NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.1
Volume:	255.566
LogP:	1.639
LogD:	1.381
LogS:	-2.026
# Rotatable Bonds:	4
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.649
Synthetic Accessibility Score:	3.806
Fsp3:	0.357
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:	-4.525
MDCK Permeability:	3.1594423489877954e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.906
Plasma Protein Binding (PPB):	48.77198028564453%
Volume Distribution (VD):	1.313
Pgp-substrate:	30.956071853637695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.145
CYP1A2-substrate:	0.183
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.241
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.142
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.2
CYP3A4-inhibitor:	0.054
CYP3A4-substrate:	0.233

ADMET: Excretion

Clearance (CL):	10.191
Half-life (T1/2):	0.582

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.188
Drug-inuced Liver Injury (DILI):	0.885
AMES Toxicity:	0.136
Rat Oral Acute Toxicity:	0.318
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.178
Carcinogencity:	0.198
Eye Corrosion:	0.044
Eye Irritation:	0.189
Respiratory Toxicity:	0.1

Download Data

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

Natural Product: NPC472316

Natural Product ID:	NPC472316
*Common Name:**	OGXADNXQFFRXMG-YUTCNCBUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OGXADNXQFFRXMG-YUTCNCBUSA-N
Standard InCHI:	InChI=1S/C14H16O4/c1-17-14(10-6-3-2-4-7-10)13(16)11-8-5-9-12(15)18-11/h2-7,9,11,13-14,16H,8H2,1H3/t11-,13+,14-/m0/s1
SMILES:	COC(C1=CC=CC=C1)C(C2CC=CC(=O)O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3358617
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002542] Benzylethers

*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
NPO33111	polyalthia parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25419616]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[548103]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[548103]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[548103]

☑ 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 NPC472316 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	190
0.1-0.2	854
0.2-0.3	2574
0.3-0.4	7320
0.4-0.5	11614
0.5-0.6	13136
0.6-0.7	6249
0.7-0.8	683
0.8-0.85	42
0.85-0.9	18
0.9-0.95	9
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472315
1.0	High Similarity	NPC474376
1.0	High Similarity	NPC475203
0.9798	High Similarity	NPC136962
0.9596	High Similarity	NPC171831
0.9596	High Similarity	NPC242913
0.9596	High Similarity	NPC280616
0.9505	High Similarity	NPC277788
0.9406	High Similarity	NPC37115
0.9238	High Similarity	NPC265002
0.9143	High Similarity	NPC234376
0.9109	High Similarity	NPC234305
0.902	High Similarity	NPC85977
0.9	High Similarity	NPC98911
0.9	High Similarity	NPC472318
0.8785	High Similarity	NPC185840
0.8738	High Similarity	NPC82426
0.8738	High Similarity	NPC91820
0.8585	High Similarity	NPC475465
0.8585	High Similarity	NPC472314
0.8571	High Similarity	NPC472919
0.85	High Similarity	NPC23453
0.8485	Intermediate Similarity	NPC472319
0.8455	Intermediate Similarity	NPC474363
0.844	Intermediate Similarity	NPC158282
0.8367	Intermediate Similarity	NPC304760
0.8318	Intermediate Similarity	NPC477251
0.8291	Intermediate Similarity	NPC471466
0.8288	Intermediate Similarity	NPC172525
0.8283	Intermediate Similarity	NPC173443
0.8142	Intermediate Similarity	NPC473507
0.8119	Intermediate Similarity	NPC119631
0.8108	Intermediate Similarity	NPC474314
0.8108	Intermediate Similarity	NPC477250
0.8073	Intermediate Similarity	NPC20485
0.8061	Intermediate Similarity	NPC58616
0.8056	Intermediate Similarity	NPC37714
0.8056	Intermediate Similarity	NPC152384
0.8037	Intermediate Similarity	NPC160382
0.8036	Intermediate Similarity	NPC272524
0.8034	Intermediate Similarity	NPC229600
0.802	Intermediate Similarity	NPC213156
0.802	Intermediate Similarity	NPC240108
0.8018	Intermediate Similarity	NPC474157
0.8018	Intermediate Similarity	NPC476003
0.8018	Intermediate Similarity	NPC323007
0.8	Intermediate Similarity	NPC182549
0.8	Intermediate Similarity	NPC114741
0.8	Intermediate Similarity	NPC469636
0.8	Intermediate Similarity	NPC476033
0.8	Intermediate Similarity	NPC184633
0.8	Intermediate Similarity	NPC154517
0.7965	Intermediate Similarity	NPC308744
0.7963	Intermediate Similarity	NPC148060
0.7946	Intermediate Similarity	NPC470825
0.7944	Intermediate Similarity	NPC154905
0.7944	Intermediate Similarity	NPC60373
0.7925	Intermediate Similarity	NPC80115
0.7921	Intermediate Similarity	NPC220893
0.79	Intermediate Similarity	NPC286608
0.79	Intermediate Similarity	NPC89377
0.79	Intermediate Similarity	NPC96625
0.79	Intermediate Similarity	NPC169050
0.7895	Intermediate Similarity	NPC474685
0.789	Intermediate Similarity	NPC269457
0.787	Intermediate Similarity	NPC301943
0.787	Intermediate Similarity	NPC474365
0.7869	Intermediate Similarity	NPC473993
0.7869	Intermediate Similarity	NPC472707
0.7857	Intermediate Similarity	NPC30563
0.7857	Intermediate Similarity	NPC127491
0.7857	Intermediate Similarity	NPC308619
0.7857	Intermediate Similarity	NPC183700
0.7857	Intermediate Similarity	NPC43584
0.7857	Intermediate Similarity	NPC324835
0.7857	Intermediate Similarity	NPC63345
0.7851	Intermediate Similarity	NPC79608
0.7838	Intermediate Similarity	NPC474364
0.7833	Intermediate Similarity	NPC138798
0.783	Intermediate Similarity	NPC135951
0.783	Intermediate Similarity	NPC35448
0.783	Intermediate Similarity	NPC78701
0.7826	Intermediate Similarity	NPC471616
0.7815	Intermediate Similarity	NPC475328
0.7807	Intermediate Similarity	NPC87069
0.7788	Intermediate Similarity	NPC139946
0.7788	Intermediate Similarity	NPC321852
0.7778	Intermediate Similarity	NPC309434
0.7778	Intermediate Similarity	NPC304538
0.7768	Intermediate Similarity	NPC276061
0.7768	Intermediate Similarity	NPC474148
0.7768	Intermediate Similarity	NPC174099
0.776	Intermediate Similarity	NPC29734
0.7757	Intermediate Similarity	NPC146351
0.775	Intermediate Similarity	NPC327070
0.775	Intermediate Similarity	NPC325301
0.7736	Intermediate Similarity	NPC249912
0.7736	Intermediate Similarity	NPC92754
0.7736	Intermediate Similarity	NPC325499
0.7736	Intermediate Similarity	NPC276775
0.7731	Intermediate Similarity	NPC470848
0.7731	Intermediate Similarity	NPC470849
0.7731	Intermediate Similarity	NPC476872
0.7727	Intermediate Similarity	NPC127676
0.7719	Intermediate Similarity	NPC128368
0.7719	Intermediate Similarity	NPC474176
0.7714	Intermediate Similarity	NPC5472
0.7706	Intermediate Similarity	NPC304638
0.7699	Intermediate Similarity	NPC260818
0.7699	Intermediate Similarity	NPC133308
0.7699	Intermediate Similarity	NPC264784
0.7692	Intermediate Similarity	NPC122117
0.7685	Intermediate Similarity	NPC42211
0.7685	Intermediate Similarity	NPC469481
0.768	Intermediate Similarity	NPC113098
0.7679	Intermediate Similarity	NPC281604
0.7679	Intermediate Similarity	NPC265407
0.7679	Intermediate Similarity	NPC206341
0.7679	Intermediate Similarity	NPC83628
0.7672	Intermediate Similarity	NPC233669
0.7672	Intermediate Similarity	NPC149691
0.7667	Intermediate Similarity	NPC11724
0.7664	Intermediate Similarity	NPC225060
0.7664	Intermediate Similarity	NPC160548
0.7664	Intermediate Similarity	NPC175852
0.7664	Intermediate Similarity	NPC210529
0.7661	Intermediate Similarity	NPC301857
0.7653	Intermediate Similarity	NPC89950
0.7652	Intermediate Similarity	NPC307651
0.7652	Intermediate Similarity	NPC153053
0.7652	Intermediate Similarity	NPC474641
0.7652	Intermediate Similarity	NPC120217
0.7647	Intermediate Similarity	NPC193193
0.7642	Intermediate Similarity	NPC61181
0.7642	Intermediate Similarity	NPC114096
0.7638	Intermediate Similarity	NPC38420
0.7638	Intermediate Similarity	NPC136608
0.7627	Intermediate Similarity	NPC203124
0.7623	Intermediate Similarity	NPC246166
0.7623	Intermediate Similarity	NPC57607
0.7619	Intermediate Similarity	NPC272650
0.7619	Intermediate Similarity	NPC267336
0.7619	Intermediate Similarity	NPC233692
0.7619	Intermediate Similarity	NPC239358
0.7611	Intermediate Similarity	NPC471954
0.7611	Intermediate Similarity	NPC273837
0.7611	Intermediate Similarity	NPC75272
0.7607	Intermediate Similarity	NPC470820
0.7607	Intermediate Similarity	NPC281277
0.7603	Intermediate Similarity	NPC223351
0.7603	Intermediate Similarity	NPC52097
0.7597	Intermediate Similarity	NPC38099
0.7597	Intermediate Similarity	NPC26954
0.7593	Intermediate Similarity	NPC325497
0.7593	Intermediate Similarity	NPC118343
0.7589	Intermediate Similarity	NPC260952
0.7589	Intermediate Similarity	NPC56493
0.7589	Intermediate Similarity	NPC156648
0.7586	Intermediate Similarity	NPC306740
0.7586	Intermediate Similarity	NPC469509
0.7586	Intermediate Similarity	NPC33749
0.7586	Intermediate Similarity	NPC328593
0.7586	Intermediate Similarity	NPC217472
0.7586	Intermediate Similarity	NPC41851
0.7586	Intermediate Similarity	NPC261453
0.7586	Intermediate Similarity	NPC210092
0.7581	Intermediate Similarity	NPC148026
0.7581	Intermediate Similarity	NPC288416
0.7581	Intermediate Similarity	NPC103533
0.7578	Intermediate Similarity	NPC204353
0.7578	Intermediate Similarity	NPC326600
0.7578	Intermediate Similarity	NPC50896
0.7578	Intermediate Similarity	NPC62366
0.7576	Intermediate Similarity	NPC103326
0.7576	Intermediate Similarity	NPC87299
0.7576	Intermediate Similarity	NPC329319
0.7576	Intermediate Similarity	NPC99394
0.7568	Intermediate Similarity	NPC209632
0.7563	Intermediate Similarity	NPC470214
0.7563	Intermediate Similarity	NPC470215
0.7563	Intermediate Similarity	NPC263386
0.7563	Intermediate Similarity	NPC141791
0.7563	Intermediate Similarity	NPC109371
0.7561	Intermediate Similarity	NPC275576
0.7559	Intermediate Similarity	NPC472248
0.7547	Intermediate Similarity	NPC130398
0.7544	Intermediate Similarity	NPC210089
0.7542	Intermediate Similarity	NPC65791
0.7542	Intermediate Similarity	NPC469574
0.7538	Intermediate Similarity	NPC153818
0.7538	Intermediate Similarity	NPC475195
0.7538	Intermediate Similarity	NPC232246
0.7538	Intermediate Similarity	NPC155963
0.7525	Intermediate Similarity	NPC475710
0.7524	Intermediate Similarity	NPC77273
0.7523	Intermediate Similarity	NPC70624
0.7523	Intermediate Similarity	NPC253746
0.7522	Intermediate Similarity	NPC85493
0.7522	Intermediate Similarity	NPC17417
0.7522	Intermediate Similarity	NPC40178

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 NPC472316 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	668
0.2-0.3	1405
0.3-0.4	2749
0.4-0.5	2294
0.5-0.6	1370
0.6-0.7	462
0.7-0.8	34
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8108	Intermediate Similarity	NPD969	Suspended
0.807	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD4198	Discontinued
0.79	Intermediate Similarity	NPD1282	Approved
0.7748	Intermediate Similarity	NPD1358	Approved
0.7739	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD2629	Approved
0.7706	Intermediate Similarity	NPD6647	Phase 2
0.7699	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD9495	Approved
0.7611	Intermediate Similarity	NPD2067	Discontinued
0.7593	Intermediate Similarity	NPD1238	Approved
0.7522	Intermediate Similarity	NPD2182	Approved
0.75	Intermediate Similarity	NPD5126	Approved
0.75	Intermediate Similarity	NPD5125	Phase 3
0.7434	Intermediate Similarity	NPD290	Approved
0.7368	Intermediate Similarity	NPD2684	Approved
0.7345	Intermediate Similarity	NPD3134	Approved
0.7323	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5909	Discontinued
0.7321	Intermediate Similarity	NPD1237	Approved
0.7321	Intermediate Similarity	NPD164	Approved
0.7265	Intermediate Similarity	NPD7843	Approved
0.7257	Intermediate Similarity	NPD5048	Discontinued
0.7238	Intermediate Similarity	NPD689	Discontinued
0.7217	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD5926	Approved
0.7132	Intermediate Similarity	NPD6798	Discontinued
0.713	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2066	Phase 3
0.7111	Intermediate Similarity	NPD1652	Phase 2
0.7105	Intermediate Similarity	NPD9697	Approved
0.709	Intermediate Similarity	NPD7266	Discontinued
0.7087	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7157	Approved
0.708	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6233	Phase 2
0.7073	Intermediate Similarity	NPD5306	Approved
0.7073	Intermediate Similarity	NPD5305	Approved
0.7071	Intermediate Similarity	NPD9294	Approved
0.7059	Intermediate Similarity	NPD4628	Phase 3
0.7059	Intermediate Similarity	NPD6010	Discontinued
0.7054	Intermediate Similarity	NPD2555	Approved
0.7054	Intermediate Similarity	NPD5454	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD2553	Approved
0.7054	Intermediate Similarity	NPD2558	Approved
0.7054	Intermediate Similarity	NPD2552	Approved
0.7054	Intermediate Similarity	NPD2550	Approved
0.7054	Intermediate Similarity	NPD2549	Approved
0.7049	Intermediate Similarity	NPD9545	Approved
0.7049	Intermediate Similarity	NPD7741	Discontinued
0.7043	Intermediate Similarity	NPD6685	Approved
0.7025	Intermediate Similarity	NPD9493	Approved
0.7023	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD4136	Approved
0.7016	Intermediate Similarity	NPD4106	Approved
0.7016	Intermediate Similarity	NPD3496	Discontinued
0.7016	Intermediate Similarity	NPD4135	Approved
0.7009	Intermediate Similarity	NPD5236	Approved
0.7009	Intermediate Similarity	NPD5240	Approved
0.7009	Intermediate Similarity	NPD5237	Approved
0.7009	Intermediate Similarity	NPD9258	Approved
0.7009	Intermediate Similarity	NPD5235	Approved
0.7009	Intermediate Similarity	NPD9256	Approved
0.7009	Intermediate Similarity	NPD5239	Approved
0.7008	Intermediate Similarity	NPD2797	Approved
0.6991	Remote Similarity	NPD4189	Approved
0.6991	Remote Similarity	NPD4188	Approved
0.6984	Remote Similarity	NPD7876	Discontinued
0.6975	Remote Similarity	NPD5535	Approved
0.6972	Remote Similarity	NPD1202	Approved
0.697	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6355	Discontinued
0.697	Remote Similarity	NPD5124	Phase 1
0.6964	Remote Similarity	NPD7798	Approved
0.696	Remote Similarity	NPD4807	Approved
0.696	Remote Similarity	NPD4480	Approved
0.696	Remote Similarity	NPD422	Phase 1
0.696	Remote Similarity	NPD1091	Approved
0.696	Remote Similarity	NPD4806	Approved
0.696	Remote Similarity	NPD6287	Discontinued
0.6949	Remote Similarity	NPD2201	Approved
0.6947	Remote Similarity	NPD4062	Phase 3
0.6923	Remote Similarity	NPD7008	Discontinued
0.6917	Remote Similarity	NPD6653	Approved
0.6916	Remote Similarity	NPD800	Approved
0.6894	Remote Similarity	NPD4060	Phase 1
0.6891	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5291	Approved
0.6885	Remote Similarity	NPD5292	Approved
0.688	Remote Similarity	NPD3847	Discontinued
0.6875	Remote Similarity	NPD2160	Approved
0.6875	Remote Similarity	NPD2626	Approved
0.6875	Remote Similarity	NPD2625	Approved
0.6875	Remote Similarity	NPD2627	Approved
0.6875	Remote Similarity	NPD2159	Approved
0.6875	Remote Similarity	NPD2628	Approved
0.687	Remote Similarity	NPD3047	Approved
0.687	Remote Similarity	NPD3268	Approved
0.687	Remote Similarity	NPD3046	Approved
0.687	Remote Similarity	NPD3048	Approved
0.6869	Remote Similarity	NPD9716	Approved
0.6864	Remote Similarity	NPD9713	Approved
0.6855	Remote Similarity	NPD4102	Approved
0.6855	Remote Similarity	NPD5691	Approved
0.6855	Remote Similarity	NPD4105	Approved
0.6852	Remote Similarity	NPD1089	Approved
0.6852	Remote Similarity	NPD1090	Approved
0.6852	Remote Similarity	NPD1086	Approved
0.6847	Remote Similarity	NPD1989	Approved
0.6842	Remote Similarity	NPD4340	Discontinued
0.6838	Remote Similarity	NPD5762	Approved
0.6838	Remote Similarity	NPD5763	Approved
0.6838	Remote Similarity	NPD9532	Phase 3
0.6827	Remote Similarity	NPD3971	Phase 1
0.6827	Remote Similarity	NPD9491	Approved
0.6822	Remote Similarity	NPD6085	Phase 2
0.6822	Remote Similarity	NPD5647	Approved
0.6822	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7033	Discontinued
0.6807	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5723	Approved
0.68	Remote Similarity	NPD4626	Approved
0.6797	Remote Similarity	NPD5667	Approved
0.6794	Remote Similarity	NPD7095	Approved
0.6792	Remote Similarity	NPD9259	Approved
0.6792	Remote Similarity	NPD9257	Approved
0.6791	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2424	Discontinued
0.6783	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5765	Approved
0.6783	Remote Similarity	NPD1930	Approved
0.6783	Remote Similarity	NPD1929	Approved
0.6783	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD1241	Discontinued
0.6774	Remote Similarity	NPD1894	Discontinued
0.6772	Remote Similarity	NPD9717	Approved
0.6769	Remote Similarity	NPD5204	Approved
0.6757	Remote Similarity	NPD1693	Approved
0.6752	Remote Similarity	NPD3524	Approved
0.6752	Remote Similarity	NPD2559	Approved
0.6752	Remote Similarity	NPD3526	Approved
0.6752	Remote Similarity	NPD2551	Approved
0.6744	Remote Similarity	NPD6362	Approved
0.6742	Remote Similarity	NPD1048	Approved
0.6741	Remote Similarity	NPD7097	Phase 1
0.6727	Remote Similarity	NPD1088	Approved
0.6721	Remote Similarity	NPD5951	Approved
0.6719	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD5201	Approved
0.6718	Remote Similarity	NPD4617	Approved
0.6718	Remote Similarity	NPD6832	Phase 2
0.6718	Remote Similarity	NPD5203	Approved
0.6718	Remote Similarity	NPD4620	Approved
0.6715	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD7236	Approved
0.6698	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD3673	Approved
0.6697	Remote Similarity	NPD3672	Approved
0.6696	Remote Similarity	NPD2860	Approved
0.6696	Remote Similarity	NPD291	Approved
0.6696	Remote Similarity	NPD2859	Approved
0.6667	Remote Similarity	NPD531	Approved
0.6667	Remote Similarity	NPD3225	Approved
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD5846	Approved
0.6667	Remote Similarity	NPD3027	Phase 3
0.6667	Remote Similarity	NPD6516	Phase 2
0.6667	Remote Similarity	NPD2199	Approved
0.6667	Remote Similarity	NPD2198	Approved
0.6643	Remote Similarity	NPD5403	Approved
0.6643	Remote Similarity	NPD6190	Approved
0.6643	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD4140	Approved
0.6642	Remote Similarity	NPD6032	Approved
0.6641	Remote Similarity	NPD3662	Phase 3
0.6641	Remote Similarity	NPD3664	Approved
0.6641	Remote Similarity	NPD3663	Approved
0.6641	Remote Similarity	NPD3661	Approved
0.6639	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD1239	Approved
0.6635	Remote Similarity	NPD226	Approved
0.662	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.662	Remote Similarity	NPD5401	Approved
0.6618	Remote Similarity	NPD2567	Approved
0.6618	Remote Similarity	NPD2569	Approved
0.6617	Remote Similarity	NPD2313	Discontinued
0.6617	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD3267	Approved
0.6615	Remote Similarity	NPD3266	Approved
0.6615	Remote Similarity	NPD1203	Approved
0.6615	Remote Similarity	NPD987	Approved
0.6612	Remote Similarity	NPD228	Approved
0.6612	Remote Similarity	NPD6912	Phase 3
0.661	Remote Similarity	NPD5706	Approved
0.661	Remote Similarity	NPD812	Approved
0.661	Remote Similarity	NPD5705	Approved
0.661	Remote Similarity	NPD968	Approved
0.661	Remote Similarity	NPD5704	Approved
0.661	Remote Similarity	NPD811	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