NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	168.09
Volume:	170.032
LogP:	-0.56
LogD:	-0.796
LogS:	0.562
# Rotatable Bonds:	2
TPSA:	79.37
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.582
Synthetic Accessibility Score:	2.641
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:	-4.961
MDCK Permeability:	4.012645149487071e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.1
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.101
Plasma Protein Binding (PPB):	10.867521286010742%
Volume Distribution (VD):	1.472
Pgp-substrate:	82.84033203125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.075
CYP1A2-substrate:	0.107
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.141
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.222
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.773
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.128

ADMET: Excretion

Clearance (CL):	6.509
Half-life (T1/2):	0.9

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.198
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.895
Carcinogencity:	0.114
Eye Corrosion:	0.008
Eye Irritation:	0.075
Respiratory Toxicity:	0.344

Download Data

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

Natural Product: NPC63338

Natural Product ID:	NPC63338
*Common Name:**	Pyridoxamine
IUPAC Name:	4-(aminomethyl)-5-(hydroxymethyl)-2-methylpyridin-3-ol
Synonyms:	Pyridoxamine
Standard InCHIKey:	NHZMQXZHNVQTQA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H12N2O2/c1-5-8(12)7(2-9)6(4-11)3-10-5/h3,11-12H,2,4,9H2,1H3
SMILES:	Cc1c(c(CN)c(cn1)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL593019
PubChem CID:	1052 11205997
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0001966] Pyridoxamines [CHEMONTID:0004259] Pyridoxamine 5'-phosphates

*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

☑ 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	6
Ki	2
Others	8
Potency	4

Activity Type	# Activity
Individual Protein	4
NON-MOLECULAR	1
ORGANISM	4
Others	9
SINGLE PROTEIN	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	446.7	nM	PMID[479505]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[479505]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[479505]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[479505]
NPT35	Others	n.a.		Activity	=	14.0	%	PMID[479503]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	32.0	%	PMID[479503]
NPT27	Others	Unspecified		Activity	=	92.0	%	PMID[479503]
NPT24311	SINGLE PROTEIN	Pyridoxal kinase	Homo sapiens	Km	=	130000.0	nM	PMID[479504]
NPT2	Others	Unspecified		IC50	=	7000000.0	nM	PMID[479506]
NPT2	Others	Unspecified		Ki	=	1400000.0	nM	PMID[479506]
NPT2	Others	Unspecified		Ki	=	1420000.0	nM	PMID[479506]
NPT2	Others	Unspecified		IC50	=	1030000.0	nM	PMID[479506]
NPT35	Others	n.a.		pKa	n.a.	10.34	n.a.	PMID[479507]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	37.34	%	PMID[479508]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.15	%	PMID[479509]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[479510]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[479510]

☑ 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 NPC63338 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	5869
0.2-0.3	12012
0.3-0.4	15655
0.4-0.5	4917
0.5-0.6	2889
0.6-0.7	900
0.7-0.8	80
0.8-0.85	2
0.85-0.9	2
0.9-0.95	3
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC324203
1.0	High Similarity	NPC322976
0.9728	High Similarity	NPC63562
0.9597	High Similarity	NPC132680
0.9597	High Similarity	NPC269919
0.9481	High Similarity	NPC256828
0.9346	High Similarity	NPC263439
0.9221	High Similarity	NPC211187
0.872	High Similarity	NPC325705
0.872	High Similarity	NPC52831
0.8304	Intermediate Similarity	NPC36498
0.8205	Intermediate Similarity	NPC220523
0.7888	Intermediate Similarity	NPC153769
0.7797	Intermediate Similarity	NPC3715
0.7706	Intermediate Similarity	NPC252590
0.7647	Intermediate Similarity	NPC473764
0.7647	Intermediate Similarity	NPC314940
0.764	Intermediate Similarity	NPC161292
0.7625	Intermediate Similarity	NPC471598
0.7604	Intermediate Similarity	NPC477110
0.7597	Intermediate Similarity	NPC174421
0.7562	Intermediate Similarity	NPC470404
0.7562	Intermediate Similarity	NPC470394
0.7562	Intermediate Similarity	NPC470403
0.7547	Intermediate Similarity	NPC318935
0.7532	Intermediate Similarity	NPC471596
0.7486	Intermediate Similarity	NPC46580
0.7485	Intermediate Similarity	NPC138018
0.7484	Intermediate Similarity	NPC280853
0.7472	Intermediate Similarity	NPC314002
0.7471	Intermediate Similarity	NPC471178
0.7469	Intermediate Similarity	NPC470395
0.7459	Intermediate Similarity	NPC476167
0.7451	Intermediate Similarity	NPC306397
0.7451	Intermediate Similarity	NPC165370
0.7451	Intermediate Similarity	NPC212125
0.7438	Intermediate Similarity	NPC285016
0.7438	Intermediate Similarity	NPC245657
0.7416	Intermediate Similarity	NPC204717
0.7412	Intermediate Similarity	NPC473057
0.7405	Intermediate Similarity	NPC192315
0.736	Intermediate Similarity	NPC220765
0.7344	Intermediate Similarity	NPC5145
0.7333	Intermediate Similarity	NPC171171
0.733	Intermediate Similarity	NPC18348
0.733	Intermediate Similarity	NPC96890
0.7326	Intermediate Similarity	NPC108469
0.7312	Intermediate Similarity	NPC471594
0.7303	Intermediate Similarity	NPC161887
0.7303	Intermediate Similarity	NPC219963
0.7296	Intermediate Similarity	NPC29702
0.7296	Intermediate Similarity	NPC328029
0.7294	Intermediate Similarity	NPC25899
0.7273	Intermediate Similarity	NPC194724
0.7251	Intermediate Similarity	NPC124542
0.7251	Intermediate Similarity	NPC59779
0.7251	Intermediate Similarity	NPC471177
0.7247	Intermediate Similarity	NPC478032
0.7246	Intermediate Similarity	NPC284348
0.7245	Intermediate Similarity	NPC470799
0.7245	Intermediate Similarity	NPC8022
0.724	Intermediate Similarity	NPC477111
0.7235	Intermediate Similarity	NPC84508
0.7232	Intermediate Similarity	NPC184964
0.7225	Intermediate Similarity	NPC477113
0.7209	Intermediate Similarity	NPC97367
0.7209	Intermediate Similarity	NPC102423
0.7204	Intermediate Similarity	NPC251090
0.72	Intermediate Similarity	NPC302647
0.7191	Intermediate Similarity	NPC42979
0.7188	Intermediate Similarity	NPC316403
0.7184	Intermediate Similarity	NPC319456
0.7184	Intermediate Similarity	NPC44161
0.7176	Intermediate Similarity	NPC116573
0.7175	Intermediate Similarity	NPC224764
0.7173	Intermediate Similarity	NPC470500
0.7158	Intermediate Similarity	NPC32771
0.7151	Intermediate Similarity	NPC48192
0.7135	Intermediate Similarity	NPC99666
0.7127	Intermediate Similarity	NPC207851
0.7112	Intermediate Similarity	NPC242209
0.7111	Intermediate Similarity	NPC266551
0.711	Intermediate Similarity	NPC469813
0.711	Intermediate Similarity	NPC476446
0.711	Intermediate Similarity	NPC78375
0.7102	Intermediate Similarity	NPC253810
0.7097	Intermediate Similarity	NPC151489
0.7097	Intermediate Similarity	NPC226202
0.7093	Intermediate Similarity	NPC131718
0.7091	Intermediate Similarity	NPC471323
0.7079	Intermediate Similarity	NPC150048
0.7079	Intermediate Similarity	NPC203754
0.7076	Intermediate Similarity	NPC212742
0.7074	Intermediate Similarity	NPC156704
0.7074	Intermediate Similarity	NPC224928
0.7072	Intermediate Similarity	NPC48938
0.7068	Intermediate Similarity	NPC470678
0.7066	Intermediate Similarity	NPC257142
0.7062	Intermediate Similarity	NPC313791
0.7059	Intermediate Similarity	NPC244536
0.7045	Intermediate Similarity	NPC126481
0.7044	Intermediate Similarity	NPC256893
0.7035	Intermediate Similarity	NPC230869
0.7033	Intermediate Similarity	NPC284559
0.7006	Intermediate Similarity	NPC158129
0.7005	Intermediate Similarity	NPC307963
0.7005	Intermediate Similarity	NPC329541
0.7005	Intermediate Similarity	NPC106937
0.7	Intermediate Similarity	NPC314270
0.6995	Remote Similarity	NPC295158
0.6984	Remote Similarity	NPC77555
0.6984	Remote Similarity	NPC267928
0.6977	Remote Similarity	NPC475870
0.6968	Remote Similarity	NPC326634
0.6966	Remote Similarity	NPC259545
0.6965	Remote Similarity	NPC313804
0.6965	Remote Similarity	NPC315804
0.6963	Remote Similarity	NPC315491
0.6963	Remote Similarity	NPC45459
0.6963	Remote Similarity	NPC19872
0.6957	Remote Similarity	NPC314573
0.6954	Remote Similarity	NPC79911
0.6952	Remote Similarity	NPC324149
0.6939	Remote Similarity	NPC185782
0.6932	Remote Similarity	NPC41717
0.6923	Remote Similarity	NPC88008
0.6919	Remote Similarity	NPC26679
0.6915	Remote Similarity	NPC173080
0.6914	Remote Similarity	NPC162268
0.691	Remote Similarity	NPC273532
0.6907	Remote Similarity	NPC47059
0.6907	Remote Similarity	NPC472259
0.6907	Remote Similarity	NPC165349
0.6907	Remote Similarity	NPC329708
0.6907	Remote Similarity	NPC118832
0.6907	Remote Similarity	NPC475070
0.6907	Remote Similarity	NPC264166
0.6907	Remote Similarity	NPC274291
0.6906	Remote Similarity	NPC232340
0.6902	Remote Similarity	NPC42591
0.6902	Remote Similarity	NPC311282
0.6902	Remote Similarity	NPC241025
0.6897	Remote Similarity	NPC120798
0.6882	Remote Similarity	NPC75544
0.6882	Remote Similarity	NPC296527
0.6878	Remote Similarity	NPC93390
0.6875	Remote Similarity	NPC249040
0.6875	Remote Similarity	NPC213308
0.6867	Remote Similarity	NPC60553
0.6857	Remote Similarity	NPC71079
0.6857	Remote Similarity	NPC47298
0.6857	Remote Similarity	NPC315214
0.6857	Remote Similarity	NPC177404
0.6856	Remote Similarity	NPC245816
0.6856	Remote Similarity	NPC200836
0.6856	Remote Similarity	NPC476138
0.6856	Remote Similarity	NPC475774
0.6848	Remote Similarity	NPC320394
0.6845	Remote Similarity	NPC76748
0.6842	Remote Similarity	NPC13880
0.6834	Remote Similarity	NPC316981
0.6825	Remote Similarity	NPC473821
0.6818	Remote Similarity	NPC159319
0.6818	Remote Similarity	NPC11464
0.6818	Remote Similarity	NPC474217
0.6818	Remote Similarity	NPC32028
0.6816	Remote Similarity	NPC142901
0.6816	Remote Similarity	NPC249614
0.6813	Remote Similarity	NPC72980
0.6811	Remote Similarity	NPC20249
0.6811	Remote Similarity	NPC62510
0.6809	Remote Similarity	NPC92111
0.6809	Remote Similarity	NPC114974
0.6806	Remote Similarity	NPC78767
0.6806	Remote Similarity	NPC473814
0.6804	Remote Similarity	NPC211813
0.68	Remote Similarity	NPC162530
0.6791	Remote Similarity	NPC472289
0.6788	Remote Similarity	NPC315957
0.678	Remote Similarity	NPC85918
0.6778	Remote Similarity	NPC471294
0.6772	Remote Similarity	NPC133140
0.6772	Remote Similarity	NPC195268
0.677	Remote Similarity	NPC315320
0.6769	Remote Similarity	NPC53144
0.6763	Remote Similarity	NPC263455
0.6751	Remote Similarity	NPC183777
0.675	Remote Similarity	NPC219087
0.6743	Remote Similarity	NPC113812
0.6742	Remote Similarity	NPC127730
0.6742	Remote Similarity	NPC54988
0.6742	Remote Similarity	NPC278366
0.6739	Remote Similarity	NPC314394
0.6737	Remote Similarity	NPC289786
0.6734	Remote Similarity	NPC309845
0.6733	Remote Similarity	NPC288349
0.6728	Remote Similarity	NPC324611
0.6723	Remote Similarity	NPC311276
0.6722	Remote Similarity	NPC121658
0.6722	Remote Similarity	NPC14651

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 NPC63338 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	728
0.2-0.3	884
0.3-0.4	1692
0.4-0.5	3231
0.5-0.6	1986
0.6-0.7	401
0.7-0.8	42
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD9398	Clinical (unspecified phase)
0.9597	High Similarity	NPD9382	Approved
0.9597	High Similarity	NPD9383	Approved
0.872	High Similarity	NPD9510	Approved
0.8466	Intermediate Similarity	NPD2123	Phase 3
0.8304	Intermediate Similarity	NPD9363	Approved
0.8304	Intermediate Similarity	NPD9364	Phase 2
0.8218	Intermediate Similarity	NPD5317	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD9362	Approved
0.7933	Intermediate Similarity	NPD1229	Phase 2
0.7888	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD861	Approved
0.7725	Intermediate Similarity	NPD863	Approved
0.7725	Intermediate Similarity	NPD862	Approved
0.7633	Intermediate Similarity	NPD424	Approved
0.7633	Intermediate Similarity	NPD425	Approved
0.7574	Intermediate Similarity	NPD926	Approved
0.7574	Intermediate Similarity	NPD925	Approved
0.7514	Intermediate Similarity	NPD9690	Approved
0.7468	Intermediate Similarity	NPD9506	Approved
0.7451	Intermediate Similarity	NPD9284	Approved
0.7451	Intermediate Similarity	NPD9080	Approved
0.744	Intermediate Similarity	NPD5255	Approved
0.743	Intermediate Similarity	NPD5256	Discontinued
0.7403	Intermediate Similarity	NPD1213	Phase 3
0.7396	Intermediate Similarity	NPD1418	Phase 2
0.7366	Intermediate Similarity	NPD2175	Phase 3
0.7366	Intermediate Similarity	NPD2176	Approved
0.7366	Intermediate Similarity	NPD2177	Approved
0.7341	Intermediate Similarity	NPD565	Phase 2
0.733	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD158	Discontinued
0.7308	Intermediate Similarity	NPD5316	Approved
0.7294	Intermediate Similarity	NPD9705	Discontinued
0.7294	Intermediate Similarity	NPD112	Approved
0.7232	Intermediate Similarity	NPD6159	Phase 2
0.7222	Intermediate Similarity	NPD534	Phase 2
0.7222	Intermediate Similarity	NPD1649	Discontinued
0.7222	Intermediate Similarity	NPD537	Phase 2
0.7205	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD1352	Discontinued
0.7189	Intermediate Similarity	NPD9695	Approved
0.7188	Intermediate Similarity	NPD796	Phase 2
0.7176	Intermediate Similarity	NPD2582	Approved
0.7176	Intermediate Similarity	NPD2581	Approved
0.7169	Intermediate Similarity	NPD4702	Approved
0.7169	Intermediate Similarity	NPD4703	Approved
0.7127	Intermediate Similarity	NPD1096	Discontinued
0.7111	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD1034	Phase 3
0.7099	Intermediate Similarity	NPD9076	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD687	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD3813	Approved
0.7086	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4699	Discontinued
0.7074	Intermediate Similarity	NPD1622	Discontinued
0.7074	Intermediate Similarity	NPD2952	Discontinued
0.7065	Intermediate Similarity	NPD4021	Phase 2
0.7059	Intermediate Similarity	NPD4086	Phase 1
0.7043	Intermediate Similarity	NPD6569	Phase 2
0.7041	Intermediate Similarity	NPD4131	Phase 3
0.703	Intermediate Similarity	NPD3717	Discontinued
0.7011	Intermediate Similarity	NPD2383	Phase 1
0.701	Intermediate Similarity	NPD1392	Approved
0.701	Intermediate Similarity	NPD6290	Phase 2
0.7005	Intermediate Similarity	NPD1038	Approved
0.7005	Intermediate Similarity	NPD802	Phase 2
0.7005	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD3082	Discontinued
0.6989	Remote Similarity	NPD2781	Approved
0.6984	Remote Similarity	NPD7948	Phase 1
0.6983	Remote Similarity	NPD5100	Phase 3
0.6977	Remote Similarity	NPD9574	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD2782	Approved
0.6971	Remote Similarity	NPD2780	Approved
0.6963	Remote Similarity	NPD484	Approved
0.6954	Remote Similarity	NPD4502	Phase 2
0.6954	Remote Similarity	NPD5939	Approved
0.6954	Remote Similarity	NPD3570	Phase 2
0.6954	Remote Similarity	NPD5936	Approved
0.6952	Remote Similarity	NPD9689	Approved
0.6935	Remote Similarity	NPD8063	Discontinued
0.6928	Remote Similarity	NPD3525	Discontinued
0.6907	Remote Similarity	NPD4039	Approved
0.6907	Remote Similarity	NPD31	Approved
0.6907	Remote Similarity	NPD4038	Approved
0.6907	Remote Similarity	NPD4035	Approved
0.6907	Remote Similarity	NPD4036	Approved
0.6907	Remote Similarity	NPD4033	Approved
0.6907	Remote Similarity	NPD4034	Approved
0.6907	Remote Similarity	NPD4037	Approved
0.6907	Remote Similarity	NPD4122	Approved
0.6907	Remote Similarity	NPD32	Approved
0.6884	Remote Similarity	NPD2615	Phase 3
0.6884	Remote Similarity	NPD2616	Phase 3
0.6879	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1684	Approved
0.6857	Remote Similarity	NPD1685	Approved
0.6851	Remote Similarity	NPD4071	Approved
0.6851	Remote Similarity	NPD4072	Approved
0.6845	Remote Similarity	NPD3321	Discontinued
0.6842	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3477	Phase 2
0.6839	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD4203	Approved
0.6831	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD4204	Approved
0.6816	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD3396	Approved
0.6789	Remote Similarity	NPD3395	Approved
0.6788	Remote Similarity	NPD1739	Approved
0.6788	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1740	Approved
0.6786	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD706	Phase 1
0.6772	Remote Similarity	NPD3923	Approved
0.6772	Remote Similarity	NPD3922	Approved
0.6772	Remote Similarity	NPD3921	Approved
0.6772	Remote Similarity	NPD3924	Approved
0.677	Remote Similarity	NPD9206	Approved
0.677	Remote Similarity	NPD9207	Approved
0.6763	Remote Similarity	NPD7603	Discontinued
0.6755	Remote Similarity	NPD2544	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD9596	Approved
0.6744	Remote Similarity	NPD9595	Approved
0.674	Remote Similarity	NPD5065	Approved
0.6737	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4551	Phase 2
0.6736	Remote Similarity	NPD5999	Phase 2
0.6736	Remote Similarity	NPD9688	Approved
0.6736	Remote Similarity	NPD9687	Approved
0.6735	Remote Similarity	NPD4795	Phase 2
0.6733	Remote Similarity	NPD5612	Discontinued
0.6732	Remote Similarity	NPD7726	Phase 1
0.6724	Remote Similarity	NPD276	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD3931	Approved
0.6718	Remote Similarity	NPD3928	Approved
0.6704	Remote Similarity	NPD5862	Discovery
0.6703	Remote Similarity	NPD5596	Phase 2
0.6703	Remote Similarity	NPD2382	Approved
0.6703	Remote Similarity	NPD2380	Approved
0.6703	Remote Similarity	NPD2381	Approved
0.6702	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.67	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD8823	Approved
0.6685	Remote Similarity	NPD2076	Approved
0.6685	Remote Similarity	NPD2077	Approved
0.6684	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4437	Phase 3
0.6667	Remote Similarity	NPD1032	Phase 2
0.6667	Remote Similarity	NPD3330	Phase 1
0.6651	Remote Similarity	NPD7558	Phase 2
0.6649	Remote Similarity	NPD1768	Approved
0.6635	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.663	Remote Similarity	NPD9548	Phase 2
0.6629	Remote Similarity	NPD1274	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD8356	Approved
0.6617	Remote Similarity	NPD5067	Phase 2
0.6617	Remote Similarity	NPD5066	Phase 2
0.6615	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD2414	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD9357	Approved
0.6598	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD4372	Phase 1
0.6596	Remote Similarity	NPD4375	Approved
0.6596	Remote Similarity	NPD4919	Phase 3
0.6596	Remote Similarity	NPD4921	Phase 3
0.6596	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5948	Phase 2
0.6583	Remote Similarity	NPD7222	Phase 2
0.6578	Remote Similarity	NPD3569	Discontinued
0.6578	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4526	Approved
0.6562	Remote Similarity	NPD4528	Approved
0.6562	Remote Similarity	NPD4529	Approved
0.6559	Remote Similarity	NPD3386	Phase 2
0.6559	Remote Similarity	NPD1570	Approved
0.6559	Remote Similarity	NPD3178	Discontinued
0.6557	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.655	Remote Similarity	NPD4612	Discontinued
0.655	Remote Similarity	NPD9075	Approved
0.655	Remote Similarity	NPD9074	Approved
0.6545	Remote Similarity	NPD4148	Approved
0.6543	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD4889	Approved
0.6538	Remote Similarity	NPD4945	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