NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.11
Volume:	276.095
LogP:	3.138
LogD:	3.14
LogS:	-4.55
# Rotatable Bonds:	5
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.771
Synthetic Accessibility Score:	1.449
Fsp3:	0.188
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:	-4.573
MDCK Permeability:	2.372840026509948e-05
Pgp-inhibitor:	0.116
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.415
Plasma Protein Binding (PPB):	96.719482421875%
Volume Distribution (VD):	0.538
Pgp-substrate:	1.7718391418457031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.843
CYP1A2-substrate:	0.961
CYP2C19-inhibitor:	0.887
CYP2C19-substrate:	0.314
CYP2C9-inhibitor:	0.809
CYP2C9-substrate:	0.923
CYP2D6-inhibitor:	0.316
CYP2D6-substrate:	0.906
CYP3A4-inhibitor:	0.737
CYP3A4-substrate:	0.799

ADMET: Excretion

Clearance (CL):	10.621
Half-life (T1/2):	0.448

ADMET: Toxicity

hERG Blockers:	0.261
Human Hepatotoxicity (H-HT):	0.229
Drug-inuced Liver Injury (DILI):	0.926
AMES Toxicity:	0.535
Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.032
Skin Sensitization:	0.255
Carcinogencity:	0.503
Eye Corrosion:	0.005
Eye Irritation:	0.519
Respiratory Toxicity:	0.068

Download Data

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

Natural Product: NPC469954

Natural Product ID:	NPC469954
*Common Name:**	1,2-Bis(4-Methoxyphenyl)Ethanone
IUPAC Name:	1,2-bis(4-methoxyphenyl)ethanone
Synonyms:
Standard InCHIKey:	SICBLYCPRWNHHP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H16O3/c1-18-14-7-3-12(4-8-14)11-16(17)13-5-9-15(19-2)10-6-13/h3-10H,11H2,1-2H3
SMILES:	COc1ccc(cc1)CC(=O)c1ccc(cc1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL13385
PubChem CID:	67120
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO12418	Myroxylon peruiferum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(79)80020-5]
NPO12418	Myroxylon peruiferum	Species	Fabaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[10328294]
NPO12418	Myroxylon peruiferum	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	>	20.0	ug.mL-1	PMID[574178]

☑ 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 NPC469954 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	327
0.1-0.2	1951
0.2-0.3	4574
0.3-0.4	11554
0.4-0.5	5955
0.5-0.6	5315
0.6-0.7	9012
0.7-0.8	3689
0.8-0.85	277
0.85-0.9	40
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.945	High Similarity	NPC23332
0.9358	High Similarity	NPC183648
0.9035	High Similarity	NPC19290
0.8929	High Similarity	NPC57879
0.8843	High Similarity	NPC177925
0.8807	High Similarity	NPC38209
0.8783	High Similarity	NPC220540
0.878	High Similarity	NPC211120
0.875	High Similarity	NPC474691
0.872	High Similarity	NPC66384
0.872	High Similarity	NPC164236
0.872	High Similarity	NPC183103
0.872	High Similarity	NPC112192
0.872	High Similarity	NPC128348
0.872	High Similarity	NPC189106
0.872	High Similarity	NPC309717
0.8716	High Similarity	NPC298224
0.871	High Similarity	NPC245395
0.8707	High Similarity	NPC470860
0.8699	High Similarity	NPC2596
0.8696	High Similarity	NPC252004
0.8689	High Similarity	NPC474264
0.8689	High Similarity	NPC474737
0.8678	High Similarity	NPC56332
0.8655	High Similarity	NPC225245
0.8644	High Similarity	NPC201284
0.8618	High Similarity	NPC428300
0.8607	High Similarity	NPC2771
0.8607	High Similarity	NPC470858
0.8595	High Similarity	NPC141252
0.8595	High Similarity	NPC11799
0.8583	High Similarity	NPC223354
0.8583	High Similarity	NPC27643
0.856	High Similarity	NPC247779
0.8548	High Similarity	NPC475017
0.8548	High Similarity	NPC125887
0.8525	High Similarity	NPC30216
0.8516	High Similarity	NPC89504
0.8516	High Similarity	NPC95485
0.8516	High Similarity	NPC88065
0.8516	High Similarity	NPC286336
0.8509	High Similarity	NPC116842
0.8504	High Similarity	NPC182428
0.8492	Intermediate Similarity	NPC164295
0.8492	Intermediate Similarity	NPC239134
0.8487	Intermediate Similarity	NPC54243
0.8487	Intermediate Similarity	NPC35744
0.8487	Intermediate Similarity	NPC61779
0.8482	Intermediate Similarity	NPC1065
0.8475	Intermediate Similarity	NPC45104
0.8468	Intermediate Similarity	NPC293387
0.8468	Intermediate Similarity	NPC37512
0.8462	Intermediate Similarity	NPC322197
0.8455	Intermediate Similarity	NPC65041
0.845	Intermediate Similarity	NPC131039
0.8448	Intermediate Similarity	NPC279916
0.8443	Intermediate Similarity	NPC473942
0.8438	Intermediate Similarity	NPC188646
0.8438	Intermediate Similarity	NPC204960
0.8438	Intermediate Similarity	NPC292998
0.8438	Intermediate Similarity	NPC472365
0.8438	Intermediate Similarity	NPC337373
0.8438	Intermediate Similarity	NPC28753
0.8438	Intermediate Similarity	NPC139813
0.8438	Intermediate Similarity	NPC20560
0.8438	Intermediate Similarity	NPC18877
0.8438	Intermediate Similarity	NPC192304
0.8438	Intermediate Similarity	NPC294593
0.8438	Intermediate Similarity	NPC82225
0.8438	Intermediate Similarity	NPC312318
0.8438	Intermediate Similarity	NPC159623
0.8438	Intermediate Similarity	NPC263670
0.8438	Intermediate Similarity	NPC144051
0.8438	Intermediate Similarity	NPC175098
0.8438	Intermediate Similarity	NPC242294
0.8438	Intermediate Similarity	NPC56031
0.843	Intermediate Similarity	NPC314329
0.8425	Intermediate Similarity	NPC474340
0.8425	Intermediate Similarity	NPC308037
0.8425	Intermediate Similarity	NPC153453
0.8425	Intermediate Similarity	NPC262359
0.8425	Intermediate Similarity	NPC284424
0.8425	Intermediate Similarity	NPC313618
0.8425	Intermediate Similarity	NPC64359
0.8421	Intermediate Similarity	NPC95172
0.8417	Intermediate Similarity	NPC470092
0.8413	Intermediate Similarity	NPC282230
0.8413	Intermediate Similarity	NPC183348
0.8413	Intermediate Similarity	NPC66905
0.8403	Intermediate Similarity	NPC249435
0.8403	Intermediate Similarity	NPC171023
0.8403	Intermediate Similarity	NPC32298
0.8387	Intermediate Similarity	NPC237868
0.8385	Intermediate Similarity	NPC98115
0.8385	Intermediate Similarity	NPC186838
0.8385	Intermediate Similarity	NPC477244
0.8385	Intermediate Similarity	NPC254741
0.8385	Intermediate Similarity	NPC249606
0.8385	Intermediate Similarity	NPC150399
0.8385	Intermediate Similarity	NPC477242
0.8385	Intermediate Similarity	NPC12165
0.8385	Intermediate Similarity	NPC186647
0.8385	Intermediate Similarity	NPC41461
0.8385	Intermediate Similarity	NPC168105
0.8385	Intermediate Similarity	NPC25287
0.8385	Intermediate Similarity	NPC1486
0.8385	Intermediate Similarity	NPC24394
0.8385	Intermediate Similarity	NPC477243
0.8385	Intermediate Similarity	NPC213603
0.8385	Intermediate Similarity	NPC66349
0.8385	Intermediate Similarity	NPC274109
0.8374	Intermediate Similarity	NPC221798
0.8372	Intermediate Similarity	NPC125269
0.8359	Intermediate Similarity	NPC257756
0.8359	Intermediate Similarity	NPC473655
0.8359	Intermediate Similarity	NPC205468
0.8359	Intermediate Similarity	NPC470406
0.8359	Intermediate Similarity	NPC212631
0.8359	Intermediate Similarity	NPC129132
0.8359	Intermediate Similarity	NPC101294
0.8359	Intermediate Similarity	NPC87231
0.8349	Intermediate Similarity	NPC175298
0.8346	Intermediate Similarity	NPC125153
0.8346	Intermediate Similarity	NPC470977
0.8346	Intermediate Similarity	NPC301717
0.8346	Intermediate Similarity	NPC196979
0.8346	Intermediate Similarity	NPC15083
0.8346	Intermediate Similarity	NPC470976
0.8333	Intermediate Similarity	NPC66246
0.8333	Intermediate Similarity	NPC264976
0.8333	Intermediate Similarity	NPC17525
0.8333	Intermediate Similarity	NPC170546
0.8321	Intermediate Similarity	NPC317119
0.8321	Intermediate Similarity	NPC23870
0.8321	Intermediate Similarity	NPC472419
0.8321	Intermediate Similarity	NPC470962
0.8321	Intermediate Similarity	NPC153979
0.832	Intermediate Similarity	NPC121104
0.8308	Intermediate Similarity	NPC13575
0.8308	Intermediate Similarity	NPC156092
0.8308	Intermediate Similarity	NPC99854
0.8306	Intermediate Similarity	NPC165556
0.8291	Intermediate Similarity	NPC53953
0.8281	Intermediate Similarity	NPC186097
0.8281	Intermediate Similarity	NPC475009
0.8281	Intermediate Similarity	NPC278556
0.8281	Intermediate Similarity	NPC475008
0.8276	Intermediate Similarity	NPC54626
0.8264	Intermediate Similarity	NPC246214
0.8261	Intermediate Similarity	NPC234639
0.8258	Intermediate Similarity	NPC124269
0.8258	Intermediate Similarity	NPC472368
0.8258	Intermediate Similarity	NPC21350
0.825	Intermediate Similarity	NPC293424
0.8246	Intermediate Similarity	NPC226699
0.8244	Intermediate Similarity	NPC473391
0.8244	Intermediate Similarity	NPC240593
0.8244	Intermediate Similarity	NPC472364
0.8244	Intermediate Similarity	NPC476333
0.8244	Intermediate Similarity	NPC161196
0.8244	Intermediate Similarity	NPC472367
0.824	Intermediate Similarity	NPC179777
0.8235	Intermediate Similarity	NPC316062
0.8231	Intermediate Similarity	NPC103842
0.8226	Intermediate Similarity	NPC107846
0.8226	Intermediate Similarity	NPC89630
0.822	Intermediate Similarity	NPC114144
0.8217	Intermediate Similarity	NPC229646
0.8211	Intermediate Similarity	NPC291189
0.8211	Intermediate Similarity	NPC69403
0.8211	Intermediate Similarity	NPC139171
0.8197	Intermediate Similarity	NPC295317
0.8195	Intermediate Similarity	NPC477956
0.8195	Intermediate Similarity	NPC472366
0.8195	Intermediate Similarity	NPC11566
0.8195	Intermediate Similarity	NPC109232
0.8195	Intermediate Similarity	NPC28398
0.8195	Intermediate Similarity	NPC470211
0.819	Intermediate Similarity	NPC473809
0.8189	Intermediate Similarity	NPC939
0.8189	Intermediate Similarity	NPC304622
0.8182	Intermediate Similarity	NPC7013
0.8182	Intermediate Similarity	NPC44573
0.8182	Intermediate Similarity	NPC188879
0.8182	Intermediate Similarity	NPC303644
0.8182	Intermediate Similarity	NPC157855
0.8182	Intermediate Similarity	NPC162680
0.8182	Intermediate Similarity	NPC209560
0.8182	Intermediate Similarity	NPC259685
0.8182	Intermediate Similarity	NPC294409
0.8182	Intermediate Similarity	NPC181124
0.8182	Intermediate Similarity	NPC116632
0.8182	Intermediate Similarity	NPC62735
0.8175	Intermediate Similarity	NPC123722
0.8175	Intermediate Similarity	NPC151167
0.8175	Intermediate Similarity	NPC123228
0.8175	Intermediate Similarity	NPC32163
0.8175	Intermediate Similarity	NPC16651
0.8175	Intermediate Similarity	NPC5018
0.8175	Intermediate Similarity	NPC286683

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 NPC469954 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	336
0.1-0.2	1038
0.2-0.3	1126
0.3-0.4	2545
0.4-0.5	2032
0.5-0.6	1347
0.6-0.7	559
0.7-0.8	150
0.8-0.85	13
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9478	High Similarity	NPD3972	Approved
0.8833	High Similarity	NPD1876	Approved
0.8772	High Similarity	NPD1241	Discontinued
0.843	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD1240	Approved
0.8387	Intermediate Similarity	NPD2798	Approved
0.8385	Intermediate Similarity	NPD2796	Approved
0.8333	Intermediate Similarity	NPD1651	Approved
0.8295	Intermediate Similarity	NPD1607	Approved
0.8281	Intermediate Similarity	NPD3140	Approved
0.8281	Intermediate Similarity	NPD3142	Approved
0.8195	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8167	Intermediate Similarity	NPD5536	Phase 2
0.811	Intermediate Similarity	NPD6832	Phase 2
0.8074	Intermediate Similarity	NPD3887	Approved
0.8045	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD2353	Approved
0.8045	Intermediate Similarity	NPD2344	Approved
0.803	Intermediate Similarity	NPD2799	Discontinued
0.803	Intermediate Similarity	NPD1510	Phase 2
0.8	Intermediate Similarity	NPD3134	Approved
0.8	Intermediate Similarity	NPD4628	Phase 3
0.7984	Intermediate Similarity	NPD1281	Approved
0.797	Intermediate Similarity	NPD2935	Discontinued
0.7967	Intermediate Similarity	NPD17	Approved
0.7951	Intermediate Similarity	NPD9545	Approved
0.7949	Intermediate Similarity	NPD5451	Approved
0.7903	Intermediate Similarity	NPD3847	Discontinued
0.7899	Intermediate Similarity	NPD5535	Approved
0.7874	Intermediate Similarity	NPD3267	Approved
0.7874	Intermediate Similarity	NPD3266	Approved
0.7852	Intermediate Similarity	NPD1549	Phase 2
0.7826	Intermediate Similarity	NPD6799	Approved
0.7815	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD2309	Approved
0.781	Intermediate Similarity	NPD2354	Approved
0.7805	Intermediate Similarity	NPD1894	Discontinued
0.7795	Intermediate Similarity	NPD1283	Approved
0.7786	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD5586	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1358	Approved
0.7778	Intermediate Similarity	NPD1608	Approved
0.7778	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD3748	Approved
0.7752	Intermediate Similarity	NPD9494	Approved
0.7737	Intermediate Similarity	NPD7003	Approved
0.7734	Intermediate Similarity	NPD2797	Approved
0.7727	Intermediate Similarity	NPD4307	Phase 2
0.7717	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD2313	Discontinued
0.771	Intermediate Similarity	NPD3268	Approved
0.771	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD5283	Phase 1
0.7676	Intermediate Similarity	NPD7458	Discontinued
0.7647	Intermediate Similarity	NPD1471	Phase 3
0.7643	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD1238	Approved
0.7622	Intermediate Similarity	NPD6599	Discontinued
0.76	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1203	Approved
0.7594	Intermediate Similarity	NPD2979	Phase 3
0.7576	Intermediate Similarity	NPD6798	Discontinued
0.7569	Intermediate Similarity	NPD7411	Suspended
0.7563	Intermediate Similarity	NPD2684	Approved
0.7537	Intermediate Similarity	NPD1933	Approved
0.7537	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD1243	Approved
0.7518	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6279	Approved
0.7517	Intermediate Similarity	NPD6280	Approved
0.7517	Intermediate Similarity	NPD7577	Discontinued
0.75	Intermediate Similarity	NPD4308	Phase 3
0.75	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD1481	Phase 2
0.75	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD9493	Approved
0.7482	Intermediate Similarity	NPD3750	Approved
0.7479	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD7819	Suspended
0.7466	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD6273	Approved
0.746	Intermediate Similarity	NPD5585	Approved
0.746	Intermediate Similarity	NPD5691	Approved
0.7447	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD3764	Approved
0.7438	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD1535	Discovery
0.7415	Intermediate Similarity	NPD5977	Approved
0.7415	Intermediate Similarity	NPD5978	Approved
0.741	Intermediate Similarity	NPD2654	Approved
0.7407	Intermediate Similarity	NPD6355	Discontinued
0.7405	Intermediate Similarity	NPD1019	Discontinued
0.7402	Intermediate Similarity	NPD4626	Approved
0.7402	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD6801	Discontinued
0.7394	Intermediate Similarity	NPD4662	Approved
0.7394	Intermediate Similarity	NPD4661	Approved
0.7391	Intermediate Similarity	NPD2346	Discontinued
0.7388	Intermediate Similarity	NPD4062	Phase 3
0.7388	Intermediate Similarity	NPD6233	Phase 2
0.7388	Intermediate Similarity	NPD8032	Phase 2
0.7376	Intermediate Similarity	NPD7440	Discontinued
0.7376	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD1237	Approved
0.7368	Intermediate Similarity	NPD2860	Approved
0.7368	Intermediate Similarity	NPD2859	Approved
0.736	Intermediate Similarity	NPD3596	Phase 2
0.7347	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD5049	Phase 3
0.7329	Intermediate Similarity	NPD6386	Approved
0.7329	Intermediate Similarity	NPD6385	Approved
0.7319	Intermediate Similarity	NPD2531	Phase 2
0.7319	Intermediate Similarity	NPD2438	Suspended
0.7319	Intermediate Similarity	NPD4476	Approved
0.7319	Intermediate Similarity	NPD4477	Approved
0.7317	Intermediate Similarity	NPD7843	Approved
0.7315	Intermediate Similarity	NPD7075	Discontinued
0.7311	Intermediate Similarity	NPD9697	Approved
0.7305	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD743	Approved
0.7297	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3869	Phase 3
0.7292	Intermediate Similarity	NPD3873	Phase 3
0.7292	Intermediate Similarity	NPD920	Approved
0.7287	Intermediate Similarity	NPD6287	Discontinued
0.7281	Intermediate Similarity	NPD2934	Approved
0.7281	Intermediate Similarity	NPD2933	Approved
0.7279	Intermediate Similarity	NPD4618	Approved
0.7279	Intermediate Similarity	NPD4622	Approved
0.7279	Intermediate Similarity	NPD1934	Approved
0.7273	Intermediate Similarity	NPD2182	Approved
0.7273	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6862	Phase 2
0.7248	Intermediate Similarity	NPD3882	Suspended
0.7244	Intermediate Similarity	NPD6581	Approved
0.7244	Intermediate Similarity	NPD6580	Approved
0.723	Intermediate Similarity	NPD2801	Approved
0.7227	Intermediate Similarity	NPD164	Approved
0.7226	Intermediate Similarity	NPD6651	Approved
0.7219	Intermediate Similarity	NPD5494	Approved
0.7214	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6873	Phase 2
0.7203	Intermediate Similarity	NPD1511	Approved
0.72	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD1202	Approved
0.7188	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD3817	Phase 2
0.7181	Intermediate Similarity	NPD2296	Approved
0.7179	Intermediate Similarity	NPD3020	Approved
0.7176	Intermediate Similarity	NPD4359	Approved
0.7174	Intermediate Similarity	NPD5688	Approved
0.7174	Intermediate Similarity	NPD5689	Approved
0.7164	Intermediate Similarity	NPD2614	Approved
0.7143	Intermediate Similarity	NPD9261	Approved
0.7143	Intermediate Similarity	NPD2557	Approved
0.7143	Intermediate Similarity	NPD7157	Approved
0.7132	Intermediate Similarity	NPD6516	Phase 2
0.7132	Intermediate Similarity	NPD2668	Approved
0.7132	Intermediate Similarity	NPD2667	Approved
0.7132	Intermediate Similarity	NPD5846	Approved
0.7124	Intermediate Similarity	NPD6808	Phase 2
0.7122	Intermediate Similarity	NPD7033	Discontinued
0.7121	Intermediate Similarity	NPD3225	Approved
0.7113	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7095	Approved
0.7107	Intermediate Similarity	NPD968	Approved
0.7103	Intermediate Similarity	NPD1512	Approved
0.7103	Intermediate Similarity	NPD2186	Approved
0.7095	Intermediate Similarity	NPD5890	Approved
0.7095	Intermediate Similarity	NPD5889	Approved
0.7092	Intermediate Similarity	NPD4534	Discontinued
0.7083	Intermediate Similarity	NPD5909	Discontinued
0.708	Intermediate Similarity	NPD943	Approved
0.7078	Intermediate Similarity	NPD3926	Phase 2
0.7075	Intermediate Similarity	NPD3226	Approved
0.7071	Intermediate Similarity	NPD1551	Phase 2
0.7068	Intermediate Similarity	NPD1164	Approved
0.7059	Intermediate Similarity	NPD1296	Phase 2
0.7055	Intermediate Similarity	NPD5403	Approved
0.7054	Intermediate Similarity	NPD3025	Approved
0.7054	Intermediate Similarity	NPD3024	Approved
0.7045	Intermediate Similarity	NPD6583	Phase 3
0.7045	Intermediate Similarity	NPD6582	Phase 2
0.7045	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD821	Approved
0.7034	Intermediate Similarity	NPD5401	Approved
0.7032	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6585	Discontinued
0.7023	Intermediate Similarity	NPD1201	Approved
0.702	Intermediate Similarity	NPD7768	Phase 2
0.702	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD6387	Discontinued
0.7007	Intermediate Similarity	NPD957	Approved
0.7	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1929	Approved
0.7	Intermediate Similarity	NPD1778	Approved
0.7	Intermediate Similarity	NPD1930	Approved
0.7	Intermediate Similarity	NPD2932	Approved

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