NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.09
Volume:	285.38
LogP:	4.488
LogD:	3.841
LogS:	-6.16
# Rotatable Bonds:	1
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.623
Synthetic Accessibility Score:	2.093
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.952
MDCK Permeability:	1.070325197360944e-05
Pgp-inhibitor:	0.644
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.571
30% Bioavailability (F30%):	0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.105
Plasma Protein Binding (PPB):	99.02413940429688%
Volume Distribution (VD):	0.627
Pgp-substrate:	0.6297675371170044%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.376
CYP2C19-inhibitor:	0.849
CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.649
CYP2C9-substrate:	0.879
CYP2D6-inhibitor:	0.221
CYP2D6-substrate:	0.575
CYP3A4-inhibitor:	0.354
CYP3A4-substrate:	0.162

ADMET: Excretion

Clearance (CL):	3.562
Half-life (T1/2):	0.112

ADMET: Toxicity

hERG Blockers:	0.257
Human Hepatotoxicity (H-HT):	0.669
Drug-inuced Liver Injury (DILI):	0.913
AMES Toxicity:	0.884
Rat Oral Acute Toxicity:	0.074
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.7
Carcinogencity:	0.817
Eye Corrosion:	0.003
Eye Irritation:	0.906
Respiratory Toxicity:	0.441

Download Data

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

Natural Product: NPC472880

Natural Product ID:	NPC472880
*Common Name:**	2-Phenylphenalen-1-One
IUPAC Name:	2-phenylphenalen-1-one
Synonyms:
Standard InCHIKey:	XLKSZOCYJIRNJT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H12O/c20-19-16-11-5-9-14-8-4-10-15(18(14)16)12-17(19)13-6-2-1-3-7-13/h1-12H
SMILES:	C1=CC=C(C=C1)C2=CC3=CC=CC4=C3C(=CC=C4)C2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3593487
PubChem CID:	12576628
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0002044] Phenylnaphthalenes

*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
NPO15254	Macropidia fuliginosa	Species	Haemodoraceae	Eukaryota	n.a.	Australian	n.a.	PMID[26151487]
NPO15254	Macropidia fuliginosa	Species	Haemodoraceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	IZ	=	2.0	mm	PMID[503912]

☑ 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 NPC472880 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	548
0.1-0.2	2303
0.2-0.3	6771
0.3-0.4	14820
0.4-0.5	12705
0.5-0.6	4856
0.6-0.7	524
0.7-0.8	106
0.8-0.85	41
0.85-0.9	15
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9432	High Similarity	NPC418308
0.9318	High Similarity	NPC267262
0.9111	High Similarity	NPC277277
0.9111	High Similarity	NPC19256
0.9053	High Similarity	NPC472879
0.9043	High Similarity	NPC49994
0.9022	High Similarity	NPC289883
0.8854	High Similarity	NPC476993
0.883	High Similarity	NPC185208
0.883	High Similarity	NPC219573
0.8737	High Similarity	NPC239185
0.8723	High Similarity	NPC260233
0.871	High Similarity	NPC155232
0.871	High Similarity	NPC153885
0.8696	High Similarity	NPC173413
0.8681	High Similarity	NPC157778
0.8667	High Similarity	NPC160339
0.8667	High Similarity	NPC307
0.8646	High Similarity	NPC134882
0.8617	High Similarity	NPC238219
0.8602	High Similarity	NPC284475
0.8602	High Similarity	NPC133461
0.8602	High Similarity	NPC103346
0.8587	High Similarity	NPC113307
0.8587	High Similarity	NPC325709
0.8571	High Similarity	NPC43945
0.8544	High Similarity	NPC186128
0.8542	High Similarity	NPC265220
0.8523	High Similarity	NPC273033
0.8523	High Similarity	NPC12936
0.8511	High Similarity	NPC188844
0.8511	High Similarity	NPC59677
0.8511	High Similarity	NPC1682
0.8511	High Similarity	NPC323420
0.8469	Intermediate Similarity	NPC109514
0.8454	Intermediate Similarity	NPC75724
0.8409	Intermediate Similarity	NPC71664
0.8381	Intermediate Similarity	NPC67377
0.837	Intermediate Similarity	NPC69057
0.8333	Intermediate Similarity	NPC215008
0.8333	Intermediate Similarity	NPC273758
0.8252	Intermediate Similarity	NPC470252
0.8191	Intermediate Similarity	NPC298115
0.8137	Intermediate Similarity	NPC134120
0.8119	Intermediate Similarity	NPC475939
0.8119	Intermediate Similarity	NPC472691
0.8119	Intermediate Similarity	NPC474866
0.8119	Intermediate Similarity	NPC471829
0.8111	Intermediate Similarity	NPC145053
0.809	Intermediate Similarity	NPC139901
0.809	Intermediate Similarity	NPC151405
0.8085	Intermediate Similarity	NPC153308
0.8068	Intermediate Similarity	NPC245966
0.8	Intermediate Similarity	NPC190567
0.8	Intermediate Similarity	NPC95868
0.7981	Intermediate Similarity	NPC203732
0.7978	Intermediate Similarity	NPC285470
0.7978	Intermediate Similarity	NPC2785
0.7978	Intermediate Similarity	NPC36342
0.7941	Intermediate Similarity	NPC247976
0.7889	Intermediate Similarity	NPC300205
0.7872	Intermediate Similarity	NPC164526
0.7865	Intermediate Similarity	NPC9796
0.7802	Intermediate Similarity	NPC164086
0.7778	Intermediate Similarity	NPC470253
0.7757	Intermediate Similarity	NPC265513
0.7742	Intermediate Similarity	NPC39600
0.7714	Intermediate Similarity	NPC472700
0.7714	Intermediate Similarity	NPC472699
0.7714	Intermediate Similarity	NPC100767
0.7692	Intermediate Similarity	NPC329282
0.7692	Intermediate Similarity	NPC272260
0.7685	Intermediate Similarity	NPC280789
0.7653	Intermediate Similarity	NPC125226
0.7642	Intermediate Similarity	NPC472696
0.7642	Intermediate Similarity	NPC472683
0.7642	Intermediate Similarity	NPC472701
0.7642	Intermediate Similarity	NPC472695
0.7619	Intermediate Similarity	NPC474910
0.7619	Intermediate Similarity	NPC172483
0.7615	Intermediate Similarity	NPC93287
0.7609	Intermediate Similarity	NPC17408
0.7609	Intermediate Similarity	NPC285716
0.7596	Intermediate Similarity	NPC274443
0.7596	Intermediate Similarity	NPC329556
0.7589	Intermediate Similarity	NPC228318
0.7582	Intermediate Similarity	NPC66270
0.7582	Intermediate Similarity	NPC245896
0.7579	Intermediate Similarity	NPC252067
0.7553	Intermediate Similarity	NPC197581
0.7545	Intermediate Similarity	NPC196673
0.7545	Intermediate Similarity	NPC471721
0.7545	Intermediate Similarity	NPC326664
0.7528	Intermediate Similarity	NPC96835
0.7528	Intermediate Similarity	NPC258492
0.7527	Intermediate Similarity	NPC73978
0.7522	Intermediate Similarity	NPC318173
0.7521	Intermediate Similarity	NPC164014
0.75	Intermediate Similarity	NPC244427
0.75	Intermediate Similarity	NPC222390
0.7477	Intermediate Similarity	NPC215419
0.7473	Intermediate Similarity	NPC179726
0.7455	Intermediate Similarity	NPC143768
0.7444	Intermediate Similarity	NPC307195
0.7419	Intermediate Similarity	NPC315216
0.7419	Intermediate Similarity	NPC50063
0.7416	Intermediate Similarity	NPC285679
0.7407	Intermediate Similarity	NPC192577
0.7407	Intermediate Similarity	NPC318327
0.7396	Intermediate Similarity	NPC123476
0.7391	Intermediate Similarity	NPC232958
0.7391	Intermediate Similarity	NPC103488
0.7386	Intermediate Similarity	NPC72670
0.7374	Intermediate Similarity	NPC110420
0.7374	Intermediate Similarity	NPC303967
0.7374	Intermediate Similarity	NPC67585
0.7368	Intermediate Similarity	NPC324624
0.7364	Intermediate Similarity	NPC218855
0.7364	Intermediate Similarity	NPC292834
0.7353	Intermediate Similarity	NPC12695
0.7345	Intermediate Similarity	NPC158157
0.7345	Intermediate Similarity	NPC469843
0.734	Intermediate Similarity	NPC100039
0.7333	Intermediate Similarity	NPC428300
0.7328	Intermediate Similarity	NPC144547
0.7327	Intermediate Similarity	NPC34243
0.7303	Intermediate Similarity	NPC74458
0.7297	Intermediate Similarity	NPC471481
0.7282	Intermediate Similarity	NPC156021
0.7273	Intermediate Similarity	NPC137315
0.7273	Intermediate Similarity	NPC474057
0.7257	Intermediate Similarity	NPC260886
0.7255	Intermediate Similarity	NPC172925
0.7241	Intermediate Similarity	NPC988
0.7241	Intermediate Similarity	NPC289432
0.7238	Intermediate Similarity	NPC112552
0.7234	Intermediate Similarity	NPC477703
0.7232	Intermediate Similarity	NPC234637
0.7232	Intermediate Similarity	NPC130591
0.7207	Intermediate Similarity	NPC66208
0.7207	Intermediate Similarity	NPC79496
0.7204	Intermediate Similarity	NPC255345
0.72	Intermediate Similarity	NPC58872
0.719	Intermediate Similarity	NPC478162
0.719	Intermediate Similarity	NPC478165
0.7174	Intermediate Similarity	NPC78500
0.7168	Intermediate Similarity	NPC474095
0.7168	Intermediate Similarity	NPC217111
0.7168	Intermediate Similarity	NPC228936
0.7156	Intermediate Similarity	NPC470007
0.7155	Intermediate Similarity	NPC202015
0.7143	Intermediate Similarity	NPC221825
0.7143	Intermediate Similarity	NPC13784
0.7143	Intermediate Similarity	NPC318067
0.713	Intermediate Similarity	NPC80605
0.713	Intermediate Similarity	NPC471186
0.713	Intermediate Similarity	NPC323440
0.713	Intermediate Similarity	NPC222968
0.713	Intermediate Similarity	NPC268930
0.713	Intermediate Similarity	NPC167336
0.7128	Intermediate Similarity	NPC159661
0.7117	Intermediate Similarity	NPC291799
0.7115	Intermediate Similarity	NPC103048
0.7115	Intermediate Similarity	NPC240042
0.7111	Intermediate Similarity	NPC1008
0.7111	Intermediate Similarity	NPC39799
0.7111	Intermediate Similarity	NPC193578
0.7111	Intermediate Similarity	NPC158028
0.7111	Intermediate Similarity	NPC135433
0.7111	Intermediate Similarity	NPC226999
0.7111	Intermediate Similarity	NPC280135
0.7111	Intermediate Similarity	NPC87099
0.7103	Intermediate Similarity	NPC255676
0.7079	Intermediate Similarity	NPC213570
0.7079	Intermediate Similarity	NPC246822
0.7079	Intermediate Similarity	NPC98880
0.7079	Intermediate Similarity	NPC139416
0.7075	Intermediate Similarity	NPC133809
0.7075	Intermediate Similarity	NPC128248
0.7075	Intermediate Similarity	NPC136810
0.7054	Intermediate Similarity	NPC212415
0.7034	Intermediate Similarity	NPC472981
0.703	Intermediate Similarity	NPC26224
0.7021	Intermediate Similarity	NPC76455
0.7021	Intermediate Similarity	NPC137847
0.701	Intermediate Similarity	NPC149263
0.7009	Intermediate Similarity	NPC476645
0.7	Intermediate Similarity	NPC477693
0.7	Intermediate Similarity	NPC251490
0.7	Intermediate Similarity	NPC477704
0.7	Intermediate Similarity	NPC95289
0.7	Intermediate Similarity	NPC473345
0.6983	Remote Similarity	NPC61651
0.6981	Remote Similarity	NPC476042
0.6975	Remote Similarity	NPC269923
0.6975	Remote Similarity	NPC167323
0.6972	Remote Similarity	NPC105899
0.6967	Remote Similarity	NPC474106
0.6966	Remote Similarity	NPC311343
0.6964	Remote Similarity	NPC210089

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 NPC472880 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	514
0.1-0.2	990
0.2-0.3	1425
0.3-0.4	3522
0.4-0.5	1980
0.5-0.6	588
0.6-0.7	113
0.7-0.8	10
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8737	High Similarity	NPD3495	Discontinued
0.8602	High Similarity	NPD7609	Phase 3
0.8571	High Similarity	NPD650	Approved
0.8523	High Similarity	NPD942	Approved
0.8511	High Similarity	NPD7631	Approved
0.8125	Intermediate Similarity	NPD1508	Approved
0.8	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD1843	Approved
0.7699	Intermediate Similarity	NPD5836	Discontinued
0.767	Intermediate Similarity	NPD1932	Approved
0.7596	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD1929	Approved
0.7596	Intermediate Similarity	NPD1930	Approved
0.7431	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD4879	Approved
0.7321	Intermediate Similarity	NPD5951	Approved
0.7255	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD2329	Discontinued
0.7245	Intermediate Similarity	NPD506	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2066	Phase 3
0.713	Intermediate Similarity	NPD7610	Discontinued
0.7069	Intermediate Similarity	NPD7009	Phase 2
0.7059	Intermediate Similarity	NPD4878	Approved
0.7054	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD2648	Phase 3
0.7009	Intermediate Similarity	NPD2193	Phase 2
0.6991	Remote Similarity	NPD7094	Approved
0.6991	Remote Similarity	NPD6858	Approved
0.699	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD1239	Approved
0.6935	Remote Similarity	NPD7008	Discontinued
0.6923	Remote Similarity	NPD4094	Approved
0.6891	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD1237	Approved
0.6857	Remote Similarity	NPD1989	Approved
0.6852	Remote Similarity	NPD2196	Discontinued
0.6827	Remote Similarity	NPD1563	Approved
0.6827	Remote Similarity	NPD1202	Approved
0.6807	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4657	Approved
0.6792	Remote Similarity	NPD4655	Approved
0.6786	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD664	Approved
0.6705	Remote Similarity	NPD675	Discontinued
0.6697	Remote Similarity	NPD6024	Approved
0.6697	Remote Similarity	NPD2171	Approved
0.6697	Remote Similarity	NPD6027	Approved
0.6694	Remote Similarity	NPD1201	Approved
0.6667	Remote Similarity	NPD2197	Approved
0.6667	Remote Similarity	NPD2192	Approved
0.6667	Remote Similarity	NPD3971	Phase 1
0.6667	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD1099	Approved
0.6636	Remote Similarity	NPD3357	Discontinued
0.6636	Remote Similarity	NPD1566	Phase 3
0.6636	Remote Similarity	NPD1565	Approved
0.6636	Remote Similarity	NPD1100	Approved
0.6636	Remote Similarity	NPD1564	Approved
0.6613	Remote Similarity	NPD1470	Approved
0.6604	Remote Similarity	NPD6049	Phase 2
0.6604	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD2508	Discontinued
0.6577	Remote Similarity	NPD5909	Discontinued
0.6569	Remote Similarity	NPD1087	Approved
0.6535	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD2345	Approved
0.6522	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD1677	Discontinued
0.6515	Remote Similarity	NPD5408	Approved
0.6515	Remote Similarity	NPD5405	Approved
0.6515	Remote Similarity	NPD5406	Approved
0.6515	Remote Similarity	NPD5404	Approved
0.6514	Remote Similarity	NPD7798	Approved
0.6514	Remote Similarity	NPD1238	Approved
0.6495	Remote Similarity	NPD225	Approved
0.6495	Remote Similarity	NPD227	Approved
0.6471	Remote Similarity	NPD9259	Approved
0.6471	Remote Similarity	NPD9257	Approved
0.6452	Remote Similarity	NPD3549	Approved
0.6452	Remote Similarity	NPD3547	Approved
0.6452	Remote Similarity	NPD3550	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD1693	Approved
0.6436	Remote Similarity	NPD4544	Approved
0.6434	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD9490	Approved
0.6429	Remote Similarity	NPD164	Approved
0.6406	Remote Similarity	NPD2754	Discontinued
0.64	Remote Similarity	NPD1482	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD8239	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD813	Approved
0.6387	Remote Similarity	NPD3317	Approved
0.6381	Remote Similarity	NPD1089	Approved
0.6381	Remote Similarity	NPD1090	Approved
0.6381	Remote Similarity	NPD1086	Approved
0.6373	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7541	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD2182	Approved
0.6341	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD9491	Approved
0.6324	Remote Similarity	NPD7003	Approved
0.6308	Remote Similarity	NPD7713	Phase 3
0.6308	Remote Similarity	NPD7961	Discontinued
0.6303	Remote Similarity	NPD2319	Discontinued
0.63	Remote Similarity	NPD226	Approved
0.6299	Remote Similarity	NPD4980	Approved
0.6293	Remote Similarity	NPD1317	Discontinued
0.6286	Remote Similarity	NPD800	Approved
0.6279	Remote Similarity	NPD6966	Discovery
0.6273	Remote Similarity	NPD5832	Phase 3
0.627	Remote Similarity	NPD1876	Approved
0.6262	Remote Similarity	NPD4407	Approved
0.6262	Remote Similarity	NPD4405	Approved
0.6262	Remote Similarity	NPD4408	Approved
0.6262	Remote Similarity	NPD1088	Approved
0.6261	Remote Similarity	NPD2342	Discontinued
0.625	Remote Similarity	NPD4321	Approved
0.625	Remote Similarity	NPD4793	Discontinued
0.624	Remote Similarity	NPD3972	Approved
0.624	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD3764	Approved
0.6226	Remote Similarity	NPD9256	Approved
0.6226	Remote Similarity	NPD3673	Approved
0.6226	Remote Similarity	NPD3672	Approved
0.6226	Remote Similarity	NPD9258	Approved
0.6218	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.621	Remote Similarity	NPD3881	Discontinued
0.6198	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD9716	Approved
0.6182	Remote Similarity	NPD5597	Approved
0.6182	Remote Similarity	NPD5598	Approved
0.6179	Remote Similarity	NPD3024	Approved
0.6179	Remote Similarity	NPD3025	Approved
0.6179	Remote Similarity	NPD1651	Approved
0.616	Remote Similarity	NPD6287	Discontinued
0.6148	Remote Similarity	NPD6065	Approved
0.6148	Remote Similarity	NPD997	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD5346	Phase 2
0.6132	Remote Similarity	NPD5347	Phase 2
0.6129	Remote Similarity	NPD3019	Approved
0.6129	Remote Similarity	NPD2932	Approved
0.6111	Remote Similarity	NPD3356	Approved
0.6111	Remote Similarity	NPD3355	Approved
0.6103	Remote Similarity	NPD2346	Discontinued
0.6094	Remote Similarity	NPD3244	Pre-registration
0.6094	Remote Similarity	NPD5653	Discontinued
0.6094	Remote Similarity	NPD1164	Approved
0.6094	Remote Similarity	NPD3245	Phase 3
0.6091	Remote Similarity	NPD6472	Discontinued
0.6091	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD2895	Discontinued
0.6082	Remote Similarity	NPD4058	Approved
0.608	Remote Similarity	NPD3023	Approved
0.608	Remote Similarity	NPD3026	Approved
0.6074	Remote Similarity	NPD3748	Approved
0.6074	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7390	Discontinued
0.6063	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD5157	Phase 1
0.6063	Remote Similarity	NPD5159	Phase 2
0.6055	Remote Similarity	NPD2878	Approved
0.6055	Remote Similarity	NPD3980	Approved
0.6055	Remote Similarity	NPD3982	Approved
0.6053	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD1245	Approved
0.6048	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD2798	Approved
0.6045	Remote Similarity	NPD7192	Discontinued
0.604	Remote Similarity	NPD3981	Approved
0.604	Remote Similarity	NPD3903	Approved
0.604	Remote Similarity	NPD3904	Approved
0.604	Remote Similarity	NPD3979	Approved
0.6036	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD1246	Approved
0.6032	Remote Similarity	NPD1281	Approved
0.6032	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD5630	Phase 1
0.6018	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD1574	Approved
0.6	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6	Remote Similarity	NPD9260	Approved
0.6	Remote Similarity	NPD7084	Phase 3
0.6	Remote Similarity	NPD4705	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD2313	Discontinued
0.5985	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD1593	Approved
0.5965	Remote Similarity	NPD4803	Discontinued
0.5957	Remote Similarity	NPD8165	Discontinued
0.5954	Remote Similarity	NPD7055	Discontinued
0.595	Remote Similarity	NPD7076	Approved
0.595	Remote Similarity	NPD6010	Discontinued
0.595	Remote Similarity	NPD7077	Approved
0.5946	Remote Similarity	NPD3093	Approved
0.5938	Remote Similarity	NPD182	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD7679	Phase 2
0.5923	Remote Similarity	NPD6007	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