NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	278.15
Volume:	286.874
LogP:	2.762
LogD:	2.371
LogS:	-4.42
# Rotatable Bonds:	1
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.546
Synthetic Accessibility Score:	5.394
Fsp3:	0.75
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:	-4.67
MDCK Permeability:	2.6381238058093004e-05
Pgp-inhibitor:	0.675
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.071
20% Bioavailability (F20%):	0.055
30% Bioavailability (F30%):	0.852

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.826
Plasma Protein Binding (PPB):	67.05850982666016%
Volume Distribution (VD):	0.734
Pgp-substrate:	42.26497268676758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.232
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.61
CYP2C9-inhibitor:	0.061
CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.367
CYP3A4-inhibitor:	0.152
CYP3A4-substrate:	0.283

ADMET: Excretion

Clearance (CL):	15.386
Half-life (T1/2):	0.278

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.497
Drug-inuced Liver Injury (DILI):	0.287
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.929
Maximum Recommended Daily Dose:	0.333
Skin Sensitization:	0.269
Carcinogencity:	0.185
Eye Corrosion:	0.261
Eye Irritation:	0.044
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC472378

Natural Product ID:	NPC472378
*Common Name:**	GDGLLDGJRBJFRQ-WNCDQNTKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GDGLLDGJRBJFRQ-WNCDQNTKSA-N
Standard InCHI:	InChI=1S/C16H22O4/c1-9-5-10-8-15(2,3)11(9)6-13(17)12-7-14(18)20-16(10,12)19-4/h5,7,10-11,13,17H,6,8H2,1-4H3/t10-,11+,13-,16+/m1/s1
SMILES:	CO[C@]12OC(=O)C=C2[C@H](O)C[C@H]2C(=C[C@@H]1CC2(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3397813
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0001656] Acetals [CHEMONTID:0004472] Ketals

*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	>	35000.0	nM	PMID[522924]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	35000.0	nM	PMID[522924]
NPT27	Others	Unspecified		IC50	>	35000.0	nM	PMID[522924]

☑ 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 NPC472378 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	1382
0.2-0.3	5287
0.3-0.4	15157
0.4-0.5	9904
0.5-0.6	7711
0.6-0.7	2746
0.7-0.8	281
0.8-0.85	22
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.939	High Similarity	NPC472377
0.8977	High Similarity	NPC141831
0.8966	High Similarity	NPC470734
0.8864	High Similarity	NPC281942
0.8864	High Similarity	NPC232426
0.8851	High Similarity	NPC472810
0.8851	High Similarity	NPC472809
0.8778	High Similarity	NPC298973
0.8778	High Similarity	NPC104925
0.8706	High Similarity	NPC474809
0.8706	High Similarity	NPC311070
0.869	High Similarity	NPC475944
0.8667	High Similarity	NPC472812
0.8588	High Similarity	NPC323251
0.8588	High Similarity	NPC471298
0.8571	High Similarity	NPC469697
0.8556	High Similarity	NPC472811
0.8554	High Similarity	NPC474816
0.8554	High Similarity	NPC209135
0.8523	High Similarity	NPC312561
0.8506	High Similarity	NPC42586
0.8506	High Similarity	NPC473251
0.8506	High Similarity	NPC163606
0.8488	Intermediate Similarity	NPC471297
0.8444	Intermediate Similarity	NPC78973
0.8434	Intermediate Similarity	NPC262747
0.8427	Intermediate Similarity	NPC474629
0.8409	Intermediate Similarity	NPC131813
0.8391	Intermediate Similarity	NPC126518
0.8391	Intermediate Similarity	NPC471301
0.8387	Intermediate Similarity	NPC165632
0.8387	Intermediate Similarity	NPC162346
0.837	Intermediate Similarity	NPC470255
0.8295	Intermediate Similarity	NPC471795
0.8276	Intermediate Similarity	NPC474193
0.8276	Intermediate Similarity	NPC12283
0.8276	Intermediate Similarity	NPC42476
0.8211	Intermediate Similarity	NPC474440
0.8182	Intermediate Similarity	NPC471302
0.8172	Intermediate Similarity	NPC474554
0.8152	Intermediate Similarity	NPC477122
0.8152	Intermediate Similarity	NPC329842
0.8125	Intermediate Similarity	NPC477721
0.8125	Intermediate Similarity	NPC477716
0.8105	Intermediate Similarity	NPC477718
0.8105	Intermediate Similarity	NPC477719
0.8105	Intermediate Similarity	NPC475709
0.809	Intermediate Similarity	NPC472442
0.8085	Intermediate Similarity	NPC472441
0.8068	Intermediate Similarity	NPC472440
0.8065	Intermediate Similarity	NPC205034
0.8065	Intermediate Similarity	NPC162615
0.8065	Intermediate Similarity	NPC152778
0.8065	Intermediate Similarity	NPC156553
0.8065	Intermediate Similarity	NPC53555
0.8065	Intermediate Similarity	NPC115021
0.8043	Intermediate Similarity	NPC469403
0.8043	Intermediate Similarity	NPC477782
0.8043	Intermediate Similarity	NPC182136
0.8043	Intermediate Similarity	NPC280149
0.8043	Intermediate Similarity	NPC221111
0.8041	Intermediate Similarity	NPC477717
0.8023	Intermediate Similarity	NPC242767
0.8	Intermediate Similarity	NPC17578
0.8	Intermediate Similarity	NPC471219
0.8	Intermediate Similarity	NPC473756
0.8	Intermediate Similarity	NPC240673
0.7979	Intermediate Similarity	NPC53685
0.7978	Intermediate Similarity	NPC31086
0.7978	Intermediate Similarity	NPC474865
0.7957	Intermediate Similarity	NPC477783
0.7957	Intermediate Similarity	NPC472814
0.7957	Intermediate Similarity	NPC177037
0.7957	Intermediate Similarity	NPC72845
0.7955	Intermediate Similarity	NPC471218
0.7955	Intermediate Similarity	NPC324170
0.7952	Intermediate Similarity	NPC16349
0.7952	Intermediate Similarity	NPC222244
0.7938	Intermediate Similarity	NPC472644
0.7935	Intermediate Similarity	NPC474396
0.7935	Intermediate Similarity	NPC5509
0.7935	Intermediate Similarity	NPC50488
0.7917	Intermediate Similarity	NPC98112
0.7917	Intermediate Similarity	NPC53844
0.7912	Intermediate Similarity	NPC476600
0.7912	Intermediate Similarity	NPC471796
0.7895	Intermediate Similarity	NPC276110
0.7879	Intermediate Similarity	NPC45897
0.7872	Intermediate Similarity	NPC472954
0.7872	Intermediate Similarity	NPC139692
0.7872	Intermediate Similarity	NPC472640
0.7872	Intermediate Similarity	NPC472641
0.7865	Intermediate Similarity	NPC23748
0.7865	Intermediate Similarity	NPC193198
0.7857	Intermediate Similarity	NPC472643
0.7849	Intermediate Similarity	NPC310479
0.7849	Intermediate Similarity	NPC220216
0.7849	Intermediate Similarity	NPC472642
0.7835	Intermediate Similarity	NPC473154
0.7812	Intermediate Similarity	NPC473153
0.7812	Intermediate Similarity	NPC134072
0.7812	Intermediate Similarity	NPC234993
0.7812	Intermediate Similarity	NPC242848
0.7812	Intermediate Similarity	NPC16967
0.7802	Intermediate Similarity	NPC329692
0.78	Intermediate Similarity	NPC471937
0.7789	Intermediate Similarity	NPC474555
0.7789	Intermediate Similarity	NPC191521
0.7789	Intermediate Similarity	NPC324078
0.7789	Intermediate Similarity	NPC57117
0.7778	Intermediate Similarity	NPC472815
0.7778	Intermediate Similarity	NPC470800
0.7778	Intermediate Similarity	NPC82297
0.7778	Intermediate Similarity	NPC474693
0.7766	Intermediate Similarity	NPC124374
0.7755	Intermediate Similarity	NPC324841
0.7755	Intermediate Similarity	NPC474012
0.7755	Intermediate Similarity	NPC38855
0.7755	Intermediate Similarity	NPC476299
0.7755	Intermediate Similarity	NPC16601
0.7753	Intermediate Similarity	NPC256112
0.7745	Intermediate Similarity	NPC470024
0.7742	Intermediate Similarity	NPC174342
0.7742	Intermediate Similarity	NPC261320
0.7742	Intermediate Similarity	NPC251528
0.7732	Intermediate Similarity	NPC205143
0.7732	Intermediate Similarity	NPC208094
0.7727	Intermediate Similarity	NPC10636
0.7717	Intermediate Similarity	NPC166857
0.7711	Intermediate Similarity	NPC4299
0.7701	Intermediate Similarity	NPC184737
0.77	Intermediate Similarity	NPC120009
0.77	Intermediate Similarity	NPC471938
0.7692	Intermediate Similarity	NPC474694
0.7692	Intermediate Similarity	NPC473659
0.7692	Intermediate Similarity	NPC106416
0.7692	Intermediate Similarity	NPC474860
0.7692	Intermediate Similarity	NPC475860
0.7692	Intermediate Similarity	NPC65661
0.7692	Intermediate Similarity	NPC35933
0.7692	Intermediate Similarity	NPC471300
0.7692	Intermediate Similarity	NPC30984
0.7692	Intermediate Similarity	NPC86316
0.7684	Intermediate Similarity	NPC99653
0.7684	Intermediate Similarity	NPC472303
0.7677	Intermediate Similarity	NPC198992
0.767	Intermediate Similarity	NPC206618
0.7667	Intermediate Similarity	NPC49208
0.7667	Intermediate Similarity	NPC477124
0.7667	Intermediate Similarity	NPC79945
0.766	Intermediate Similarity	NPC470817
0.766	Intermediate Similarity	NPC51486
0.7653	Intermediate Similarity	NPC222303
0.7653	Intermediate Similarity	NPC471610
0.7653	Intermediate Similarity	NPC159763
0.7653	Intermediate Similarity	NPC275086
0.7653	Intermediate Similarity	NPC325229
0.7653	Intermediate Similarity	NPC278386
0.7653	Intermediate Similarity	NPC124512
0.7647	Intermediate Similarity	NPC109376
0.764	Intermediate Similarity	NPC159148
0.764	Intermediate Similarity	NPC170303
0.7629	Intermediate Similarity	NPC470801
0.7609	Intermediate Similarity	NPC474062
0.7609	Intermediate Similarity	NPC477668
0.7609	Intermediate Similarity	NPC311163
0.7604	Intermediate Similarity	NPC477722
0.7604	Intermediate Similarity	NPC469491
0.7604	Intermediate Similarity	NPC475572
0.7604	Intermediate Similarity	NPC105490
0.7604	Intermediate Similarity	NPC470521
0.76	Intermediate Similarity	NPC238397
0.76	Intermediate Similarity	NPC58329
0.76	Intermediate Similarity	NPC471914
0.76	Intermediate Similarity	NPC471363
0.759	Intermediate Similarity	NPC101622
0.7586	Intermediate Similarity	NPC283619
0.7582	Intermediate Similarity	NPC46320
0.7582	Intermediate Similarity	NPC474359
0.7582	Intermediate Similarity	NPC96055
0.7579	Intermediate Similarity	NPC470520
0.7579	Intermediate Similarity	NPC2882
0.7579	Intermediate Similarity	NPC78594
0.7579	Intermediate Similarity	NPC234335
0.7579	Intermediate Similarity	NPC289479
0.7576	Intermediate Similarity	NPC476767
0.7576	Intermediate Similarity	NPC227865
0.7576	Intermediate Similarity	NPC477720
0.7576	Intermediate Similarity	NPC472826
0.7573	Intermediate Similarity	NPC38948
0.7573	Intermediate Similarity	NPC224660
0.7556	Intermediate Similarity	NPC122945
0.7556	Intermediate Similarity	NPC109938
0.7553	Intermediate Similarity	NPC246028
0.7553	Intermediate Similarity	NPC314727
0.7553	Intermediate Similarity	NPC470819
0.7553	Intermediate Similarity	NPC293044
0.7553	Intermediate Similarity	NPC20946
0.7553	Intermediate Similarity	NPC168131
0.7551	Intermediate Similarity	NPC73911

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 NPC472378 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	1917
0.2-0.3	3921
0.3-0.4	2304
0.4-0.5	520
0.5-0.6	273
0.6-0.7	37
0.7-0.8	0
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
0.8391	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD4225	Approved
0.7404	Intermediate Similarity	NPD6686	Approved
0.7363	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7640	Approved
0.7228	Intermediate Similarity	NPD7639	Approved
0.7129	Intermediate Similarity	NPD7638	Approved
0.6939	Remote Similarity	NPD5785	Approved
0.6869	Remote Similarity	NPD7637	Suspended
0.6837	Remote Similarity	NPD6051	Approved
0.6832	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD5344	Discontinued
0.6814	Remote Similarity	NPD7328	Approved
0.6814	Remote Similarity	NPD7327	Approved
0.68	Remote Similarity	NPD5778	Approved
0.68	Remote Similarity	NPD5779	Approved
0.6796	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD8033	Approved
0.6774	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7838	Discovery
0.6768	Remote Similarity	NPD6698	Approved
0.6768	Remote Similarity	NPD46	Approved
0.6754	Remote Similarity	NPD7516	Approved
0.6737	Remote Similarity	NPD6695	Phase 3
0.6737	Remote Similarity	NPD7154	Phase 3
0.6726	Remote Similarity	NPD7115	Discovery
0.6706	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6411	Approved
0.6699	Remote Similarity	NPD6084	Phase 2
0.6699	Remote Similarity	NPD6083	Phase 2
0.6696	Remote Similarity	NPD8377	Approved
0.6696	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7503	Approved
0.6638	Remote Similarity	NPD8378	Approved
0.6638	Remote Similarity	NPD8296	Approved
0.6638	Remote Similarity	NPD8335	Approved
0.6638	Remote Similarity	NPD8380	Approved
0.6638	Remote Similarity	NPD8379	Approved
0.6634	Remote Similarity	NPD6399	Phase 3
0.6604	Remote Similarity	NPD7632	Discontinued
0.6598	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD1694	Approved
0.6596	Remote Similarity	NPD4822	Approved
0.6596	Remote Similarity	NPD4821	Approved
0.6596	Remote Similarity	NPD4819	Approved
0.6596	Remote Similarity	NPD4820	Approved
0.6593	Remote Similarity	NPD8264	Approved
0.6571	Remote Similarity	NPD6648	Approved
0.6569	Remote Similarity	NPD7748	Approved
0.6562	Remote Similarity	NPD5362	Discontinued
0.6559	Remote Similarity	NPD4271	Approved
0.6559	Remote Similarity	NPD4268	Approved
0.6559	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7515	Phase 2
0.6531	Remote Similarity	NPD7521	Approved
0.6531	Remote Similarity	NPD5330	Approved
0.6531	Remote Similarity	NPD6684	Approved
0.6531	Remote Similarity	NPD7334	Approved
0.6531	Remote Similarity	NPD6409	Approved
0.6531	Remote Similarity	NPD7146	Approved
0.6522	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6882	Approved
0.6518	Remote Similarity	NPD6053	Discontinued
0.6514	Remote Similarity	NPD6412	Phase 2
0.65	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6101	Approved
0.6495	Remote Similarity	NPD3666	Approved
0.6495	Remote Similarity	NPD3665	Phase 1
0.6495	Remote Similarity	NPD3133	Approved
0.6489	Remote Similarity	NPD6929	Approved
0.6486	Remote Similarity	NPD6371	Approved
0.6476	Remote Similarity	NPD5696	Approved
0.6465	Remote Similarity	NPD7524	Approved
0.6465	Remote Similarity	NPD7750	Discontinued
0.6458	Remote Similarity	NPD5209	Approved
0.6458	Remote Similarity	NPD3667	Approved
0.6429	Remote Similarity	NPD5363	Approved
0.6422	Remote Similarity	NPD6675	Approved
0.6422	Remote Similarity	NPD6402	Approved
0.6422	Remote Similarity	NPD5739	Approved
0.6422	Remote Similarity	NPD7128	Approved
0.6421	Remote Similarity	NPD6931	Approved
0.6421	Remote Similarity	NPD6930	Phase 2
0.6417	Remote Similarity	NPD7507	Approved
0.6413	Remote Similarity	NPD6942	Approved
0.6413	Remote Similarity	NPD7339	Approved
0.6413	Remote Similarity	NPD8039	Approved
0.64	Remote Similarity	NPD5737	Approved
0.64	Remote Similarity	NPD6672	Approved
0.64	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6903	Approved
0.6395	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5332	Approved
0.6392	Remote Similarity	NPD5331	Approved
0.6381	Remote Similarity	NPD7902	Approved
0.6373	Remote Similarity	NPD5693	Phase 1
0.6364	Remote Similarity	NPD5279	Phase 3
0.6364	Remote Similarity	NPD3618	Phase 1
0.6364	Remote Similarity	NPD4249	Approved
0.6364	Remote Similarity	NPD5697	Approved
0.6364	Remote Similarity	NPD5701	Approved
0.6354	Remote Similarity	NPD4790	Discontinued
0.6353	Remote Similarity	NPD4192	Approved
0.6353	Remote Similarity	NPD4193	Approved
0.6353	Remote Similarity	NPD4191	Approved
0.6353	Remote Similarity	NPD4194	Approved
0.6339	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD4753	Phase 2
0.6327	Remote Similarity	NPD4786	Approved
0.6316	Remote Similarity	NPD7645	Phase 2
0.6306	Remote Similarity	NPD7320	Approved
0.6306	Remote Similarity	NPD6899	Approved
0.6306	Remote Similarity	NPD6881	Approved
0.6304	Remote Similarity	NPD6926	Approved
0.6304	Remote Similarity	NPD6924	Approved
0.63	Remote Similarity	NPD4251	Approved
0.63	Remote Similarity	NPD4250	Approved
0.63	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4269	Approved
0.6289	Remote Similarity	NPD4270	Approved
0.6286	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7839	Suspended
0.6283	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5776	Phase 2
0.6277	Remote Similarity	NPD6925	Approved
0.6263	Remote Similarity	NPD1696	Phase 3
0.626	Remote Similarity	NPD7319	Approved
0.625	Remote Similarity	NPD6373	Approved
0.625	Remote Similarity	NPD6012	Approved
0.625	Remote Similarity	NPD7332	Phase 2
0.625	Remote Similarity	NPD7514	Phase 3
0.625	Remote Similarity	NPD4695	Discontinued
0.625	Remote Similarity	NPD6014	Approved
0.625	Remote Similarity	NPD6372	Approved
0.625	Remote Similarity	NPD6013	Approved
0.6214	Remote Similarity	NPD7087	Discontinued
0.6211	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7145	Approved
0.62	Remote Similarity	NPD4519	Discontinued
0.62	Remote Similarity	NPD5786	Approved
0.62	Remote Similarity	NPD4623	Approved
0.6195	Remote Similarity	NPD7290	Approved
0.6195	Remote Similarity	NPD6883	Approved
0.6195	Remote Similarity	NPD7102	Approved
0.6186	Remote Similarity	NPD6902	Approved
0.6176	Remote Similarity	NPD5328	Approved
0.617	Remote Similarity	NPD6933	Approved
0.6163	Remote Similarity	NPD368	Approved
0.6161	Remote Similarity	NPD6011	Approved
0.6147	Remote Similarity	NPD5211	Phase 2
0.6146	Remote Similarity	NPD4195	Approved
0.614	Remote Similarity	NPD6650	Approved
0.614	Remote Similarity	NPD6847	Approved
0.614	Remote Similarity	NPD8130	Phase 1
0.614	Remote Similarity	NPD6617	Approved
0.614	Remote Similarity	NPD6869	Approved
0.614	Remote Similarity	NPD6649	Approved
0.6126	Remote Similarity	NPD4211	Phase 1
0.6122	Remote Similarity	NPD6435	Approved
0.61	Remote Similarity	NPD6893	Approved
0.6095	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5282	Discontinued
0.6095	Remote Similarity	NPD7900	Approved
0.6087	Remote Similarity	NPD8297	Approved
0.6082	Remote Similarity	NPD7525	Registered
0.6082	Remote Similarity	NPD4252	Approved
0.6075	Remote Similarity	NPD4755	Approved
0.6071	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6079	Approved
0.6058	Remote Similarity	NPD5284	Approved
0.6058	Remote Similarity	NPD7983	Approved
0.6058	Remote Similarity	NPD5281	Approved
0.6044	Remote Similarity	NPD6923	Approved
0.6044	Remote Similarity	NPD6922	Approved
0.6038	Remote Similarity	NPD4629	Approved
0.6038	Remote Similarity	NPD5210	Approved
0.6036	Remote Similarity	NPD5141	Approved
0.6024	Remote Similarity	NPD342	Phase 1
0.602	Remote Similarity	NPD6898	Phase 1
0.602	Remote Similarity	NPD5369	Approved
0.6019	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6904	Approved
0.6019	Remote Similarity	NPD6080	Approved
0.6019	Remote Similarity	NPD6673	Approved
0.6017	Remote Similarity	NPD7505	Discontinued
0.6017	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD3668	Phase 3
0.6	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4202	Approved
0.5981	Remote Similarity	NPD4697	Phase 3
0.5981	Remote Similarity	NPD5221	Approved
0.5981	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD5222	Approved
0.5978	Remote Similarity	NPD7143	Approved
0.5978	Remote Similarity	NPD7144	Approved
0.5963	Remote Similarity	NPD4700	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