NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.09
Volume:	282.198
LogP:	3.949
LogD:	3.215
LogS:	-5.177
# Rotatable Bonds:	2
TPSA:	39.44
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.708
Synthetic Accessibility Score:	1.858
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.675
MDCK Permeability:	2.2109272322268225e-05
Pgp-inhibitor:	0.455
Pgp-substrate:	0.577
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.031
30% Bioavailability (F30%):	0.922

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079
Plasma Protein Binding (PPB):	97.58110809326172%
Volume Distribution (VD):	0.585
Pgp-substrate:	1.8724281787872314%

ADMET: Metabolism

CYP1A2-inhibitor:	0.922
CYP1A2-substrate:	0.938
CYP2C19-inhibitor:	0.638
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.577
CYP2C9-substrate:	0.903
CYP2D6-inhibitor:	0.659
CYP2D6-substrate:	0.932
CYP3A4-inhibitor:	0.584
CYP3A4-substrate:	0.426

ADMET: Excretion

Clearance (CL):	3.428
Half-life (T1/2):	0.166

ADMET: Toxicity

hERG Blockers:	0.242
Human Hepatotoxicity (H-HT):	0.121
Drug-inuced Liver Injury (DILI):	0.859
AMES Toxicity:	0.524
Rat Oral Acute Toxicity:	0.316
Maximum Recommended Daily Dose:	0.201
Skin Sensitization:	0.401
Carcinogencity:	0.527
Eye Corrosion:	0.011
Eye Irritation:	0.958
Respiratory Toxicity:	0.296

Download Data

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

Natural Product: NPC474264

Natural Product ID:	NPC474264
*Common Name:**	7-O-Methylformononetin
IUPAC Name:	3-(4-methoxyphenyl)-7-methylchromen-4-one
Synonyms:	7-O-Methylformononetin
Standard InCHIKey:	PJZVNCZNTQDLPS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O3/c1-11-3-8-14-16(9-11)20-10-15(17(14)18)12-4-6-13(19-2)7-5-12/h3-10H,1-2H3
SMILES:	CC1=CC2=C(C=C1)C(=O)C(=CO2)C3=CC=C(C=C3)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464456
PubChem CID:	584452
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002606] 4'-O-methylated isoflavonoids [CHEMONTID:0002687] 4'-O-methylisoflavones

*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
NPO20912	Wisteria brachybotrys	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2853205]
NPO20912	Wisteria brachybotrys	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
Others	10

Activity Type	# Activity
Cell Line	5
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	34.3	%	PMID[473481]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	100.0	%	PMID[473481]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	80.0	%	PMID[473481]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[473481]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[473481]
NPT2	Others	Unspecified		Activity	=	90.2	%	PMID[473481]
NPT2	Others	Unspecified		Activity	=	30.3	%	PMID[473481]

☑ 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 NPC474264 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	492
0.1-0.2	1878
0.2-0.3	4788
0.3-0.4	12499
0.4-0.5	5152
0.5-0.6	5141
0.6-0.7	7419
0.7-0.8	4911
0.8-0.85	360
0.85-0.9	52
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.952	High Similarity	NPC474340
0.944	High Similarity	NPC301717
0.9344	High Similarity	NPC56332
0.9328	High Similarity	NPC201284
0.9244	High Similarity	NPC171023
0.8976	High Similarity	NPC57552
0.8968	High Similarity	NPC298884
0.896	High Similarity	NPC2771
0.8898	High Similarity	NPC125887
0.8852	High Similarity	NPC54243
0.8846	High Similarity	NPC182428
0.8824	High Similarity	NPC279916
0.879	High Similarity	NPC314329
0.8779	High Similarity	NPC223354
0.8779	High Similarity	NPC1249
0.877	High Similarity	NPC32298
0.8769	High Similarity	NPC183103
0.8699	High Similarity	NPC35744
0.8689	High Similarity	NPC469954
0.8651	High Similarity	NPC182646
0.8647	High Similarity	NPC77955
0.8647	High Similarity	NPC324929
0.8636	High Similarity	NPC292998
0.8603	High Similarity	NPC171094
0.8594	High Similarity	NPC177925
0.8594	High Similarity	NPC474737
0.8593	High Similarity	NPC223336
0.8582	High Similarity	NPC254741
0.855	High Similarity	NPC239134
0.855	High Similarity	NPC164295
0.854	High Similarity	NPC185607
0.8529	High Similarity	NPC109232
0.8527	High Similarity	NPC428300
0.8519	High Similarity	NPC303644
0.8519	High Similarity	NPC7013
0.8519	High Similarity	NPC116632
0.8519	High Similarity	NPC209560
0.8519	High Similarity	NPC181124
0.8519	High Similarity	NPC294409
0.8519	High Similarity	NPC162680
0.8519	High Similarity	NPC212767
0.8516	High Similarity	NPC224657
0.8512	High Similarity	NPC53953
0.8489	Intermediate Similarity	NPC49282
0.8489	Intermediate Similarity	NPC469764
0.8485	Intermediate Similarity	NPC284424
0.848	Intermediate Similarity	NPC470092
0.8473	Intermediate Similarity	NPC7569
0.8462	Intermediate Similarity	NPC475017
0.8456	Intermediate Similarity	NPC309154
0.8456	Intermediate Similarity	NPC55162
0.8456	Intermediate Similarity	NPC278323
0.8456	Intermediate Similarity	NPC1268
0.8456	Intermediate Similarity	NPC12175
0.8456	Intermediate Similarity	NPC279668
0.8456	Intermediate Similarity	NPC90665
0.8444	Intermediate Similarity	NPC186647
0.8444	Intermediate Similarity	NPC193792
0.8429	Intermediate Similarity	NPC469758
0.8421	Intermediate Similarity	NPC470406
0.8409	Intermediate Similarity	NPC477412
0.8397	Intermediate Similarity	NPC211120
0.8394	Intermediate Similarity	NPC136095
0.8394	Intermediate Similarity	NPC295384
0.8385	Intermediate Similarity	NPC45537
0.8385	Intermediate Similarity	NPC22783
0.8385	Intermediate Similarity	NPC41721
0.8385	Intermediate Similarity	NPC470841
0.838	Intermediate Similarity	NPC474052
0.837	Intermediate Similarity	NPC234560
0.837	Intermediate Similarity	NPC39426
0.837	Intermediate Similarity	NPC141934
0.8359	Intermediate Similarity	NPC93730
0.8357	Intermediate Similarity	NPC478019
0.8357	Intermediate Similarity	NPC471590
0.8347	Intermediate Similarity	NPC23332
0.8346	Intermediate Similarity	NPC278556
0.8345	Intermediate Similarity	NPC167663
0.8345	Intermediate Similarity	NPC53016
0.8345	Intermediate Similarity	NPC476054
0.8333	Intermediate Similarity	NPC101366
0.8333	Intermediate Similarity	NPC48624
0.8333	Intermediate Similarity	NPC259166
0.8333	Intermediate Similarity	NPC219917
0.8333	Intermediate Similarity	NPC172250
0.8333	Intermediate Similarity	NPC204985
0.8333	Intermediate Similarity	NPC213659
0.8333	Intermediate Similarity	NPC149780
0.8333	Intermediate Similarity	NPC124365
0.8333	Intermediate Similarity	NPC80962
0.8333	Intermediate Similarity	NPC326109
0.8333	Intermediate Similarity	NPC215311
0.8333	Intermediate Similarity	NPC228184
0.8333	Intermediate Similarity	NPC144118
0.8333	Intermediate Similarity	NPC278787
0.8309	Intermediate Similarity	NPC235428
0.8309	Intermediate Similarity	NPC472364
0.8309	Intermediate Similarity	NPC284184
0.8309	Intermediate Similarity	NPC473391
0.8309	Intermediate Similarity	NPC301341
0.8309	Intermediate Similarity	NPC87545
0.8308	Intermediate Similarity	NPC237868
0.8298	Intermediate Similarity	NPC120924
0.8298	Intermediate Similarity	NPC12377
0.8298	Intermediate Similarity	NPC130176
0.8298	Intermediate Similarity	NPC99454
0.8298	Intermediate Similarity	NPC196114
0.8298	Intermediate Similarity	NPC216314
0.8298	Intermediate Similarity	NPC195919
0.8296	Intermediate Similarity	NPC125269
0.8296	Intermediate Similarity	NPC217914
0.8295	Intermediate Similarity	NPC470162
0.8295	Intermediate Similarity	NPC75432
0.8295	Intermediate Similarity	NPC470163
0.8295	Intermediate Similarity	NPC193805
0.8286	Intermediate Similarity	NPC189650
0.8284	Intermediate Similarity	NPC101294
0.8284	Intermediate Similarity	NPC473655
0.8273	Intermediate Similarity	NPC55832
0.8273	Intermediate Similarity	NPC69755
0.8273	Intermediate Similarity	NPC24075
0.8273	Intermediate Similarity	NPC469404
0.8273	Intermediate Similarity	NPC268204
0.8273	Intermediate Similarity	NPC52789
0.8273	Intermediate Similarity	NPC26051
0.8271	Intermediate Similarity	NPC141549
0.8271	Intermediate Similarity	NPC279596
0.8264	Intermediate Similarity	NPC183648
0.8261	Intermediate Similarity	NPC283429
0.8261	Intermediate Similarity	NPC109007
0.8248	Intermediate Similarity	NPC228661
0.8248	Intermediate Similarity	NPC44573
0.8248	Intermediate Similarity	NPC103001
0.824	Intermediate Similarity	NPC217423
0.824	Intermediate Similarity	NPC45104
0.8239	Intermediate Similarity	NPC474999
0.8239	Intermediate Similarity	NPC478018
0.8235	Intermediate Similarity	NPC471670
0.8235	Intermediate Similarity	NPC99854
0.8235	Intermediate Similarity	NPC232996
0.8226	Intermediate Similarity	NPC188907
0.8217	Intermediate Similarity	NPC141252
0.8217	Intermediate Similarity	NPC11799
0.8214	Intermediate Similarity	NPC215451
0.8214	Intermediate Similarity	NPC1534
0.8214	Intermediate Similarity	NPC277369
0.8209	Intermediate Similarity	NPC308037
0.8209	Intermediate Similarity	NPC262359
0.8209	Intermediate Similarity	NPC313618
0.8209	Intermediate Similarity	NPC186097
0.8209	Intermediate Similarity	NPC475009
0.8209	Intermediate Similarity	NPC475008
0.8209	Intermediate Similarity	NPC64359
0.8201	Intermediate Similarity	NPC472409
0.8201	Intermediate Similarity	NPC253822
0.8197	Intermediate Similarity	NPC54626
0.8195	Intermediate Similarity	NPC245395
0.8194	Intermediate Similarity	NPC255641
0.8194	Intermediate Similarity	NPC290954
0.8188	Intermediate Similarity	NPC470407
0.8182	Intermediate Similarity	NPC80710
0.8182	Intermediate Similarity	NPC203747
0.8182	Intermediate Similarity	NPC139364
0.8182	Intermediate Similarity	NPC254702
0.8182	Intermediate Similarity	NPC194653
0.8175	Intermediate Similarity	NPC161196
0.8175	Intermediate Similarity	NPC41567
0.8175	Intermediate Similarity	NPC213603
0.8169	Intermediate Similarity	NPC300540
0.8162	Intermediate Similarity	NPC95485
0.8162	Intermediate Similarity	NPC22222
0.8162	Intermediate Similarity	NPC22644
0.8162	Intermediate Similarity	NPC281513
0.8162	Intermediate Similarity	NPC89504
0.8162	Intermediate Similarity	NPC286336
0.8162	Intermediate Similarity	NPC66705
0.8162	Intermediate Similarity	NPC88065
0.816	Intermediate Similarity	NPC19290
0.816	Intermediate Similarity	NPC316062
0.8156	Intermediate Similarity	NPC293201
0.8156	Intermediate Similarity	NPC38065
0.8156	Intermediate Similarity	NPC242893
0.8156	Intermediate Similarity	NPC117836
0.8156	Intermediate Similarity	NPC113089
0.8156	Intermediate Similarity	NPC476178
0.8156	Intermediate Similarity	NPC182842
0.8156	Intermediate Similarity	NPC475705
0.8156	Intermediate Similarity	NPC51887
0.8154	Intermediate Similarity	NPC4012
0.8148	Intermediate Similarity	NPC205468
0.8148	Intermediate Similarity	NPC257756
0.8148	Intermediate Similarity	NPC212631
0.8148	Intermediate Similarity	NPC87231
0.8148	Intermediate Similarity	NPC129132
0.8143	Intermediate Similarity	NPC49108
0.8138	Intermediate Similarity	NPC118427
0.8134	Intermediate Similarity	NPC205360
0.8134	Intermediate Similarity	NPC324488
0.8129	Intermediate Similarity	NPC11566
0.8125	Intermediate Similarity	NPC38545

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 NPC474264 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	457
0.1-0.2	992
0.2-0.3	1356
0.3-0.4	2680
0.4-0.5	1894
0.5-0.6	1155
0.6-0.7	470
0.7-0.8	132
0.8-0.85	12
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.879	High Similarity	NPD1547	Clinical (unspecified phase)
0.874	High Similarity	NPD2798	Approved
0.8582	High Similarity	NPD2796	Approved
0.8571	High Similarity	NPD3972	Approved
0.837	Intermediate Similarity	NPD1510	Phase 2
0.8358	Intermediate Similarity	NPD1607	Approved
0.8309	Intermediate Similarity	NPD2935	Discontinued
0.8295	Intermediate Similarity	NPD1876	Approved
0.8254	Intermediate Similarity	NPD1651	Approved
0.8248	Intermediate Similarity	NPD2346	Discontinued
0.8211	Intermediate Similarity	NPD1241	Discontinued
0.8209	Intermediate Similarity	NPD1240	Approved
0.8195	Intermediate Similarity	NPD2313	Discontinued
0.8182	Intermediate Similarity	NPD6832	Phase 2
0.8148	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD2799	Discontinued
0.8074	Intermediate Similarity	NPD4307	Phase 2
0.8062	Intermediate Similarity	NPD1281	Approved
0.7986	Intermediate Similarity	NPD2344	Approved
0.7929	Intermediate Similarity	NPD1549	Phase 2
0.7879	Intermediate Similarity	NPD1283	Approved
0.7857	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD3748	Approved
0.7842	Intermediate Similarity	NPD4308	Phase 3
0.7829	Intermediate Similarity	NPD5691	Approved
0.7817	Intermediate Similarity	NPD7003	Approved
0.7812	Intermediate Similarity	NPD5536	Phase 2
0.7786	Intermediate Similarity	NPD1201	Approved
0.7785	Intermediate Similarity	NPD7819	Suspended
0.7762	Intermediate Similarity	NPD2309	Approved
0.7755	Intermediate Similarity	NPD3226	Approved
0.7754	Intermediate Similarity	NPD1933	Approved
0.7746	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1471	Phase 3
0.7718	Intermediate Similarity	NPD1934	Approved
0.7703	Intermediate Similarity	NPD4380	Phase 2
0.7703	Intermediate Similarity	NPD6599	Discontinued
0.7687	Intermediate Similarity	NPD3266	Approved
0.7687	Intermediate Similarity	NPD3267	Approved
0.7687	Intermediate Similarity	NPD1203	Approved
0.7687	Intermediate Similarity	NPD1470	Approved
0.7681	Intermediate Similarity	NPD2979	Phase 3
0.7667	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD411	Approved
0.766	Intermediate Similarity	NPD1551	Phase 2
0.7655	Intermediate Similarity	NPD6799	Approved
0.7655	Intermediate Similarity	NPD1511	Approved
0.7639	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD7458	Discontinued
0.7634	Intermediate Similarity	NPD4626	Approved
0.763	Intermediate Similarity	NPD1019	Discontinued
0.7622	Intermediate Similarity	NPD1243	Approved
0.7616	Intermediate Similarity	NPD3817	Phase 2
0.7603	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6844	Discontinued
0.7597	Intermediate Similarity	NPD9493	Approved
0.7594	Intermediate Similarity	NPD9717	Approved
0.7586	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD3750	Approved
0.7569	Intermediate Similarity	NPD4628	Phase 3
0.7569	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD2797	Approved
0.7552	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1512	Approved
0.7551	Intermediate Similarity	NPD6273	Approved
0.755	Intermediate Similarity	NPD2801	Approved
0.755	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD7411	Suspended
0.7532	Intermediate Similarity	NPD5494	Approved
0.75	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD17	Approved
0.7483	Intermediate Similarity	NPD6280	Approved
0.7483	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5401	Approved
0.7483	Intermediate Similarity	NPD4661	Approved
0.7483	Intermediate Similarity	NPD6279	Approved
0.7483	Intermediate Similarity	NPD6801	Discontinued
0.7483	Intermediate Similarity	NPD4662	Approved
0.7465	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD3882	Suspended
0.7445	Intermediate Similarity	NPD9494	Approved
0.7429	Intermediate Similarity	NPD3140	Approved
0.7429	Intermediate Similarity	NPD3142	Approved
0.7413	Intermediate Similarity	NPD2531	Phase 2
0.7413	Intermediate Similarity	NPD2438	Suspended
0.741	Intermediate Similarity	NPD6798	Discontinued
0.741	Intermediate Similarity	NPD3268	Approved
0.7407	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7075	Discontinued
0.7403	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5402	Approved
0.7386	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5403	Approved
0.7383	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD447	Suspended
0.7372	Intermediate Similarity	NPD6959	Discontinued
0.7364	Intermediate Similarity	NPD5283	Phase 1
0.736	Intermediate Similarity	NPD3134	Approved
0.7357	Intermediate Similarity	NPD8032	Phase 2
0.7355	Intermediate Similarity	NPD919	Approved
0.7348	Intermediate Similarity	NPD1894	Discontinued
0.7344	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7768	Phase 2
0.7333	Intermediate Similarity	NPD1608	Approved
0.7325	Intermediate Similarity	NPD6232	Discontinued
0.7323	Intermediate Similarity	NPD5451	Approved
0.7305	Intermediate Similarity	NPD943	Approved
0.7303	Intermediate Similarity	NPD5889	Approved
0.7303	Intermediate Similarity	NPD5890	Approved
0.7299	Intermediate Similarity	NPD1164	Approved
0.7296	Intermediate Similarity	NPD7473	Discontinued
0.7293	Intermediate Similarity	NPD5585	Approved
0.7292	Intermediate Similarity	NPD5408	Approved
0.7292	Intermediate Similarity	NPD5404	Approved
0.7292	Intermediate Similarity	NPD5406	Approved
0.7292	Intermediate Similarity	NPD5405	Approved
0.7287	Intermediate Similarity	NPD5535	Approved
0.7284	Intermediate Similarity	NPD6559	Discontinued
0.7279	Intermediate Similarity	NPD3887	Approved
0.7261	Intermediate Similarity	NPD1247	Approved
0.7258	Intermediate Similarity	NPD9261	Approved
0.7254	Intermediate Similarity	NPD6355	Discontinued
0.725	Intermediate Similarity	NPD3818	Discontinued
0.7248	Intermediate Similarity	NPD2532	Approved
0.7248	Intermediate Similarity	NPD2533	Approved
0.7248	Intermediate Similarity	NPD2534	Approved
0.7241	Intermediate Similarity	NPD2353	Approved
0.7241	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1778	Approved
0.7239	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6166	Phase 2
0.7218	Intermediate Similarity	NPD9545	Approved
0.7185	Intermediate Similarity	NPD3847	Discontinued
0.7172	Intermediate Similarity	NPD4476	Approved
0.7172	Intermediate Similarity	NPD4477	Approved
0.717	Intermediate Similarity	NPD3926	Phase 2
0.7165	Intermediate Similarity	NPD1358	Approved
0.7163	Intermediate Similarity	NPD3764	Approved
0.7163	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2296	Approved
0.7154	Intermediate Similarity	NPD1238	Approved
0.7143	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2654	Approved
0.7143	Intermediate Similarity	NPD9697	Approved
0.7133	Intermediate Similarity	NPD4618	Approved
0.7133	Intermediate Similarity	NPD4622	Approved
0.7132	Intermediate Similarity	NPD1611	Approved
0.7125	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6585	Discontinued
0.7107	Intermediate Similarity	NPD6808	Phase 2
0.7103	Intermediate Similarity	NPD7033	Discontinued
0.7099	Intermediate Similarity	NPD7054	Approved
0.707	Intermediate Similarity	NPD3749	Approved
0.7067	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7390	Discontinued
0.7059	Intermediate Similarity	NPD2649	Approved
0.7059	Intermediate Similarity	NPD3496	Discontinued
0.7059	Intermediate Similarity	NPD2651	Approved
0.7055	Intermediate Similarity	NPD7074	Phase 3
0.7055	Intermediate Similarity	NPD6100	Approved
0.7055	Intermediate Similarity	NPD6099	Approved
0.7055	Intermediate Similarity	NPD7472	Approved
0.7051	Intermediate Similarity	NPD5977	Approved
0.7051	Intermediate Similarity	NPD5978	Approved
0.7047	Intermediate Similarity	NPD2354	Approved
0.7039	Intermediate Similarity	NPD3869	Phase 3
0.7039	Intermediate Similarity	NPD3873	Phase 3
0.7039	Intermediate Similarity	NPD5586	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3024	Approved
0.7037	Intermediate Similarity	NPD3025	Approved
0.7034	Intermediate Similarity	NPD5689	Approved
0.7034	Intermediate Similarity	NPD5688	Approved
0.7031	Intermediate Similarity	NPD9263	Approved
0.7031	Intermediate Similarity	NPD9264	Approved
0.7031	Intermediate Similarity	NPD9267	Approved
0.7029	Intermediate Similarity	NPD5327	Phase 3
0.7029	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4359	Approved
0.7025	Intermediate Similarity	NPD3252	Approved
0.702	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6797	Phase 2
0.7007	Intermediate Similarity	NPD6287	Discontinued
0.7006	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7440	Discontinued
0.6994	Remote Similarity	NPD5844	Phase 1
0.6994	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6233	Phase 2
0.6985	Remote Similarity	NPD3019	Approved
0.6985	Remote Similarity	NPD2932	Approved
0.6982	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6398	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