NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.15
Volume:	307.766
LogP:	3.357
LogD:	3.709
LogS:	-3.489
# 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:	0.709
Synthetic Accessibility Score:	1.855
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.806
MDCK Permeability:	1.4982484572101384e-05
Pgp-inhibitor:	0.943
Pgp-substrate:	0.095
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.901
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.889
Plasma Protein Binding (PPB):	97.52954864501953%
Volume Distribution (VD):	0.539
Pgp-substrate:	0.6721677780151367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.675
CYP2C19-inhibitor:	0.94
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.836
CYP2C9-substrate:	0.908
CYP2D6-inhibitor:	0.14
CYP2D6-substrate:	0.823
CYP3A4-inhibitor:	0.258
CYP3A4-substrate:	0.314

ADMET: Excretion

Clearance (CL):	6.864
Half-life (T1/2):	0.842

ADMET: Toxicity

hERG Blockers:	0.326
Human Hepatotoxicity (H-HT):	0.464
Drug-inuced Liver Injury (DILI):	0.154
AMES Toxicity:	0.351
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.123
Skin Sensitization:	0.901
Carcinogencity:	0.56
Eye Corrosion:	0.036
Eye Irritation:	0.961
Respiratory Toxicity:	0.127

Download Data

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

Natural Product: NPC9796

Natural Product ID:	NPC9796
*Common Name:**	1,7-Enyl-6(E)-Hepten-3-One
IUPAC Name:	(E)-1,7-diphenylhept-6-en-3-one
Synonyms:
Standard InCHIKey:	VNFWNGSEJXPCSW-NTUHNPAUSA-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/h1-7,9-13H,8,14-16H2/b13-7+
SMILES:	O=C(CCc1ccccc1)CC/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470676
PubChem CID:	44593373
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
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np100392m]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	rhizomes	Kampaengsaen district, Nakhon Pathom province, Thailand	n.a.	PMID[18554915]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[20196571]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23910596]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176399]
NPO22901	Curcuma comosa	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
Others	3

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	74.3	%	PMID[544660]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	85.45	%	PMID[544660]
NPT530	Organism	Caenorhabditis elegans	Caenorhabditis elegans	EC95	=	9.0	ug ml-1	PMID[544659]

☑ 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 NPC9796 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	274
0.1-0.2	2252
0.2-0.3	6638
0.3-0.4	15666
0.4-0.5	13832
0.5-0.6	3298
0.6-0.7	506
0.7-0.8	171
0.8-0.85	36
0.85-0.9	16
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9726	High Similarity	NPC272260
0.9459	High Similarity	NPC139901
0.9459	High Similarity	NPC151405
0.9079	High Similarity	NPC95868
0.9079	High Similarity	NPC477703
0.9028	High Similarity	NPC74458
0.8961	High Similarity	NPC12936
0.8961	High Similarity	NPC273033
0.8904	High Similarity	NPC285679
0.8831	High Similarity	NPC71664
0.8816	High Similarity	NPC103488
0.8765	High Similarity	NPC69057
0.875	High Similarity	NPC123476
0.8734	High Similarity	NPC273758
0.8684	High Similarity	NPC179726
0.859	High Similarity	NPC17408
0.859	High Similarity	NPC285716
0.8554	High Similarity	NPC231591
0.8442	Intermediate Similarity	NPC245966
0.84	Intermediate Similarity	NPC271437
0.8354	Intermediate Similarity	NPC190567
0.8353	Intermediate Similarity	NPC187725
0.8353	Intermediate Similarity	NPC141607
0.8333	Intermediate Similarity	NPC298115
0.8333	Intermediate Similarity	NPC36342
0.8333	Intermediate Similarity	NPC285470
0.8333	Intermediate Similarity	NPC2785
0.8289	Intermediate Similarity	NPC208075
0.825	Intermediate Similarity	NPC145053
0.8228	Intermediate Similarity	NPC300205
0.8214	Intermediate Similarity	NPC267262
0.8205	Intermediate Similarity	NPC298023
0.8169	Intermediate Similarity	NPC22786
0.8125	Intermediate Similarity	NPC164086
0.8125	Intermediate Similarity	NPC157055
0.8118	Intermediate Similarity	NPC418308
0.8118	Intermediate Similarity	NPC113307
0.8101	Intermediate Similarity	NPC76455
0.8101	Intermediate Similarity	NPC137847
0.8068	Intermediate Similarity	NPC206764
0.8049	Intermediate Similarity	NPC44830
0.8046	Intermediate Similarity	NPC59677
0.8028	Intermediate Similarity	NPC246588
0.8023	Intermediate Similarity	NPC19256
0.8023	Intermediate Similarity	NPC277277
0.8	Intermediate Similarity	NPC477693
0.8	Intermediate Similarity	NPC477704
0.8	Intermediate Similarity	NPC98880
0.7975	Intermediate Similarity	NPC329318
0.7931	Intermediate Similarity	NPC284475
0.7927	Intermediate Similarity	NPC230068
0.7907	Intermediate Similarity	NPC9822
0.7895	Intermediate Similarity	NPC95289
0.7867	Intermediate Similarity	NPC311343
0.7865	Intermediate Similarity	NPC472880
0.7841	Intermediate Similarity	NPC1682
0.7841	Intermediate Similarity	NPC188844
0.7841	Intermediate Similarity	NPC323420
0.7841	Intermediate Similarity	NPC153885
0.7841	Intermediate Similarity	NPC155232
0.7831	Intermediate Similarity	NPC215008
0.7816	Intermediate Similarity	NPC303967
0.7816	Intermediate Similarity	NPC67585
0.7816	Intermediate Similarity	NPC110420
0.7808	Intermediate Similarity	NPC113670
0.7805	Intermediate Similarity	NPC73978
0.7802	Intermediate Similarity	NPC49994
0.7791	Intermediate Similarity	NPC157778
0.7778	Intermediate Similarity	NPC219573
0.7778	Intermediate Similarity	NPC185208
0.7778	Intermediate Similarity	NPC210849
0.7765	Intermediate Similarity	NPC307
0.7765	Intermediate Similarity	NPC160339
0.7753	Intermediate Similarity	NPC238219
0.7753	Intermediate Similarity	NPC34243
0.7753	Intermediate Similarity	NPC289883
0.7746	Intermediate Similarity	NPC36357
0.7746	Intermediate Similarity	NPC114327
0.7727	Intermediate Similarity	NPC133461
0.7727	Intermediate Similarity	NPC125226
0.7717	Intermediate Similarity	NPC476042
0.7701	Intermediate Similarity	NPC325709
0.7692	Intermediate Similarity	NPC239185
0.7692	Intermediate Similarity	NPC103048
0.7692	Intermediate Similarity	NPC289201
0.7683	Intermediate Similarity	NPC164449
0.7683	Intermediate Similarity	NPC184030
0.7683	Intermediate Similarity	NPC127343
0.7674	Intermediate Similarity	NPC43945
0.7667	Intermediate Similarity	NPC260233
0.7647	Intermediate Similarity	NPC475710
0.7647	Intermediate Similarity	NPC95965
0.764	Intermediate Similarity	NPC77273
0.7619	Intermediate Similarity	NPC324624
0.7619	Intermediate Similarity	NPC197581
0.7614	Intermediate Similarity	NPC84288
0.7614	Intermediate Similarity	NPC173413
0.7609	Intermediate Similarity	NPC134882
0.7582	Intermediate Similarity	NPC12695
0.7528	Intermediate Similarity	NPC103346
0.75	Intermediate Similarity	NPC267443
0.75	Intermediate Similarity	NPC73637
0.75	Intermediate Similarity	NPC265220
0.75	Intermediate Similarity	NPC121478
0.7471	Intermediate Similarity	NPC194326
0.7467	Intermediate Similarity	NPC291066
0.7465	Intermediate Similarity	NPC198841
0.7447	Intermediate Similarity	NPC109514
0.7447	Intermediate Similarity	NPC476993
0.7447	Intermediate Similarity	NPC472879
0.7442	Intermediate Similarity	NPC252067
0.7432	Intermediate Similarity	NPC200745
0.7432	Intermediate Similarity	NPC71009
0.7419	Intermediate Similarity	NPC75724
0.7419	Intermediate Similarity	NPC145052
0.7412	Intermediate Similarity	NPC288903
0.7412	Intermediate Similarity	NPC39600
0.7412	Intermediate Similarity	NPC285773
0.7407	Intermediate Similarity	NPC78500
0.7396	Intermediate Similarity	NPC261573
0.7396	Intermediate Similarity	NPC120693
0.7396	Intermediate Similarity	NPC8931
0.7381	Intermediate Similarity	NPC100039
0.7361	Intermediate Similarity	NPC212114
0.7361	Intermediate Similarity	NPC300345
0.7361	Intermediate Similarity	NPC120441
0.7361	Intermediate Similarity	NPC65873
0.7342	Intermediate Similarity	NPC155429
0.7342	Intermediate Similarity	NPC326200
0.734	Intermediate Similarity	NPC54647
0.7333	Intermediate Similarity	NPC476484
0.7326	Intermediate Similarity	NPC95429
0.7324	Intermediate Similarity	NPC149436
0.732	Intermediate Similarity	NPC167336
0.7312	Intermediate Similarity	NPC240042
0.7312	Intermediate Similarity	NPC477767
0.7312	Intermediate Similarity	NPC226041
0.7308	Intermediate Similarity	NPC169222
0.7308	Intermediate Similarity	NPC16190
0.7308	Intermediate Similarity	NPC246822
0.7308	Intermediate Similarity	NPC235059
0.7308	Intermediate Similarity	NPC213570
0.7308	Intermediate Similarity	NPC139416
0.7308	Intermediate Similarity	NPC473206
0.7297	Intermediate Similarity	NPC135924
0.7297	Intermediate Similarity	NPC248705
0.7297	Intermediate Similarity	NPC150196
0.7297	Intermediate Similarity	NPC54368
0.7294	Intermediate Similarity	NPC283012
0.7294	Intermediate Similarity	NPC475199
0.7292	Intermediate Similarity	NPC472691
0.7292	Intermediate Similarity	NPC329556
0.7292	Intermediate Similarity	NPC475939
0.7292	Intermediate Similarity	NPC474866
0.7292	Intermediate Similarity	NPC471829
0.7283	Intermediate Similarity	NPC172925
0.7273	Intermediate Similarity	NPC322387
0.7263	Intermediate Similarity	NPC225079
0.725	Intermediate Similarity	NPC54269
0.7245	Intermediate Similarity	NPC188677
0.7241	Intermediate Similarity	NPC99482
0.7241	Intermediate Similarity	NPC294134
0.7237	Intermediate Similarity	NPC155172
0.7237	Intermediate Similarity	NPC198023
0.7237	Intermediate Similarity	NPC32312
0.7234	Intermediate Similarity	NPC271475
0.7234	Intermediate Similarity	NPC329387
0.7234	Intermediate Similarity	NPC317280
0.7222	Intermediate Similarity	NPC86670
0.7222	Intermediate Similarity	NPC58872
0.7222	Intermediate Similarity	NPC274455
0.7222	Intermediate Similarity	NPC269586
0.7222	Intermediate Similarity	NPC70940
0.7215	Intermediate Similarity	NPC251490
0.7215	Intermediate Similarity	NPC263385
0.7215	Intermediate Similarity	NPC72670
0.7209	Intermediate Similarity	NPC208183
0.7209	Intermediate Similarity	NPC243289
0.72	Intermediate Similarity	NPC29680
0.7191	Intermediate Similarity	NPC473345
0.7191	Intermediate Similarity	NPC329064
0.7191	Intermediate Similarity	NPC153308
0.7172	Intermediate Similarity	NPC470007
0.7162	Intermediate Similarity	NPC147062
0.7159	Intermediate Similarity	NPC164526
0.7158	Intermediate Similarity	NPC221825
0.7143	Intermediate Similarity	NPC36440
0.7143	Intermediate Similarity	NPC178527
0.7143	Intermediate Similarity	NPC471186
0.7143	Intermediate Similarity	NPC474307
0.7143	Intermediate Similarity	NPC86987
0.7128	Intermediate Similarity	NPC270654
0.7126	Intermediate Similarity	NPC267704
0.7125	Intermediate Similarity	NPC39799
0.7125	Intermediate Similarity	NPC1008
0.7125	Intermediate Similarity	NPC135433
0.7125	Intermediate Similarity	NPC226999
0.7125	Intermediate Similarity	NPC193578
0.7125	Intermediate Similarity	NPC158028
0.7125	Intermediate Similarity	NPC280135

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 NPC9796 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	1105
0.2-0.3	1448
0.3-0.4	3473
0.4-0.5	1868
0.5-0.6	769
0.6-0.7	160
0.7-0.8	41
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9079	High Similarity	NPD1507	Clinical (unspecified phase)
0.8961	High Similarity	NPD942	Approved
0.8068	Intermediate Similarity	NPD4094	Approved
0.7931	Intermediate Similarity	NPD7609	Phase 3
0.7889	Intermediate Similarity	NPD4657	Approved
0.7889	Intermediate Similarity	NPD4655	Approved
0.7875	Intermediate Similarity	NPD225	Approved
0.7875	Intermediate Similarity	NPD227	Approved
0.7841	Intermediate Similarity	NPD7631	Approved
0.7841	Intermediate Similarity	NPD1508	Approved
0.7808	Intermediate Similarity	NPD675	Discontinued
0.7753	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3495	Discontinued
0.7674	Intermediate Similarity	NPD650	Approved
0.7674	Intermediate Similarity	NPD4793	Discontinued
0.759	Intermediate Similarity	NPD226	Approved
0.7582	Intermediate Similarity	NPD1989	Approved
0.7582	Intermediate Similarity	NPD1843	Approved
0.7561	Intermediate Similarity	NPD9490	Approved
0.7553	Intermediate Similarity	NPD6027	Approved
0.7553	Intermediate Similarity	NPD6024	Approved
0.7528	Intermediate Similarity	NPD1239	Approved
0.7527	Intermediate Similarity	NPD2066	Phase 3
0.75	Intermediate Similarity	NPD5346	Phase 2
0.75	Intermediate Similarity	NPD5347	Phase 2
0.7471	Intermediate Similarity	NPD506	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD1087	Approved
0.7416	Intermediate Similarity	NPD3673	Approved
0.7416	Intermediate Similarity	NPD3672	Approved
0.7412	Intermediate Similarity	NPD9491	Approved
0.7391	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1932	Approved
0.7363	Intermediate Similarity	NPD1563	Approved
0.734	Intermediate Similarity	NPD7798	Approved
0.7303	Intermediate Similarity	NPD800	Approved
0.7292	Intermediate Similarity	NPD1929	Approved
0.7292	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1930	Approved
0.7283	Intermediate Similarity	NPD1693	Approved
0.7283	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1090	Approved
0.7222	Intermediate Similarity	NPD1089	Approved
0.7222	Intermediate Similarity	NPD1086	Approved
0.7216	Intermediate Similarity	NPD5909	Discontinued
0.7209	Intermediate Similarity	NPD3971	Phase 1
0.7188	Intermediate Similarity	NPD2193	Phase 2
0.7188	Intermediate Similarity	NPD2648	Phase 3
0.7128	Intermediate Similarity	NPD1564	Approved
0.7128	Intermediate Similarity	NPD1565	Approved
0.7128	Intermediate Similarity	NPD1566	Phase 3
0.7083	Intermediate Similarity	NPD3135	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD1088	Approved
0.7041	Intermediate Similarity	NPD2577	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD1237	Approved
0.701	Intermediate Similarity	NPD2196	Discontinued
0.701	Intermediate Similarity	NPD2171	Approved
0.6989	Remote Similarity	NPD1202	Approved
0.697	Remote Similarity	NPD5048	Discontinued
0.6947	Remote Similarity	NPD1100	Approved
0.6947	Remote Similarity	NPD1099	Approved
0.6939	Remote Similarity	NPD3357	Discontinued
0.6931	Remote Similarity	NPD2329	Discontinued
0.6905	Remote Similarity	NPD4144	Approved
0.6905	Remote Similarity	NPD4147	Approved
0.6867	Remote Similarity	NPD9716	Approved
0.686	Remote Similarity	NPD3981	Approved
0.686	Remote Similarity	NPD3979	Approved
0.686	Remote Similarity	NPD3904	Approved
0.686	Remote Similarity	NPD3903	Approved
0.6854	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4803	Discontinued
0.6804	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2192	Approved
0.68	Remote Similarity	NPD2197	Approved
0.6795	Remote Similarity	NPD173	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4027	Approved
0.6782	Remote Similarity	NPD3035	Approved
0.6782	Remote Similarity	NPD4026	Approved
0.6735	Remote Similarity	NPD5630	Phase 1
0.6705	Remote Similarity	NPD4169	Approved
0.6705	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4170	Approved
0.6701	Remote Similarity	NPD5926	Approved
0.6667	Remote Similarity	NPD1673	Approved
0.6667	Remote Similarity	NPD7094	Approved
0.6667	Remote Similarity	NPD6588	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6858	Approved
0.6667	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD1677	Discontinued
0.6633	Remote Similarity	NPD1238	Approved
0.6629	Remote Similarity	NPD4635	Approved
0.6629	Remote Similarity	NPD2001	Discontinued
0.6593	Remote Similarity	NPD9257	Approved
0.6593	Remote Similarity	NPD9259	Approved
0.6562	Remote Similarity	NPD6049	Phase 2
0.6562	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD3429	Approved
0.6556	Remote Similarity	NPD5178	Approved
0.6556	Remote Similarity	NPD4544	Approved
0.6556	Remote Similarity	NPD3427	Approved
0.6552	Remote Similarity	NPD1475	Approved
0.6538	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD466	Approved
0.6531	Remote Similarity	NPD253	Approved
0.6531	Remote Similarity	NPD9495	Approved
0.6506	Remote Similarity	NPD294	Approved
0.6506	Remote Similarity	NPD292	Approved
0.6495	Remote Similarity	NPD2860	Approved
0.6495	Remote Similarity	NPD2859	Approved
0.6484	Remote Similarity	NPD5916	Discontinued
0.6481	Remote Similarity	NPD3317	Approved
0.6477	Remote Similarity	NPD1617	Discontinued
0.6476	Remote Similarity	NPD3643	Approved
0.6476	Remote Similarity	NPD3642	Approved
0.6476	Remote Similarity	NPD3644	Approved
0.6465	Remote Similarity	NPD742	Approved
0.6444	Remote Similarity	NPD5288	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD6647	Phase 2
0.6436	Remote Similarity	NPD5765	Approved
0.6429	Remote Similarity	NPD9566	Approved
0.6422	Remote Similarity	NPD4574	Approved
0.6422	Remote Similarity	NPD4576	Approved
0.6421	Remote Similarity	NPD1007	Discontinued
0.6413	Remote Similarity	NPD4406	Approved
0.6413	Remote Similarity	NPD4636	Approved
0.6413	Remote Similarity	NPD4409	Approved
0.6392	Remote Similarity	NPD2934	Approved
0.6392	Remote Similarity	NPD2933	Approved
0.6389	Remote Similarity	NPD3867	Phase 2
0.6389	Remote Similarity	NPD1023	Approved
0.6389	Remote Similarity	NPD2508	Discontinued
0.6389	Remote Similarity	NPD1021	Approved
0.6389	Remote Similarity	NPD1711	Phase 2
0.6389	Remote Similarity	NPD5951	Approved
0.6389	Remote Similarity	NPD1020	Approved
0.6389	Remote Similarity	NPD1022	Approved
0.6389	Remote Similarity	NPD2629	Approved
0.6383	Remote Similarity	NPD1628	Approved
0.6383	Remote Similarity	NPD1629	Approved
0.6381	Remote Similarity	NPD5278	Discontinued
0.6381	Remote Similarity	NPD2067	Discontinued
0.6381	Remote Similarity	NPD3581	Discontinued
0.6381	Remote Similarity	NPD1317	Discontinued
0.6374	Remote Similarity	NPD2539	Approved
0.6374	Remote Similarity	NPD2538	Approved
0.6364	Remote Similarity	NPD7610	Discontinued
0.6364	Remote Similarity	NPD6065	Approved
0.6344	Remote Similarity	NPD3428	Approved
0.6344	Remote Similarity	NPD4145	Approved
0.6344	Remote Similarity	NPD4146	Approved
0.6344	Remote Similarity	NPD2002	Discontinued
0.6344	Remote Similarity	NPD1282	Approved
0.6344	Remote Similarity	NPD3426	Approved
0.6339	Remote Similarity	NPD5836	Discontinued
0.6337	Remote Similarity	NPD813	Approved
0.6327	Remote Similarity	NPD2895	Discontinued
0.6327	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5927	Discontinued
0.6321	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD2811	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD9258	Approved
0.6316	Remote Similarity	NPD9256	Approved
0.6311	Remote Similarity	NPD1766	Approved
0.6311	Remote Similarity	NPD1761	Approved
0.6311	Remote Similarity	NPD1765	Approved
0.6311	Remote Similarity	NPD1018	Approved
0.6311	Remote Similarity	NPD1767	Approved
0.6311	Remote Similarity	NPD1763	Approved
0.6306	Remote Similarity	NPD7009	Phase 2
0.63	Remote Similarity	NPD3020	Approved
0.6296	Remote Similarity	NPD7077	Approved
0.6296	Remote Similarity	NPD3598	Phase 3
0.6296	Remote Similarity	NPD7076	Approved
0.6292	Remote Similarity	NPD914	Suspended
0.6289	Remote Similarity	NPD1066	Discontinued
0.6283	Remote Similarity	NPD4879	Approved
0.6277	Remote Similarity	NPD5675	Discontinued
0.6277	Remote Similarity	NPD3345	Approved
0.6275	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD7679	Phase 2
0.6273	Remote Similarity	NPD5162	Approved
0.6264	Remote Similarity	NPD1185	Approved
0.6263	Remote Similarity	NPD1875	Phase 1
0.6263	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD2124	Approved
0.6262	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6685	Approved
0.625	Remote Similarity	NPD4102	Approved
0.625	Remote Similarity	NPD5706	Approved
0.625	Remote Similarity	NPD467	Phase 1
0.625	Remote Similarity	NPD1651	Approved
0.625	Remote Similarity	NPD5705	Approved
0.625	Remote Similarity	NPD4105	Approved
0.625	Remote Similarity	NPD3025	Approved
0.625	Remote Similarity	NPD5704	Approved
0.625	Remote Similarity	NPD3024	Approved
0.6239	Remote Similarity	NPD2319	Discontinued
0.6238	Remote Similarity	NPD2558	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