NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.14
Volume:	281.368
LogP:	1.79
LogD:	1.531
LogS:	-2.198
# Rotatable Bonds:	4
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.845
Synthetic Accessibility Score:	3.979
Fsp3:	0.438
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:	-4.469
MDCK Permeability:	2.312559081474319e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.142
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.401
Plasma Protein Binding (PPB):	86.98745727539062%
Volume Distribution (VD):	0.877
Pgp-substrate:	9.506438255310059%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.597
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.889
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.187
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.319
CYP3A4-inhibitor:	0.128
CYP3A4-substrate:	0.569

ADMET: Excretion

Clearance (CL):	4.999
Half-life (T1/2):	0.511

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.527
Drug-inuced Liver Injury (DILI):	0.549
AMES Toxicity:	0.214
Rat Oral Acute Toxicity:	0.27
Maximum Recommended Daily Dose:	0.273
Skin Sensitization:	0.083
Carcinogencity:	0.138
Eye Corrosion:	0.009
Eye Irritation:	0.161
Respiratory Toxicity:	0.12

Download Data

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

Natural Product: NPC25385

Natural Product ID:	NPC25385
*Common Name:**	(2S,4R,5S)-4-Hydroxy-5-Methoxy-2-((R)-1-Phenylallyl)Cyclohexanone
IUPAC Name:	(2S,4R,5S)-4-hydroxy-5-methoxy-2-[(1R)-1-phenylprop-2-enyl]cyclohexan-1-one
Synonyms:
Standard InCHIKey:	XFQZPZFTYDDJIR-UGQVUOCMSA-N
Standard InCHI:	InChI=1S/C16H20O3/c1-3-12(11-7-5-4-6-8-11)13-9-15(18)16(19-2)10-14(13)17/h3-8,12-13,15-16,18H,1,9-10H2,2H3/t12-,13-,15+,16-/m0/s1
SMILES:	C=C[C@@H](c1ccccc1)[C@@H]1C[C@H]([C@H](CC1=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464973
PubChem CID:	11470966
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives

*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	=	13200.0	nM	PMID[500727]

☑ 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 NPC25385 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	193
0.1-0.2	795
0.2-0.3	1877
0.3-0.4	6301
0.4-0.5	12458
0.5-0.6	17502
0.6-0.7	3370
0.7-0.8	192
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC193640
1.0	High Similarity	NPC475905
0.8911	High Similarity	NPC158623
0.8679	High Similarity	NPC475282
0.8485	Intermediate Similarity	NPC187725
0.8485	Intermediate Similarity	NPC141607
0.8396	Intermediate Similarity	NPC474307
0.8302	Intermediate Similarity	NPC19136
0.8283	Intermediate Similarity	NPC231591
0.8235	Intermediate Similarity	NPC206764
0.8019	Intermediate Similarity	NPC266343
0.8	Intermediate Similarity	NPC329387
0.8	Intermediate Similarity	NPC317280
0.7925	Intermediate Similarity	NPC476042
0.7886	Intermediate Similarity	NPC262819
0.7845	Intermediate Similarity	NPC471553
0.783	Intermediate Similarity	NPC271475
0.7788	Intermediate Similarity	NPC471189
0.7727	Intermediate Similarity	NPC471186
0.7705	Intermediate Similarity	NPC294050
0.7705	Intermediate Similarity	NPC328997
0.768	Intermediate Similarity	NPC471334
0.7658	Intermediate Similarity	NPC474111
0.7658	Intermediate Similarity	NPC329705
0.7642	Intermediate Similarity	NPC146239
0.7593	Intermediate Similarity	NPC474308
0.7586	Intermediate Similarity	NPC215419
0.7583	Intermediate Similarity	NPC98305
0.7583	Intermediate Similarity	NPC476234
0.7581	Intermediate Similarity	NPC316553
0.757	Intermediate Similarity	NPC289201
0.7568	Intermediate Similarity	NPC321670
0.7563	Intermediate Similarity	NPC476645
0.7544	Intermediate Similarity	NPC265513
0.7541	Intermediate Similarity	NPC138798
0.75	Intermediate Similarity	NPC34634
0.75	Intermediate Similarity	NPC265454
0.748	Intermediate Similarity	NPC317163
0.7478	Intermediate Similarity	NPC471188
0.7476	Intermediate Similarity	NPC477693
0.7476	Intermediate Similarity	NPC477704
0.7459	Intermediate Similarity	NPC108286
0.7458	Intermediate Similarity	NPC108532
0.7455	Intermediate Similarity	NPC474820
0.7455	Intermediate Similarity	NPC475978
0.7434	Intermediate Similarity	NPC20485
0.7431	Intermediate Similarity	NPC54647
0.7429	Intermediate Similarity	NPC317645
0.7422	Intermediate Similarity	NPC144257
0.7407	Intermediate Similarity	NPC477767
0.74	Intermediate Similarity	NPC73637
0.74	Intermediate Similarity	NPC121478
0.7398	Intermediate Similarity	NPC325740
0.7391	Intermediate Similarity	NPC252544
0.7391	Intermediate Similarity	NPC321252
0.7374	Intermediate Similarity	NPC184030
0.7374	Intermediate Similarity	NPC164449
0.7373	Intermediate Similarity	NPC9274
0.7373	Intermediate Similarity	NPC210531
0.7368	Intermediate Similarity	NPC317305
0.7364	Intermediate Similarity	NPC225079
0.7364	Intermediate Similarity	NPC94487
0.736	Intermediate Similarity	NPC171007
0.736	Intermediate Similarity	NPC190849
0.7355	Intermediate Similarity	NPC183339
0.7355	Intermediate Similarity	NPC133389
0.7355	Intermediate Similarity	NPC234337
0.735	Intermediate Similarity	NPC172525
0.7345	Intermediate Similarity	NPC94751
0.7345	Intermediate Similarity	NPC142326
0.7344	Intermediate Similarity	NPC209851
0.7339	Intermediate Similarity	NPC145052
0.7328	Intermediate Similarity	NPC177576
0.7328	Intermediate Similarity	NPC218855
0.7327	Intermediate Similarity	NPC44830
0.7323	Intermediate Similarity	NPC473443
0.7317	Intermediate Similarity	NPC86900
0.7308	Intermediate Similarity	NPC477896
0.7297	Intermediate Similarity	NPC474112
0.7281	Intermediate Similarity	NPC470007
0.7281	Intermediate Similarity	NPC211439
0.728	Intermediate Similarity	NPC476033
0.728	Intermediate Similarity	NPC79608
0.7266	Intermediate Similarity	NPC137427
0.7266	Intermediate Similarity	NPC244246
0.7266	Intermediate Similarity	NPC215941
0.7266	Intermediate Similarity	NPC123196
0.7266	Intermediate Similarity	NPC319282
0.7266	Intermediate Similarity	NPC275724
0.7266	Intermediate Similarity	NPC65935
0.7266	Intermediate Similarity	NPC311419
0.7265	Intermediate Similarity	NPC477476
0.7265	Intermediate Similarity	NPC470253
0.7265	Intermediate Similarity	NPC477475
0.7258	Intermediate Similarity	NPC244876
0.7258	Intermediate Similarity	NPC472681
0.7258	Intermediate Similarity	NPC140118
0.7258	Intermediate Similarity	NPC12881
0.725	Intermediate Similarity	NPC61651
0.7248	Intermediate Similarity	NPC226041
0.7248	Intermediate Similarity	NPC324602
0.7244	Intermediate Similarity	NPC225103
0.7236	Intermediate Similarity	NPC293831
0.7236	Intermediate Similarity	NPC369
0.7232	Intermediate Similarity	NPC247976
0.7232	Intermediate Similarity	NPC329556
0.7232	Intermediate Similarity	NPC160382
0.7231	Intermediate Similarity	NPC136994
0.7231	Intermediate Similarity	NPC88255
0.7227	Intermediate Similarity	NPC471616
0.7227	Intermediate Similarity	NPC23402
0.7227	Intermediate Similarity	NPC62138
0.7227	Intermediate Similarity	NPC188010
0.7222	Intermediate Similarity	NPC81135
0.7213	Intermediate Similarity	NPC472680
0.7213	Intermediate Similarity	NPC475804
0.7213	Intermediate Similarity	NPC472679
0.7213	Intermediate Similarity	NPC105709
0.7213	Intermediate Similarity	NPC474222
0.7212	Intermediate Similarity	NPC322387
0.7209	Intermediate Similarity	NPC80599
0.7207	Intermediate Similarity	NPC136810
0.7207	Intermediate Similarity	NPC133809
0.7207	Intermediate Similarity	NPC128248
0.7206	Intermediate Similarity	NPC277053
0.7206	Intermediate Similarity	NPC301946
0.7203	Intermediate Similarity	NPC294458
0.7203	Intermediate Similarity	NPC474363
0.7203	Intermediate Similarity	NPC234637
0.7203	Intermediate Similarity	NPC130591
0.72	Intermediate Similarity	NPC478108
0.72	Intermediate Similarity	NPC231767
0.7193	Intermediate Similarity	NPC244933
0.7193	Intermediate Similarity	NPC85560
0.719	Intermediate Similarity	NPC249435
0.719	Intermediate Similarity	NPC318173
0.7188	Intermediate Similarity	NPC472388
0.7188	Intermediate Similarity	NPC475138
0.7184	Intermediate Similarity	NPC99482
0.7184	Intermediate Similarity	NPC475710
0.7179	Intermediate Similarity	NPC477250
0.7176	Intermediate Similarity	NPC477893
0.717	Intermediate Similarity	NPC86670
0.717	Intermediate Similarity	NPC70940
0.717	Intermediate Similarity	NPC274455
0.717	Intermediate Similarity	NPC84288
0.7167	Intermediate Similarity	NPC212891
0.7165	Intermediate Similarity	NPC20287
0.7165	Intermediate Similarity	NPC20404
0.7165	Intermediate Similarity	NPC12022
0.7165	Intermediate Similarity	NPC293641
0.7164	Intermediate Similarity	NPC77493
0.7154	Intermediate Similarity	NPC472981
0.7153	Intermediate Similarity	NPC474241
0.7143	Intermediate Similarity	NPC127975
0.7143	Intermediate Similarity	NPC285350
0.7143	Intermediate Similarity	NPC236405
0.7143	Intermediate Similarity	NPC217111
0.7132	Intermediate Similarity	NPC80895
0.7132	Intermediate Similarity	NPC471912
0.7131	Intermediate Similarity	NPC182240
0.7131	Intermediate Similarity	NPC202015
0.7119	Intermediate Similarity	NPC471481
0.7117	Intermediate Similarity	NPC221825
0.7111	Intermediate Similarity	NPC182869
0.7109	Intermediate Similarity	NPC767
0.7109	Intermediate Similarity	NPC278308
0.7109	Intermediate Similarity	NPC247250
0.7107	Intermediate Similarity	NPC80605
0.7107	Intermediate Similarity	NPC323440
0.7107	Intermediate Similarity	NPC222968
0.7107	Intermediate Similarity	NPC152812
0.71	Intermediate Similarity	NPC272260
0.709	Intermediate Similarity	NPC473440
0.709	Intermediate Similarity	NPC474250
0.7087	Intermediate Similarity	NPC269598
0.7087	Intermediate Similarity	NPC253681
0.7087	Intermediate Similarity	NPC473423
0.708	Intermediate Similarity	NPC239608
0.708	Intermediate Similarity	NPC127857
0.708	Intermediate Similarity	NPC46161
0.7075	Intermediate Similarity	NPC9822
0.7073	Intermediate Similarity	NPC474223
0.7073	Intermediate Similarity	NPC475827
0.7071	Intermediate Similarity	NPC9796
0.7059	Intermediate Similarity	NPC475199
0.7059	Intermediate Similarity	NPC283012
0.7054	Intermediate Similarity	NPC264728
0.705	Intermediate Similarity	NPC81698
0.705	Intermediate Similarity	NPC250046
0.705	Intermediate Similarity	NPC471970
0.705	Intermediate Similarity	NPC60509
0.7043	Intermediate Similarity	NPC100767
0.7043	Intermediate Similarity	NPC83409
0.7043	Intermediate Similarity	NPC185763
0.704	Intermediate Similarity	NPC469927
0.704	Intermediate Similarity	NPC139171
0.7037	Intermediate Similarity	NPC474784
0.703	Intermediate Similarity	NPC477703
0.703	Intermediate Similarity	NPC127343

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 NPC25385 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	728
0.2-0.3	1291
0.3-0.4	3040
0.4-0.5	2365
0.5-0.6	1313
0.6-0.7	224
0.7-0.8	15
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
0.7739	Intermediate Similarity	NPD2629	Approved
0.7727	Intermediate Similarity	NPD5048	Discontinued
0.7699	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD3317	Approved
0.7431	Intermediate Similarity	NPD2066	Phase 3
0.7333	Intermediate Similarity	NPD3673	Approved
0.7333	Intermediate Similarity	NPD3672	Approved
0.7273	Intermediate Similarity	NPD7798	Approved
0.7238	Intermediate Similarity	NPD5347	Phase 2
0.7238	Intermediate Similarity	NPD5346	Phase 2
0.7232	Intermediate Similarity	NPD1930	Approved
0.7232	Intermediate Similarity	NPD1929	Approved
0.7232	Intermediate Similarity	NPD6647	Phase 2
0.7232	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1693	Approved
0.7193	Intermediate Similarity	NPD6685	Approved
0.717	Intermediate Similarity	NPD1090	Approved
0.717	Intermediate Similarity	NPD1089	Approved
0.717	Intermediate Similarity	NPD1086	Approved
0.7156	Intermediate Similarity	NPD1989	Approved
0.7154	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1932	Approved
0.7129	Intermediate Similarity	NPD226	Approved
0.708	Intermediate Similarity	NPD5765	Approved
0.7075	Intermediate Similarity	NPD800	Approved
0.7069	Intermediate Similarity	NPD2329	Discontinued
0.7059	Intermediate Similarity	NPD6010	Discontinued
0.7048	Intermediate Similarity	NPD4793	Discontinued
0.7037	Intermediate Similarity	NPD1088	Approved
0.7027	Intermediate Similarity	NPD9495	Approved
0.7018	Intermediate Similarity	NPD1237	Approved
0.7018	Intermediate Similarity	NPD5909	Discontinued
0.7	Intermediate Similarity	NPD1711	Phase 2
0.6975	Remote Similarity	NPD6858	Approved
0.6975	Remote Similarity	NPD7094	Approved
0.6944	Remote Similarity	NPD1239	Approved
0.6937	Remote Similarity	NPD1564	Approved
0.6937	Remote Similarity	NPD1566	Phase 3
0.6937	Remote Similarity	NPD1565	Approved
0.6935	Remote Similarity	NPD5306	Approved
0.6935	Remote Similarity	NPD5305	Approved
0.6917	Remote Similarity	NPD2652	Approved
0.6917	Remote Similarity	NPD2650	Approved
0.6909	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1087	Approved
0.6832	Remote Similarity	NPD227	Approved
0.6832	Remote Similarity	NPD225	Approved
0.6829	Remote Similarity	NPD7610	Discontinued
0.6827	Remote Similarity	NPD9491	Approved
0.6825	Remote Similarity	NPD4216	Approved
0.6825	Remote Similarity	NPD4218	Approved
0.6825	Remote Similarity	NPD2609	Approved
0.6825	Remote Similarity	NPD4807	Approved
0.6825	Remote Similarity	NPD4217	Approved
0.6825	Remote Similarity	NPD3131	Approved
0.6825	Remote Similarity	NPD4215	Approved
0.6825	Remote Similarity	NPD2612	Approved
0.6825	Remote Similarity	NPD2610	Approved
0.6825	Remote Similarity	NPD3132	Approved
0.6825	Remote Similarity	NPD2611	Approved
0.6825	Remote Similarity	NPD4806	Approved
0.6825	Remote Similarity	NPD2608	Approved
0.6822	Remote Similarity	NPD6085	Phase 2
0.6822	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4198	Discontinued
0.6783	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6912	Phase 3
0.6746	Remote Similarity	NPD4136	Approved
0.6746	Remote Similarity	NPD4135	Approved
0.6746	Remote Similarity	NPD4106	Approved
0.6723	Remote Similarity	NPD2067	Discontinued
0.6696	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6065	Approved
0.6667	Remote Similarity	NPD3643	Approved
0.6667	Remote Similarity	NPD2932	Approved
0.6667	Remote Similarity	NPD1563	Approved
0.6667	Remote Similarity	NPD3644	Approved
0.6667	Remote Similarity	NPD3019	Approved
0.6667	Remote Similarity	NPD3642	Approved
0.6639	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.661	Remote Similarity	NPD467	Phase 1
0.6593	Remote Similarity	NPD6355	Discontinued
0.6587	Remote Similarity	NPD5981	Approved
0.6587	Remote Similarity	NPD4105	Approved
0.6587	Remote Similarity	NPD4102	Approved
0.6583	Remote Similarity	NPD1317	Discontinued
0.6583	Remote Similarity	NPD3021	Approved
0.6583	Remote Similarity	NPD3022	Approved
0.6577	Remote Similarity	NPD7631	Approved
0.6569	Remote Similarity	NPD7305	Phase 1
0.6567	Remote Similarity	NPD7961	Discontinued
0.6565	Remote Similarity	NPD5647	Approved
0.6538	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD1018	Approved
0.6522	Remote Similarity	NPD3020	Approved
0.6515	Remote Similarity	NPD5204	Approved
0.6508	Remote Similarity	NPD7009	Phase 2
0.6491	Remote Similarity	NPD3495	Discontinued
0.6486	Remote Similarity	NPD7609	Phase 3
0.648	Remote Similarity	NPD4574	Approved
0.648	Remote Similarity	NPD4576	Approved
0.6476	Remote Similarity	NPD942	Approved
0.6466	Remote Similarity	NPD4620	Approved
0.6466	Remote Similarity	NPD5201	Approved
0.6466	Remote Similarity	NPD5203	Approved
0.6466	Remote Similarity	NPD4617	Approved
0.6466	Remote Similarity	NPD2613	Approved
0.646	Remote Similarity	NPD4814	Discontinued
0.6454	Remote Similarity	NPD4628	Phase 3
0.6446	Remote Similarity	NPD4233	Approved
0.6446	Remote Similarity	NPD4234	Approved
0.6444	Remote Similarity	NPD6663	Approved
0.6442	Remote Similarity	NPD9490	Approved
0.6435	Remote Similarity	NPD253	Approved
0.641	Remote Similarity	NPD4719	Phase 2
0.6397	Remote Similarity	NPD943	Approved
0.6397	Remote Similarity	NPD5120	Approved
0.6397	Remote Similarity	NPD5121	Approved
0.6397	Remote Similarity	NPD5119	Approved
0.6391	Remote Similarity	NPD3664	Approved
0.6391	Remote Similarity	NPD5736	Approved
0.6391	Remote Similarity	NPD3662	Phase 3
0.6391	Remote Similarity	NPD3663	Approved
0.6391	Remote Similarity	NPD7084	Phase 3
0.6391	Remote Similarity	NPD3661	Approved
0.6385	Remote Similarity	NPD1608	Approved
0.6379	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD4479	Discontinued
0.6378	Remote Similarity	NPD2218	Phase 2
0.6378	Remote Similarity	NPD2217	Approved
0.6372	Remote Similarity	NPD3719	Approved
0.6372	Remote Similarity	NPD3718	Approved
0.6372	Remote Similarity	NPD1066	Discontinued
0.6371	Remote Similarity	NPD3598	Phase 3
0.637	Remote Similarity	NPD6798	Discontinued
0.6364	Remote Similarity	NPD7236	Approved
0.6364	Remote Similarity	NPD2628	Approved
0.6364	Remote Similarity	NPD2160	Approved
0.6364	Remote Similarity	NPD2627	Approved
0.6364	Remote Similarity	NPD2625	Approved
0.6364	Remote Similarity	NPD2159	Approved
0.6364	Remote Similarity	NPD2626	Approved
0.6357	Remote Similarity	NPD3026	Approved
0.6357	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD3023	Approved
0.6343	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD8166	Discontinued
0.6338	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD4110	Phase 3
0.6336	Remote Similarity	NPD5159	Phase 2
0.6336	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD5157	Phase 1
0.6328	Remote Similarity	NPD1651	Approved
0.6328	Remote Similarity	NPD3024	Approved
0.6328	Remote Similarity	NPD3025	Approved
0.6324	Remote Similarity	NPD3614	Approved
0.6324	Remote Similarity	NPD3616	Approved
0.6324	Remote Similarity	NPD3088	Approved
0.6324	Remote Similarity	NPD2574	Discontinued
0.6324	Remote Similarity	NPD2573	Approved
0.6324	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD2570	Approved
0.6324	Remote Similarity	NPD3615	Approved
0.6324	Remote Similarity	NPD2566	Approved
0.6324	Remote Similarity	NPD4746	Phase 3
0.6324	Remote Similarity	NPD3087	Approved
0.6324	Remote Similarity	NPD3090	Approved
0.6324	Remote Similarity	NPD2571	Approved
0.6324	Remote Similarity	NPD4745	Approved
0.6324	Remote Similarity	NPD3089	Approved
0.632	Remote Similarity	NPD690	Clinical (unspecified phase)
0.632	Remote Similarity	NPD5951	Approved
0.6316	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD2798	Approved
0.6316	Remote Similarity	NPD4094	Approved
0.6311	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD3092	Approved
0.6306	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6101	Approved
0.6296	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD6190	Approved
0.6293	Remote Similarity	NPD5926	Approved
0.6288	Remote Similarity	NPD1283	Approved
0.6283	Remote Similarity	NPD1508	Approved
0.6279	Remote Similarity	NPD5126	Approved
0.6279	Remote Similarity	NPD5125	Phase 3
0.6279	Remote Similarity	NPD2345	Approved
0.6276	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD650	Approved
0.6269	Remote Similarity	NPD9494	Approved
0.6261	Remote Similarity	NPD2860	Approved
0.6261	Remote Similarity	NPD2859	Approved
0.626	Remote Similarity	NPD3972	Approved
0.626	Remote Similarity	NPD4878	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