NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	228.12
Volume:	252.645
LogP:	3.649
LogD:	3.401
LogS:	-3.26
# Rotatable Bonds:	3
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.787
Synthetic Accessibility Score:	2.398
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.642
MDCK Permeability:	1.5871353753027506e-05
Pgp-inhibitor:	0.035
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.974
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.145
Plasma Protein Binding (PPB):	96.41699981689453%
Volume Distribution (VD):	1.302
Pgp-substrate:	2.420398235321045%

ADMET: Metabolism

CYP1A2-inhibitor:	0.736
CYP1A2-substrate:	0.927
CYP2C19-inhibitor:	0.914
CYP2C19-substrate:	0.674
CYP2C9-inhibitor:	0.827
CYP2C9-substrate:	0.969
CYP2D6-inhibitor:	0.909
CYP2D6-substrate:	0.875
CYP3A4-inhibitor:	0.578
CYP3A4-substrate:	0.528

ADMET: Excretion

Clearance (CL):	12.1
Half-life (T1/2):	0.769

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.074
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.157
Rat Oral Acute Toxicity:	0.692
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.808
Carcinogencity:	0.098
Eye Corrosion:	0.005
Eye Irritation:	0.848
Respiratory Toxicity:	0.615

Download Data

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

Natural Product: NPC329387

Natural Product ID:	NPC329387
*Common Name:**	(4R,6R)-4-Hydroxy-6-(1-Phenylallyl)Cyclohex-2-Enone
IUPAC Name:	(4R,6R)-4-hydroxy-6-(1-phenylprop-2-enyl)cyclohex-2-en-1-one
Synonyms:
Standard InCHIKey:	RTLQJCZEXLLNLE-SMEJFCCLSA-N
Standard InCHI:	InChI=1S/C15H16O2/c1-2-13(11-6-4-3-5-7-11)14-10-12(16)8-9-15(14)17/h2-9,12-14,16H,1,10H2/t12-,13?,14+/m0/s1
SMILES:	C=CC([C@H]1C[C@@H](O)C=CC1=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463733
PubChem CID:	11183777
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO29804	Nepalese propolis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[15974608]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
CELL-LINE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20763	CELL-LINE	J774.1	Mus musculus	IC50	=	500.0	nM	PMID[485699]

☑ 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 NPC329387 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	203
0.1-0.2	883
0.2-0.3	2270
0.3-0.4	7304
0.4-0.5	13376
0.5-0.6	14886
0.6-0.7	3252
0.7-0.8	499
0.8-0.85	18
0.85-0.9	3
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC317280
0.8911	High Similarity	NPC475282
0.8854	High Similarity	NPC289201
0.8646	High Similarity	NPC206764
0.8495	Intermediate Similarity	NPC194326
0.8447	Intermediate Similarity	NPC211439
0.8396	Intermediate Similarity	NPC306977
0.8396	Intermediate Similarity	NPC206414
0.8396	Intermediate Similarity	NPC242957
0.8396	Intermediate Similarity	NPC287055
0.8333	Intermediate Similarity	NPC249067
0.8333	Intermediate Similarity	NPC141607
0.8333	Intermediate Similarity	NPC187725
0.8211	Intermediate Similarity	NPC477704
0.8211	Intermediate Similarity	NPC477693
0.8208	Intermediate Similarity	NPC474057
0.8077	Intermediate Similarity	NPC474307
0.8077	Intermediate Similarity	NPC321670
0.8058	Intermediate Similarity	NPC247976
0.802	Intermediate Similarity	NPC145052
0.8	Intermediate Similarity	NPC25385
0.8	Intermediate Similarity	NPC475905
0.8	Intermediate Similarity	NPC193640
0.7963	Intermediate Similarity	NPC471188
0.7895	Intermediate Similarity	NPC99482
0.7895	Intermediate Similarity	NPC123476
0.789	Intermediate Similarity	NPC470253
0.787	Intermediate Similarity	NPC265513
0.7843	Intermediate Similarity	NPC179411
0.783	Intermediate Similarity	NPC100767
0.7818	Intermediate Similarity	NPC196673
0.781	Intermediate Similarity	NPC329282
0.7807	Intermediate Similarity	NPC470585
0.7788	Intermediate Similarity	NPC304873
0.7788	Intermediate Similarity	NPC25458
0.7778	Intermediate Similarity	NPC476484
0.7767	Intermediate Similarity	NPC474308
0.7766	Intermediate Similarity	NPC475199
0.7766	Intermediate Similarity	NPC283012
0.7757	Intermediate Similarity	NPC20485
0.7755	Intermediate Similarity	NPC231591
0.7748	Intermediate Similarity	NPC285350
0.7739	Intermediate Similarity	NPC472981
0.7736	Intermediate Similarity	NPC471186
0.7714	Intermediate Similarity	NPC329556
0.7714	Intermediate Similarity	NPC255676
0.7699	Intermediate Similarity	NPC471553
0.7692	Intermediate Similarity	NPC12881
0.7692	Intermediate Similarity	NPC140118
0.7684	Intermediate Similarity	NPC44830
0.767	Intermediate Similarity	NPC210529
0.767	Intermediate Similarity	NPC175852
0.767	Intermediate Similarity	NPC160548
0.767	Intermediate Similarity	NPC476120
0.7664	Intermediate Similarity	NPC83409
0.7664	Intermediate Similarity	NPC185763
0.7664	Intermediate Similarity	NPC477251
0.7664	Intermediate Similarity	NPC51174
0.7636	Intermediate Similarity	NPC477250
0.7632	Intermediate Similarity	NPC318173
0.7624	Intermediate Similarity	NPC34243
0.7611	Intermediate Similarity	NPC325646
0.7611	Intermediate Similarity	NPC28951
0.7604	Intermediate Similarity	NPC304538
0.76	Intermediate Similarity	NPC317645
0.7596	Intermediate Similarity	NPC217621
0.7596	Intermediate Similarity	NPC54647
0.7596	Intermediate Similarity	NPC476042
0.7589	Intermediate Similarity	NPC93181
0.7589	Intermediate Similarity	NPC215419
0.7579	Intermediate Similarity	NPC121478
0.7579	Intermediate Similarity	NPC73637
0.7576	Intermediate Similarity	NPC1793
0.7573	Intermediate Similarity	NPC156021
0.7573	Intermediate Similarity	NPC278228
0.757	Intermediate Similarity	NPC134120
0.757	Intermediate Similarity	NPC105899
0.7565	Intermediate Similarity	NPC472708
0.7553	Intermediate Similarity	NPC184030
0.7553	Intermediate Similarity	NPC127343
0.7553	Intermediate Similarity	NPC164449
0.7553	Intermediate Similarity	NPC285716
0.7553	Intermediate Similarity	NPC17408
0.7551	Intermediate Similarity	NPC322387
0.7547	Intermediate Similarity	NPC274443
0.7545	Intermediate Similarity	NPC252544
0.7545	Intermediate Similarity	NPC321252
0.7544	Intermediate Similarity	NPC80605
0.7544	Intermediate Similarity	NPC323440
0.7544	Intermediate Similarity	NPC222968
0.7526	Intermediate Similarity	NPC95965
0.7525	Intermediate Similarity	NPC77273
0.7523	Intermediate Similarity	NPC317305
0.7522	Intermediate Similarity	NPC23402
0.7522	Intermediate Similarity	NPC322197
0.75	Intermediate Similarity	NPC95178
0.75	Intermediate Similarity	NPC29989
0.75	Intermediate Similarity	NPC472680
0.75	Intermediate Similarity	NPC474222
0.75	Intermediate Similarity	NPC274455
0.75	Intermediate Similarity	NPC475804
0.75	Intermediate Similarity	NPC110420
0.75	Intermediate Similarity	NPC70940
0.75	Intermediate Similarity	NPC67585
0.75	Intermediate Similarity	NPC133302
0.75	Intermediate Similarity	NPC303967
0.75	Intermediate Similarity	NPC229242
0.75	Intermediate Similarity	NPC86670
0.75	Intermediate Similarity	NPC69332
0.75	Intermediate Similarity	NPC472679
0.7478	Intermediate Similarity	NPC249435
0.7477	Intermediate Similarity	NPC292834
0.7477	Intermediate Similarity	NPC177576
0.7477	Intermediate Similarity	NPC66208
0.7477	Intermediate Similarity	NPC19136
0.7477	Intermediate Similarity	NPC218855
0.7477	Intermediate Similarity	NPC158282
0.7477	Intermediate Similarity	NPC471189
0.7474	Intermediate Similarity	NPC117180
0.7459	Intermediate Similarity	NPC472388
0.7458	Intermediate Similarity	NPC65627
0.7455	Intermediate Similarity	NPC88141
0.7453	Intermediate Similarity	NPC244427
0.7453	Intermediate Similarity	NPC222390
0.7449	Intermediate Similarity	NPC93843
0.7447	Intermediate Similarity	NPC139901
0.7447	Intermediate Similarity	NPC151405
0.7438	Intermediate Similarity	NPC116057
0.7436	Intermediate Similarity	NPC476234
0.7434	Intermediate Similarity	NPC186933
0.7431	Intermediate Similarity	NPC470007
0.7431	Intermediate Similarity	NPC34715
0.7431	Intermediate Similarity	NPC112903
0.7431	Intermediate Similarity	NPC249811
0.7426	Intermediate Similarity	NPC110704
0.7426	Intermediate Similarity	NPC133461
0.7417	Intermediate Similarity	NPC236405
0.7414	Intermediate Similarity	NPC473767
0.7411	Intermediate Similarity	NPC272524
0.7411	Intermediate Similarity	NPC128368
0.7407	Intermediate Similarity	NPC172483
0.7404	Intermediate Similarity	NPC253423
0.7396	Intermediate Similarity	NPC329319
0.7396	Intermediate Similarity	NPC99394
0.7396	Intermediate Similarity	NPC87299
0.7396	Intermediate Similarity	NPC103326
0.7391	Intermediate Similarity	NPC152812
0.7387	Intermediate Similarity	NPC476003
0.7387	Intermediate Similarity	NPC133308
0.7387	Intermediate Similarity	NPC477247
0.7383	Intermediate Similarity	NPC160382
0.7377	Intermediate Similarity	NPC225103
0.7373	Intermediate Similarity	NPC18785
0.7368	Intermediate Similarity	NPC471616
0.7368	Intermediate Similarity	NPC477703
0.7368	Intermediate Similarity	NPC9274
0.7368	Intermediate Similarity	NPC190567
0.7364	Intermediate Similarity	NPC318327
0.7358	Intermediate Similarity	NPC158623
0.7358	Intermediate Similarity	NPC264728
0.7358	Intermediate Similarity	NPC282895
0.7358	Intermediate Similarity	NPC225079
0.7358	Intermediate Similarity	NPC469481
0.7355	Intermediate Similarity	NPC471935
0.7355	Intermediate Similarity	NPC471929
0.7355	Intermediate Similarity	NPC81135
0.7355	Intermediate Similarity	NPC471930
0.7355	Intermediate Similarity	NPC169913
0.7355	Intermediate Similarity	NPC477365
0.7353	Intermediate Similarity	NPC153885
0.7353	Intermediate Similarity	NPC1682
0.7353	Intermediate Similarity	NPC188844
0.735	Intermediate Similarity	NPC474223
0.735	Intermediate Similarity	NPC475827
0.735	Intermediate Similarity	NPC473662
0.735	Intermediate Similarity	NPC7151
0.735	Intermediate Similarity	NPC216297
0.7345	Intermediate Similarity	NPC477411
0.7345	Intermediate Similarity	NPC474363
0.7345	Intermediate Similarity	NPC153053
0.7345	Intermediate Similarity	NPC234637
0.7345	Intermediate Similarity	NPC130591
0.7345	Intermediate Similarity	NPC87069
0.734	Intermediate Similarity	NPC103488
0.734	Intermediate Similarity	NPC224544
0.734	Intermediate Similarity	NPC76455
0.734	Intermediate Similarity	NPC137847
0.7339	Intermediate Similarity	NPC136962
0.7339	Intermediate Similarity	NPC85560
0.7339	Intermediate Similarity	NPC142326
0.7339	Intermediate Similarity	NPC94751
0.7339	Intermediate Similarity	NPC37115
0.7339	Intermediate Similarity	NPC70843
0.7339	Intermediate Similarity	NPC244933
0.7333	Intermediate Similarity	NPC234890
0.7333	Intermediate Similarity	NPC74507
0.7327	Intermediate Similarity	NPC62765
0.7321	Intermediate Similarity	NPC212718
0.7321	Intermediate Similarity	NPC321852
0.7321	Intermediate Similarity	NPC114682

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 NPC329387 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	796
0.2-0.3	1302
0.3-0.4	2842
0.4-0.5	2441
0.5-0.6	1261
0.6-0.7	274
0.7-0.8	45
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8351	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1237	Approved
0.8235	Intermediate Similarity	NPD6647	Phase 2
0.8208	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD2066	Phase 3
0.7788	Intermediate Similarity	NPD1932	Approved
0.7714	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD1929	Approved
0.7714	Intermediate Similarity	NPD1930	Approved
0.767	Intermediate Similarity	NPD9495	Approved
0.766	Intermediate Similarity	NPD226	Approved
0.7642	Intermediate Similarity	NPD5909	Discontinued
0.7549	Intermediate Similarity	NPD1693	Approved
0.7547	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD2329	Discontinued
0.75	Intermediate Similarity	NPD1086	Approved
0.75	Intermediate Similarity	NPD1089	Approved
0.75	Intermediate Similarity	NPD1090	Approved
0.7434	Intermediate Similarity	NPD2629	Approved
0.7407	Intermediate Similarity	NPD5048	Discontinued
0.74	Intermediate Similarity	NPD5347	Phase 2
0.74	Intermediate Similarity	NPD5346	Phase 2
0.74	Intermediate Similarity	NPD800	Approved
0.7383	Intermediate Similarity	NPD5765	Approved
0.7374	Intermediate Similarity	NPD4793	Discontinued
0.7364	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7631	Approved
0.7353	Intermediate Similarity	NPD1088	Approved
0.734	Intermediate Similarity	NPD227	Approved
0.734	Intermediate Similarity	NPD225	Approved
0.7327	Intermediate Similarity	NPD3672	Approved
0.7327	Intermediate Similarity	NPD9258	Approved
0.7327	Intermediate Similarity	NPD9256	Approved
0.7327	Intermediate Similarity	NPD3673	Approved
0.732	Intermediate Similarity	NPD9491	Approved
0.7297	Intermediate Similarity	NPD1317	Discontinued
0.7292	Intermediate Similarity	NPD942	Approved
0.7257	Intermediate Similarity	NPD6858	Approved
0.7257	Intermediate Similarity	NPD7094	Approved
0.7255	Intermediate Similarity	NPD1239	Approved
0.7255	Intermediate Similarity	NPD7609	Phase 3
0.7232	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1087	Approved
0.72	Intermediate Similarity	NPD650	Approved
0.7188	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6685	Approved
0.7167	Intermediate Similarity	NPD4878	Approved
0.7155	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5951	Approved
0.7107	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5157	Phase 1
0.7107	Intermediate Similarity	NPD5159	Phase 2
0.7075	Intermediate Similarity	NPD3495	Discontinued
0.7075	Intermediate Similarity	NPD1566	Phase 3
0.7075	Intermediate Similarity	NPD1565	Approved
0.7075	Intermediate Similarity	NPD1564	Approved
0.7073	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD3317	Approved
0.7064	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD9294	Approved
0.7034	Intermediate Similarity	NPD7009	Phase 2
0.7021	Intermediate Similarity	NPD9716	Approved
0.7019	Intermediate Similarity	NPD1508	Approved
0.7018	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD2067	Discontinued
0.6981	Remote Similarity	NPD1989	Approved
0.697	Remote Similarity	NPD3971	Phase 1
0.6952	Remote Similarity	NPD1202	Approved
0.6949	Remote Similarity	NPD7610	Discontinued
0.6944	Remote Similarity	NPD1238	Approved
0.6944	Remote Similarity	NPD7798	Approved
0.6935	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6085	Phase 2
0.6931	Remote Similarity	NPD9259	Approved
0.6931	Remote Similarity	NPD9257	Approved
0.6917	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD2932	Approved
0.6917	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD9490	Approved
0.6903	Remote Similarity	NPD2182	Approved
0.6897	Remote Similarity	NPD6010	Discontinued
0.6875	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6912	Phase 3
0.686	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD253	Approved
0.6847	Remote Similarity	NPD164	Approved
0.6838	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1843	Approved
0.6822	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1563	Approved
0.6789	Remote Similarity	NPD3020	Approved
0.6777	Remote Similarity	NPD5305	Approved
0.6777	Remote Similarity	NPD5306	Approved
0.6777	Remote Similarity	NPD3019	Approved
0.6772	Remote Similarity	NPD7008	Discontinued
0.6752	Remote Similarity	NPD1241	Discontinued
0.6727	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD467	Phase 1
0.6721	Remote Similarity	NPD4879	Approved
0.672	Remote Similarity	NPD1470	Approved
0.6697	Remote Similarity	NPD5926	Approved
0.6694	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4807	Approved
0.6667	Remote Similarity	NPD4806	Approved
0.6667	Remote Similarity	NPD1201	Approved
0.6641	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD2345	Approved
0.6638	Remote Similarity	NPD3643	Approved
0.6638	Remote Similarity	NPD3644	Approved
0.6638	Remote Similarity	NPD3642	Approved
0.6637	Remote Similarity	NPD1018	Approved
0.6636	Remote Similarity	NPD845	Approved
0.6636	Remote Similarity	NPD1066	Discontinued
0.6636	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6637	Approved
0.661	Remote Similarity	NPD2652	Approved
0.661	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.661	Remote Similarity	NPD2650	Approved
0.6585	Remote Similarity	NPD4106	Approved
0.6585	Remote Similarity	NPD4135	Approved
0.6585	Remote Similarity	NPD4136	Approved
0.6581	Remote Similarity	NPD9508	Approved
0.6574	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD4814	Discontinued
0.6574	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6049	Phase 2
0.6571	Remote Similarity	NPD689	Discontinued
0.6555	Remote Similarity	NPD1246	Approved
0.6555	Remote Similarity	NPD1711	Phase 2
0.6541	Remote Similarity	NPD7305	Phase 1
0.6538	Remote Similarity	NPD7714	Approved
0.6538	Remote Similarity	NPD7961	Discontinued
0.6538	Remote Similarity	NPD7715	Approved
0.6538	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1282	Approved
0.6535	Remote Similarity	NPD2798	Approved
0.6535	Remote Similarity	NPD4980	Approved
0.6532	Remote Similarity	NPD4215	Approved
0.6532	Remote Similarity	NPD2608	Approved
0.6532	Remote Similarity	NPD4216	Approved
0.6532	Remote Similarity	NPD2610	Approved
0.6532	Remote Similarity	NPD2611	Approved
0.6532	Remote Similarity	NPD3131	Approved
0.6532	Remote Similarity	NPD4218	Approved
0.6532	Remote Similarity	NPD4217	Approved
0.6532	Remote Similarity	NPD2609	Approved
0.6532	Remote Similarity	NPD3132	Approved
0.6532	Remote Similarity	NPD2612	Approved
0.6529	Remote Similarity	NPD6065	Approved
0.6525	Remote Similarity	NPD5277	Phase 2
0.6522	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD9264	Approved
0.6522	Remote Similarity	NPD6406	Approved
0.6522	Remote Similarity	NPD9267	Approved
0.6522	Remote Similarity	NPD9263	Approved
0.6522	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD2860	Approved
0.6514	Remote Similarity	NPD2859	Approved
0.6481	Remote Similarity	NPD3719	Approved
0.6481	Remote Similarity	NPD3718	Approved
0.6476	Remote Similarity	NPD1101	Approved
0.6476	Remote Similarity	NPD531	Approved
0.6475	Remote Similarity	NPD9545	Approved
0.6471	Remote Similarity	NPD3598	Phase 3
0.6466	Remote Similarity	NPD9266	Approved
0.6466	Remote Similarity	NPD74	Approved
0.6457	Remote Similarity	NPD2797	Approved
0.6457	Remote Similarity	NPD1164	Approved
0.6455	Remote Similarity	NPD288	Approved
0.6455	Remote Similarity	NPD9566	Approved
0.6449	Remote Similarity	NPD7236	Approved
0.6446	Remote Similarity	NPD9493	Approved
0.6434	Remote Similarity	NPD7055	Discontinued
0.6429	Remote Similarity	NPD1755	Approved
0.6423	Remote Similarity	NPD5981	Approved
0.6423	Remote Similarity	NPD1245	Approved
0.6423	Remote Similarity	NPD4105	Approved
0.6423	Remote Similarity	NPD4102	Approved
0.6423	Remote Similarity	NPD8166	Discontinued
0.6422	Remote Similarity	NPD9260	Approved
0.6422	Remote Similarity	NPD2933	Approved
0.6422	Remote Similarity	NPD2934	Approved
0.6418	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD6663	Approved
0.64	Remote Similarity	NPD6287	Discontinued
0.64	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD9611	Approved
0.6396	Remote Similarity	NPD9612	Approved
0.6396	Remote Similarity	NPD9609	Approved
0.6391	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD1876	Approved
0.6372	Remote Similarity	NPD2193	Phase 2
0.6372	Remote Similarity	NPD855	Approved
0.6372	Remote Similarity	NPD4818	Approved
0.6372	Remote Similarity	NPD854	Approved
0.6372	Remote Similarity	NPD4719	Phase 2
0.6372	Remote Similarity	NPD4817	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