NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	226.12
Volume:	228.883
LogP:	0.383
LogD:	0.353
LogS:	-1.914
# Rotatable Bonds:	2
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.724
Synthetic Accessibility Score:	4.994
Fsp3:	0.667
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:	-4.682
MDCK Permeability:	3.817738615907729e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.771
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.276
Plasma Protein Binding (PPB):	26.856355667114258%
Volume Distribution (VD):	0.99
Pgp-substrate:	65.2854995727539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.448
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.756
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.341
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	4.026
Half-life (T1/2):	0.724

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.319
Drug-inuced Liver Injury (DILI):	0.296
AMES Toxicity:	0.693
Rat Oral Acute Toxicity:	0.184
Maximum Recommended Daily Dose:	0.102
Skin Sensitization:	0.555
Carcinogencity:	0.876
Eye Corrosion:	0.239
Eye Irritation:	0.818
Respiratory Toxicity:	0.816

Download Data

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

Natural Product: NPC472379

Natural Product ID:	NPC472379
*Common Name:**	WWUDJTFAAXAXAE-ITMYLUJXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WWUDJTFAAXAXAE-ITMYLUJXSA-N
Standard InCHI:	InChI=1S/C12H18O4/c1-3-4-8-7-16-12(15-2)6-5-9(13)11(14)10(8)12/h3-4,9-11,13-14H,1,5-7H2,2H3/b8-4-/t9-,10-,11-,12-/m1/s1
SMILES:	COC12CCC(C(C1C(=CC=C)CO2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3397814
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO33203	euryspongia sp.	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23434422]
NPO33203	euryspongia sp.	Species	Dysideidae	Eukaryota	n.a.	Iriomote Island	n.a.	PMID[25600405]

☑ 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	1
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	40000.0	nM	PMID[533884]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	40000.0	nM	PMID[533884]
NPT27	Others	Unspecified		IC50	>	40000.0	nM	PMID[533884]

☑ 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 NPC472379 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	167
0.1-0.2	1230
0.2-0.3	4478
0.3-0.4	9581
0.4-0.5	15108
0.5-0.6	9240
0.6-0.7	2689
0.7-0.8	200
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8276	Intermediate Similarity	NPC298595
0.7723	Intermediate Similarity	NPC311223
0.7717	Intermediate Similarity	NPC470819
0.7708	Intermediate Similarity	NPC120446
0.7647	Intermediate Similarity	NPC316974
0.7634	Intermediate Similarity	NPC470817
0.7624	Intermediate Similarity	NPC125423
0.7624	Intermediate Similarity	NPC88013
0.7579	Intermediate Similarity	NPC256368
0.7573	Intermediate Similarity	NPC316708
0.7573	Intermediate Similarity	NPC119550
0.7549	Intermediate Similarity	NPC48548
0.7549	Intermediate Similarity	NPC217921
0.7549	Intermediate Similarity	NPC135015
0.7549	Intermediate Similarity	NPC128795
0.7526	Intermediate Similarity	NPC26307
0.75	Intermediate Similarity	NPC470026
0.75	Intermediate Similarity	NPC134270
0.7476	Intermediate Similarity	NPC40728
0.7449	Intermediate Similarity	NPC312325
0.7447	Intermediate Similarity	NPC477866
0.7447	Intermediate Similarity	NPC477865
0.7447	Intermediate Similarity	NPC191323
0.7429	Intermediate Similarity	NPC321272
0.7429	Intermediate Similarity	NPC317460
0.7429	Intermediate Similarity	NPC328074
0.7429	Intermediate Similarity	NPC470025
0.7426	Intermediate Similarity	NPC201880
0.7426	Intermediate Similarity	NPC473207
0.7426	Intermediate Similarity	NPC264867
0.7426	Intermediate Similarity	NPC81567
0.7426	Intermediate Similarity	NPC470321
0.7423	Intermediate Similarity	NPC472995
0.7416	Intermediate Similarity	NPC471270
0.7404	Intermediate Similarity	NPC177047
0.74	Intermediate Similarity	NPC238397
0.74	Intermediate Similarity	NPC471363
0.7386	Intermediate Similarity	NPC476701
0.7358	Intermediate Similarity	NPC470027
0.7353	Intermediate Similarity	NPC252296
0.7347	Intermediate Similarity	NPC98112
0.7347	Intermediate Similarity	NPC472998
0.734	Intermediate Similarity	NPC133450
0.7333	Intermediate Similarity	NPC17791
0.7333	Intermediate Similarity	NPC208189
0.7333	Intermediate Similarity	NPC65034
0.7327	Intermediate Similarity	NPC127933
0.7327	Intermediate Similarity	NPC475889
0.7327	Intermediate Similarity	NPC7644
0.7327	Intermediate Similarity	NPC471450
0.7327	Intermediate Similarity	NPC7613
0.7303	Intermediate Similarity	NPC236707
0.7303	Intermediate Similarity	NPC471266
0.7303	Intermediate Similarity	NPC95124
0.7292	Intermediate Similarity	NPC475098
0.7292	Intermediate Similarity	NPC189651
0.7283	Intermediate Similarity	NPC119001
0.7283	Intermediate Similarity	NPC470658
0.7282	Intermediate Similarity	NPC184512
0.7282	Intermediate Similarity	NPC109376
0.7264	Intermediate Similarity	NPC231797
0.7263	Intermediate Similarity	NPC177668
0.7255	Intermediate Similarity	NPC473068
0.7245	Intermediate Similarity	NPC165632
0.7241	Intermediate Similarity	NPC229655
0.7228	Intermediate Similarity	NPC11956
0.7228	Intermediate Similarity	NPC471889
0.7212	Intermediate Similarity	NPC224660
0.7212	Intermediate Similarity	NPC470024
0.7209	Intermediate Similarity	NPC24590
0.7204	Intermediate Similarity	NPC311163
0.72	Intermediate Similarity	NPC272223
0.7184	Intermediate Similarity	NPC172867
0.7184	Intermediate Similarity	NPC218158
0.7184	Intermediate Similarity	NPC82251
0.7174	Intermediate Similarity	NPC83702
0.7172	Intermediate Similarity	NPC218064
0.7158	Intermediate Similarity	NPC477917
0.7158	Intermediate Similarity	NPC309310
0.7158	Intermediate Similarity	NPC49783
0.7158	Intermediate Similarity	NPC299527
0.7157	Intermediate Similarity	NPC45897
0.7157	Intermediate Similarity	NPC471888
0.7157	Intermediate Similarity	NPC471887
0.7157	Intermediate Similarity	NPC23584
0.7157	Intermediate Similarity	NPC471885
0.7157	Intermediate Similarity	NPC473070
0.7157	Intermediate Similarity	NPC471886
0.7143	Intermediate Similarity	NPC13924
0.7143	Intermediate Similarity	NPC259858
0.7143	Intermediate Similarity	NPC477969
0.7143	Intermediate Similarity	NPC469583
0.7143	Intermediate Similarity	NPC206618
0.7143	Intermediate Similarity	NPC477385
0.7143	Intermediate Similarity	NPC135224
0.7143	Intermediate Similarity	NPC477970
0.7143	Intermediate Similarity	NPC471372
0.7143	Intermediate Similarity	NPC477390
0.7143	Intermediate Similarity	NPC471362
0.7143	Intermediate Similarity	NPC100892
0.7143	Intermediate Similarity	NPC472189
0.7129	Intermediate Similarity	NPC198992
0.7128	Intermediate Similarity	NPC316138
0.7128	Intermediate Similarity	NPC313658
0.7113	Intermediate Similarity	NPC474792
0.7113	Intermediate Similarity	NPC67398
0.7113	Intermediate Similarity	NPC91654
0.7108	Intermediate Similarity	NPC476650
0.71	Intermediate Similarity	NPC203627
0.7097	Intermediate Similarity	NPC471494
0.7087	Intermediate Similarity	NPC194941
0.7083	Intermediate Similarity	NPC159876
0.7079	Intermediate Similarity	NPC477089
0.7075	Intermediate Similarity	NPC191439
0.7075	Intermediate Similarity	NPC170974
0.7075	Intermediate Similarity	NPC103627
0.7071	Intermediate Similarity	NPC171598
0.7071	Intermediate Similarity	NPC472996
0.7071	Intermediate Similarity	NPC173329
0.7071	Intermediate Similarity	NPC472997
0.7071	Intermediate Similarity	NPC288350
0.7059	Intermediate Similarity	NPC37207
0.7059	Intermediate Similarity	NPC300399
0.7059	Intermediate Similarity	NPC471482
0.7053	Intermediate Similarity	NPC248312
0.7048	Intermediate Similarity	NPC80210
0.7048	Intermediate Similarity	NPC38948
0.7048	Intermediate Similarity	NPC38376
0.7048	Intermediate Similarity	NPC181994
0.7048	Intermediate Similarity	NPC473069
0.7041	Intermediate Similarity	NPC189513
0.7033	Intermediate Similarity	NPC246621
0.7033	Intermediate Similarity	NPC474894
0.703	Intermediate Similarity	NPC244878
0.703	Intermediate Similarity	NPC473204
0.703	Intermediate Similarity	NPC188968
0.703	Intermediate Similarity	NPC473790
0.7021	Intermediate Similarity	NPC323209
0.7021	Intermediate Similarity	NPC255143
0.7019	Intermediate Similarity	NPC239961
0.7019	Intermediate Similarity	NPC51719
0.7011	Intermediate Similarity	NPC472173
0.7	Intermediate Similarity	NPC86971
0.7	Intermediate Similarity	NPC240372
0.7	Intermediate Similarity	NPC472188
0.6991	Remote Similarity	NPC471082
0.6991	Remote Similarity	NPC196130
0.699	Remote Similarity	NPC120009
0.699	Remote Similarity	NPC281378
0.6989	Remote Similarity	NPC266718
0.6989	Remote Similarity	NPC46320
0.6981	Remote Similarity	NPC473318
0.6981	Remote Similarity	NPC473328
0.6981	Remote Similarity	NPC285253
0.6981	Remote Similarity	NPC28844
0.6981	Remote Similarity	NPC221110
0.6981	Remote Similarity	NPC180459
0.6981	Remote Similarity	NPC128133
0.6981	Remote Similarity	NPC195116
0.6979	Remote Similarity	NPC249408
0.6979	Remote Similarity	NPC115607
0.6979	Remote Similarity	NPC104129
0.6979	Remote Similarity	NPC128066
0.6979	Remote Similarity	NPC473058
0.6979	Remote Similarity	NPC97103
0.6972	Remote Similarity	NPC73314
0.697	Remote Similarity	NPC8774
0.697	Remote Similarity	NPC476720
0.6966	Remote Similarity	NPC476703
0.6961	Remote Similarity	NPC84042
0.6961	Remote Similarity	NPC176406
0.6961	Remote Similarity	NPC475617
0.6961	Remote Similarity	NPC21568
0.6961	Remote Similarity	NPC305085
0.6961	Remote Similarity	NPC20673
0.6961	Remote Similarity	NPC472554
0.6961	Remote Similarity	NPC285231
0.6957	Remote Similarity	NPC109938
0.6957	Remote Similarity	NPC122945
0.6952	Remote Similarity	NPC122816
0.6952	Remote Similarity	NPC33053
0.6952	Remote Similarity	NPC471205
0.6952	Remote Similarity	NPC475074
0.6947	Remote Similarity	NPC471056
0.6947	Remote Similarity	NPC476948
0.6947	Remote Similarity	NPC471055
0.6941	Remote Similarity	NPC472947
0.6939	Remote Similarity	NPC156553
0.6939	Remote Similarity	NPC472195
0.6939	Remote Similarity	NPC119379
0.6939	Remote Similarity	NPC110022
0.6939	Remote Similarity	NPC238090
0.6939	Remote Similarity	NPC472196
0.6931	Remote Similarity	NPC476800
0.6931	Remote Similarity	NPC151093
0.6931	Remote Similarity	NPC471366
0.6931	Remote Similarity	NPC475068
0.6931	Remote Similarity	NPC472186
0.6931	Remote Similarity	NPC474440
0.6931	Remote Similarity	NPC318917

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 NPC472379 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	1416
0.2-0.3	3947
0.3-0.4	2395
0.4-0.5	960
0.5-0.6	226
0.6-0.7	55
0.7-0.8	1
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
0.73	Intermediate Similarity	NPD5344	Discontinued
0.72	Intermediate Similarity	NPD6648	Approved
0.7083	Intermediate Similarity	NPD7838	Discovery
0.6947	Remote Similarity	NPD7524	Approved
0.6907	Remote Similarity	NPD3168	Discontinued
0.6809	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6695	Phase 3
0.6667	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7516	Approved
0.6566	Remote Similarity	NPD46	Approved
0.6566	Remote Similarity	NPD6698	Approved
0.6545	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7983	Approved
0.6491	Remote Similarity	NPD7327	Approved
0.6491	Remote Similarity	NPD7328	Approved
0.6466	Remote Similarity	NPD8513	Phase 3
0.6466	Remote Similarity	NPD7503	Approved
0.6466	Remote Similarity	NPD8517	Approved
0.6466	Remote Similarity	NPD8516	Approved
0.6466	Remote Similarity	NPD8515	Approved
0.6452	Remote Similarity	NPD6929	Approved
0.6442	Remote Similarity	NPD4225	Approved
0.6429	Remote Similarity	NPD7750	Discontinued
0.6422	Remote Similarity	NPD6686	Approved
0.6383	Remote Similarity	NPD7514	Phase 3
0.6383	Remote Similarity	NPD7332	Phase 2
0.6383	Remote Similarity	NPD6930	Phase 2
0.6383	Remote Similarity	NPD6931	Approved
0.6344	Remote Similarity	NPD7145	Approved
0.6337	Remote Similarity	NPD7637	Suspended
0.6333	Remote Similarity	NPD4732	Discontinued
0.6327	Remote Similarity	NPD4249	Approved
0.6316	Remote Similarity	NPD6902	Approved
0.6275	Remote Similarity	NPD5778	Approved
0.6275	Remote Similarity	NPD5779	Approved
0.6271	Remote Similarity	NPD5125	Phase 3
0.6271	Remote Similarity	NPD5126	Approved
0.6263	Remote Similarity	NPD4251	Approved
0.6263	Remote Similarity	NPD4250	Approved
0.6239	Remote Similarity	NPD5357	Phase 1
0.6237	Remote Similarity	NPD6932	Approved
0.6237	Remote Similarity	NPD6925	Approved
0.6237	Remote Similarity	NPD5776	Phase 2
0.6216	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD8074	Phase 3
0.6186	Remote Similarity	NPD8033	Approved
0.6186	Remote Similarity	NPD8296	Approved
0.6186	Remote Similarity	NPD8335	Approved
0.6186	Remote Similarity	NPD8380	Approved
0.6186	Remote Similarity	NPD8379	Approved
0.6186	Remote Similarity	NPD8378	Approved
0.6176	Remote Similarity	NPD7087	Discontinued
0.6132	Remote Similarity	NPD7638	Approved
0.6129	Remote Similarity	NPD6933	Approved
0.6102	Remote Similarity	NPD8377	Approved
0.6102	Remote Similarity	NPD8294	Approved
0.6095	Remote Similarity	NPD7839	Suspended
0.6091	Remote Similarity	NPD6640	Phase 3
0.6075	Remote Similarity	NPD7639	Approved
0.6075	Remote Similarity	NPD7640	Approved
0.6061	Remote Similarity	NPD6893	Approved
0.6042	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1145	Discontinued
0.5979	Remote Similarity	NPD6898	Phase 1
0.5963	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.596	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD6683	Phase 2
0.593	Remote Similarity	NPD368	Approved
0.5914	Remote Similarity	NPD6924	Approved
0.5914	Remote Similarity	NPD6926	Approved
0.5893	Remote Similarity	NPD6412	Phase 2
0.5893	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD7509	Discontinued
0.5859	Remote Similarity	NPD7154	Phase 3
0.5854	Remote Similarity	NPD7507	Approved
0.5851	Remote Similarity	NPD8264	Approved
0.5849	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.584	Remote Similarity	NPD7319	Approved
0.5833	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4268	Approved
0.5833	Remote Similarity	NPD4271	Approved
0.5825	Remote Similarity	NPD6101	Approved
0.5825	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD371	Approved
0.5794	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD8444	Approved
0.5783	Remote Similarity	NPD342	Phase 1
0.5769	Remote Similarity	NPD7136	Phase 2
0.5769	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD7144	Approved
0.5761	Remote Similarity	NPD7143	Approved
0.5755	Remote Similarity	NPD5282	Discontinued
0.5743	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD1694	Approved
0.5739	Remote Similarity	NPD6371	Approved
0.5727	Remote Similarity	NPD4159	Approved
0.5726	Remote Similarity	NPD8451	Approved
0.5714	Remote Similarity	NPD4819	Approved
0.5714	Remote Similarity	NPD6411	Approved
0.5714	Remote Similarity	NPD4822	Approved
0.5714	Remote Similarity	NPD7525	Registered
0.5714	Remote Similarity	NPD4820	Approved
0.5714	Remote Similarity	NPD4821	Approved
0.5702	Remote Similarity	NPD6054	Approved
0.5699	Remote Similarity	NPD7150	Approved
0.5699	Remote Similarity	NPD7151	Approved
0.5699	Remote Similarity	NPD7152	Approved
0.5691	Remote Similarity	NPD7829	Approved
0.5691	Remote Similarity	NPD7830	Approved
0.568	Remote Similarity	NPD8448	Approved
0.5673	Remote Similarity	NPD1695	Approved
0.5656	Remote Similarity	NPD6016	Approved
0.5656	Remote Similarity	NPD6015	Approved
0.5652	Remote Similarity	NPD6922	Approved
0.5652	Remote Similarity	NPD6923	Approved
0.5652	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5649	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD1091	Approved
0.5641	Remote Similarity	NPD969	Suspended
0.5614	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD7645	Phase 2
0.561	Remote Similarity	NPD5988	Approved
0.561	Remote Similarity	NPD6370	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