316	Approved
0.7303	Intermediate Similarity	NPD9080	Approved
0.7299	Intermediate Similarity	NPD6159	Phase 2
0.7296	Intermediate Similarity	NPD1649	Discontinued
0.7278	Intermediate Similarity	NPD9076	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1352	Discontinued
0.7253	Intermediate Similarity	NPD9695	Approved
0.7246	Intermediate Similarity	NPD2581	Approved
0.7246	Intermediate Similarity	NPD2582	Approved
0.7207	Intermediate Similarity	NPD5256	Discontinued
0.7167	Intermediate Similarity	NPD1034	Phase 3
0.7167	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1418	Phase 2
0.716	Intermediate Similarity	NPD3813	Approved
0.7151	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2176	Approved
0.7151	Intermediate Similarity	NPD2177	Approved
0.7151	Intermediate Similarity	NPD2175	Phase 3
0.7151	Intermediate Similarity	NPD2781	Approved
0.7135	Intermediate Similarity	NPD2782	Approved
0.7135	Intermediate Similarity	NPD2780	Approved
0.7135	Intermediate Similarity	NPD1622	Discontinued
0.711	Intermediate Similarity	NPD565	Phase 2
0.7104	Intermediate Similarity	NPD6569	Phase 2
0.7104	Intermediate Similarity	NPD9689	Approved
0.7099	Intermediate Similarity	NPD3525	Discontinued
0.7072	Intermediate Similarity	NPD2383	Phase 1
0.7045	Intermediate Similarity	NPD5100	Phase 3
0.703	Intermediate Similarity	NPD4703	Approved
0.703	Intermediate Similarity	NPD4702	Approved
0.702	Intermediate Similarity	NPD534	Phase 2
0.702	Intermediate Similarity	NPD537	Phase 2
0.6995	Remote Similarity	NPD8063	Discontinued
0.6979	Remote Similarity	NPD796	Phase 2
0.6963	Remote Similarity	NPD4038	Approved
0.6963	Remote Similarity	NPD4122	Approved
0.6963	Remote Similarity	NPD4035	Approved
0.6963	Remote Similarity	NPD4039	Approved
0.6963	Remote Similarity	NPD4037	Approved
0.6963	Remote Similarity	NPD31	Approved
0.6963	Remote Similarity	NPD32	Approved
0.6963	Remote Similarity	NPD4033	Approved
0.6963	Remote Similarity	NPD4034	Approved
0.6963	Remote Similarity	NPD4036	Approved
0.6959	Remote Similarity	NPD687	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD2952	Discontinued
0.6943	Remote Similarity	NPD9206	Approved
0.6943	Remote Similarity	NPD9207	Approved
0.6941	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3924	Approved
0.6919	Remote Similarity	NPD3921	Approved
0.6919	Remote Similarity	NPD3923	Approved
0.6919	Remote Similarity	NPD3922	Approved
0.6906	Remote Similarity	NPD1096	Discontinued
0.6902	Remote Similarity	NPD3321	Discontinued
0.6898	Remote Similarity	NPD3477	Phase 2
0.6898	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.689	Remote Similarity	NPD3717	Discontinued
0.6889	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4203	Approved
0.6889	Remote Similarity	NPD4204	Approved
0.6878	Remote Similarity	NPD9687	Approved
0.6878	Remote Similarity	NPD9688	Approved
0.6875	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD3082	Discontinued
0.6865	Remote Similarity	NPD4699	Discontinued
0.6863	Remote Similarity	NPD4086	Phase 1
0.6848	Remote Similarity	NPD8823	Approved
0.6848	Remote Similarity	NPD4021	Phase 2
0.6845	Remote Similarity	NPD3395	Approved
0.6845	Remote Similarity	NPD3396	Approved
0.6842	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4131	Phase 3
0.6837	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD9595	Approved
0.6805	Remote Similarity	NPD9596	Approved
0.6804	Remote Similarity	NPD6290	Phase 2
0.6804	Remote Similarity	NPD1392	Approved
0.6791	Remote Similarity	NPD4551	Phase 2
0.6791	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD1038	Approved
0.6791	Remote Similarity	NPD802	Phase 2
0.6776	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7948	Phase 1
0.6761	Remote Similarity	NPD5862	Discovery
0.6757	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD484	Approved
0.6751	Remote Similarity	NPD5936	Approved
0.6751	Remote Similarity	NPD3570	Phase 2
0.6751	Remote Similarity	NPD4502	Phase 2
0.6751	Remote Similarity	NPD5939	Approved
0.6744	Remote Similarity	NPD9574	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD2077	Approved
0.6742	Remote Similarity	NPD2076	Approved
0.6739	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD1685	Approved
0.6724	Remote Similarity	NPD1684	Approved
0.6722	Remote Similarity	NPD1032	Phase 2
0.6721	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD9075	Approved
0.6707	Remote Similarity	NPD9074	Approved
0.6705	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1274	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4889	Approved
0.6683	Remote Similarity	NPD2616	Phase 3
0.6683	Remote Similarity	NPD2615	Phase 3
0.6667	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8356	Approved
0.6667	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD2414	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4375	Approved
0.6649	Remote Similarity	NPD4372	Phase 1
0.6649	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7222	Phase 2
0.6631	Remote Similarity	NPD2544	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4071	Approved
0.663	Remote Similarity	NPD4072	Approved
0.6618	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5999	Phase 2
0.6614	Remote Similarity	NPD4529	Approved
0.6614	Remote Similarity	NPD4526	Approved
0.6614	Remote Similarity	NPD4528	Approved
0.6612	Remote Similarity	NPD1570	Approved
0.6612	Remote Similarity	NPD3386	Phase 2
0.6611	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD3931	Approved
0.6598	Remote Similarity	NPD3928	Approved
0.6596	Remote Similarity	NPD4148	Approved
0.6593	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3576	Approved
0.6588	Remote Similarity	NPD3575	Approved
0.6585	Remote Similarity	NPD4945	Discontinued
0.658	Remote Similarity	NPD1739	Approved
0.658	Remote Similarity	NPD1740	Approved
0.6576	Remote Similarity	NPD5596	Phase 2
0.6571	Remote Similarity	NPD2511	Approved
0.657	Remote Similarity	NPD7603	Discontinued
0.657	Remote Similarity	NPD5640	Discontinued
0.6566	Remote Similarity	NPD4437	Phase 3
0.6559	Remote Similarity	NPD706	Phase 1
0.6557	Remote Similarity	NPD2600	Approved
0.6557	Remote Similarity	NPD2599	Approved
0.6557	Remote Similarity	NPD2601	Approved
0.6552	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.655	Remote Similarity	NPD3330	Phase 1
0.6548	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD1380	Discovery
0.6543	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD8430	Approved
0.6537	Remote Similarity	NPD7726	Phase 1
0.6536	Remote Similarity	NPD7474	Suspended
0.6536	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5612	Discontinued
0.6531	Remote Similarity	NPD4795	Phase 2
0.6526	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6361	Phase 2
0.6524	Remote Similarity	NPD8020	Approved
0.6524	Remote Similarity	NPD8021	Approved
0.6519	Remote Similarity	NPD5065	Approved
0.6512	Remote Similarity	NPD2882	Phase 1
0.6512	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6158	Phase 2
0.6508	Remote Similarity	NPD2334	Discontinued

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