NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	208.11
Volume:	223.377
LogP:	2.48
LogD:	2.511
LogS:	-3.044
# Rotatable Bonds:	4
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.713
Synthetic Accessibility Score:	1.655
Fsp3:	0.417
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.505
MDCK Permeability:	2.4222192223533057e-05
Pgp-inhibitor:	0.479
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.125
30% Bioavailability (F30%):	0.641

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.689
Plasma Protein Binding (PPB):	91.51512908935547%
Volume Distribution (VD):	0.692
Pgp-substrate:	6.455566883087158%

ADMET: Metabolism

CYP1A2-inhibitor:	0.959
CYP1A2-substrate:	0.954
CYP2C19-inhibitor:	0.701
CYP2C19-substrate:	0.882
CYP2C9-inhibitor:	0.261
CYP2C9-substrate:	0.781
CYP2D6-inhibitor:	0.087
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.198
CYP3A4-substrate:	0.574

ADMET: Excretion

Clearance (CL):	7.744
Half-life (T1/2):	0.827

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.048
Drug-inuced Liver Injury (DILI):	0.653
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.077
Carcinogencity:	0.239
Eye Corrosion:	0.01
Eye Irritation:	0.24
Respiratory Toxicity:	0.129

Download Data

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

Natural Product: NPC474691

Natural Product ID:	NPC474691
*Common Name:**	1-(3,4-Dimethoxyphenyl)-2-Methylpropan-1-One
IUPAC Name:	1-(3,4-dimethoxyphenyl)-2-methylpropan-1-one
Synonyms:
Standard InCHIKey:	FGVRUUHJVIWSEN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H16O3/c1-8(2)12(13)9-5-6-10(14-3)11(7-9)15-4/h5-8H,1-4H3
SMILES:	CC(C)C(=O)C1=CC(=C(C=C1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479494
PubChem CID:	26422
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO13877	Wedelia forsteriana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO13877	Wedelia forsteriana	Species	Asteraceae	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	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1819	Organism	Microsporum canis	Arthroderma otae	MIC	>	50.0	ug.mL-1	PMID[454239]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	>	50.0	ug.mL-1	PMID[454239]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	50.0	ug.mL-1	PMID[454239]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	=	50.0	ug.mL-1	PMID[454239]
NPT328	Organism	Epidermophyton floccosum	Epidermophyton floccosum	MIC	=	50.0	ug.mL-1	PMID[454239]

☑ 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 NPC474691 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	388
0.1-0.2	1732
0.2-0.3	4952
0.3-0.4	11664
0.4-0.5	5808
0.5-0.6	4604
0.6-0.7	9512
0.7-0.8	3783
0.8-0.85	186
0.85-0.9	52
0.9-0.95	14
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9741	High Similarity	NPC225245
0.9256	High Similarity	NPC30216
0.9244	High Similarity	NPC295317
0.9187	High Similarity	NPC16651
0.9187	High Similarity	NPC32163
0.9187	High Similarity	NPC286683
0.9127	High Similarity	NPC153453
0.9062	High Similarity	NPC95485
0.9062	High Similarity	NPC88065
0.9062	High Similarity	NPC89504
0.9024	High Similarity	NPC473626
0.8952	High Similarity	NPC154275
0.8879	High Similarity	NPC23332
0.8828	High Similarity	NPC50763
0.8793	High Similarity	NPC183648
0.878	High Similarity	NPC114298
0.875	High Similarity	NPC469954
0.873	High Similarity	NPC203719
0.873	High Similarity	NPC117237
0.8712	High Similarity	NPC470962
0.871	High Similarity	NPC242372
0.871	High Similarity	NPC257976
0.871	High Similarity	NPC4181
0.871	High Similarity	NPC164778
0.8672	High Similarity	NPC285776
0.8672	High Similarity	NPC66905
0.864	High Similarity	NPC273686
0.864	High Similarity	NPC312404
0.8626	High Similarity	NPC139519
0.8593	High Similarity	NPC169214
0.8593	High Similarity	NPC176030
0.8593	High Similarity	NPC86455
0.8593	High Similarity	NPC229218
0.8593	High Similarity	NPC125134
0.8593	High Similarity	NPC137920
0.8593	High Similarity	NPC141817
0.8593	High Similarity	NPC192597
0.8582	High Similarity	NPC138438
0.8582	High Similarity	NPC908
0.8582	High Similarity	NPC28398
0.8571	High Similarity	NPC120066
0.8548	High Similarity	NPC201777
0.8538	High Similarity	NPC111888
0.8529	High Similarity	NPC46161
0.8529	High Similarity	NPC46880
0.8529	High Similarity	NPC239608
0.8527	High Similarity	NPC298268
0.8527	High Similarity	NPC299010
0.8516	High Similarity	NPC304747
0.8512	High Similarity	NPC268317
0.8507	High Similarity	NPC223336
0.8504	High Similarity	NPC177925
0.8504	High Similarity	NPC179777
0.8504	High Similarity	NPC474737
0.8485	Intermediate Similarity	NPC208760
0.8485	Intermediate Similarity	NPC204592
0.8473	Intermediate Similarity	NPC288743
0.8473	Intermediate Similarity	NPC283823
0.8473	Intermediate Similarity	NPC159418
0.8473	Intermediate Similarity	NPC327410
0.8455	Intermediate Similarity	NPC299406
0.845	Intermediate Similarity	NPC304622
0.8443	Intermediate Similarity	NPC185738
0.8438	Intermediate Similarity	NPC276466
0.8438	Intermediate Similarity	NPC151167
0.8438	Intermediate Similarity	NPC5018
0.8438	Intermediate Similarity	NPC123228
0.8438	Intermediate Similarity	NPC123722
0.8433	Intermediate Similarity	NPC44573
0.8433	Intermediate Similarity	NPC325625
0.8425	Intermediate Similarity	NPC470858
0.8413	Intermediate Similarity	NPC163083
0.8413	Intermediate Similarity	NPC244876
0.8406	Intermediate Similarity	NPC30890
0.8403	Intermediate Similarity	NPC57879
0.8403	Intermediate Similarity	NPC54626
0.8397	Intermediate Similarity	NPC239302
0.8385	Intermediate Similarity	NPC172673
0.8374	Intermediate Similarity	NPC205502
0.8374	Intermediate Similarity	NPC171023
0.8359	Intermediate Similarity	NPC303680
0.8359	Intermediate Similarity	NPC84076
0.8359	Intermediate Similarity	NPC90128
0.8346	Intermediate Similarity	NPC143649
0.8345	Intermediate Similarity	NPC153620
0.8345	Intermediate Similarity	NPC24257
0.8333	Intermediate Similarity	NPC207732
0.8333	Intermediate Similarity	NPC327052
0.8321	Intermediate Similarity	NPC185607
0.8321	Intermediate Similarity	NPC28326
0.832	Intermediate Similarity	NPC158949
0.8319	Intermediate Similarity	NPC179309
0.8308	Intermediate Similarity	NPC150809
0.8295	Intermediate Similarity	NPC223807
0.8295	Intermediate Similarity	NPC64948
0.8293	Intermediate Similarity	NPC150919
0.8281	Intermediate Similarity	NPC53305
0.8281	Intermediate Similarity	NPC257589
0.8279	Intermediate Similarity	NPC220540
0.8276	Intermediate Similarity	NPC292792
0.8276	Intermediate Similarity	NPC38209
0.8273	Intermediate Similarity	NPC213482
0.8271	Intermediate Similarity	NPC144662
0.8271	Intermediate Similarity	NPC155098
0.8271	Intermediate Similarity	NPC311339
0.8271	Intermediate Similarity	NPC37065
0.8268	Intermediate Similarity	NPC141252
0.8268	Intermediate Similarity	NPC11799
0.8261	Intermediate Similarity	NPC469615
0.8261	Intermediate Similarity	NPC50954
0.8258	Intermediate Similarity	NPC183103
0.8248	Intermediate Similarity	NPC84273
0.8248	Intermediate Similarity	NPC58229
0.8244	Intermediate Similarity	NPC477705
0.8244	Intermediate Similarity	NPC477694
0.8235	Intermediate Similarity	NPC4796
0.8227	Intermediate Similarity	NPC474903
0.8226	Intermediate Similarity	NPC166591
0.8217	Intermediate Similarity	NPC127937
0.8217	Intermediate Similarity	NPC92207
0.8214	Intermediate Similarity	NPC195919
0.8214	Intermediate Similarity	NPC216314
0.8214	Intermediate Similarity	NPC120924
0.8211	Intermediate Similarity	NPC470860
0.8201	Intermediate Similarity	NPC196941
0.8201	Intermediate Similarity	NPC309169
0.8201	Intermediate Similarity	NPC469683
0.8201	Intermediate Similarity	NPC472836
0.8197	Intermediate Similarity	NPC252004
0.819	Intermediate Similarity	NPC298224
0.8188	Intermediate Similarity	NPC11314
0.8188	Intermediate Similarity	NPC27220
0.8188	Intermediate Similarity	NPC312256
0.8182	Intermediate Similarity	NPC164295
0.8182	Intermediate Similarity	NPC477706
0.8182	Intermediate Similarity	NPC239134
0.8175	Intermediate Similarity	NPC471877
0.8175	Intermediate Similarity	NPC50823
0.8169	Intermediate Similarity	NPC237441
0.8168	Intermediate Similarity	NPC261759
0.8162	Intermediate Similarity	NPC284409
0.8162	Intermediate Similarity	NPC46947
0.8156	Intermediate Similarity	NPC470511
0.8156	Intermediate Similarity	NPC469539
0.8156	Intermediate Similarity	NPC469540
0.8154	Intermediate Similarity	NPC20404
0.8154	Intermediate Similarity	NPC293641
0.8154	Intermediate Similarity	NPC281020
0.8154	Intermediate Similarity	NPC12022
0.8154	Intermediate Similarity	NPC20287
0.8148	Intermediate Similarity	NPC324929
0.8148	Intermediate Similarity	NPC90431
0.8148	Intermediate Similarity	NPC77955
0.8145	Intermediate Similarity	NPC280001
0.8145	Intermediate Similarity	NPC240664
0.8143	Intermediate Similarity	NPC224687
0.8143	Intermediate Similarity	NPC157133
0.8143	Intermediate Similarity	NPC73416
0.8143	Intermediate Similarity	NPC136278
0.8143	Intermediate Similarity	NPC160777
0.8143	Intermediate Similarity	NPC471590
0.8134	Intermediate Similarity	NPC45404
0.8134	Intermediate Similarity	NPC237330
0.8129	Intermediate Similarity	NPC473090
0.8129	Intermediate Similarity	NPC476054
0.8129	Intermediate Similarity	NPC469978
0.8129	Intermediate Similarity	NPC119663
0.8116	Intermediate Similarity	NPC110419
0.8115	Intermediate Similarity	NPC165106
0.8112	Intermediate Similarity	NPC472279
0.8112	Intermediate Similarity	NPC62354
0.811	Intermediate Similarity	NPC177291
0.811	Intermediate Similarity	NPC194416
0.8106	Intermediate Similarity	NPC233961
0.8106	Intermediate Similarity	NPC339621
0.8106	Intermediate Similarity	NPC142985
0.8106	Intermediate Similarity	NPC280399
0.8106	Intermediate Similarity	NPC195292
0.8103	Intermediate Similarity	NPC12714
0.8103	Intermediate Similarity	NPC310905
0.8102	Intermediate Similarity	NPC474784
0.8102	Intermediate Similarity	NPC322021
0.8099	Intermediate Similarity	NPC10304
0.8099	Intermediate Similarity	NPC63256
0.8092	Intermediate Similarity	NPC226661
0.8092	Intermediate Similarity	NPC278308
0.8088	Intermediate Similarity	NPC157944
0.8088	Intermediate Similarity	NPC125417
0.8088	Intermediate Similarity	NPC95679
0.8088	Intermediate Similarity	NPC112068
0.8088	Intermediate Similarity	NPC25305
0.8088	Intermediate Similarity	NPC110899
0.8088	Intermediate Similarity	NPC474274
0.8085	Intermediate Similarity	NPC231013
0.8085	Intermediate Similarity	NPC165389
0.8077	Intermediate Similarity	NPC276014
0.8077	Intermediate Similarity	NPC474264
0.8074	Intermediate Similarity	NPC274613
0.8074	Intermediate Similarity	NPC38101
0.8071	Intermediate Similarity	NPC113089

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 NPC474691 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	381
0.1-0.2	1006
0.2-0.3	1522
0.3-0.4	2661
0.4-0.5	1849
0.5-0.6	1109
0.6-0.7	513
0.7-0.8	102
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.873	High Similarity	NPD9494	Approved
0.8443	Intermediate Similarity	NPD5536	Phase 2
0.8333	Intermediate Similarity	NPD3972	Approved
0.8115	Intermediate Similarity	NPD1241	Discontinued
0.8115	Intermediate Similarity	NPD5283	Phase 1
0.8062	Intermediate Similarity	NPD1876	Approved
0.8028	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD5978	Approved
0.7891	Intermediate Similarity	NPD5977	Approved
0.7874	Intermediate Similarity	NPD1651	Approved
0.7805	Intermediate Similarity	NPD228	Approved
0.7794	Intermediate Similarity	NPD447	Suspended
0.7692	Intermediate Similarity	NPD1281	Approved
0.7692	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD6386	Approved
0.7687	Intermediate Similarity	NPD6385	Approved
0.7682	Intermediate Similarity	NPD5494	Approved
0.7674	Intermediate Similarity	NPD17	Approved
0.7669	Intermediate Similarity	NPD2798	Approved
0.7623	Intermediate Similarity	NPD1358	Approved
0.76	Intermediate Similarity	NPD3882	Suspended
0.7591	Intermediate Similarity	NPD3140	Approved
0.7591	Intermediate Similarity	NPD1240	Approved
0.7591	Intermediate Similarity	NPD3142	Approved
0.7584	Intermediate Similarity	NPD2801	Approved
0.7571	Intermediate Similarity	NPD2796	Approved
0.7568	Intermediate Similarity	NPD6873	Phase 2
0.7557	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD824	Approved
0.7541	Intermediate Similarity	NPD3134	Approved
0.7536	Intermediate Similarity	NPD230	Phase 1
0.7519	Intermediate Similarity	NPD9545	Approved
0.7519	Intermediate Similarity	NPD1283	Approved
0.7517	Intermediate Similarity	NPD1934	Approved
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD2799	Discontinued
0.7483	Intermediate Similarity	NPD4628	Phase 3
0.7482	Intermediate Similarity	NPD1607	Approved
0.7447	Intermediate Similarity	NPD2935	Discontinued
0.7431	Intermediate Similarity	NPD3887	Approved
0.7419	Intermediate Similarity	NPD3926	Phase 2
0.7417	Intermediate Similarity	NPD5353	Approved
0.7417	Intermediate Similarity	NPD3817	Phase 2
0.741	Intermediate Similarity	NPD1933	Approved
0.7403	Intermediate Similarity	NPD1247	Approved
0.7394	Intermediate Similarity	NPD2353	Approved
0.7394	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2344	Approved
0.7386	Intermediate Similarity	NPD919	Approved
0.7383	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1510	Phase 2
0.7361	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD4110	Phase 3
0.7351	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD943	Approved
0.7329	Intermediate Similarity	NPD1511	Approved
0.7328	Intermediate Similarity	NPD5691	Approved
0.7325	Intermediate Similarity	NPD7473	Discontinued
0.7315	Intermediate Similarity	NPD7458	Discontinued
0.7308	Intermediate Similarity	NPD5242	Approved
0.7292	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD2684	Approved
0.7279	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD3146	Approved
0.7273	Intermediate Similarity	NPD4626	Approved
0.7273	Intermediate Similarity	NPD1471	Phase 3
0.7267	Intermediate Similarity	NPD7028	Phase 2
0.7255	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6232	Discontinued
0.723	Intermediate Similarity	NPD1512	Approved
0.7222	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD2979	Phase 3
0.7211	Intermediate Similarity	NPD6799	Approved
0.7203	Intermediate Similarity	NPD2438	Suspended
0.7197	Intermediate Similarity	NPD9268	Approved
0.7197	Intermediate Similarity	NPD1357	Approved
0.7192	Intermediate Similarity	NPD2354	Approved
0.7192	Intermediate Similarity	NPD2309	Approved
0.7181	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6832	Phase 2
0.717	Intermediate Similarity	NPD3818	Discontinued
0.7164	Intermediate Similarity	NPD3705	Approved
0.7152	Intermediate Similarity	NPD6166	Phase 2
0.7152	Intermediate Similarity	NPD6876	Approved
0.7152	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6875	Approved
0.7152	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8032	Phase 2
0.7123	Intermediate Similarity	NPD7003	Approved
0.7114	Intermediate Similarity	NPD6273	Approved
0.7111	Intermediate Similarity	NPD9269	Phase 2
0.7111	Intermediate Similarity	NPD9717	Approved
0.7105	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7110	Phase 1
0.7103	Intermediate Similarity	NPD1549	Phase 2
0.7099	Intermediate Similarity	NPD9493	Approved
0.708	Intermediate Similarity	NPD3266	Approved
0.708	Intermediate Similarity	NPD3267	Approved
0.7071	Intermediate Similarity	NPD5111	Phase 2
0.7071	Intermediate Similarity	NPD2313	Discontinued
0.7071	Intermediate Similarity	NPD5110	Phase 2
0.7071	Intermediate Similarity	NPD5109	Approved
0.7068	Intermediate Similarity	NPD5585	Approved
0.7068	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3640	Phase 3
0.7067	Intermediate Similarity	NPD3639	Approved
0.7067	Intermediate Similarity	NPD3641	Approved
0.7063	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1243	Approved
0.7054	Intermediate Similarity	NPD7843	Approved
0.7047	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD6355	Discontinued
0.7042	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6599	Discontinued
0.7039	Intermediate Similarity	NPD4380	Phase 2
0.7034	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD2346	Discontinued
0.7031	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD1019	Discontinued
0.7023	Intermediate Similarity	NPD7157	Approved
0.7019	Intermediate Similarity	NPD5844	Phase 1
0.7015	Intermediate Similarity	NPD1778	Approved
0.7015	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD3748	Approved
0.7014	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7819	Suspended
0.7013	Intermediate Similarity	NPD1465	Phase 2
0.7007	Intermediate Similarity	NPD8166	Discontinued
0.7	Intermediate Similarity	NPD3027	Phase 3
0.6993	Remote Similarity	NPD2653	Approved
0.6985	Remote Similarity	NPD2981	Phase 2
0.6975	Remote Similarity	NPD7074	Phase 3
0.6974	Remote Similarity	NPD2649	Approved
0.6974	Remote Similarity	NPD2651	Approved
0.6972	Remote Similarity	NPD4307	Phase 2
0.697	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD2531	Phase 2
0.6963	Remote Similarity	NPD3847	Discontinued
0.696	Remote Similarity	NPD164	Approved
0.6957	Remote Similarity	NPD2797	Approved
0.6954	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD920	Approved
0.6953	Remote Similarity	NPD5451	Approved
0.695	Remote Similarity	NPD3268	Approved
0.695	Remote Similarity	NPD411	Approved
0.695	Remote Similarity	NPD6798	Discontinued
0.6948	Remote Similarity	NPD6280	Approved
0.6948	Remote Similarity	NPD6279	Approved
0.6944	Remote Similarity	NPD743	Approved
0.6939	Remote Similarity	NPD2654	Approved
0.6934	Remote Similarity	NPD2983	Phase 2
0.6934	Remote Similarity	NPD2982	Phase 2
0.6933	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5535	Approved
0.6914	Remote Similarity	NPD7054	Approved
0.6913	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD957	Approved
0.689	Remote Similarity	NPD7685	Pre-registration
0.6879	Remote Similarity	NPD7095	Approved
0.6879	Remote Similarity	NPD7075	Discontinued
0.6875	Remote Similarity	NPD2182	Approved
0.6875	Remote Similarity	NPD2492	Phase 1
0.6871	Remote Similarity	NPD7472	Approved
0.6867	Remote Similarity	NPD4357	Discontinued
0.6866	Remote Similarity	NPD1894	Discontinued
0.6863	Remote Similarity	NPD3455	Phase 2
0.6857	Remote Similarity	NPD3018	Phase 2
0.6855	Remote Similarity	NPD8127	Discontinued
0.6855	Remote Similarity	NPD2821	Approved
0.6853	Remote Similarity	NPD3620	Phase 2
0.6853	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD2163	Approved
0.6846	Remote Similarity	NPD6190	Approved
0.6839	Remote Similarity	NPD37	Approved
0.6839	Remote Similarity	NPD7577	Discontinued
0.6839	Remote Similarity	NPD6801	Discontinued
0.6838	Remote Similarity	NPD3496	Discontinued
0.6835	Remote Similarity	NPD1203	Approved
0.6831	Remote Similarity	NPD5718	Phase 2
0.6831	Remote Similarity	NPD3764	Approved
0.6831	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6896	Approved
0.6828	Remote Similarity	NPD6895	Approved
0.6826	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD3022	Approved
0.6822	Remote Similarity	NPD3021	Approved
0.6821	Remote Similarity	NPD4662	Approved
0.6821	Remote Similarity	NPD2533	Approved
0.6821	Remote Similarity	NPD4661	Approved
0.6821	Remote Similarity	NPD2534	Approved
0.6821	Remote Similarity	NPD7410	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