NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	134.07
Volume:	153.908
LogP:	1.505
LogD:	1.046
LogS:	-1.982
# Rotatable Bonds:	2
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.603
Synthetic Accessibility Score:	1.372
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.272
MDCK Permeability:	4.1871837311191484e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.38
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.479
Plasma Protein Binding (PPB):	53.747474670410156%
Volume Distribution (VD):	0.707
Pgp-substrate:	32.60582733154297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.531
CYP1A2-substrate:	0.669
CYP2C19-inhibitor:	0.685
CYP2C19-substrate:	0.686
CYP2C9-inhibitor:	0.161
CYP2C9-substrate:	0.33
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.464
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.481

ADMET: Excretion

Clearance (CL):	11.192
Half-life (T1/2):	0.834

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.507
Drug-inuced Liver Injury (DILI):	0.756
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.419
Carcinogencity:	0.185
Eye Corrosion:	0.705
Eye Irritation:	0.978
Respiratory Toxicity:	0.022

Download Data

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

Natural Product: NPC285679

Natural Product ID:	NPC285679
*Common Name:**	1-Phenylpropan-2-One
IUPAC Name:	1-phenylpropan-2-one
Synonyms:
Standard InCHIKey:	QCCDLTOVEPVEJK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H10O/c1-8(10)7-9-5-3-2-4-6-9/h2-6H,7H2,1H3
SMILES:	CC(=O)Cc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3800510
PubChem CID:	7678
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002811] Phenylpropanes

*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
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562834]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[24155209]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24959987]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25302569]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	leaves and stems	n.a.	n.a.	PMID[25442304]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29812	Panax quinquefolium	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29812	Panax quinquefolium	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8187	Schisandra chinensis	Species	Schisandraceae	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
NPT4109	Individual Protein	C-terminal-binding protein 2	Homo sapiens	IC50	>	300000.0	nM	PMID[490330]

☑ 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 NPC285679 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	324
0.1-0.2	2544
0.2-0.3	8445
0.3-0.4	16214
0.4-0.5	11870
0.5-0.6	2549
0.6-0.7	532
0.7-0.8	162
0.8-0.85	30
0.85-0.9	20
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9851	High Similarity	NPC74458
0.9306	High Similarity	NPC36342
0.9306	High Similarity	NPC285470
0.9306	High Similarity	NPC2785
0.9178	High Similarity	NPC300205
0.9167	High Similarity	NPC245966
0.9054	High Similarity	NPC190567
0.9054	High Similarity	NPC164086
0.9041	High Similarity	NPC103488
0.9014	High Similarity	NPC208075
0.8933	High Similarity	NPC145053
0.8904	High Similarity	NPC9796
0.8873	High Similarity	NPC271437
0.88	High Similarity	NPC17408
0.88	High Similarity	NPC71664
0.88	High Similarity	NPC285716
0.88	High Similarity	NPC95868
0.8714	High Similarity	NPC98880
0.8684	High Similarity	NPC273033
0.8684	High Similarity	NPC12936
0.8667	High Similarity	NPC151405
0.8667	High Similarity	NPC139901
0.8667	High Similarity	NPC272260
0.8649	High Similarity	NPC298023
0.8592	High Similarity	NPC95289
0.8571	High Similarity	NPC311343
0.8553	High Similarity	NPC477703
0.8533	High Similarity	NPC76455
0.8533	High Similarity	NPC137847
0.8462	Intermediate Similarity	NPC273758
0.8442	Intermediate Similarity	NPC73978
0.84	Intermediate Similarity	NPC329318
0.8375	Intermediate Similarity	NPC160339
0.8375	Intermediate Similarity	NPC307
0.8312	Intermediate Similarity	NPC157055
0.8272	Intermediate Similarity	NPC69057
0.8272	Intermediate Similarity	NPC43945
0.825	Intermediate Similarity	NPC95965
0.8228	Intermediate Similarity	NPC288903
0.8228	Intermediate Similarity	NPC39600
0.8228	Intermediate Similarity	NPC324624
0.8228	Intermediate Similarity	NPC215008
0.8228	Intermediate Similarity	NPC197581
0.8205	Intermediate Similarity	NPC100039
0.8171	Intermediate Similarity	NPC157778
0.8101	Intermediate Similarity	NPC230068
0.8077	Intermediate Similarity	NPC127343
0.806	Intermediate Similarity	NPC300345
0.806	Intermediate Similarity	NPC120441
0.806	Intermediate Similarity	NPC212114
0.806	Intermediate Similarity	NPC65873
0.8026	Intermediate Similarity	NPC78500
0.8025	Intermediate Similarity	NPC252067
0.8025	Intermediate Similarity	NPC294134
0.8025	Intermediate Similarity	NPC123476
0.8	Intermediate Similarity	NPC285773
0.7976	Intermediate Similarity	NPC277277
0.7976	Intermediate Similarity	NPC173413
0.7973	Intermediate Similarity	NPC326200
0.7952	Intermediate Similarity	NPC473345
0.7952	Intermediate Similarity	NPC267262
0.7922	Intermediate Similarity	NPC179726
0.791	Intermediate Similarity	NPC269586
0.791	Intermediate Similarity	NPC198841
0.7882	Intermediate Similarity	NPC284475
0.7882	Intermediate Similarity	NPC133461
0.7857	Intermediate Similarity	NPC231591
0.7857	Intermediate Similarity	NPC418308
0.7857	Intermediate Similarity	NPC113307
0.7857	Intermediate Similarity	NPC298115
0.7831	Intermediate Similarity	NPC322387
0.7791	Intermediate Similarity	NPC155232
0.7791	Intermediate Similarity	NPC1682
0.7791	Intermediate Similarity	NPC188844
0.7791	Intermediate Similarity	NPC59677
0.7791	Intermediate Similarity	NPC153885
0.7778	Intermediate Similarity	NPC44830
0.7778	Intermediate Similarity	NPC149263
0.7765	Intermediate Similarity	NPC19256
0.7765	Intermediate Similarity	NPC110420
0.7765	Intermediate Similarity	NPC303967
0.7765	Intermediate Similarity	NPC67585
0.7761	Intermediate Similarity	NPC277704
0.7761	Intermediate Similarity	NPC149436
0.7738	Intermediate Similarity	NPC329064
0.7738	Intermediate Similarity	NPC153308
0.7738	Intermediate Similarity	NPC477704
0.7738	Intermediate Similarity	NPC477693
0.7733	Intermediate Similarity	NPC155429
0.7714	Intermediate Similarity	NPC150196
0.7714	Intermediate Similarity	NPC54368
0.7714	Intermediate Similarity	NPC238023
0.7714	Intermediate Similarity	NPC135924
0.7714	Intermediate Similarity	NPC310758
0.7714	Intermediate Similarity	NPC210849
0.7714	Intermediate Similarity	NPC248705
0.7711	Intermediate Similarity	NPC164526
0.7703	Intermediate Similarity	NPC169222
0.7703	Intermediate Similarity	NPC16190
0.7703	Intermediate Similarity	NPC235059
0.7701	Intermediate Similarity	NPC246757
0.7701	Intermediate Similarity	NPC289883
0.7701	Intermediate Similarity	NPC238219
0.7701	Intermediate Similarity	NPC291070
0.7681	Intermediate Similarity	NPC8235
0.7674	Intermediate Similarity	NPC476484
0.7614	Intermediate Similarity	NPC260233
0.7606	Intermediate Similarity	NPC29680
0.7586	Intermediate Similarity	NPC323420
0.7571	Intermediate Similarity	NPC147062
0.7571	Intermediate Similarity	NPC169110
0.7558	Intermediate Similarity	NPC70940
0.7558	Intermediate Similarity	NPC274455
0.7558	Intermediate Similarity	NPC84288
0.7558	Intermediate Similarity	NPC58872
0.7558	Intermediate Similarity	NPC86670
0.7528	Intermediate Similarity	NPC185208
0.7528	Intermediate Similarity	NPC219573
0.7528	Intermediate Similarity	NPC12695
0.75	Intermediate Similarity	NPC88566
0.75	Intermediate Similarity	NPC34243
0.7471	Intermediate Similarity	NPC187725
0.7471	Intermediate Similarity	NPC110704
0.7471	Intermediate Similarity	NPC141607
0.7465	Intermediate Similarity	NPC246588
0.7444	Intermediate Similarity	NPC240042
0.7444	Intermediate Similarity	NPC239185
0.7444	Intermediate Similarity	NPC103048
0.7442	Intermediate Similarity	NPC325709
0.7442	Intermediate Similarity	NPC9822
0.7439	Intermediate Similarity	NPC323103
0.7436	Intermediate Similarity	NPC189371
0.7429	Intermediate Similarity	NPC114327
0.7429	Intermediate Similarity	NPC64270
0.7429	Intermediate Similarity	NPC36357
0.7416	Intermediate Similarity	NPC472880
0.7412	Intermediate Similarity	NPC194326
0.7407	Intermediate Similarity	NPC121800
0.7397	Intermediate Similarity	NPC155172
0.7397	Intermediate Similarity	NPC32312
0.7397	Intermediate Similarity	NPC198023
0.7386	Intermediate Similarity	NPC77273
0.7363	Intermediate Similarity	NPC134882
0.7363	Intermediate Similarity	NPC49994
0.7363	Intermediate Similarity	NPC75724
0.7361	Intermediate Similarity	NPC22786
0.7361	Intermediate Similarity	NPC71009
0.7361	Intermediate Similarity	NPC66517
0.7349	Intermediate Similarity	NPC270507
0.7342	Intermediate Similarity	NPC175393
0.7333	Intermediate Similarity	NPC82770
0.7333	Intermediate Similarity	NPC78954
0.7333	Intermediate Similarity	NPC239931
0.7303	Intermediate Similarity	NPC71140
0.7297	Intermediate Similarity	NPC178527
0.7284	Intermediate Similarity	NPC170484
0.7283	Intermediate Similarity	NPC476042
0.7283	Intermediate Similarity	NPC280869
0.7273	Intermediate Similarity	NPC317645
0.7273	Intermediate Similarity	NPC125226
0.7273	Intermediate Similarity	NPC103346
0.7273	Intermediate Similarity	NPC208302
0.726	Intermediate Similarity	NPC21211
0.726	Intermediate Similarity	NPC113670
0.726	Intermediate Similarity	NPC45756
0.7253	Intermediate Similarity	NPC265220
0.725	Intermediate Similarity	NPC3672
0.725	Intermediate Similarity	NPC287790
0.7229	Intermediate Similarity	NPC103387
0.7222	Intermediate Similarity	NPC206764
0.7215	Intermediate Similarity	NPC206800
0.7215	Intermediate Similarity	NPC32203
0.7204	Intermediate Similarity	NPC476993
0.7204	Intermediate Similarity	NPC112552
0.7204	Intermediate Similarity	NPC109514
0.72	Intermediate Similarity	NPC6107
0.72	Intermediate Similarity	NPC267443
0.7174	Intermediate Similarity	NPC145052
0.7174	Intermediate Similarity	NPC260000
0.7162	Intermediate Similarity	NPC291066
0.716	Intermediate Similarity	NPC50192
0.7128	Intermediate Similarity	NPC222390
0.7128	Intermediate Similarity	NPC244427
0.7128	Intermediate Similarity	NPC25458
0.7123	Intermediate Similarity	NPC200745
0.7108	Intermediate Similarity	NPC89950
0.7097	Intermediate Similarity	NPC54647
0.7093	Intermediate Similarity	NPC318107
0.7089	Intermediate Similarity	NPC108218
0.7079	Intermediate Similarity	NPC86987
0.7073	Intermediate Similarity	NPC78517
0.7073	Intermediate Similarity	NPC167577
0.7067	Intermediate Similarity	NPC289915
0.7067	Intermediate Similarity	NPC113837
0.7065	Intermediate Similarity	NPC477767
0.7065	Intermediate Similarity	NPC156021
0.7065	Intermediate Similarity	NPC289201
0.7059	Intermediate Similarity	NPC267704
0.7053	Intermediate Similarity	NPC472691
0.7053	Intermediate Similarity	NPC475939

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 NPC285679 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	317
0.1-0.2	1105
0.2-0.3	1908
0.3-0.4	3402
0.4-0.5	1660
0.5-0.6	610
0.6-0.7	107
0.7-0.8	35
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.88	High Similarity	NPD1507	Clinical (unspecified phase)
0.8684	High Similarity	NPD942	Approved
0.8289	Intermediate Similarity	NPD225	Approved
0.8289	Intermediate Similarity	NPD227	Approved
0.8272	Intermediate Similarity	NPD650	Approved
0.8272	Intermediate Similarity	NPD506	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD9490	Approved
0.8	Intermediate Similarity	NPD9491	Approved
0.7975	Intermediate Similarity	NPD226	Approved
0.7882	Intermediate Similarity	NPD7609	Phase 3
0.7831	Intermediate Similarity	NPD1087	Approved
0.7791	Intermediate Similarity	NPD7631	Approved
0.7647	Intermediate Similarity	NPD800	Approved
0.7614	Intermediate Similarity	NPD1693	Approved
0.7614	Intermediate Similarity	NPD4094	Approved
0.7586	Intermediate Similarity	NPD1508	Approved
0.7558	Intermediate Similarity	NPD1089	Approved
0.7558	Intermediate Similarity	NPD1086	Approved
0.7558	Intermediate Similarity	NPD1090	Approved
0.75	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD4657	Approved
0.7444	Intermediate Similarity	NPD3495	Discontinued
0.7444	Intermediate Similarity	NPD1100	Approved
0.7444	Intermediate Similarity	NPD4655	Approved
0.7444	Intermediate Similarity	NPD1099	Approved
0.7442	Intermediate Similarity	NPD5347	Phase 2
0.7442	Intermediate Similarity	NPD5346	Phase 2
0.7412	Intermediate Similarity	NPD4793	Discontinued
0.7386	Intermediate Similarity	NPD1088	Approved
0.7356	Intermediate Similarity	NPD3672	Approved
0.7356	Intermediate Similarity	NPD3673	Approved
0.7333	Intermediate Similarity	NPD1843	Approved
0.7303	Intermediate Similarity	NPD1563	Approved
0.7283	Intermediate Similarity	NPD2066	Phase 3
0.7273	Intermediate Similarity	NPD1239	Approved
0.726	Intermediate Similarity	NPD675	Discontinued
0.7215	Intermediate Similarity	NPD9716	Approved
0.7162	Intermediate Similarity	NPD173	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1989	Approved
0.7128	Intermediate Similarity	NPD2196	Discontinued
0.7128	Intermediate Similarity	NPD6024	Approved
0.7128	Intermediate Similarity	NPD2648	Phase 3
0.7128	Intermediate Similarity	NPD2171	Approved
0.7128	Intermediate Similarity	NPD6027	Approved
0.7128	Intermediate Similarity	NPD2193	Phase 2
0.7093	Intermediate Similarity	NPD9257	Approved
0.7093	Intermediate Similarity	NPD9259	Approved
0.7065	Intermediate Similarity	NPD1566	Phase 3
0.7065	Intermediate Similarity	NPD1564	Approved
0.7065	Intermediate Similarity	NPD1565	Approved
0.7053	Intermediate Similarity	NPD3357	Discontinued
0.7053	Intermediate Similarity	NPD1929	Approved
0.7053	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD1930	Approved
0.7033	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD9497	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD9495	Approved
0.6989	Remote Similarity	NPD466	Approved
0.6947	Remote Similarity	NPD1932	Approved
0.6941	Remote Similarity	NPD3971	Phase 1
0.6923	Remote Similarity	NPD1202	Approved
0.6915	Remote Similarity	NPD742	Approved
0.6907	Remote Similarity	NPD1677	Discontinued
0.6907	Remote Similarity	NPD2197	Approved
0.6907	Remote Similarity	NPD2192	Approved
0.6889	Remote Similarity	NPD1007	Discontinued
0.6835	Remote Similarity	NPD294	Approved
0.6835	Remote Similarity	NPD292	Approved
0.6804	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD1237	Approved
0.6782	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD9256	Approved
0.6778	Remote Similarity	NPD9258	Approved
0.6774	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4803	Discontinued
0.6737	Remote Similarity	NPD7798	Approved
0.6702	Remote Similarity	NPD9566	Approved
0.67	Remote Similarity	NPD2329	Discontinued
0.6667	Remote Similarity	NPD9588	Approved
0.6667	Remote Similarity	NPD9591	Approved
0.6667	Remote Similarity	NPD80	Approved
0.6667	Remote Similarity	NPD9589	Approved
0.6667	Remote Similarity	NPD9592	Approved
0.6667	Remote Similarity	NPD9590	Approved
0.6667	Remote Similarity	NPD9594	Approved
0.6667	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9593	Approved
0.6634	Remote Similarity	NPD1317	Discontinued
0.6633	Remote Similarity	NPD5909	Discontinued
0.6633	Remote Similarity	NPD164	Approved
0.6632	Remote Similarity	NPD253	Approved
0.6629	Remote Similarity	NPD1282	Approved
0.6598	Remote Similarity	NPD813	Approved
0.6582	Remote Similarity	NPD1673	Approved
0.6569	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD1018	Approved
0.6566	Remote Similarity	NPD1763	Approved
0.6566	Remote Similarity	NPD1761	Approved
0.6566	Remote Similarity	NPD1767	Approved
0.6566	Remote Similarity	NPD1766	Approved
0.6566	Remote Similarity	NPD1765	Approved
0.6562	Remote Similarity	NPD1238	Approved
0.6562	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD1066	Discontinued
0.6543	Remote Similarity	NPD9728	Phase 1
0.6531	Remote Similarity	NPD6647	Phase 2
0.6505	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD9260	Approved
0.6471	Remote Similarity	NPD664	Approved
0.6463	Remote Similarity	NPD505	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD9294	Approved
0.6429	Remote Similarity	NPD4144	Approved
0.6429	Remote Similarity	NPD4147	Approved
0.6408	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5048	Discontinued
0.6381	Remote Similarity	NPD1241	Discontinued
0.6373	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD2182	Approved
0.6353	Remote Similarity	NPD296	Approved
0.6353	Remote Similarity	NPD295	Approved
0.6353	Remote Similarity	NPD293	Approved
0.6337	Remote Similarity	NPD467	Phase 1
0.6321	Remote Similarity	NPD1246	Approved
0.6321	Remote Similarity	NPD1023	Approved
0.6321	Remote Similarity	NPD1074	Approved
0.6321	Remote Similarity	NPD1075	Approved
0.6321	Remote Similarity	NPD1021	Approved
0.6321	Remote Similarity	NPD1073	Approved
0.6321	Remote Similarity	NPD1022	Approved
0.6321	Remote Similarity	NPD1020	Approved
0.6321	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4233	Approved
0.6311	Remote Similarity	NPD1756	Approved
0.6311	Remote Similarity	NPD4234	Approved
0.6311	Remote Similarity	NPD1752	Approved
0.6311	Remote Similarity	NPD2067	Discontinued
0.6286	Remote Similarity	NPD7094	Approved
0.6286	Remote Similarity	NPD6858	Approved
0.6279	Remote Similarity	NPD1051	Approved
0.6279	Remote Similarity	NPD1053	Approved
0.6279	Remote Similarity	NPD589	Approved
0.6279	Remote Similarity	NPD1052	Approved
0.6279	Remote Similarity	NPD590	Approved
0.6235	Remote Similarity	NPD603	Approved
0.6226	Remote Similarity	NPD2650	Approved
0.6226	Remote Similarity	NPD7076	Approved
0.6226	Remote Similarity	NPD2652	Approved
0.6226	Remote Similarity	NPD7077	Approved
0.6222	Remote Similarity	NPD111	Approved
0.6207	Remote Similarity	NPD260	Discontinued
0.6207	Remote Similarity	NPD3981	Approved
0.6207	Remote Similarity	NPD3979	Approved
0.6207	Remote Similarity	NPD3904	Approved
0.6207	Remote Similarity	NPD5371	Approved
0.6207	Remote Similarity	NPD3903	Approved
0.6207	Remote Similarity	NPD5372	Approved
0.62	Remote Similarity	NPD5765	Approved
0.62	Remote Similarity	NPD9261	Approved
0.62	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD1101	Approved
0.619	Remote Similarity	NPD2124	Approved
0.619	Remote Similarity	NPD753	Approved
0.6176	Remote Similarity	NPD6685	Approved
0.6168	Remote Similarity	NPD2629	Approved
0.6168	Remote Similarity	NPD1711	Phase 2
0.6163	Remote Similarity	NPD9393	Approved
0.6163	Remote Similarity	NPD9564	Approved
0.6163	Remote Similarity	NPD79	Approved
0.6163	Remote Similarity	NPD9397	Approved
0.6163	Remote Similarity	NPD9563	Approved
0.6162	Remote Similarity	NPD5630	Phase 1
0.6154	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD3581	Discontinued
0.6154	Remote Similarity	NPD5278	Discontinued
0.6147	Remote Similarity	NPD7610	Discontinued
0.6146	Remote Similarity	NPD6049	Phase 2
0.6146	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD472	Approved
0.6136	Remote Similarity	NPD3035	Approved
0.6136	Remote Similarity	NPD4026	Approved
0.6136	Remote Similarity	NPD4027	Approved
0.6132	Remote Similarity	NPD2607	Approved
0.6132	Remote Similarity	NPD1279	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD480	Approved
0.6132	Remote Similarity	NPD181	Approved
0.6129	Remote Similarity	NPD689	Discontinued
0.6122	Remote Similarity	NPD5926	Approved
0.6111	Remote Similarity	NPD3317	Approved
0.6095	Remote Similarity	NPD3643	Approved
0.6095	Remote Similarity	NPD3642	Approved
0.6095	Remote Similarity	NPD3644	Approved
0.6092	Remote Similarity	NPD508	Approved
0.6092	Remote Similarity	NPD507	Approved
0.6092	Remote Similarity	NPD1475	Approved
0.6091	Remote Similarity	NPD7009	Phase 2
0.6087	Remote Similarity	NPD9538	Approved
0.6075	Remote Similarity	NPD1374	Approved
0.6075	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD1370	Approved
0.6075	Remote Similarity	NPD1371	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