NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	228.12
Volume:	252.645
LogP:	1.674
LogD:	1.848
LogS:	-3.502
# Rotatable Bonds:	3
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.863
Synthetic Accessibility Score:	3.224
Fsp3:	0.267
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.653
MDCK Permeability:	1.8077653294312768e-05
Pgp-inhibitor:	0.459
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.645
Plasma Protein Binding (PPB):	93.1456069946289%
Volume Distribution (VD):	0.754
Pgp-substrate:	2.4147205352783203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.548
CYP1A2-substrate:	0.517
CYP2C19-inhibitor:	0.198
CYP2C19-substrate:	0.42
CYP2C9-inhibitor:	0.081
CYP2C9-substrate:	0.75
CYP2D6-inhibitor:	0.143
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.205
CYP3A4-substrate:	0.38

ADMET: Excretion

Clearance (CL):	8.527
Half-life (T1/2):	0.748

ADMET: Toxicity

hERG Blockers:	0.083
Human Hepatotoxicity (H-HT):	0.457
Drug-inuced Liver Injury (DILI):	0.067
AMES Toxicity:	0.345
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.864
Skin Sensitization:	0.961
Carcinogencity:	0.784
Eye Corrosion:	0.306
Eye Irritation:	0.979
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC194326

Natural Product ID:	NPC194326
*Common Name:**	(1'r)-Candenatenin B
IUPAC Name:	(4R)-4-hydroxy-4-[(E)-3-phenylprop-2-enyl]cyclohex-2-en-1-one
Synonyms:
Standard InCHIKey:	MNSSTBQBMIUDKC-NFBGWVBBSA-N
Standard InCHI:	InChI=1S/C15H16O2/c16-14-8-11-15(17,12-9-14)10-4-7-13-5-2-1-3-6-13/h1-8,11,17H,9-10,12H2/b7-4+/t15-/m1/s1
SMILES:	c1ccc(cc1)/C=C/C[C@]1(C=CC(=O)CC1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078028
PubChem CID:	44254876
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000037] Styrenes

*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
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[19653666]
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	n.a.	Thai	n.a.	PMID[3430167]
NPO13784	Dalbergia candenatensis	Species	Fabaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	19700.0	nM	PMID[510627]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	83700.0	nM	PMID[510627]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	54400.0	nM	PMID[510627]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	55700.0	nM	PMID[510627]

☑ 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 NPC194326 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	180
0.1-0.2	1528
0.2-0.3	4010
0.3-0.4	11673
0.4-0.5	15325
0.5-0.6	8152
0.6-0.7	1587
0.7-0.8	226
0.8-0.85	13
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8602	High Similarity	NPC474308
0.8495	Intermediate Similarity	NPC329387
0.8495	Intermediate Similarity	NPC317280
0.8391	Intermediate Similarity	NPC123476
0.8387	Intermediate Similarity	NPC289201
0.8315	Intermediate Similarity	NPC477704
0.8315	Intermediate Similarity	NPC477693
0.8276	Intermediate Similarity	NPC44546
0.8105	Intermediate Similarity	NPC179411
0.8105	Intermediate Similarity	NPC476120
0.8	Intermediate Similarity	NPC278228
0.7979	Intermediate Similarity	NPC473347
0.7941	Intermediate Similarity	NPC474057
0.7907	Intermediate Similarity	NPC151405
0.7907	Intermediate Similarity	NPC139901
0.7882	Intermediate Similarity	NPC179726
0.7872	Intermediate Similarity	NPC34243
0.7857	Intermediate Similarity	NPC206800
0.7857	Intermediate Similarity	NPC32203
0.7812	Intermediate Similarity	NPC240042
0.7789	Intermediate Similarity	NPC206764
0.7742	Intermediate Similarity	NPC62765
0.7723	Intermediate Similarity	NPC69332
0.7723	Intermediate Similarity	NPC51174
0.7723	Intermediate Similarity	NPC29989
0.7723	Intermediate Similarity	NPC95178
0.7701	Intermediate Similarity	NPC300205
0.77	Intermediate Similarity	NPC249067
0.7683	Intermediate Similarity	NPC98880
0.7677	Intermediate Similarity	NPC25458
0.7674	Intermediate Similarity	NPC245966
0.766	Intermediate Similarity	NPC476484
0.766	Intermediate Similarity	NPC110704
0.7647	Intermediate Similarity	NPC211439
0.7642	Intermediate Similarity	NPC114144
0.7629	Intermediate Similarity	NPC156021
0.7629	Intermediate Similarity	NPC253423
0.7614	Intermediate Similarity	NPC127343
0.7614	Intermediate Similarity	NPC164086
0.7614	Intermediate Similarity	NPC71664
0.76	Intermediate Similarity	NPC68269
0.76	Intermediate Similarity	NPC247976
0.7596	Intermediate Similarity	NPC222905
0.759	Intermediate Similarity	NPC95289
0.7586	Intermediate Similarity	NPC36342
0.7586	Intermediate Similarity	NPC50192
0.7586	Intermediate Similarity	NPC285470
0.7586	Intermediate Similarity	NPC2785
0.7582	Intermediate Similarity	NPC95965
0.7579	Intermediate Similarity	NPC77273
0.7573	Intermediate Similarity	NPC475282
0.7561	Intermediate Similarity	NPC311343
0.7556	Intermediate Similarity	NPC215008
0.7556	Intermediate Similarity	NPC273758
0.7556	Intermediate Similarity	NPC44830
0.7556	Intermediate Similarity	NPC285773
0.7551	Intermediate Similarity	NPC201967
0.7551	Intermediate Similarity	NPC229242
0.7549	Intermediate Similarity	NPC70843
0.7528	Intermediate Similarity	NPC12936
0.7528	Intermediate Similarity	NPC273033
0.7526	Intermediate Similarity	NPC61944
0.75	Intermediate Similarity	NPC472585
0.75	Intermediate Similarity	NPC244427
0.75	Intermediate Similarity	NPC88141
0.75	Intermediate Similarity	NPC155429
0.75	Intermediate Similarity	NPC74458
0.75	Intermediate Similarity	NPC222390
0.75	Intermediate Similarity	NPC272260
0.75	Intermediate Similarity	NPC181709
0.7477	Intermediate Similarity	NPC93181
0.7476	Intermediate Similarity	NPC141523
0.7476	Intermediate Similarity	NPC20485
0.7476	Intermediate Similarity	NPC34715
0.7475	Intermediate Similarity	NPC54647
0.7475	Intermediate Similarity	NPC130193
0.7475	Intermediate Similarity	NPC217621
0.7474	Intermediate Similarity	NPC187725
0.7474	Intermediate Similarity	NPC141607
0.7471	Intermediate Similarity	NPC329318
0.7471	Intermediate Similarity	NPC9796
0.7429	Intermediate Similarity	NPC116842
0.7426	Intermediate Similarity	NPC274443
0.7426	Intermediate Similarity	NPC255676
0.7419	Intermediate Similarity	NPC69057
0.7419	Intermediate Similarity	NPC43945
0.7416	Intermediate Similarity	NPC95868
0.7416	Intermediate Similarity	NPC190567
0.7416	Intermediate Similarity	NPC477703
0.7416	Intermediate Similarity	NPC17408
0.7416	Intermediate Similarity	NPC285716
0.7412	Intermediate Similarity	NPC285679
0.7404	Intermediate Similarity	NPC17525
0.74	Intermediate Similarity	NPC158623
0.74	Intermediate Similarity	NPC282895
0.7386	Intermediate Similarity	NPC137847
0.7386	Intermediate Similarity	NPC76455
0.7379	Intermediate Similarity	NPC6984
0.7379	Intermediate Similarity	NPC100767
0.7374	Intermediate Similarity	NPC145052
0.7374	Intermediate Similarity	NPC260000
0.7368	Intermediate Similarity	NPC110420
0.7368	Intermediate Similarity	NPC303967
0.7368	Intermediate Similarity	NPC67585
0.7353	Intermediate Similarity	NPC120693
0.7353	Intermediate Similarity	NPC329282
0.7353	Intermediate Similarity	NPC261573
0.7353	Intermediate Similarity	NPC8931
0.7347	Intermediate Similarity	NPC12695
0.734	Intermediate Similarity	NPC157778
0.7339	Intermediate Similarity	NPC108532
0.7333	Intermediate Similarity	NPC133050
0.7333	Intermediate Similarity	NPC73978
0.7333	Intermediate Similarity	NPC145053
0.7333	Intermediate Similarity	NPC95172
0.7327	Intermediate Similarity	NPC304873
0.7327	Intermediate Similarity	NPC284477
0.732	Intermediate Similarity	NPC261181
0.7312	Intermediate Similarity	NPC474211
0.7312	Intermediate Similarity	NPC318107
0.7308	Intermediate Similarity	NPC226699
0.7303	Intermediate Similarity	NPC469894
0.73	Intermediate Similarity	NPC280869
0.73	Intermediate Similarity	NPC325497
0.73	Intermediate Similarity	NPC228435
0.7292	Intermediate Similarity	NPC284475
0.7292	Intermediate Similarity	NPC133461
0.7292	Intermediate Similarity	NPC472319
0.7282	Intermediate Similarity	NPC321670
0.7282	Intermediate Similarity	NPC134120
0.7282	Intermediate Similarity	NPC172483
0.7282	Intermediate Similarity	NPC105899
0.7273	Intermediate Similarity	NPC472788
0.7273	Intermediate Similarity	NPC103048
0.7264	Intermediate Similarity	NPC21162
0.7255	Intermediate Similarity	NPC329556
0.7255	Intermediate Similarity	NPC135784
0.7253	Intermediate Similarity	NPC283012
0.7253	Intermediate Similarity	NPC475199
0.7245	Intermediate Similarity	NPC81010
0.7245	Intermediate Similarity	NPC32977
0.7241	Intermediate Similarity	NPC189371
0.7238	Intermediate Similarity	NPC224584
0.7234	Intermediate Similarity	NPC322387
0.7216	Intermediate Similarity	NPC188844
0.7216	Intermediate Similarity	NPC153885
0.7216	Intermediate Similarity	NPC1682
0.7216	Intermediate Similarity	NPC155232
0.7212	Intermediate Similarity	NPC188677
0.7204	Intermediate Similarity	NPC99482
0.7204	Intermediate Similarity	NPC474354
0.72	Intermediate Similarity	NPC160548
0.72	Intermediate Similarity	NPC210529
0.72	Intermediate Similarity	NPC175852
0.7196	Intermediate Similarity	NPC268388
0.7196	Intermediate Similarity	NPC292834
0.7191	Intermediate Similarity	NPC103488
0.7188	Intermediate Similarity	NPC274455
0.7188	Intermediate Similarity	NPC86670
0.7188	Intermediate Similarity	NPC173413
0.7188	Intermediate Similarity	NPC70940
0.7184	Intermediate Similarity	NPC472222
0.7184	Intermediate Similarity	NPC472221
0.7174	Intermediate Similarity	NPC308619
0.7174	Intermediate Similarity	NPC324835
0.7174	Intermediate Similarity	NPC127491
0.7172	Intermediate Similarity	NPC257182
0.7172	Intermediate Similarity	NPC286006
0.7172	Intermediate Similarity	NPC246679
0.7158	Intermediate Similarity	NPC329064
0.7156	Intermediate Similarity	NPC186933
0.7156	Intermediate Similarity	NPC285350
0.7143	Intermediate Similarity	NPC249811
0.7143	Intermediate Similarity	NPC156648
0.7143	Intermediate Similarity	NPC238219
0.7143	Intermediate Similarity	NPC71795
0.7143	Intermediate Similarity	NPC82770
0.7143	Intermediate Similarity	NPC239931
0.7143	Intermediate Similarity	NPC117180
0.7143	Intermediate Similarity	NPC78954
0.713	Intermediate Similarity	NPC306977
0.713	Intermediate Similarity	NPC287055
0.713	Intermediate Similarity	NPC206414
0.713	Intermediate Similarity	NPC242957
0.7129	Intermediate Similarity	NPC245561
0.7115	Intermediate Similarity	NPC163734
0.7113	Intermediate Similarity	NPC317645
0.7103	Intermediate Similarity	NPC476003
0.71	Intermediate Similarity	NPC477767
0.71	Intermediate Similarity	NPC133135
0.71	Intermediate Similarity	NPC283711
0.71	Intermediate Similarity	NPC251579
0.7097	Intermediate Similarity	NPC168855
0.7097	Intermediate Similarity	NPC304538
0.7093	Intermediate Similarity	NPC326200
0.7091	Intermediate Similarity	NPC322197
0.7091	Intermediate Similarity	NPC23402
0.7087	Intermediate Similarity	NPC13426
0.7087	Intermediate Similarity	NPC474365
0.7087	Intermediate Similarity	NPC301943

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 NPC194326 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	948
0.2-0.3	1396
0.3-0.4	3187
0.4-0.5	2361
0.5-0.6	891
0.6-0.7	159
0.7-0.8	31
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7872	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD9716	Approved
0.7742	Intermediate Similarity	NPD9258	Approved
0.7742	Intermediate Similarity	NPD9256	Approved
0.77	Intermediate Similarity	NPD1237	Approved
0.7653	Intermediate Similarity	NPD2066	Phase 3
0.7556	Intermediate Similarity	NPD9491	Approved
0.7528	Intermediate Similarity	NPD942	Approved
0.7528	Intermediate Similarity	NPD226	Approved
0.7426	Intermediate Similarity	NPD6647	Phase 2
0.7419	Intermediate Similarity	NPD650	Approved
0.7416	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD3971	Phase 1
0.7327	Intermediate Similarity	NPD1932	Approved
0.732	Intermediate Similarity	NPD1202	Approved
0.7312	Intermediate Similarity	NPD9257	Approved
0.7312	Intermediate Similarity	NPD9259	Approved
0.7292	Intermediate Similarity	NPD7609	Phase 3
0.7263	Intermediate Similarity	NPD800	Approved
0.7255	Intermediate Similarity	NPD1929	Approved
0.7255	Intermediate Similarity	NPD1930	Approved
0.7255	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD1693	Approved
0.7234	Intermediate Similarity	NPD4793	Discontinued
0.7216	Intermediate Similarity	NPD7631	Approved
0.72	Intermediate Similarity	NPD9495	Approved
0.7191	Intermediate Similarity	NPD227	Approved
0.7191	Intermediate Similarity	NPD225	Approved
0.7188	Intermediate Similarity	NPD1086	Approved
0.7188	Intermediate Similarity	NPD1090	Approved
0.7188	Intermediate Similarity	NPD1089	Approved
0.7184	Intermediate Similarity	NPD5909	Discontinued
0.7113	Intermediate Similarity	NPD1239	Approved
0.7111	Intermediate Similarity	NPD9490	Approved
0.7103	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5346	Phase 2
0.7083	Intermediate Similarity	NPD5347	Phase 2
0.7079	Intermediate Similarity	NPD9294	Approved
0.7041	Intermediate Similarity	NPD1088	Approved
0.7037	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD1238	Approved
0.6952	Remote Similarity	NPD5048	Discontinued
0.6931	Remote Similarity	NPD3495	Discontinued
0.6923	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD2329	Discontinued
0.6907	Remote Similarity	NPD689	Discontinued
0.69	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4878	Approved
0.6875	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1087	Approved
0.6875	Remote Similarity	NPD1282	Approved
0.6869	Remote Similarity	NPD1508	Approved
0.6852	Remote Similarity	NPD1317	Discontinued
0.6847	Remote Similarity	NPD5951	Approved
0.6847	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD9264	Approved
0.6822	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD9263	Approved
0.6822	Remote Similarity	NPD9267	Approved
0.6818	Remote Similarity	NPD5277	Phase 2
0.6765	Remote Similarity	NPD1566	Phase 3
0.6765	Remote Similarity	NPD1564	Approved
0.6765	Remote Similarity	NPD1565	Approved
0.6759	Remote Similarity	NPD9266	Approved
0.6759	Remote Similarity	NPD74	Approved
0.6733	Remote Similarity	NPD9260	Approved
0.6733	Remote Similarity	NPD2933	Approved
0.6733	Remote Similarity	NPD2934	Approved
0.6727	Remote Similarity	NPD9508	Approved
0.6698	Remote Similarity	NPD164	Approved
0.6667	Remote Similarity	NPD2859	Approved
0.6667	Remote Similarity	NPD111	Approved
0.6667	Remote Similarity	NPD1843	Approved
0.6667	Remote Similarity	NPD2860	Approved
0.6638	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7009	Phase 2
0.6607	Remote Similarity	NPD1241	Discontinued
0.6606	Remote Similarity	NPD2182	Approved
0.6579	Remote Similarity	NPD9493	Approved
0.6569	Remote Similarity	NPD6049	Phase 2
0.6569	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5159	Phase 2
0.6555	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5157	Phase 1
0.6552	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD2629	Approved
0.6545	Remote Similarity	NPD2067	Discontinued
0.6529	Remote Similarity	NPD4980	Approved
0.6522	Remote Similarity	NPD7610	Discontinued
0.6505	Remote Similarity	NPD1989	Approved
0.65	Remote Similarity	NPD3672	Approved
0.65	Remote Similarity	NPD3673	Approved
0.6496	Remote Similarity	NPD2932	Approved
0.6476	Remote Similarity	NPD3020	Approved
0.6476	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1066	Discontinued
0.6471	Remote Similarity	NPD1563	Approved
0.6471	Remote Similarity	NPD845	Approved
0.6466	Remote Similarity	NPD9545	Approved
0.646	Remote Similarity	NPD6010	Discontinued
0.6449	Remote Similarity	NPD9261	Approved
0.6446	Remote Similarity	NPD1470	Approved
0.6442	Remote Similarity	NPD1099	Approved
0.6442	Remote Similarity	NPD1100	Approved
0.6442	Remote Similarity	NPD9566	Approved
0.6441	Remote Similarity	NPD4879	Approved
0.6436	Remote Similarity	NPD1007	Discontinued
0.641	Remote Similarity	NPD4102	Approved
0.641	Remote Similarity	NPD4105	Approved
0.6408	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD1246	Approved
0.6404	Remote Similarity	NPD9281	Approved
0.6396	Remote Similarity	NPD664	Approved
0.6387	Remote Similarity	NPD1201	Approved
0.6381	Remote Similarity	NPD5926	Approved
0.6381	Remote Similarity	NPD253	Approved
0.6373	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD5305	Approved
0.6356	Remote Similarity	NPD5306	Approved
0.6356	Remote Similarity	NPD3019	Approved
0.6356	Remote Similarity	NPD1104	Approved
0.6355	Remote Similarity	NPD4817	Approved
0.6355	Remote Similarity	NPD2648	Phase 3
0.6355	Remote Similarity	NPD2171	Approved
0.6355	Remote Similarity	NPD2193	Phase 2
0.6355	Remote Similarity	NPD4818	Approved
0.6346	Remote Similarity	NPD844	Approved
0.6321	Remote Similarity	NPD7798	Approved
0.6321	Remote Similarity	NPD9712	Approved
0.6303	Remote Similarity	NPD4135	Approved
0.6303	Remote Similarity	NPD4106	Approved
0.6303	Remote Similarity	NPD4136	Approved
0.6303	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.63	Remote Similarity	NPD1101	Approved
0.6296	Remote Similarity	NPD4658	Approved
0.6296	Remote Similarity	NPD4231	Approved
0.6296	Remote Similarity	NPD5765	Approved
0.6296	Remote Similarity	NPD3681	Approved
0.6296	Remote Similarity	NPD3683	Approved
0.6296	Remote Similarity	NPD4229	Approved
0.6296	Remote Similarity	NPD4656	Approved
0.6296	Remote Similarity	NPD3680	Approved
0.6296	Remote Similarity	NPD3682	Approved
0.6281	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD1616	Discontinued
0.6262	Remote Similarity	NPD1242	Phase 1
0.626	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4806	Approved
0.625	Remote Similarity	NPD4807	Approved
0.625	Remote Similarity	NPD9250	Approved
0.625	Remote Similarity	NPD4094	Approved
0.6239	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD1758	Phase 1
0.6228	Remote Similarity	NPD6858	Approved
0.6228	Remote Similarity	NPD7094	Approved
0.6226	Remote Similarity	NPD9710	Approved
0.6226	Remote Similarity	NPD9711	Approved
0.622	Remote Similarity	NPD4445	Approved
0.622	Remote Similarity	NPD4453	Approved
0.622	Remote Similarity	NPD4452	Approved
0.6218	Remote Similarity	NPD2345	Approved
0.6218	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD256	Approved
0.6207	Remote Similarity	NPD3317	Approved
0.6207	Remote Similarity	NPD255	Approved
0.6204	Remote Similarity	NPD940	Approved
0.6204	Remote Similarity	NPD2196	Discontinued
0.6204	Remote Similarity	NPD846	Approved
0.62	Remote Similarity	NPD9538	Approved
0.6198	Remote Similarity	NPD9717	Approved
0.619	Remote Similarity	NPD3764	Approved
0.619	Remote Similarity	NPD1809	Phase 2
0.6186	Remote Similarity	NPD1759	Phase 1
0.6182	Remote Similarity	NPD1018	Approved
0.6182	Remote Similarity	NPD999	Phase 2
0.6179	Remote Similarity	NPD1164	Approved
0.6179	Remote Similarity	NPD1203	Approved
0.6179	Remote Similarity	NPD2797	Approved
0.6174	Remote Similarity	NPD2652	Approved
0.6174	Remote Similarity	NPD2650	Approved
0.6154	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD719	Approved
0.6154	Remote Similarity	NPD720	Approved
0.6154	Remote Similarity	NPD9568	Approved
0.6148	Remote Similarity	NPD1755	Approved
0.6147	Remote Similarity	NPD3357	Discontinued
0.6147	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD1245	Approved
0.6132	Remote Similarity	NPD4655	Approved
0.6132	Remote Similarity	NPD288	Approved
0.6132	Remote Similarity	NPD4657	Approved
0.6129	Remote Similarity	NPD2798	Approved
0.6126	Remote Similarity	NPD6685	Approved
0.6126	Remote Similarity	NPD3134	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