NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	206.02
Volume:	192.536
LogP:	1.061
LogD:	1.032
LogS:	-3.118
# Rotatable Bonds:	0
TPSA:	91.67
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.474
Synthetic Accessibility Score:	2.693
Fsp3:	0.1
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.699
MDCK Permeability:	1.2857375622843392e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.038
20% Bioavailability (F20%):	0.458
30% Bioavailability (F30%):	0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	78.76947784423828%
Volume Distribution (VD):	0.78
Pgp-substrate:	23.8076229095459%

ADMET: Metabolism

CYP1A2-inhibitor:	0.783
CYP1A2-substrate:	0.086
CYP2C19-inhibitor:	0.07
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.216
CYP2C9-substrate:	0.727
CYP2D6-inhibitor:	0.072
CYP2D6-substrate:	0.155
CYP3A4-inhibitor:	0.441
CYP3A4-substrate:	0.145

ADMET: Excretion

Clearance (CL):	12.869
Half-life (T1/2):	0.757

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.039
Drug-inuced Liver Injury (DILI):	0.935
AMES Toxicity:	0.683
Rat Oral Acute Toxicity:	0.167
Maximum Recommended Daily Dose:	0.084
Skin Sensitization:	0.841
Carcinogencity:	0.107
Eye Corrosion:	0.318
Eye Irritation:	0.971
Respiratory Toxicity:	0.354

Download Data

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

Natural Product: NPC179898

Natural Product ID:	NPC179898
*Common Name:**	Flaviolin
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RROPNRTUMVVUED-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H6O5/c11-4-1-5-9(6(12)2-4)7(13)3-8(14)10(5)15/h1-3,11-12,14H
SMILES:	c1c(cc(c2c1C(=O)C(=CC2=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1232770
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO12318	Ayapana amygdalina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19908	Fejervarya limnocharis	Species	Dicroglossidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3748	Astragalus eremophilus	Species	Fabaceae	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
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	43651.58	nM	PMID[478034]

☑ 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 NPC179898 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	391
0.1-0.2	1760
0.2-0.3	4838
0.3-0.4	11734
0.4-0.5	6832
0.5-0.6	5435
0.6-0.7	6282
0.7-0.8	4711
0.8-0.85	518
0.85-0.9	166
0.9-0.95	29
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9219	High Similarity	NPC478190
0.9154	High Similarity	NPC129752
0.912	High Similarity	NPC10926
0.9077	High Similarity	NPC44437
0.9062	High Similarity	NPC147757
0.9048	High Similarity	NPC8745
0.904	High Similarity	NPC13238
0.8968	High Similarity	NPC201728
0.8968	High Similarity	NPC477454
0.8968	High Similarity	NPC262671
0.8939	High Similarity	NPC254847
0.8931	High Similarity	NPC282780
0.8931	High Similarity	NPC166480
0.8906	High Similarity	NPC41263
0.8898	High Similarity	NPC473691
0.8898	High Similarity	NPC231774
0.8872	High Similarity	NPC471905
0.8872	High Similarity	NPC53206
0.8872	High Similarity	NPC53414
0.8837	High Similarity	NPC92624
0.8824	High Similarity	NPC291078
0.8815	High Similarity	NPC156872
0.88	High Similarity	NPC115159
0.88	High Similarity	NPC19174
0.88	High Similarity	NPC267552
0.88	High Similarity	NPC73532
0.88	High Similarity	NPC143427
0.88	High Similarity	NPC224273
0.88	High Similarity	NPC45438
0.878	High Similarity	NPC40649
0.878	High Similarity	NPC209486
0.877	High Similarity	NPC108288
0.8769	High Similarity	NPC259942
0.876	High Similarity	NPC165257
0.8741	High Similarity	NPC190457
0.8741	High Similarity	NPC242994
0.8741	High Similarity	NPC143438
0.8741	High Similarity	NPC138099
0.874	High Similarity	NPC310540
0.8731	High Similarity	NPC471452
0.873	High Similarity	NPC133909
0.873	High Similarity	NPC32032
0.872	High Similarity	NPC297186
0.872	High Similarity	NPC146642
0.8712	High Similarity	NPC267205
0.871	High Similarity	NPC161617
0.8702	High Similarity	NPC469526
0.8702	High Similarity	NPC34070
0.8696	High Similarity	NPC471906
0.8676	High Similarity	NPC203063
0.8676	High Similarity	NPC169452
0.8676	High Similarity	NPC181560
0.8651	High Similarity	NPC242895
0.8651	High Similarity	NPC156139
0.864	High Similarity	NPC294037
0.8636	High Similarity	NPC17843
0.8636	High Similarity	NPC135801
0.8633	High Similarity	NPC28632
0.8626	High Similarity	NPC17840
0.8626	High Similarity	NPC26697
0.8626	High Similarity	NPC247477
0.8615	High Similarity	NPC24869
0.8613	High Similarity	NPC204045
0.8613	High Similarity	NPC305845
0.8613	High Similarity	NPC290550
0.8613	High Similarity	NPC110810
0.8613	High Similarity	NPC246638
0.8605	High Similarity	NPC51037
0.8605	High Similarity	NPC1991
0.8603	High Similarity	NPC52358
0.8593	High Similarity	NPC290030
0.8582	High Similarity	NPC290803
0.8571	High Similarity	NPC48036
0.8571	High Similarity	NPC248363
0.8571	High Similarity	NPC149246
0.8561	High Similarity	NPC475201
0.8561	High Similarity	NPC219892
0.8561	High Similarity	NPC189823
0.856	High Similarity	NPC232178
0.856	High Similarity	NPC158222
0.8551	High Similarity	NPC193555
0.8551	High Similarity	NPC73061
0.8551	High Similarity	NPC135524
0.855	High Similarity	NPC102829
0.855	High Similarity	NPC278928
0.855	High Similarity	NPC120488
0.8519	High Similarity	NPC191976
0.8519	High Similarity	NPC86524
0.8507	High Similarity	NPC175943
0.8507	High Similarity	NPC474519
0.8504	High Similarity	NPC215392
0.8496	Intermediate Similarity	NPC175738
0.8496	Intermediate Similarity	NPC309430
0.8492	Intermediate Similarity	NPC285829
0.8492	Intermediate Similarity	NPC159525
0.8492	Intermediate Similarity	NPC206778
0.8489	Intermediate Similarity	NPC238629
0.8485	Intermediate Similarity	NPC117609
0.8485	Intermediate Similarity	NPC62219
0.8485	Intermediate Similarity	NPC233056
0.848	Intermediate Similarity	NPC241089
0.8473	Intermediate Similarity	NPC237225
0.8473	Intermediate Similarity	NPC95537
0.8467	Intermediate Similarity	NPC92655
0.8467	Intermediate Similarity	NPC472903
0.8462	Intermediate Similarity	NPC3224
0.8444	Intermediate Similarity	NPC161632
0.8444	Intermediate Similarity	NPC14377
0.8438	Intermediate Similarity	NPC309765
0.8438	Intermediate Similarity	NPC91105
0.8433	Intermediate Similarity	NPC180261
0.8433	Intermediate Similarity	NPC37299
0.8433	Intermediate Similarity	NPC153783
0.8429	Intermediate Similarity	NPC244691
0.8429	Intermediate Similarity	NPC48762
0.8429	Intermediate Similarity	NPC193703
0.8429	Intermediate Similarity	NPC21599
0.8429	Intermediate Similarity	NPC19896
0.8421	Intermediate Similarity	NPC198249
0.8417	Intermediate Similarity	NPC137649
0.8417	Intermediate Similarity	NPC49108
0.8409	Intermediate Similarity	NPC474998
0.8409	Intermediate Similarity	NPC109123
0.8409	Intermediate Similarity	NPC99731
0.84	Intermediate Similarity	NPC230349
0.8397	Intermediate Similarity	NPC100067
0.8397	Intermediate Similarity	NPC209959
0.8397	Intermediate Similarity	NPC190043
0.8397	Intermediate Similarity	NPC169250
0.8397	Intermediate Similarity	NPC324209
0.8397	Intermediate Similarity	NPC23126
0.8397	Intermediate Similarity	NPC103356
0.8397	Intermediate Similarity	NPC266689
0.8397	Intermediate Similarity	NPC98254
0.8397	Intermediate Similarity	NPC30501
0.8397	Intermediate Similarity	NPC162612
0.8397	Intermediate Similarity	NPC105157
0.8397	Intermediate Similarity	NPC72158
0.8394	Intermediate Similarity	NPC472403
0.8394	Intermediate Similarity	NPC9121
0.8394	Intermediate Similarity	NPC177307
0.8394	Intermediate Similarity	NPC175552
0.8385	Intermediate Similarity	NPC103540
0.8385	Intermediate Similarity	NPC475733
0.8382	Intermediate Similarity	NPC242712
0.8382	Intermediate Similarity	NPC223836
0.8382	Intermediate Similarity	NPC118919
0.8382	Intermediate Similarity	NPC235115
0.8382	Intermediate Similarity	NPC315275
0.8372	Intermediate Similarity	NPC65761
0.8372	Intermediate Similarity	NPC472029
0.8369	Intermediate Similarity	NPC34482
0.8359	Intermediate Similarity	NPC226275
0.8359	Intermediate Similarity	NPC198336
0.8359	Intermediate Similarity	NPC196976
0.8359	Intermediate Similarity	NPC303737
0.8358	Intermediate Similarity	NPC65060
0.8346	Intermediate Similarity	NPC198305
0.8345	Intermediate Similarity	NPC244923
0.8345	Intermediate Similarity	NPC472904
0.8333	Intermediate Similarity	NPC21305
0.8333	Intermediate Similarity	NPC162939
0.8333	Intermediate Similarity	NPC247250
0.8333	Intermediate Similarity	NPC283844
0.8333	Intermediate Similarity	NPC473017
0.8333	Intermediate Similarity	NPC57380
0.8333	Intermediate Similarity	NPC268052
0.8333	Intermediate Similarity	NPC767
0.8333	Intermediate Similarity	NPC221777
0.8321	Intermediate Similarity	NPC170742
0.8321	Intermediate Similarity	NPC15837
0.8321	Intermediate Similarity	NPC474849
0.8321	Intermediate Similarity	NPC474771
0.8321	Intermediate Similarity	NPC149372
0.8321	Intermediate Similarity	NPC53001
0.8321	Intermediate Similarity	NPC178467
0.8321	Intermediate Similarity	NPC267846
0.8321	Intermediate Similarity	NPC65837
0.8321	Intermediate Similarity	NPC62952
0.831	Intermediate Similarity	NPC470570
0.8309	Intermediate Similarity	NPC61153
0.8309	Intermediate Similarity	NPC283590
0.8309	Intermediate Similarity	NPC182496
0.8309	Intermediate Similarity	NPC180905
0.8309	Intermediate Similarity	NPC70859
0.8309	Intermediate Similarity	NPC130899
0.8309	Intermediate Similarity	NPC278375
0.8306	Intermediate Similarity	NPC276111
0.8306	Intermediate Similarity	NPC118288
0.8296	Intermediate Similarity	NPC254603
0.8296	Intermediate Similarity	NPC171968
0.8295	Intermediate Similarity	NPC283514
0.8295	Intermediate Similarity	NPC307174
0.8286	Intermediate Similarity	NPC474961
0.8273	Intermediate Similarity	NPC183345
0.8264	Intermediate Similarity	NPC84142
0.8264	Intermediate Similarity	NPC77325
0.8264	Intermediate Similarity	NPC4423
0.8261	Intermediate Similarity	NPC33144
0.8261	Intermediate Similarity	NPC191835

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 NPC179898 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	1003
0.2-0.3	1774
0.3-0.4	2927
0.4-0.5	1830
0.5-0.6	876
0.6-0.7	282
0.7-0.8	85
0.8-0.85	3
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8939	High Similarity	NPD651	Clinical (unspecified phase)
0.8939	High Similarity	NPD1509	Clinical (unspecified phase)
0.877	High Similarity	NPD405	Clinical (unspecified phase)
0.8636	High Similarity	NPD943	Approved
0.8385	Intermediate Similarity	NPD1470	Approved
0.8201	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD1201	Approved
0.8042	Intermediate Similarity	NPD7390	Discontinued
0.8015	Intermediate Similarity	NPD9269	Phase 2
0.7986	Intermediate Similarity	NPD1510	Phase 2
0.7984	Intermediate Similarity	NPD9268	Approved
0.7956	Intermediate Similarity	NPD1240	Approved
0.7842	Intermediate Similarity	NPD1607	Approved
0.7808	Intermediate Similarity	NPD1512	Approved
0.7692	Intermediate Similarity	NPD1549	Phase 2
0.768	Intermediate Similarity	NPD74	Approved
0.768	Intermediate Similarity	NPD9266	Approved
0.7676	Intermediate Similarity	NPD5408	Approved
0.7676	Intermediate Similarity	NPD5406	Approved
0.7676	Intermediate Similarity	NPD5404	Approved
0.7676	Intermediate Similarity	NPD5405	Approved
0.7671	Intermediate Similarity	NPD1511	Approved
0.7622	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD9263	Approved
0.76	Intermediate Similarity	NPD9264	Approved
0.76	Intermediate Similarity	NPD9267	Approved
0.7586	Intermediate Similarity	NPD3750	Approved
0.7582	Intermediate Similarity	NPD3882	Suspended
0.7574	Intermediate Similarity	NPD1164	Approved
0.7518	Intermediate Similarity	NPD230	Phase 1
0.7517	Intermediate Similarity	NPD2800	Approved
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD2533	Approved
0.7466	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7819	Suspended
0.7419	Intermediate Similarity	NPD3749	Approved
0.7365	Intermediate Similarity	NPD3300	Phase 2
0.7348	Intermediate Similarity	NPD9493	Approved
0.7342	Intermediate Similarity	NPD6232	Discontinued
0.7338	Intermediate Similarity	NPD2801	Approved
0.7328	Intermediate Similarity	NPD9281	Approved
0.7315	Intermediate Similarity	NPD6799	Approved
0.7313	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7473	Discontinued
0.728	Intermediate Similarity	NPD9261	Approved
0.7273	Intermediate Similarity	NPD1934	Approved
0.7267	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD2344	Approved
0.7255	Intermediate Similarity	NPD4380	Phase 2
0.7241	Intermediate Similarity	NPD3748	Approved
0.7241	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1465	Phase 2
0.7222	Intermediate Similarity	NPD6651	Approved
0.7209	Intermediate Similarity	NPD4750	Phase 3
0.7197	Intermediate Similarity	NPD7075	Discontinued
0.7192	Intermediate Similarity	NPD1551	Phase 2
0.7192	Intermediate Similarity	NPD2796	Approved
0.7192	Intermediate Similarity	NPD2935	Discontinued
0.7183	Intermediate Similarity	NPD3764	Approved
0.717	Intermediate Similarity	NPD6959	Discontinued
0.7143	Intermediate Similarity	NPD6599	Discontinued
0.712	Intermediate Similarity	NPD1242	Phase 1
0.7115	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD9545	Approved
0.7078	Intermediate Similarity	NPD3226	Approved
0.7071	Intermediate Similarity	NPD1203	Approved
0.707	Intermediate Similarity	NPD3817	Phase 2
0.707	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2309	Approved
0.7063	Intermediate Similarity	NPD846	Approved
0.7063	Intermediate Similarity	NPD940	Approved
0.7047	Intermediate Similarity	NPD1243	Approved
0.7039	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6166	Phase 2
0.7037	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1471	Phase 3
0.7007	Intermediate Similarity	NPD2932	Approved
0.6987	Remote Similarity	NPD7411	Suspended
0.6981	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD9717	Approved
0.6975	Remote Similarity	NPD3926	Phase 2
0.6962	Remote Similarity	NPD5402	Approved
0.6959	Remote Similarity	NPD6099	Approved
0.6959	Remote Similarity	NPD6100	Approved
0.6951	Remote Similarity	NPD3818	Discontinued
0.6951	Remote Similarity	NPD3751	Discontinued
0.6944	Remote Similarity	NPD411	Approved
0.6943	Remote Similarity	NPD6801	Discontinued
0.6928	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD447	Suspended
0.6918	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5710	Approved
0.6914	Remote Similarity	NPD5711	Approved
0.6913	Remote Similarity	NPD2346	Discontinued
0.6908	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2799	Discontinued
0.6887	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3019	Approved
0.6852	Remote Similarity	NPD1247	Approved
0.6845	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5403	Approved
0.6839	Remote Similarity	NPD920	Approved
0.6832	Remote Similarity	NPD919	Approved
0.6829	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6797	Phase 2
0.6821	Remote Similarity	NPD2654	Approved
0.6818	Remote Similarity	NPD5401	Approved
0.6813	Remote Similarity	NPD7768	Phase 2
0.679	Remote Similarity	NPD5494	Approved
0.6786	Remote Similarity	NPD7251	Discontinued
0.6783	Remote Similarity	NPD2798	Approved
0.6781	Remote Similarity	NPD520	Approved
0.6746	Remote Similarity	NPD7808	Phase 3
0.6736	Remote Similarity	NPD9494	Approved
0.6732	Remote Similarity	NPD6190	Approved
0.6726	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5953	Discontinued
0.6724	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD2313	Discontinued
0.6707	Remote Similarity	NPD6020	Phase 2
0.6707	Remote Similarity	NPD7054	Approved
0.6707	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1237	Approved
0.6686	Remote Similarity	NPD8150	Discontinued
0.6667	Remote Similarity	NPD7074	Phase 3
0.6667	Remote Similarity	NPD7472	Approved
0.6667	Remote Similarity	NPD422	Phase 1
0.6646	Remote Similarity	NPD4288	Approved
0.6643	Remote Similarity	NPD1876	Approved
0.6607	Remote Similarity	NPD5844	Phase 1
0.6601	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD1755	Approved
0.6554	Remote Similarity	NPD6534	Approved
0.6554	Remote Similarity	NPD6535	Approved
0.6549	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD2296	Approved
0.6527	Remote Similarity	NPD2403	Approved
0.6519	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4287	Approved
0.6509	Remote Similarity	NPD7286	Phase 2
0.6506	Remote Similarity	NPD3787	Discontinued
0.6503	Remote Similarity	NPD1608	Approved
0.6503	Remote Similarity	NPD3972	Approved
0.6496	Remote Similarity	NPD1241	Discontinued
0.6491	Remote Similarity	NPD6559	Discontinued
0.6491	Remote Similarity	NPD5029	Approved
0.6491	Remote Similarity	NPD5027	Approved
0.6491	Remote Similarity	NPD5031	Approved
0.6484	Remote Similarity	NPD288	Approved
0.6479	Remote Similarity	NPD3026	Approved
0.6479	Remote Similarity	NPD3023	Approved
0.6467	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD6777	Approved
0.6464	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD6780	Approved
0.6464	Remote Similarity	NPD6778	Approved
0.6464	Remote Similarity	NPD6781	Approved
0.6464	Remote Similarity	NPD6779	Approved
0.6464	Remote Similarity	NPD6782	Approved
0.6464	Remote Similarity	NPD6776	Approved
0.6463	Remote Similarity	NPD6832	Phase 2
0.6462	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4749	Approved
0.6454	Remote Similarity	NPD3024	Approved
0.6454	Remote Similarity	NPD3025	Approved
0.6453	Remote Similarity	NPD4955	Approved
0.6453	Remote Similarity	NPD5034	Approved
0.6453	Remote Similarity	NPD36	Approved
0.6453	Remote Similarity	NPD5026	Approved
0.6453	Remote Similarity	NPD5028	Approved
0.6453	Remote Similarity	NPD4954	Approved
0.6453	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4628	Phase 3
0.6444	Remote Similarity	NPD7699	Phase 2
0.6444	Remote Similarity	NPD7700	Phase 2
0.6434	Remote Similarity	NPD1610	Phase 2
0.6416	Remote Similarity	NPD5035	Approved
0.6414	Remote Similarity	NPD1283	Approved
0.6406	Remote Similarity	NPD844	Approved
0.64	Remote Similarity	NPD5037	Approved
0.64	Remote Similarity	NPD5038	Approved
0.64	Remote Similarity	NPD9258	Approved
0.64	Remote Similarity	NPD9256	Approved
0.6395	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD5030	Phase 2
0.6395	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4878	Approved
0.6385	Remote Similarity	NPD3020	Approved
0.6383	Remote Similarity	NPD1759	Phase 1
0.6383	Remote Similarity	NPD1548	Phase 1
0.6376	Remote Similarity	NPD3268	Approved
0.6376	Remote Similarity	NPD1296	Phase 2

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