NPASS Compound

Structure

NPC281207 OpenBabel07101718242D 21 23 0 0 0 0 0 0 0 0999 V2000 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 5 1 0 0 0 0 2 9 2 0 0 0 0 3 6 2 0 0 0 0 3 9 1 0 0 0 0 4 7 2 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 8 10 2 0 0 0 0 8 13 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 20 1 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 18 2 0 0 0 0 15 16 2 0 0 0 0 15 19 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	284.07
Volume:	282.482
LogP:	3.39
LogD:	2.609
LogS:	-3.743
# Rotatable Bonds:	2
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.756
Synthetic Accessibility Score:	2.061
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.746
MDCK Permeability:	1.475593580835266e-05
Pgp-inhibitor:	0.282
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.807

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	97.44541931152344%
Volume Distribution (VD):	0.523
Pgp-substrate:	3.5445141792297363%

ADMET: Metabolism

CYP1A2-inhibitor:	0.953
CYP1A2-substrate:	0.779
CYP2C19-inhibitor:	0.873
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.647
CYP2C9-substrate:	0.933
CYP2D6-inhibitor:	0.745
CYP2D6-substrate:	0.885
CYP3A4-inhibitor:	0.82
CYP3A4-substrate:	0.189

ADMET: Excretion

Clearance (CL):	4.578
Half-life (T1/2):	0.722

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.128
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.591
Rat Oral Acute Toxicity:	0.181
Maximum Recommended Daily Dose:	0.217
Skin Sensitization:	0.552
Carcinogencity:	0.275
Eye Corrosion:	0.004
Eye Irritation:	0.829
Respiratory Toxicity:	0.161

Download Data

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

Natural Product: NPC281207

Natural Product ID:	NPC281207
*Common Name:**	3,7-Dihydroxy-4'-Methoxyflavone
IUPAC Name:	3,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one
Synonyms:
Standard InCHIKey:	IYFVCSURXCCUSJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O5/c1-20-11-5-2-9(3-6-11)16-15(19)14(18)12-7-4-10(17)8-13(12)21-16/h2-8,17,19H,1H3
SMILES:	COc1ccc(cc1)c1oc2cc(O)ccc2c(=O)c1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2017116
PubChem CID:	12314892
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0001136] Flavonols

*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
NPO33390	broussonetia kanzinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22450131]

☑ 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	1
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1120	Individual Protein	Pancreatic triacylglycerol lipase	Sus scrofa	Inhibition	=	21.8	%	PMID[478047]
NPT1120	Individual Protein	Pancreatic triacylglycerol lipase	Sus scrofa	IC50	>	100000.0	nM	PMID[478047]

☑ 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 NPC281207 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	485
0.1-0.2	2014
0.2-0.3	5293
0.3-0.4	11452
0.4-0.5	5692
0.5-0.6	4237
0.6-0.7	5551
0.7-0.8	4053
0.8-0.85	2162
0.85-0.9	1255
0.9-0.95	418
0.95-1	85

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC269652
0.9926	High Similarity	NPC136840
0.9925	High Similarity	NPC152042
0.9925	High Similarity	NPC143799
0.9925	High Similarity	NPC241838
0.9852	High Similarity	NPC103342
0.9852	High Similarity	NPC230285
0.9852	High Similarity	NPC146679
0.9852	High Similarity	NPC103904
0.9852	High Similarity	NPC59951
0.9852	High Similarity	NPC184536
0.9779	High Similarity	NPC90582
0.9779	High Similarity	NPC262094
0.9776	High Similarity	NPC299379
0.9776	High Similarity	NPC266597
0.9776	High Similarity	NPC250266
0.9704	High Similarity	NPC276905
0.9701	High Similarity	NPC216361
0.9701	High Similarity	NPC281917
0.9701	High Similarity	NPC116775
0.9701	High Similarity	NPC194281
0.9701	High Similarity	NPC47815
0.9701	High Similarity	NPC127447
0.9701	High Similarity	NPC187432
0.9701	High Similarity	NPC29353
0.9701	High Similarity	NPC234133
0.9701	High Similarity	NPC256042
0.9701	High Similarity	NPC473887
0.9701	High Similarity	NPC124784
0.9701	High Similarity	NPC231772
0.9638	High Similarity	NPC470216
0.9568	High Similarity	NPC273538
0.9568	High Similarity	NPC216538
0.9565	High Similarity	NPC200694
0.9565	High Similarity	NPC473042
0.9559	High Similarity	NPC280284
0.9559	High Similarity	NPC188947
0.9559	High Similarity	NPC99333
0.9556	High Similarity	NPC13408
0.9552	High Similarity	NPC248872
0.9552	High Similarity	NPC172262
0.95	High Similarity	NPC5820
0.95	High Similarity	NPC178343
0.95	High Similarity	NPC124729
0.95	High Similarity	NPC306488
0.9496	High Similarity	NPC212932
0.9496	High Similarity	NPC9117
0.9496	High Similarity	NPC190637
0.9496	High Similarity	NPC158874
0.9496	High Similarity	NPC293053
0.9496	High Similarity	NPC24821
0.9493	High Similarity	NPC110969
0.9489	High Similarity	NPC18260
0.9489	High Similarity	NPC78913
0.9485	High Similarity	NPC275055
0.9485	High Similarity	NPC290291
0.9485	High Similarity	NPC188879
0.9485	High Similarity	NPC228661
0.9478	High Similarity	NPC50898
0.9478	High Similarity	NPC78540
0.9478	High Similarity	NPC274121
0.9478	High Similarity	NPC213216
0.9478	High Similarity	NPC57601
0.9429	High Similarity	NPC326500
0.9424	High Similarity	NPC11561
0.9424	High Similarity	NPC226636
0.942	High Similarity	NPC172986
0.942	High Similarity	NPC270883
0.942	High Similarity	NPC159275
0.942	High Similarity	NPC241100
0.942	High Similarity	NPC261227
0.9416	High Similarity	NPC201395
0.9416	High Similarity	NPC124269
0.9412	High Similarity	NPC72452
0.9412	High Similarity	NPC240593
0.9412	High Similarity	NPC61546
0.9403	High Similarity	NPC212631
0.9403	High Similarity	NPC205468
0.9403	High Similarity	NPC129132
0.9403	High Similarity	NPC257756
0.9403	High Similarity	NPC87231
0.9403	High Similarity	NPC128216
0.9371	High Similarity	NPC61258
0.9366	High Similarity	NPC244407
0.9366	High Similarity	NPC296869
0.9362	High Similarity	NPC229190
0.9362	High Similarity	NPC153758
0.9362	High Similarity	NPC470458
0.9353	High Similarity	NPC156590
0.9353	High Similarity	NPC147688
0.9353	High Similarity	NPC103362
0.9353	High Similarity	NPC205006
0.9353	High Similarity	NPC118840
0.9353	High Similarity	NPC64908
0.9353	High Similarity	NPC282300
0.9353	High Similarity	NPC3188
0.9348	High Similarity	NPC261234
0.9348	High Similarity	NPC220062
0.9348	High Similarity	NPC222342
0.9348	High Similarity	NPC310135
0.9348	High Similarity	NPC150648
0.9348	High Similarity	NPC225153
0.9348	High Similarity	NPC217186
0.9348	High Similarity	NPC96565
0.9348	High Similarity	NPC301217
0.9348	High Similarity	NPC216978
0.9348	High Similarity	NPC303633
0.9348	High Similarity	NPC274784
0.9348	High Similarity	NPC53181
0.9348	High Similarity	NPC20709
0.9348	High Similarity	NPC55018
0.9348	High Similarity	NPC329203
0.9348	High Similarity	NPC265871
0.9343	High Similarity	NPC116632
0.9343	High Similarity	NPC303644
0.9343	High Similarity	NPC254841
0.9343	High Similarity	NPC7013
0.9343	High Similarity	NPC209560
0.9343	High Similarity	NPC294409
0.9343	High Similarity	NPC162680
0.9343	High Similarity	NPC181124
0.9338	High Similarity	NPC9985
0.9338	High Similarity	NPC239495
0.9333	High Similarity	NPC188646
0.9333	High Similarity	NPC56031
0.9333	High Similarity	NPC192304
0.9333	High Similarity	NPC139813
0.9333	High Similarity	NPC175098
0.9333	High Similarity	NPC263670
0.9333	High Similarity	NPC472365
0.9333	High Similarity	NPC242294
0.9333	High Similarity	NPC312318
0.9333	High Similarity	NPC337373
0.9328	High Similarity	NPC473584
0.9328	High Similarity	NPC262359
0.9328	High Similarity	NPC113006
0.9328	High Similarity	NPC475589
0.9328	High Similarity	NPC64359
0.9328	High Similarity	NPC308037
0.9328	High Similarity	NPC284424
0.9328	High Similarity	NPC31872
0.9328	High Similarity	NPC278556
0.9306	High Similarity	NPC260895
0.9301	High Similarity	NPC470461
0.9301	High Similarity	NPC159103
0.9301	High Similarity	NPC270465
0.9301	High Similarity	NPC87125
0.9296	High Similarity	NPC476182
0.9296	High Similarity	NPC211466
0.9296	High Similarity	NPC166757
0.9296	High Similarity	NPC44721
0.9296	High Similarity	NPC472918
0.9296	High Similarity	NPC122828
0.9296	High Similarity	NPC259632
0.9296	High Similarity	NPC40086
0.9296	High Similarity	NPC14001
0.9296	High Similarity	NPC176869
0.9296	High Similarity	NPC3779
0.9291	High Similarity	NPC71210
0.9291	High Similarity	NPC234629
0.9291	High Similarity	NPC184649
0.9291	High Similarity	NPC303185
0.9291	High Similarity	NPC311741
0.9286	High Similarity	NPC202981
0.9281	High Similarity	NPC150522
0.9281	High Similarity	NPC284550
0.9281	High Similarity	NPC305355
0.9281	High Similarity	NPC129853
0.9281	High Similarity	NPC188243
0.9281	High Similarity	NPC110228
0.9281	High Similarity	NPC6407
0.9281	High Similarity	NPC475680
0.9281	High Similarity	NPC235239
0.9281	High Similarity	NPC69769
0.9281	High Similarity	NPC76445
0.9275	High Similarity	NPC55162
0.9275	High Similarity	NPC147686
0.9275	High Similarity	NPC90665
0.9275	High Similarity	NPC118813
0.9275	High Similarity	NPC12175
0.9275	High Similarity	NPC472460
0.9275	High Similarity	NPC329225
0.9275	High Similarity	NPC278323
0.9275	High Similarity	NPC309154
0.9275	High Similarity	NPC279668
0.927	High Similarity	NPC121243
0.927	High Similarity	NPC240147
0.9265	High Similarity	NPC286336
0.9259	High Similarity	NPC101294
0.9259	High Similarity	NPC25937
0.9259	High Similarity	NPC473655
0.9259	High Similarity	NPC10971
0.9254	High Similarity	NPC5515
0.9254	High Similarity	NPC270369
0.9254	High Similarity	NPC137264
0.9241	High Similarity	NPC55205
0.9236	High Similarity	NPC267117
0.9236	High Similarity	NPC50728
0.9236	High Similarity	NPC149127
0.9236	High Similarity	NPC188871

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 NPC281207 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	455
0.1-0.2	982
0.2-0.3	1787
0.3-0.4	2715
0.4-0.5	1739
0.5-0.6	1000
0.6-0.7	322
0.7-0.8	96
0.8-0.85	33
0.85-0.9	15
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9568	High Similarity	NPD4378	Clinical (unspecified phase)
0.9275	High Similarity	NPD1549	Phase 2
0.9203	High Similarity	NPD1552	Clinical (unspecified phase)
0.9203	High Similarity	NPD1550	Clinical (unspecified phase)
0.9197	High Similarity	NPD1510	Phase 2
0.9185	High Similarity	NPD1240	Approved
0.9091	High Similarity	NPD1512	Approved
0.9051	High Similarity	NPD1607	Approved
0.9021	High Similarity	NPD7410	Clinical (unspecified phase)
0.8993	High Similarity	NPD2796	Approved
0.8951	High Similarity	NPD6799	Approved
0.8951	High Similarity	NPD1511	Approved
0.8792	High Similarity	NPD2801	Approved
0.8742	High Similarity	NPD7075	Discontinued
0.8725	High Similarity	NPD6801	Discontinued
0.8725	High Similarity	NPD1934	Approved
0.8716	High Similarity	NPD4380	Phase 2
0.8675	High Similarity	NPD3882	Suspended
0.8667	High Similarity	NPD7096	Clinical (unspecified phase)
0.8667	High Similarity	NPD2393	Clinical (unspecified phase)
0.8658	High Similarity	NPD7411	Suspended
0.8618	High Similarity	NPD4381	Clinical (unspecified phase)
0.8611	High Similarity	NPD3750	Approved
0.8609	High Similarity	NPD3817	Phase 2
0.8591	High Similarity	NPD6599	Discontinued
0.8514	High Similarity	NPD5403	Approved
0.8503	High Similarity	NPD5401	Approved
0.8487	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD1551	Phase 2
0.8421	Intermediate Similarity	NPD7819	Suspended
0.8408	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD6166	Phase 2
0.8408	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8357	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD2800	Approved
0.8288	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD3748	Approved
0.8261	Intermediate Similarity	NPD1203	Approved
0.8261	Intermediate Similarity	NPD6797	Phase 2
0.8258	Intermediate Similarity	NPD3749	Approved
0.8247	Intermediate Similarity	NPD5402	Approved
0.8231	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD7251	Discontinued
0.8194	Intermediate Similarity	NPD7768	Phase 2
0.8187	Intermediate Similarity	NPD3818	Discontinued
0.8176	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1243	Approved
0.816	Intermediate Similarity	NPD7808	Phase 3
0.8151	Intermediate Similarity	NPD2344	Approved
0.8146	Intermediate Similarity	NPD920	Approved
0.8137	Intermediate Similarity	NPD7054	Approved
0.8101	Intermediate Similarity	NPD6959	Discontinued
0.8099	Intermediate Similarity	NPD2313	Discontinued
0.8086	Intermediate Similarity	NPD7472	Approved
0.8082	Intermediate Similarity	NPD2935	Discontinued
0.8074	Intermediate Similarity	NPD1548	Phase 1
0.8049	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD9717	Approved
0.8013	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6651	Approved
0.7975	Intermediate Similarity	NPD7074	Phase 3
0.7971	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD422	Phase 1
0.7962	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD6832	Phase 2
0.7933	Intermediate Similarity	NPD2309	Approved
0.7925	Intermediate Similarity	NPD5494	Approved
0.7914	Intermediate Similarity	NPD7286	Phase 2
0.7891	Intermediate Similarity	NPD2799	Discontinued
0.7875	Intermediate Similarity	NPD1247	Approved
0.7862	Intermediate Similarity	NPD919	Approved
0.7862	Intermediate Similarity	NPD943	Approved
0.7847	Intermediate Similarity	NPD3268	Approved
0.7831	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6232	Discontinued
0.7818	Intermediate Similarity	NPD5953	Discontinued
0.7817	Intermediate Similarity	NPD2798	Approved
0.7806	Intermediate Similarity	NPD3226	Approved
0.7801	Intermediate Similarity	NPD3225	Approved
0.7791	Intermediate Similarity	NPD7473	Discontinued
0.7778	Intermediate Similarity	NPD2533	Approved
0.7778	Intermediate Similarity	NPD3926	Phase 2
0.7778	Intermediate Similarity	NPD2534	Approved
0.7778	Intermediate Similarity	NPD2532	Approved
0.7771	Intermediate Similarity	NPD6559	Discontinued
0.777	Intermediate Similarity	NPD4308	Phase 3
0.777	Intermediate Similarity	NPD7033	Discontinued
0.777	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD4628	Phase 3
0.7746	Intermediate Similarity	NPD2797	Approved
0.7718	Intermediate Similarity	NPD6099	Approved
0.7718	Intermediate Similarity	NPD6100	Approved
0.7714	Intermediate Similarity	NPD1610	Phase 2
0.7711	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD4908	Phase 1
0.7687	Intermediate Similarity	NPD1933	Approved
0.7687	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD2654	Approved
0.7681	Intermediate Similarity	NPD9545	Approved
0.7667	Intermediate Similarity	NPD2346	Discontinued
0.7664	Intermediate Similarity	NPD9493	Approved
0.7651	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3266	Approved
0.7622	Intermediate Similarity	NPD3267	Approved
0.761	Intermediate Similarity	NPD1465	Phase 2
0.7603	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5844	Phase 1
0.7574	Intermediate Similarity	NPD1241	Discontinued
0.7569	Intermediate Similarity	NPD1019	Discontinued
0.7568	Intermediate Similarity	NPD447	Suspended
0.7568	Intermediate Similarity	NPD230	Phase 1
0.7562	Intermediate Similarity	NPD4288	Approved
0.7535	Intermediate Similarity	NPD3972	Approved
0.753	Intermediate Similarity	NPD3751	Discontinued
0.7516	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4307	Phase 2
0.7486	Intermediate Similarity	NPD4363	Phase 3
0.7486	Intermediate Similarity	NPD4360	Phase 2
0.7484	Intermediate Similarity	NPD7390	Discontinued
0.7483	Intermediate Similarity	NPD1296	Phase 2
0.7483	Intermediate Similarity	NPD411	Approved
0.7483	Intermediate Similarity	NPD6798	Discontinued
0.7468	Intermediate Similarity	NPD2354	Approved
0.7466	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1471	Phase 3
0.7432	Intermediate Similarity	NPD6233	Phase 2
0.7413	Intermediate Similarity	NPD1481	Phase 2
0.7413	Intermediate Similarity	NPD1608	Approved
0.7397	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1613	Approved
0.7375	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD3764	Approved
0.7346	Intermediate Similarity	NPD2296	Approved
0.7345	Intermediate Similarity	NPD4361	Phase 2
0.7345	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1535	Discovery
0.7337	Intermediate Similarity	NPD1729	Discontinued
0.7333	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5124	Phase 1
0.7329	Intermediate Similarity	NPD6844	Discontinued
0.732	Intermediate Similarity	NPD2353	Approved
0.732	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2403	Approved
0.7289	Intermediate Similarity	NPD3787	Discontinued
0.7273	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1470	Approved
0.7257	Intermediate Similarity	NPD4287	Approved
0.7251	Intermediate Similarity	NPD6104	Discontinued
0.7244	Intermediate Similarity	NPD3887	Approved
0.723	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1652	Phase 2
0.7222	Intermediate Similarity	NPD1201	Approved
0.7219	Intermediate Similarity	NPD6355	Discontinued
0.7215	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD17	Approved
0.7197	Intermediate Similarity	NPD7440	Discontinued
0.7192	Intermediate Similarity	NPD1876	Approved
0.7186	Intermediate Similarity	NPD5711	Approved
0.7186	Intermediate Similarity	NPD5710	Approved
0.7183	Intermediate Similarity	NPD1894	Discontinued
0.7181	Intermediate Similarity	NPD4625	Phase 3
0.717	Intermediate Similarity	NPD5049	Phase 3
0.716	Intermediate Similarity	NPD5890	Approved
0.716	Intermediate Similarity	NPD5889	Approved
0.7152	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3140	Approved
0.7152	Intermediate Similarity	NPD6971	Discontinued
0.7152	Intermediate Similarity	NPD3142	Approved
0.7143	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1164	Approved
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD8434	Phase 2
0.7135	Intermediate Similarity	NPD7584	Approved
0.7134	Intermediate Similarity	NPD6190	Approved
0.7123	Intermediate Similarity	NPD4749	Approved
0.7118	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4661	Approved
0.7107	Intermediate Similarity	NPD4662	Approved
0.7105	Intermediate Similarity	NPD4340	Discontinued
0.7099	Intermediate Similarity	NPD6585	Discontinued
0.7088	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4062	Phase 3
0.7083	Intermediate Similarity	NPD7229	Phase 3
0.708	Intermediate Similarity	NPD74	Approved
0.708	Intermediate Similarity	NPD9266	Approved
0.707	Intermediate Similarity	NPD7003	Approved
0.7067	Intermediate Similarity	NPD3027	Phase 3
0.7047	Intermediate Similarity	NPD2861	Phase 2
0.7047	Intermediate Similarity	NPD9494	Approved
0.7044	Intermediate Similarity	NPD7213	Phase 3
0.7044	Intermediate Similarity	NPD7212	Phase 2
0.7037	Intermediate Similarity	NPD5808	Clinical (unspecified phase)

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