NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.06
Volume:	216.23
LogP:	-2.354
LogD:	-0.85
LogS:	0.371
# Rotatable Bonds:	4
TPSA:	122.74
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.656
Synthetic Accessibility Score:	4.077
Fsp3:	0.375
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:	-5.404
MDCK Permeability:	3.627508704084903e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.056
30% Bioavailability (F30%):	0.044

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.073
Plasma Protein Binding (PPB):	10.020467758178711%
Volume Distribution (VD):	1.132
Pgp-substrate:	82.61737823486328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.086
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.434
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.257
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.042

ADMET: Excretion

Clearance (CL):	1.655
Half-life (T1/2):	0.883

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.155
Drug-inuced Liver Injury (DILI):	0.009
AMES Toxicity:	0.19
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.739
Skin Sensitization:	0.533
Carcinogencity:	0.172
Eye Corrosion:	0.023
Eye Irritation:	0.075
Respiratory Toxicity:	0.348

Download Data

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

Natural Product: NPC256828

Natural Product ID:	NPC256828
*Common Name:**	Pyridoxamine Phosphate
IUPAC Name:	[4-(aminomethyl)-5-hydroxy-6-methylpyridin-3-yl]methyl dihydrogen phosphate
Synonyms:	Pyridoxamine Phosphate
Standard InCHIKey:	ZMJGSOSNSPKHNH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H13N2O5P/c1-5-8(11)7(2-9)6(3-10-5)4-15-16(12,13)14/h3,11H,2,4,9H2,1H3,(H2,12,13,14)
SMILES:	Cc1c(c(CN)c(cn1)COP(=O)(O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1235353
PubChem CID:	1053
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
NPO21556	NPC256828	n.a.	Sclerotia	0.057 ± 0.014	n.a.	n.a.	%	PMID[20527951]

☑ 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
Potency	4

Activity Type	# Activity
Individual Protein	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	28695.4	nM	PMID[454862]
NPT100	Individual Protein	Glutaminase kidney isoform, mitochondrial	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[454862]
NPT2	Others	Unspecified		Potency	n.a.	15089	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21131.7	nM	PubChem BioAssay data set

☑ 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 NPC256828 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	409
0.1-0.2	7167
0.2-0.3	11162
0.3-0.4	15856
0.4-0.5	4719
0.5-0.6	2663
0.6-0.7	673
0.7-0.8	36
0.8-0.85	2
0.85-0.9	2
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9739	High Similarity	NPC211187
0.9481	High Similarity	NPC63338
0.9481	High Similarity	NPC322976
0.9481	High Similarity	NPC324203
0.9221	High Similarity	NPC63562
0.9103	High Similarity	NPC269919
0.9103	High Similarity	NPC132680
0.8875	High Similarity	NPC263439
0.8765	High Similarity	NPC36498
0.8304	Intermediate Similarity	NPC325705
0.8304	Intermediate Similarity	NPC52831
0.7791	Intermediate Similarity	NPC220523
0.7529	Intermediate Similarity	NPC319456
0.75	Intermediate Similarity	NPC153769
0.7446	Intermediate Similarity	NPC3715
0.7443	Intermediate Similarity	NPC252590
0.7419	Intermediate Similarity	NPC106937
0.7386	Intermediate Similarity	NPC314940
0.7386	Intermediate Similarity	NPC473764
0.7312	Intermediate Similarity	NPC174421
0.7286	Intermediate Similarity	NPC477110
0.7273	Intermediate Similarity	NPC318935
0.7262	Intermediate Similarity	NPC161292
0.7256	Intermediate Similarity	NPC471596
0.7246	Intermediate Similarity	NPC471598
0.7243	Intermediate Similarity	NPC46580
0.7228	Intermediate Similarity	NPC314002
0.7225	Intermediate Similarity	NPC138018
0.7225	Intermediate Similarity	NPC476167
0.7216	Intermediate Similarity	NPC471178
0.7212	Intermediate Similarity	NPC280853
0.7186	Intermediate Similarity	NPC470404
0.7186	Intermediate Similarity	NPC470403
0.7186	Intermediate Similarity	NPC470394
0.7174	Intermediate Similarity	NPC204717
0.7173	Intermediate Similarity	NPC192315
0.717	Intermediate Similarity	NPC306397
0.717	Intermediate Similarity	NPC212125
0.7169	Intermediate Similarity	NPC285016
0.7169	Intermediate Similarity	NPC245657
0.7159	Intermediate Similarity	NPC473057
0.7143	Intermediate Similarity	NPC315320
0.712	Intermediate Similarity	NPC220765
0.7107	Intermediate Similarity	NPC18348
0.7101	Intermediate Similarity	NPC470395
0.7097	Intermediate Similarity	NPC171171
0.7088	Intermediate Similarity	NPC96890
0.7079	Intermediate Similarity	NPC108469
0.7065	Intermediate Similarity	NPC161887
0.7063	Intermediate Similarity	NPC165370
0.7049	Intermediate Similarity	NPC42979
0.7048	Intermediate Similarity	NPC471594
0.7045	Intermediate Similarity	NPC25899
0.7035	Intermediate Similarity	NPC5145
0.7033	Intermediate Similarity	NPC194724
0.7033	Intermediate Similarity	NPC224764
0.703	Intermediate Similarity	NPC29702
0.703	Intermediate Similarity	NPC8022
0.703	Intermediate Similarity	NPC328029
0.703	Intermediate Similarity	NPC470799
0.702	Intermediate Similarity	NPC477111
0.7006	Intermediate Similarity	NPC59779
0.7006	Intermediate Similarity	NPC124542
0.7006	Intermediate Similarity	NPC471177
0.7005	Intermediate Similarity	NPC477113
0.6995	Remote Similarity	NPC184964
0.6973	Remote Similarity	NPC219963
0.697	Remote Similarity	NPC316403
0.6966	Remote Similarity	NPC97367
0.6961	Remote Similarity	NPC302647
0.6944	Remote Similarity	NPC44161
0.6943	Remote Similarity	NPC156704
0.6932	Remote Similarity	NPC116573
0.6931	Remote Similarity	NPC32771
0.6919	Remote Similarity	NPC478032
0.6911	Remote Similarity	NPC99666
0.691	Remote Similarity	NPC48192
0.6897	Remote Similarity	NPC284348
0.6893	Remote Similarity	NPC84508
0.6891	Remote Similarity	NPC242209
0.6891	Remote Similarity	NPC251090
0.6882	Remote Similarity	NPC266551
0.6872	Remote Similarity	NPC102423
0.6869	Remote Similarity	NPC470500
0.6868	Remote Similarity	NPC253810
0.6857	Remote Similarity	NPC244536
0.6856	Remote Similarity	NPC224928
0.6854	Remote Similarity	NPC131718
0.6853	Remote Similarity	NPC470678
0.6842	Remote Similarity	NPC471323
0.6836	Remote Similarity	NPC212742
0.6832	Remote Similarity	NPC151489
0.6829	Remote Similarity	NPC473513
0.6821	Remote Similarity	NPC257142
0.6809	Remote Similarity	NPC284559
0.6809	Remote Similarity	NPC207851
0.6796	Remote Similarity	NPC314270
0.6788	Remote Similarity	NPC307963
0.6788	Remote Similarity	NPC329541
0.6788	Remote Similarity	NPC226202
0.6778	Remote Similarity	NPC78375
0.6778	Remote Similarity	NPC476446
0.6778	Remote Similarity	NPC469813
0.6776	Remote Similarity	NPC273532
0.6769	Remote Similarity	NPC267928
0.6769	Remote Similarity	NPC77555
0.6763	Remote Similarity	NPC313804
0.6763	Remote Similarity	NPC315804
0.6757	Remote Similarity	NPC203754
0.6757	Remote Similarity	NPC150048
0.6755	Remote Similarity	NPC48938
0.6753	Remote Similarity	NPC326634
0.6751	Remote Similarity	NPC315491
0.6751	Remote Similarity	NPC45459
0.6751	Remote Similarity	NPC19872
0.6742	Remote Similarity	NPC475870
0.6739	Remote Similarity	NPC259545
0.6739	Remote Similarity	NPC313791
0.6737	Remote Similarity	NPC314573
0.6736	Remote Similarity	NPC324149
0.6733	Remote Similarity	NPC185782
0.6722	Remote Similarity	NPC79911
0.6721	Remote Similarity	NPC126481
0.672	Remote Similarity	NPC320394
0.6716	Remote Similarity	NPC26679
0.6716	Remote Similarity	NPC88008
0.6715	Remote Similarity	NPC173080
0.6704	Remote Similarity	NPC230869
0.6703	Remote Similarity	NPC41717
0.67	Remote Similarity	NPC475070
0.67	Remote Similarity	NPC472259
0.6687	Remote Similarity	NPC256893
0.6685	Remote Similarity	NPC158129
0.6685	Remote Similarity	NPC162268
0.6684	Remote Similarity	NPC295158
0.6684	Remote Similarity	NPC311282
0.6684	Remote Similarity	NPC232340
0.6684	Remote Similarity	NPC42591
0.6667	Remote Similarity	NPC213308
0.6667	Remote Similarity	NPC75544
0.6667	Remote Similarity	NPC296527
0.6667	Remote Similarity	NPC120798
0.6667	Remote Similarity	NPC93390
0.665	Remote Similarity	NPC200836
0.665	Remote Similarity	NPC476138
0.665	Remote Similarity	NPC245816
0.665	Remote Similarity	NPC475774
0.6649	Remote Similarity	NPC133140
0.6649	Remote Similarity	NPC195268
0.6634	Remote Similarity	NPC316981
0.6633	Remote Similarity	NPC13880
0.6632	Remote Similarity	NPC76748
0.663	Remote Similarity	NPC47298
0.663	Remote Similarity	NPC71079
0.663	Remote Similarity	NPC315214
0.663	Remote Similarity	NPC177404
0.6628	Remote Similarity	NPC60553
0.6618	Remote Similarity	NPC11464
0.6618	Remote Similarity	NPC142901
0.6617	Remote Similarity	NPC329708
0.6617	Remote Similarity	NPC264166
0.6617	Remote Similarity	NPC274291
0.6617	Remote Similarity	NPC118832
0.6617	Remote Similarity	NPC165349
0.6617	Remote Similarity	NPC47059
0.6615	Remote Similarity	NPC473821
0.6602	Remote Similarity	NPC162530
0.66	Remote Similarity	NPC211813
0.6599	Remote Similarity	NPC78767
0.6599	Remote Similarity	NPC473814
0.6598	Remote Similarity	NPC114974
0.6598	Remote Similarity	NPC92111
0.6597	Remote Similarity	NPC20249
0.6597	Remote Similarity	NPC241025
0.6597	Remote Similarity	NPC62510
0.6596	Remote Similarity	NPC72980
0.6595	Remote Similarity	NPC249614
0.6593	Remote Similarity	NPC159319
0.6593	Remote Similarity	NPC32028
0.6593	Remote Similarity	NPC474217
0.6583	Remote Similarity	NPC249040
0.6583	Remote Similarity	NPC315957
0.658	Remote Similarity	NPC472289
0.6567	Remote Similarity	NPC53144
0.6559	Remote Similarity	NPC471294
0.6557	Remote Similarity	NPC85918
0.6553	Remote Similarity	NPC202605
0.6553	Remote Similarity	NPC112206
0.6552	Remote Similarity	NPC183777
0.6538	Remote Similarity	NPC288349
0.6538	Remote Similarity	NPC476161
0.6537	Remote Similarity	NPC309845
0.6531	Remote Similarity	NPC289786
0.6526	Remote Similarity	NPC470474
0.6524	Remote Similarity	NPC95898
0.6524	Remote Similarity	NPC213530
0.6524	Remote Similarity	NPC193267
0.6522	Remote Similarity	NPC127730
0.6522	Remote Similarity	NPC266931
0.6522	Remote Similarity	NPC278366

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 NPC256828 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	787
0.2-0.3	877
0.3-0.4	1898
0.4-0.5	3302
0.5-0.6	1799
0.6-0.7	277
0.7-0.8	24
0.8-0.85	4
0.85-0.9	2
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9481	High Similarity	NPD9398	Clinical (unspecified phase)
0.9103	High Similarity	NPD9383	Approved
0.9103	High Similarity	NPD9382	Approved
0.8765	High Similarity	NPD9363	Approved
0.8765	High Similarity	NPD9364	Phase 2
0.8671	High Similarity	NPD5317	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD9362	Approved
0.8304	Intermediate Similarity	NPD9510	Approved
0.8166	Intermediate Similarity	NPD2123	Phase 3
0.7798	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD5316	Approved
0.7676	Intermediate Similarity	NPD1229	Phase 2
0.7605	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD802	Phase 2
0.7371	Intermediate Similarity	NPD425	Approved
0.7371	Intermediate Similarity	NPD424	Approved
0.7356	Intermediate Similarity	NPD863	Approved
0.7356	Intermediate Similarity	NPD862	Approved
0.7356	Intermediate Similarity	NPD861	Approved
0.7314	Intermediate Similarity	NPD925	Approved
0.7314	Intermediate Similarity	NPD926	Approved
0.7301	Intermediate Similarity	NPD9506	Approved
0.7263	Intermediate Similarity	NPD9690	Approved
0.7258	Intermediate Similarity	NPD1213	Phase 3
0.7189	Intermediate Similarity	NPD5256	Discontinued
0.7184	Intermediate Similarity	NPD5255	Approved
0.717	Intermediate Similarity	NPD9080	Approved
0.717	Intermediate Similarity	NPD9284	Approved
0.7143	Intermediate Similarity	NPD9206	Approved
0.7143	Intermediate Similarity	NPD1418	Phase 2
0.7143	Intermediate Similarity	NPD9207	Approved
0.7095	Intermediate Similarity	NPD565	Phase 2
0.7088	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD2544	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD158	Discontinued
0.7047	Intermediate Similarity	NPD2176	Approved
0.7047	Intermediate Similarity	NPD2177	Approved
0.7047	Intermediate Similarity	NPD2175	Phase 3
0.7045	Intermediate Similarity	NPD112	Approved
0.7045	Intermediate Similarity	NPD9705	Discontinued
0.7041	Intermediate Similarity	NPD1352	Discontinued
0.701	Intermediate Similarity	NPD537	Phase 2
0.701	Intermediate Similarity	NPD534	Phase 2
0.6995	Remote Similarity	NPD6159	Phase 2
0.6989	Remote Similarity	NPD1096	Discontinued
0.6973	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD1649	Discontinued
0.6963	Remote Similarity	NPD9695	Approved
0.6946	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1622	Discontinued
0.6932	Remote Similarity	NPD2582	Approved
0.6932	Remote Similarity	NPD2581	Approved
0.6919	Remote Similarity	NPD4702	Approved
0.6919	Remote Similarity	NPD4703	Approved
0.6915	Remote Similarity	NPD4131	Phase 3
0.6884	Remote Similarity	NPD796	Phase 2
0.6878	Remote Similarity	NPD1034	Phase 3
0.6878	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4086	Phase 1
0.6856	Remote Similarity	NPD2952	Discontinued
0.6856	Remote Similarity	NPD7948	Phase 1
0.6854	Remote Similarity	NPD687	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD2781	Approved
0.6842	Remote Similarity	NPD3813	Approved
0.6842	Remote Similarity	NPD4021	Phase 2
0.6833	Remote Similarity	NPD2782	Approved
0.6833	Remote Similarity	NPD2780	Approved
0.6823	Remote Similarity	NPD6569	Phase 2
0.68	Remote Similarity	NPD6290	Phase 2
0.6788	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1038	Approved
0.6784	Remote Similarity	NPD3717	Discontinued
0.6774	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4699	Discontinued
0.6757	Remote Similarity	NPD5100	Phase 3
0.6751	Remote Similarity	NPD484	Approved
0.6749	Remote Similarity	NPD4502	Phase 2
0.6746	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD9574	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD9689	Approved
0.6719	Remote Similarity	NPD8063	Discontinued
0.6716	Remote Similarity	NPD1392	Approved
0.6702	Remote Similarity	NPD2383	Phase 1
0.6684	Remote Similarity	NPD3082	Discontinued
0.6683	Remote Similarity	NPD2615	Phase 3
0.6683	Remote Similarity	NPD2616	Phase 3
0.6667	Remote Similarity	NPD5939	Approved
0.6667	Remote Similarity	NPD3570	Phase 2
0.6667	Remote Similarity	NPD5936	Approved
0.6651	Remote Similarity	NPD7603	Discontinued
0.6649	Remote Similarity	NPD3922	Approved
0.6649	Remote Similarity	NPD3923	Approved
0.6649	Remote Similarity	NPD3924	Approved
0.6649	Remote Similarity	NPD3921	Approved
0.6648	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD3477	Phase 2
0.6633	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3321	Discontinued
0.6631	Remote Similarity	NPD4072	Approved
0.6631	Remote Similarity	NPD4071	Approved
0.663	Remote Similarity	NPD1685	Approved
0.663	Remote Similarity	NPD1684	Approved
0.6618	Remote Similarity	NPD5612	Discontinued
0.6617	Remote Similarity	NPD4034	Approved
0.6617	Remote Similarity	NPD4033	Approved
0.6617	Remote Similarity	NPD4039	Approved
0.6617	Remote Similarity	NPD4035	Approved
0.6617	Remote Similarity	NPD32	Approved
0.6617	Remote Similarity	NPD4038	Approved
0.6617	Remote Similarity	NPD31	Approved
0.6617	Remote Similarity	NPD4122	Approved
0.6617	Remote Similarity	NPD4037	Approved
0.6617	Remote Similarity	NPD4036	Approved
0.6614	Remote Similarity	NPD4204	Approved
0.6614	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD4203	Approved
0.6611	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD276	Clinical (unspecified phase)
0.659	Remote Similarity	NPD3525	Discontinued
0.6584	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD1739	Approved
0.6583	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD1740	Approved
0.6582	Remote Similarity	NPD3395	Approved
0.6582	Remote Similarity	NPD3396	Approved
0.6562	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD706	Phase 1
0.6555	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4795	Phase 2
0.6533	Remote Similarity	NPD5999	Phase 2
0.6533	Remote Similarity	NPD9687	Approved
0.6533	Remote Similarity	NPD9688	Approved
0.6531	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4551	Phase 2
0.6524	Remote Similarity	NPD5065	Approved
0.6517	Remote Similarity	NPD9596	Approved
0.6517	Remote Similarity	NPD3928	Approved
0.6517	Remote Similarity	NPD9595	Approved
0.6517	Remote Similarity	NPD3931	Approved
0.651	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD8356	Approved
0.6505	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD8129	Discovery
0.6495	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD5596	Phase 2
0.6488	Remote Similarity	NPD4437	Phase 3
0.6486	Remote Similarity	NPD5862	Discovery
0.6482	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD3330	Phase 1
0.6471	Remote Similarity	NPD2077	Approved
0.6471	Remote Similarity	NPD2076	Approved
0.6468	Remote Similarity	NPD7558	Phase 2
0.6465	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD7726	Phase 1
0.6457	Remote Similarity	NPD8823	Approved
0.6455	Remote Similarity	NPD1032	Phase 2
0.6452	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.644	Remote Similarity	NPD1570	Approved
0.6432	Remote Similarity	NPD4945	Discontinued
0.6425	Remote Similarity	NPD2414	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4889	Approved
0.6419	Remote Similarity	NPD5640	Discontinued
0.6418	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD9548	Phase 2
0.6409	Remote Similarity	NPD1274	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD3575	Approved
0.6404	Remote Similarity	NPD3576	Approved
0.6402	Remote Similarity	NPD2380	Approved
0.6402	Remote Similarity	NPD2381	Approved
0.6402	Remote Similarity	NPD2382	Approved
0.6398	Remote Similarity	NPD5948	Phase 2
0.6398	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD4372	Phase 1
0.6396	Remote Similarity	NPD6665	Discontinued
0.6393	Remote Similarity	NPD6494	Phase 2
0.6392	Remote Similarity	NPD4919	Phase 3
0.6392	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4921	Phase 3
0.6392	Remote Similarity	NPD4375	Approved
0.639	Remote Similarity	NPD7222	Phase 2
0.6389	Remote Similarity	NPD8430	Approved
0.6381	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD3569	Discontinued
0.6368	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD1768	Approved
0.6364	Remote Similarity	NPD4526	Approved
0.6364	Remote Similarity	NPD4528	Approved
0.6364	Remote Similarity	NPD4529	Approved
0.6364	Remote Similarity	NPD9357	Approved
0.6359	Remote Similarity	NPD8026	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