NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.15
Volume:	307.766
LogP:	4.32
LogD:	4.006
LogS:	-4.997
# Rotatable Bonds:	7
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.678
Synthetic Accessibility Score:	1.855
Fsp3:	0.211
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:	-4.737
MDCK Permeability:	1.694109414529521e-05
Pgp-inhibitor:	0.969
Pgp-substrate:	0.039
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.786
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.287
Plasma Protein Binding (PPB):	98.08971405029297%
Volume Distribution (VD):	0.713
Pgp-substrate:	0.47979164123535156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.961
CYP1A2-substrate:	0.48
CYP2C19-inhibitor:	0.957
CYP2C19-substrate:	0.091
CYP2C9-inhibitor:	0.905
CYP2C9-substrate:	0.28
CYP2D6-inhibitor:	0.34
CYP2D6-substrate:	0.441
CYP3A4-inhibitor:	0.372
CYP3A4-substrate:	0.495

ADMET: Excretion

Clearance (CL):	8.096
Half-life (T1/2):	0.753

ADMET: Toxicity

hERG Blockers:	0.318
Human Hepatotoxicity (H-HT):	0.484
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.073
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.968
Carcinogencity:	0.366
Eye Corrosion:	0.326
Eye Irritation:	0.981
Respiratory Toxicity:	0.921

Download Data

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

Natural Product: NPC151405

Natural Product ID:	NPC151405
*Common Name:**	1,7-Diphenyl-4-En-3-Heptanone
IUPAC Name:	(E)-1,7-diphenylhept-4-en-3-one
Synonyms:
Standard InCHIKey:	UDNMYDZHPMNIEQ-RIYZIHGNSA-N
Standard InCHI:	InChI=1S/C19H20O/c20-19(16-15-18-11-5-2-6-12-18)14-8-7-13-17-9-3-1-4-10-17/h1-6,8-12,14H,7,13,15-16H2/b14-8+
SMILES:	O=C(CCc1ccccc1)/C=C/CCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL240484
PubChem CID:	5316932
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19615910]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29323912]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[731398]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[731398]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	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	3

Activity Type	# Activity
Others	2
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	5000.0	nM	PMID[465019]
NPT24402	SINGLE PROTEIN	Probable G-protein coupled receptor 52	Homo sapiens	IC50	=	5450.0	nM	PMID[465020]
NPT2	Others	Unspecified		IC50	=	6000.0	nM	PMID[465021]

☑ 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 NPC151405 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	288
0.1-0.2	2488
0.2-0.3	6600
0.3-0.4	15084
0.4-0.5	13638
0.5-0.6	3781
0.6-0.7	609
0.7-0.8	141
0.8-0.85	30
0.85-0.9	25
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC139901
0.9459	High Similarity	NPC9796
0.9342	High Similarity	NPC71664
0.9221	High Similarity	NPC12936
0.9221	High Similarity	NPC273033
0.9211	High Similarity	NPC272260
0.92	High Similarity	NPC179726
0.9091	High Similarity	NPC95868
0.9012	High Similarity	NPC69057
0.9	High Similarity	NPC123476
0.8987	High Similarity	NPC273758
0.8947	High Similarity	NPC245966
0.8831	High Similarity	NPC2785
0.8831	High Similarity	NPC36342
0.8831	High Similarity	NPC285470
0.8784	High Similarity	NPC74458
0.8718	High Similarity	NPC300205
0.8667	High Similarity	NPC285679
0.8608	High Similarity	NPC17408
0.8608	High Similarity	NPC164086
0.8608	High Similarity	NPC190567
0.8608	High Similarity	NPC477703
0.8608	High Similarity	NPC285716
0.859	High Similarity	NPC137847
0.859	High Similarity	NPC76455
0.8514	High Similarity	NPC98880
0.85	High Similarity	NPC145053
0.8462	Intermediate Similarity	NPC329318
0.8452	Intermediate Similarity	NPC267262
0.84	Intermediate Similarity	NPC95289
0.8378	Intermediate Similarity	NPC311343
0.8354	Intermediate Similarity	NPC103488
0.8353	Intermediate Similarity	NPC418308
0.8353	Intermediate Similarity	NPC113307
0.8293	Intermediate Similarity	NPC215008
0.8276	Intermediate Similarity	NPC59677
0.8272	Intermediate Similarity	NPC73978
0.8256	Intermediate Similarity	NPC19256
0.8256	Intermediate Similarity	NPC277277
0.8235	Intermediate Similarity	NPC477704
0.8235	Intermediate Similarity	NPC477693
0.8182	Intermediate Similarity	NPC271437
0.8161	Intermediate Similarity	NPC284475
0.814	Intermediate Similarity	NPC231591
0.8118	Intermediate Similarity	NPC43945
0.8111	Intermediate Similarity	NPC289201
0.809	Intermediate Similarity	NPC472880
0.8077	Intermediate Similarity	NPC208075
0.8072	Intermediate Similarity	NPC324624
0.8068	Intermediate Similarity	NPC155232
0.8068	Intermediate Similarity	NPC153885
0.8068	Intermediate Similarity	NPC1682
0.8068	Intermediate Similarity	NPC323420
0.8068	Intermediate Similarity	NPC188844
0.8068	Intermediate Similarity	NPC77273
0.8046	Intermediate Similarity	NPC303967
0.8046	Intermediate Similarity	NPC67585
0.8046	Intermediate Similarity	NPC110420
0.8023	Intermediate Similarity	NPC157778
0.8022	Intermediate Similarity	NPC49994
0.8	Intermediate Similarity	NPC185208
0.8	Intermediate Similarity	NPC307
0.8	Intermediate Similarity	NPC12695
0.8	Intermediate Similarity	NPC160339
0.8	Intermediate Similarity	NPC219573
0.7978	Intermediate Similarity	NPC34243
0.7978	Intermediate Similarity	NPC289883
0.7978	Intermediate Similarity	NPC238219
0.7955	Intermediate Similarity	NPC141607
0.7955	Intermediate Similarity	NPC187725
0.7955	Intermediate Similarity	NPC133461
0.7945	Intermediate Similarity	NPC22786
0.7931	Intermediate Similarity	NPC298115
0.7931	Intermediate Similarity	NPC325709
0.7912	Intermediate Similarity	NPC239185
0.7912	Intermediate Similarity	NPC103048
0.7907	Intermediate Similarity	NPC194326
0.7889	Intermediate Similarity	NPC260233
0.7875	Intermediate Similarity	NPC78500
0.7857	Intermediate Similarity	NPC39600
0.7857	Intermediate Similarity	NPC197581
0.7841	Intermediate Similarity	NPC173413
0.7831	Intermediate Similarity	NPC100039
0.7826	Intermediate Similarity	NPC134882
0.7821	Intermediate Similarity	NPC326200
0.7792	Intermediate Similarity	NPC169222
0.7792	Intermediate Similarity	NPC16190
0.7792	Intermediate Similarity	NPC235059
0.7778	Intermediate Similarity	NPC298023
0.7753	Intermediate Similarity	NPC476484
0.7753	Intermediate Similarity	NPC103346
0.7727	Intermediate Similarity	NPC9822
0.7717	Intermediate Similarity	NPC240042
0.7717	Intermediate Similarity	NPC265220
0.7711	Intermediate Similarity	NPC157055
0.7692	Intermediate Similarity	NPC206764
0.7674	Intermediate Similarity	NPC252067
0.766	Intermediate Similarity	NPC476993
0.766	Intermediate Similarity	NPC472879
0.766	Intermediate Similarity	NPC109514
0.7647	Intermediate Similarity	NPC243289
0.7647	Intermediate Similarity	NPC44830
0.7647	Intermediate Similarity	NPC208183
0.7634	Intermediate Similarity	NPC145052
0.7634	Intermediate Similarity	NPC75724
0.7614	Intermediate Similarity	NPC473345
0.7568	Intermediate Similarity	NPC246588
0.7534	Intermediate Similarity	NPC36357
0.7534	Intermediate Similarity	NPC114327
0.7529	Intermediate Similarity	NPC230068
0.7526	Intermediate Similarity	NPC167336
0.75	Intermediate Similarity	NPC127343
0.75	Intermediate Similarity	NPC329556
0.75	Intermediate Similarity	NPC472691
0.75	Intermediate Similarity	NPC471829
0.75	Intermediate Similarity	NPC474866
0.75	Intermediate Similarity	NPC475939
0.7471	Intermediate Similarity	NPC95965
0.7449	Intermediate Similarity	NPC69332
0.7449	Intermediate Similarity	NPC95178
0.7449	Intermediate Similarity	NPC29989
0.7447	Intermediate Similarity	NPC317280
0.7447	Intermediate Similarity	NPC329387
0.7444	Intermediate Similarity	NPC58872
0.7442	Intermediate Similarity	NPC149263
0.7416	Intermediate Similarity	NPC153308
0.7391	Intermediate Similarity	NPC291070
0.7391	Intermediate Similarity	NPC261181
0.7391	Intermediate Similarity	NPC246757
0.7374	Intermediate Similarity	NPC470007
0.7368	Intermediate Similarity	NPC113670
0.7368	Intermediate Similarity	NPC54647
0.7368	Intermediate Similarity	NPC476042
0.7363	Intermediate Similarity	NPC110704
0.7363	Intermediate Similarity	NPC125226
0.734	Intermediate Similarity	NPC270654
0.7333	Intermediate Similarity	NPC210849
0.732	Intermediate Similarity	NPC247976
0.7317	Intermediate Similarity	NPC206800
0.7317	Intermediate Similarity	NPC32203
0.7294	Intermediate Similarity	NPC164449
0.7294	Intermediate Similarity	NPC184030
0.7273	Intermediate Similarity	NPC472700
0.7273	Intermediate Similarity	NPC291066
0.7273	Intermediate Similarity	NPC475710
0.7273	Intermediate Similarity	NPC53299
0.7273	Intermediate Similarity	NPC472699
0.7273	Intermediate Similarity	NPC70843
0.7263	Intermediate Similarity	NPC179411
0.726	Intermediate Similarity	NPC198841
0.7253	Intermediate Similarity	NPC240108
0.7253	Intermediate Similarity	NPC213156
0.7253	Intermediate Similarity	NPC108026
0.7253	Intermediate Similarity	NPC84288
0.7245	Intermediate Similarity	NPC249067
0.7245	Intermediate Similarity	NPC329282
0.7241	Intermediate Similarity	NPC285773
0.7241	Intermediate Similarity	NPC288903
0.7237	Intermediate Similarity	NPC71009
0.7237	Intermediate Similarity	NPC200745
0.7228	Intermediate Similarity	NPC88141
0.7209	Intermediate Similarity	NPC71795
0.72	Intermediate Similarity	NPC472683
0.72	Intermediate Similarity	NPC472695
0.72	Intermediate Similarity	NPC472696
0.72	Intermediate Similarity	NPC472701
0.7191	Intermediate Similarity	NPC164526
0.7172	Intermediate Similarity	NPC134120
0.7162	Intermediate Similarity	NPC120441
0.7162	Intermediate Similarity	NPC300345
0.7162	Intermediate Similarity	NPC65873
0.7162	Intermediate Similarity	NPC212114
0.716	Intermediate Similarity	NPC155429
0.7158	Intermediate Similarity	NPC156021
0.7158	Intermediate Similarity	NPC278228
0.7157	Intermediate Similarity	NPC116842
0.7143	Intermediate Similarity	NPC287790
0.7143	Intermediate Similarity	NPC3672
0.7129	Intermediate Similarity	NPC470252
0.7128	Intermediate Similarity	NPC256452
0.7126	Intermediate Similarity	NPC73637
0.7126	Intermediate Similarity	NPC475199
0.7126	Intermediate Similarity	NPC283012
0.7126	Intermediate Similarity	NPC121478
0.7123	Intermediate Similarity	NPC149436
0.7113	Intermediate Similarity	NPC112552
0.7113	Intermediate Similarity	NPC42211
0.71	Intermediate Similarity	NPC100767
0.7089	Intermediate Similarity	NPC267443
0.7083	Intermediate Similarity	NPC476120
0.7079	Intermediate Similarity	NPC294134
0.7071	Intermediate Similarity	NPC261573
0.7071	Intermediate Similarity	NPC269644
0.7071	Intermediate Similarity	NPC8931
0.7071	Intermediate Similarity	NPC120693
0.7065	Intermediate Similarity	NPC26224
0.7059	Intermediate Similarity	NPC176228
0.7059	Intermediate Similarity	NPC50192
0.7045	Intermediate Similarity	NPC324835
0.7045	Intermediate Similarity	NPC127491

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 NPC151405 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	294
0.1-0.2	1105
0.2-0.3	1459
0.3-0.4	3471
0.4-0.5	1953
0.5-0.6	712
0.6-0.7	116
0.7-0.8	33
0.8-0.85	5
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9221	High Similarity	NPD942	Approved
0.9091	High Similarity	NPD1507	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD7609	Phase 3
0.8118	Intermediate Similarity	NPD650	Approved
0.8068	Intermediate Similarity	NPD7631	Approved
0.8068	Intermediate Similarity	NPD1508	Approved
0.7912	Intermediate Similarity	NPD3495	Discontinued
0.7907	Intermediate Similarity	NPD506	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD1843	Approved
0.7778	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2066	Phase 3
0.7692	Intermediate Similarity	NPD4094	Approved
0.7683	Intermediate Similarity	NPD227	Approved
0.7683	Intermediate Similarity	NPD225	Approved
0.7579	Intermediate Similarity	NPD1932	Approved
0.7527	Intermediate Similarity	NPD4657	Approved
0.7527	Intermediate Similarity	NPD4655	Approved
0.75	Intermediate Similarity	NPD1929	Approved
0.75	Intermediate Similarity	NPD1930	Approved
0.75	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD3971	Phase 1
0.7412	Intermediate Similarity	NPD226	Approved
0.7396	Intermediate Similarity	NPD2171	Approved
0.7396	Intermediate Similarity	NPD2193	Phase 2
0.7396	Intermediate Similarity	NPD2648	Phase 3
0.7391	Intermediate Similarity	NPD1202	Approved
0.7381	Intermediate Similarity	NPD9490	Approved
0.7368	Intermediate Similarity	NPD675	Discontinued
0.734	Intermediate Similarity	NPD1100	Approved
0.734	Intermediate Similarity	NPD1099	Approved
0.7317	Intermediate Similarity	NPD9716	Approved
0.7303	Intermediate Similarity	NPD4793	Discontinued
0.7245	Intermediate Similarity	NPD1237	Approved
0.7245	Intermediate Similarity	NPD2577	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD5909	Discontinued
0.7241	Intermediate Similarity	NPD9491	Approved
0.7234	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1989	Approved
0.7216	Intermediate Similarity	NPD6027	Approved
0.7216	Intermediate Similarity	NPD6024	Approved
0.7216	Intermediate Similarity	NPD2196	Discontinued
0.7188	Intermediate Similarity	NPD7798	Approved
0.7174	Intermediate Similarity	NPD1239	Approved
0.7143	Intermediate Similarity	NPD3357	Discontinued
0.7143	Intermediate Similarity	NPD5347	Phase 2
0.7143	Intermediate Similarity	NPD5346	Phase 2
0.7129	Intermediate Similarity	NPD2329	Discontinued
0.7111	Intermediate Similarity	NPD1087	Approved
0.7065	Intermediate Similarity	NPD3672	Approved
0.7065	Intermediate Similarity	NPD3673	Approved
0.7021	Intermediate Similarity	NPD1563	Approved
0.701	Intermediate Similarity	NPD1238	Approved
0.7	Intermediate Similarity	NPD2192	Approved
0.7	Intermediate Similarity	NPD9259	Approved
0.7	Intermediate Similarity	NPD2197	Approved
0.7	Intermediate Similarity	NPD9257	Approved
0.6957	Remote Similarity	NPD800	Approved
0.6947	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1693	Approved
0.6889	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD1086	Approved
0.6882	Remote Similarity	NPD1090	Approved
0.6882	Remote Similarity	NPD1089	Approved
0.6832	Remote Similarity	NPD1677	Discontinued
0.6827	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1007	Discontinued
0.6804	Remote Similarity	NPD1565	Approved
0.6804	Remote Similarity	NPD1564	Approved
0.6804	Remote Similarity	NPD1566	Phase 3
0.68	Remote Similarity	NPD6647	Phase 2
0.6768	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4144	Approved
0.6744	Remote Similarity	NPD4147	Approved
0.6737	Remote Similarity	NPD1088	Approved
0.6735	Remote Similarity	NPD5926	Approved
0.6702	Remote Similarity	NPD9258	Approved
0.6702	Remote Similarity	NPD9256	Approved
0.6698	Remote Similarity	NPD7094	Approved
0.6698	Remote Similarity	NPD6858	Approved
0.6667	Remote Similarity	NPD5048	Discontinued
0.6635	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD173	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6049	Phase 2
0.6574	Remote Similarity	NPD5951	Approved
0.6571	Remote Similarity	NPD664	Approved
0.6571	Remote Similarity	NPD1317	Discontinued
0.6559	Remote Similarity	NPD1282	Approved
0.6545	Remote Similarity	NPD7610	Discontinued
0.6535	Remote Similarity	NPD813	Approved
0.6535	Remote Similarity	NPD4803	Discontinued
0.6518	Remote Similarity	NPD5836	Discontinued
0.6517	Remote Similarity	NPD3903	Approved
0.6517	Remote Similarity	NPD3904	Approved
0.6517	Remote Similarity	NPD3979	Approved
0.6517	Remote Similarity	NPD3981	Approved
0.6509	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7009	Phase 2
0.6481	Remote Similarity	NPD7076	Approved
0.6481	Remote Similarity	NPD7077	Approved
0.6476	Remote Similarity	NPD2182	Approved
0.646	Remote Similarity	NPD4879	Approved
0.6449	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4026	Approved
0.6444	Remote Similarity	NPD3035	Approved
0.6444	Remote Similarity	NPD4027	Approved
0.6436	Remote Similarity	NPD5630	Phase 1
0.6429	Remote Similarity	NPD9260	Approved
0.6415	Remote Similarity	NPD2067	Discontinued
0.6408	Remote Similarity	NPD164	Approved
0.6404	Remote Similarity	NPD6287	Discontinued
0.64	Remote Similarity	NPD9495	Approved
0.6374	Remote Similarity	NPD4169	Approved
0.6374	Remote Similarity	NPD4170	Approved
0.6374	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6588	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD2345	Approved
0.6348	Remote Similarity	NPD4878	Approved
0.6348	Remote Similarity	NPD3972	Approved
0.633	Remote Similarity	NPD1241	Discontinued
0.6316	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.631	Remote Similarity	NPD1673	Approved
0.6304	Remote Similarity	NPD4635	Approved
0.6304	Remote Similarity	NPD2001	Discontinued
0.63	Remote Similarity	NPD9566	Approved
0.6293	Remote Similarity	NPD5157	Phase 1
0.6293	Remote Similarity	NPD5159	Phase 2
0.6293	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD1246	Approved
0.6273	Remote Similarity	NPD2319	Discontinued
0.6273	Remote Similarity	NPD1074	Approved
0.6273	Remote Similarity	NPD1073	Approved
0.6273	Remote Similarity	NPD1075	Approved
0.6263	Remote Similarity	NPD2933	Approved
0.6263	Remote Similarity	NPD2934	Approved
0.6262	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD253	Approved
0.6238	Remote Similarity	NPD466	Approved
0.6237	Remote Similarity	NPD2539	Approved
0.6237	Remote Similarity	NPD4544	Approved
0.6237	Remote Similarity	NPD3427	Approved
0.6237	Remote Similarity	NPD2538	Approved
0.6237	Remote Similarity	NPD5178	Approved
0.6237	Remote Similarity	NPD3429	Approved
0.6228	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD4733	Approved
0.6228	Remote Similarity	NPD1727	Approved
0.6222	Remote Similarity	NPD1475	Approved
0.6216	Remote Similarity	NPD3317	Approved
0.6204	Remote Similarity	NPD3643	Approved
0.6204	Remote Similarity	NPD3642	Approved
0.6204	Remote Similarity	NPD3644	Approved
0.62	Remote Similarity	NPD2859	Approved
0.62	Remote Similarity	NPD2860	Approved
0.6182	Remote Similarity	NPD1175	Approved
0.6176	Remote Similarity	NPD742	Approved
0.6174	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.617	Remote Similarity	NPD5916	Discontinued
0.6163	Remote Similarity	NPD294	Approved
0.6163	Remote Similarity	NPD292	Approved
0.6162	Remote Similarity	NPD1066	Discontinued
0.6161	Remote Similarity	NPD4574	Approved
0.6161	Remote Similarity	NPD4576	Approved
0.6154	Remote Similarity	NPD5765	Approved
0.6154	Remote Similarity	NPD9261	Approved
0.6154	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1617	Discontinued
0.6134	Remote Similarity	NPD2798	Approved
0.6134	Remote Similarity	NPD4980	Approved
0.6129	Remote Similarity	NPD5288	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD2629	Approved
0.6126	Remote Similarity	NPD1023	Approved
0.6126	Remote Similarity	NPD1022	Approved
0.6126	Remote Similarity	NPD1020	Approved
0.6126	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD2508	Discontinued
0.6126	Remote Similarity	NPD1711	Phase 2
0.6126	Remote Similarity	NPD3867	Phase 2
0.6126	Remote Similarity	NPD1021	Approved
0.6121	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5278	Discontinued
0.6111	Remote Similarity	NPD3581	Discontinued
0.6106	Remote Similarity	NPD2347	Approved
0.6106	Remote Similarity	NPD5536	Phase 2
0.6106	Remote Similarity	NPD6065	Approved
0.6105	Remote Similarity	NPD4636	Approved
0.6105	Remote Similarity	NPD4406	Approved
0.6105	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4409	Approved
0.6102	Remote Similarity	NPD1876	Approved
0.6102	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD9728	Phase 1
0.6091	Remote Similarity	NPD5277	Phase 2
0.6087	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD1629	Approved
0.6082	Remote Similarity	NPD689	Discontinued
0.6082	Remote Similarity	NPD1628	Approved
0.6075	Remote Similarity	NPD3420	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