NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	214.14
Volume:	240.571
LogP:	4.911
LogD:	4.191
LogS:	-4.893
# Rotatable Bonds:	0
TPSA:	13.14
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.584
Synthetic Accessibility Score:	5.144
Fsp3:	0.467
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.662
MDCK Permeability:	3.295236820122227e-05
Pgp-inhibitor:	0.98
Pgp-substrate:	0.047
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.805
30% Bioavailability (F30%):	0.939

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	97.39095306396484%
Volume Distribution (VD):	3.526
Pgp-substrate:	4.214893817901611%

ADMET: Metabolism

CYP1A2-inhibitor:	0.743
CYP1A2-substrate:	0.558
CYP2C19-inhibitor:	0.862
CYP2C19-substrate:	0.845
CYP2C9-inhibitor:	0.811
CYP2C9-substrate:	0.249
CYP2D6-inhibitor:	0.099
CYP2D6-substrate:	0.787
CYP3A4-inhibitor:	0.444
CYP3A4-substrate:	0.582

ADMET: Excretion

Clearance (CL):	12.117
Half-life (T1/2):	0.163

ADMET: Toxicity

hERG Blockers:	0.121
Human Hepatotoxicity (H-HT):	0.801
Drug-inuced Liver Injury (DILI):	0.241
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.906
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.084
Carcinogencity:	0.244
Eye Corrosion:	0.017
Eye Irritation:	0.056
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC471074

Natural Product ID:	NPC471074
*Common Name:**	Rel-Dehydroeuryspongin A
IUPAC Name:	n.a.
Synonyms:	Rel-Dehydroeuryspongin A
Standard InCHIKey:	DLJMTCDCFXWRNP-CIUCYMIDSA-N
Standard InCHI:	InChI=1S/C15H18O/c1-10-8-12-9-15(2,3)13(10)5-4-11-6-7-16-14(11)12/h4-8,12-13H,9H2,1-3H3/b5-4-/t12-,13+/m1/s1
SMILES:	CC1=C[C@@H]2CC(C)(C)[C@H]1C=Cc1ccoc21
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2347643
PubChem CID:	71719571
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004144] Heteroaromatic compounds

*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	5

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Others	2

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	=	3600.0	nM	PMID[462902]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	3580.0	nM	PMID[462903]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	45000.0	nM	PMID[462903]
NPT27	Others	Unspecified		IC50	>	100000.0	nM	PMID[462903]
NPT27	Others	Unspecified		IC50	>	45000.0	nM	PMID[462903]

☑ 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 NPC471074 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	416
0.1-0.2	1636
0.2-0.3	4484
0.3-0.4	11157
0.4-0.5	8545
0.5-0.6	9330
0.6-0.7	6473
0.7-0.8	573
0.8-0.85	60
0.85-0.9	19
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473885
0.935	High Similarity	NPC59502
0.9167	High Similarity	NPC97566
0.9	High Similarity	NPC472376
0.8983	High Similarity	NPC150895
0.8824	High Similarity	NPC205523
0.879	High Similarity	NPC118853
0.879	High Similarity	NPC178382
0.876	High Similarity	NPC243704
0.8682	High Similarity	NPC473982
0.8678	High Similarity	NPC312525
0.8678	High Similarity	NPC217180
0.8661	High Similarity	NPC329707
0.864	High Similarity	NPC188377
0.864	High Similarity	NPC65735
0.8636	High Similarity	NPC307401
0.8629	High Similarity	NPC317217
0.8629	High Similarity	NPC477967
0.8607	High Similarity	NPC87466
0.8595	High Similarity	NPC59035
0.8595	High Similarity	NPC79202
0.8583	High Similarity	NPC290955
0.8583	High Similarity	NPC246392
0.8571	High Similarity	NPC22678
0.856	High Similarity	NPC16922
0.8516	High Similarity	NPC26532
0.8507	High Similarity	NPC202260
0.8504	High Similarity	NPC23086
0.8492	Intermediate Similarity	NPC477038
0.8492	Intermediate Similarity	NPC477965
0.8473	Intermediate Similarity	NPC293253
0.845	Intermediate Similarity	NPC208389
0.8444	Intermediate Similarity	NPC148374
0.8438	Intermediate Similarity	NPC83178
0.8425	Intermediate Similarity	NPC179354
0.8387	Intermediate Similarity	NPC137710
0.8376	Intermediate Similarity	NPC42471
0.8372	Intermediate Similarity	NPC279877
0.8372	Intermediate Similarity	NPC207294
0.8372	Intermediate Similarity	NPC477039
0.8372	Intermediate Similarity	NPC477123
0.8372	Intermediate Similarity	NPC477966
0.8372	Intermediate Similarity	NPC112706
0.8359	Intermediate Similarity	NPC83301
0.8359	Intermediate Similarity	NPC138139
0.8359	Intermediate Similarity	NPC74612
0.8359	Intermediate Similarity	NPC46536
0.8358	Intermediate Similarity	NPC170604
0.8358	Intermediate Similarity	NPC215109
0.8346	Intermediate Similarity	NPC209858
0.8333	Intermediate Similarity	NPC471006
0.8333	Intermediate Similarity	NPC470740
0.8321	Intermediate Similarity	NPC61788
0.8321	Intermediate Similarity	NPC298190
0.8321	Intermediate Similarity	NPC263337
0.8306	Intermediate Similarity	NPC206007
0.8295	Intermediate Similarity	NPC141059
0.8231	Intermediate Similarity	NPC476917
0.8231	Intermediate Similarity	NPC327527
0.8231	Intermediate Similarity	NPC477040
0.8226	Intermediate Similarity	NPC212918
0.8226	Intermediate Similarity	NPC227660
0.8217	Intermediate Similarity	NPC470858
0.8211	Intermediate Similarity	NPC28054
0.8209	Intermediate Similarity	NPC324117
0.8209	Intermediate Similarity	NPC158525
0.8203	Intermediate Similarity	NPC243269
0.8195	Intermediate Similarity	NPC218838
0.8182	Intermediate Similarity	NPC277525
0.8182	Intermediate Similarity	NPC477645
0.8175	Intermediate Similarity	NPC201370
0.8175	Intermediate Similarity	NPC473983
0.8162	Intermediate Similarity	NPC177262
0.8154	Intermediate Similarity	NPC95567
0.8154	Intermediate Similarity	NPC319140
0.8148	Intermediate Similarity	NPC146872
0.8145	Intermediate Similarity	NPC45536
0.8134	Intermediate Similarity	NPC106247
0.812	Intermediate Similarity	NPC471817
0.811	Intermediate Similarity	NPC115859
0.8106	Intermediate Similarity	NPC476925
0.8102	Intermediate Similarity	NPC233707
0.8095	Intermediate Similarity	NPC473969
0.8074	Intermediate Similarity	NPC92941
0.8062	Intermediate Similarity	NPC141252
0.8062	Intermediate Similarity	NPC11799
0.8045	Intermediate Similarity	NPC475092
0.8045	Intermediate Similarity	NPC89133
0.8031	Intermediate Similarity	NPC246214
0.803	Intermediate Similarity	NPC50583
0.8029	Intermediate Similarity	NPC236532
0.8029	Intermediate Similarity	NPC220094
0.8028	Intermediate Similarity	NPC71821
0.8016	Intermediate Similarity	NPC21831
0.8016	Intermediate Similarity	NPC187547
0.8015	Intermediate Similarity	NPC46896
0.8014	Intermediate Similarity	NPC290038
0.8014	Intermediate Similarity	NPC56731
0.8	Intermediate Similarity	NPC300098
0.8	Intermediate Similarity	NPC290193
0.7985	Intermediate Similarity	NPC279596
0.797	Intermediate Similarity	NPC21460
0.7958	Intermediate Similarity	NPC233763
0.7956	Intermediate Similarity	NPC310830
0.7956	Intermediate Similarity	NPC470742
0.7956	Intermediate Similarity	NPC473268
0.7956	Intermediate Similarity	NPC42400
0.7949	Intermediate Similarity	NPC156768
0.7943	Intermediate Similarity	NPC84479
0.7941	Intermediate Similarity	NPC476947
0.7937	Intermediate Similarity	NPC208906
0.7937	Intermediate Similarity	NPC144745
0.7937	Intermediate Similarity	NPC131801
0.7914	Intermediate Similarity	NPC56197
0.7907	Intermediate Similarity	NPC36255
0.7902	Intermediate Similarity	NPC224418
0.7899	Intermediate Similarity	NPC476943
0.7887	Intermediate Similarity	NPC114513
0.7887	Intermediate Similarity	NPC245522
0.7879	Intermediate Similarity	NPC184391
0.7862	Intermediate Similarity	NPC212257
0.7862	Intermediate Similarity	NPC228842
0.7857	Intermediate Similarity	NPC476031
0.7857	Intermediate Similarity	NPC476014
0.7852	Intermediate Similarity	NPC196979
0.7852	Intermediate Similarity	NPC470977
0.7852	Intermediate Similarity	NPC470976
0.7847	Intermediate Similarity	NPC93666
0.7846	Intermediate Similarity	NPC272899
0.7842	Intermediate Similarity	NPC474722
0.7842	Intermediate Similarity	NPC90953
0.784	Intermediate Similarity	NPC252004
0.7836	Intermediate Similarity	NPC66246
0.7836	Intermediate Similarity	NPC170546
0.7832	Intermediate Similarity	NPC478166
0.7829	Intermediate Similarity	NPC79557
0.7826	Intermediate Similarity	NPC64157
0.7826	Intermediate Similarity	NPC278832
0.7823	Intermediate Similarity	NPC471863
0.781	Intermediate Similarity	NPC265793
0.7803	Intermediate Similarity	NPC216810
0.7801	Intermediate Similarity	NPC473152
0.7793	Intermediate Similarity	NPC95526
0.7786	Intermediate Similarity	NPC90296
0.7786	Intermediate Similarity	NPC130275
0.7786	Intermediate Similarity	NPC83115
0.7778	Intermediate Similarity	NPC183348
0.7778	Intermediate Similarity	NPC281398
0.7778	Intermediate Similarity	NPC282230
0.7778	Intermediate Similarity	NPC136340
0.777	Intermediate Similarity	NPC25351
0.7755	Intermediate Similarity	NPC294511
0.7755	Intermediate Similarity	NPC121615
0.7742	Intermediate Similarity	NPC54626
0.7742	Intermediate Similarity	NPC105249
0.774	Intermediate Similarity	NPC472298
0.7727	Intermediate Similarity	NPC71274
0.7727	Intermediate Similarity	NPC230979
0.7727	Intermediate Similarity	NPC474829
0.7727	Intermediate Similarity	NPC303010
0.7727	Intermediate Similarity	NPC75557
0.7721	Intermediate Similarity	NPC471995
0.7721	Intermediate Similarity	NPC15083
0.7717	Intermediate Similarity	NPC316062
0.7717	Intermediate Similarity	NPC474987
0.7708	Intermediate Similarity	NPC62799
0.7704	Intermediate Similarity	NPC939
0.7704	Intermediate Similarity	NPC45947
0.7698	Intermediate Similarity	NPC292036
0.7692	Intermediate Similarity	NPC142113
0.7692	Intermediate Similarity	NPC199044
0.7692	Intermediate Similarity	NPC158871
0.7692	Intermediate Similarity	NPC117674
0.7692	Intermediate Similarity	NPC238843
0.7687	Intermediate Similarity	NPC474438
0.7687	Intermediate Similarity	NPC474279
0.7676	Intermediate Similarity	NPC52412
0.7671	Intermediate Similarity	NPC329180
0.7669	Intermediate Similarity	NPC474260
0.7669	Intermediate Similarity	NPC81912
0.7669	Intermediate Similarity	NPC329694
0.7669	Intermediate Similarity	NPC329922
0.766	Intermediate Similarity	NPC18904
0.766	Intermediate Similarity	NPC67003
0.766	Intermediate Similarity	NPC218204
0.766	Intermediate Similarity	NPC473681
0.766	Intermediate Similarity	NPC61157
0.7643	Intermediate Similarity	NPC130976
0.7642	Intermediate Similarity	NPC471521
0.7642	Intermediate Similarity	NPC473356
0.7639	Intermediate Similarity	NPC247221
0.7639	Intermediate Similarity	NPC185456
0.7635	Intermediate Similarity	NPC246164
0.7634	Intermediate Similarity	NPC471549
0.7634	Intermediate Similarity	NPC473379
0.763	Intermediate Similarity	NPC198904
0.7622	Intermediate Similarity	NPC80635
0.7622	Intermediate Similarity	NPC223415
0.7622	Intermediate Similarity	NPC267632
0.7622	Intermediate Similarity	NPC243577

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 NPC471074 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	1000
0.2-0.3	1548
0.3-0.4	2840
0.4-0.5	1999
0.5-0.6	1066
0.6-0.7	270
0.7-0.8	26
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
0.7903	Intermediate Similarity	NPD1241	Discontinued
0.7842	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD1876	Approved
0.7576	Intermediate Similarity	NPD3972	Approved
0.75	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD1471	Phase 3
0.7407	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6273	Approved
0.7244	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2798	Approved
0.7222	Intermediate Similarity	NPD2344	Approved
0.7214	Intermediate Similarity	NPD8032	Phase 2
0.7211	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD2799	Discontinued
0.7143	Intermediate Similarity	NPD5585	Approved
0.7143	Intermediate Similarity	NPD1651	Approved
0.7133	Intermediate Similarity	NPD920	Approved
0.7122	Intermediate Similarity	NPD6832	Phase 2
0.7114	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD17	Approved
0.7075	Intermediate Similarity	NPD4628	Phase 3
0.7054	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3142	Approved
0.7042	Intermediate Similarity	NPD3140	Approved
0.7034	Intermediate Similarity	NPD2796	Approved
0.7027	Intermediate Similarity	NPD2309	Approved
0.7007	Intermediate Similarity	NPD1243	Approved
0.7006	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1281	Approved
0.6978	Remote Similarity	NPD1019	Discontinued
0.6968	Remote Similarity	NPD5761	Phase 2
0.6968	Remote Similarity	NPD5760	Phase 2
0.6966	Remote Similarity	NPD3748	Approved
0.6959	Remote Similarity	NPD7003	Approved
0.6951	Remote Similarity	NPD6764	Approved
0.6951	Remote Similarity	NPD6765	Approved
0.6946	Remote Similarity	NPD8434	Phase 2
0.6934	Remote Similarity	NPD9717	Approved
0.6934	Remote Similarity	NPD1608	Approved
0.6929	Remote Similarity	NPD3134	Approved
0.6912	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD3873	Phase 3
0.6908	Remote Similarity	NPD3869	Phase 3
0.6906	Remote Similarity	NPD2797	Approved
0.6906	Remote Similarity	NPD3266	Approved
0.6906	Remote Similarity	NPD3267	Approved
0.6903	Remote Similarity	NPD6280	Approved
0.6903	Remote Similarity	NPD6279	Approved
0.6901	Remote Similarity	NPD2313	Discontinued
0.6892	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5691	Approved
0.6884	Remote Similarity	NPD5327	Phase 3
0.6884	Remote Similarity	NPD4359	Approved
0.6871	Remote Similarity	NPD2346	Discontinued
0.6842	Remote Similarity	NPD7157	Approved
0.6838	Remote Similarity	NPD1778	Approved
0.6835	Remote Similarity	NPD1283	Approved
0.6822	Remote Similarity	NPD2182	Approved
0.6809	Remote Similarity	NPD9494	Approved
0.6806	Remote Similarity	NPD4307	Phase 2
0.6806	Remote Similarity	NPD2979	Phase 3
0.6792	Remote Similarity	NPD919	Approved
0.6786	Remote Similarity	NPD6784	Approved
0.6786	Remote Similarity	NPD6785	Approved
0.6783	Remote Similarity	NPD3268	Approved
0.6759	Remote Similarity	NPD6355	Discontinued
0.6759	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD1358	Approved
0.6741	Remote Similarity	NPD9092	Discovery
0.6733	Remote Similarity	NPD3750	Approved
0.6733	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.671	Remote Similarity	NPD7458	Discontinued
0.671	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD1247	Approved
0.6692	Remote Similarity	NPD2684	Approved
0.6691	Remote Similarity	NPD9545	Approved
0.669	Remote Similarity	NPD4140	Approved
0.6689	Remote Similarity	NPD4476	Approved
0.6689	Remote Similarity	NPD1551	Phase 2
0.6689	Remote Similarity	NPD3887	Approved
0.6689	Remote Similarity	NPD4477	Approved
0.6667	Remote Similarity	NPD3496	Discontinued
0.6667	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1203	Approved
0.6667	Remote Similarity	NPD6599	Discontinued
0.6667	Remote Similarity	NPD2800	Approved
0.6646	Remote Similarity	NPD5494	Approved
0.6646	Remote Similarity	NPD7819	Suspended
0.6644	Remote Similarity	NPD4622	Approved
0.6644	Remote Similarity	NPD6005	Phase 3
0.6644	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6004	Phase 3
0.6644	Remote Similarity	NPD4618	Approved
0.6644	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6002	Phase 3
0.6641	Remote Similarity	NPD164	Approved
0.6623	Remote Similarity	NPD4110	Phase 3
0.6623	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD4308	Phase 3
0.6621	Remote Similarity	NPD4870	Approved
0.662	Remote Similarity	NPD5647	Approved
0.6603	Remote Similarity	NPD2649	Approved
0.6603	Remote Similarity	NPD2651	Approved
0.66	Remote Similarity	NPD1549	Phase 2
0.6594	Remote Similarity	NPD2932	Approved
0.6594	Remote Similarity	NPD4626	Approved
0.6589	Remote Similarity	NPD9697	Approved
0.6587	Remote Similarity	NPD1238	Approved
0.6577	Remote Similarity	NPD2935	Discontinued
0.6577	Remote Similarity	NPD2438	Suspended
0.6577	Remote Similarity	NPD6099	Approved
0.6577	Remote Similarity	NPD6100	Approved
0.6577	Remote Similarity	NPD2531	Phase 2
0.6575	Remote Similarity	NPD1240	Approved
0.6569	Remote Similarity	NPD1894	Discontinued
0.6566	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6808	Phase 2
0.6561	Remote Similarity	NPD7028	Phase 2
0.6558	Remote Similarity	NPD4662	Approved
0.6558	Remote Similarity	NPD4661	Approved
0.6558	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD5689	Approved
0.6554	Remote Similarity	NPD5688	Approved
0.6552	Remote Similarity	NPD411	Approved
0.6552	Remote Similarity	NPD3764	Approved
0.6544	Remote Similarity	NPD9493	Approved
0.6533	Remote Similarity	NPD2353	Approved
0.6533	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD1933	Approved
0.6531	Remote Similarity	NPD447	Suspended
0.6522	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3024	Approved
0.6522	Remote Similarity	NPD3445	Approved
0.6522	Remote Similarity	NPD3443	Approved
0.6522	Remote Similarity	NPD3444	Approved
0.6522	Remote Similarity	NPD3025	Approved
0.6519	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD8166	Discontinued
0.651	Remote Similarity	NPD1510	Phase 2
0.6506	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2296	Approved
0.65	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6287	Discontinued
0.6497	Remote Similarity	NPD3226	Approved
0.6496	Remote Similarity	NPD5536	Phase 2
0.6494	Remote Similarity	NPD6799	Approved
0.6493	Remote Similarity	NPD5535	Approved
0.6493	Remote Similarity	NPD7843	Approved
0.649	Remote Similarity	NPD4534	Discontinued
0.649	Remote Similarity	NPD2897	Discontinued
0.6486	Remote Similarity	NPD1607	Approved
0.6485	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD8651	Approved
0.6478	Remote Similarity	NPD7577	Discontinued
0.6475	Remote Similarity	NPD3019	Approved
0.6474	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD1712	Approved
0.6452	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.645	Remote Similarity	NPD6559	Discontinued
0.6442	Remote Similarity	NPD710	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD6798	Discontinued
0.6438	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD6362	Approved
0.6429	Remote Similarity	NPD3023	Approved
0.6429	Remote Similarity	NPD3026	Approved
0.6424	Remote Similarity	NPD3926	Phase 2
0.6423	Remote Similarity	NPD405	Clinical (unspecified phase)
0.642	Remote Similarity	NPD3749	Approved
0.6419	Remote Similarity	NPD5735	Approved
0.6415	Remote Similarity	NPD6873	Phase 2
0.6415	Remote Similarity	NPD7411	Suspended
0.6402	Remote Similarity	NPD8127	Discontinued
0.6383	Remote Similarity	NPD1611	Approved
0.6382	Remote Similarity	NPD2424	Discontinued
0.6382	Remote Similarity	NPD5958	Discontinued
0.6382	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD6653	Approved
0.6376	Remote Similarity	NPD6353	Approved
0.637	Remote Similarity	NPD821	Approved
0.637	Remote Similarity	NPD7095	Approved
0.637	Remote Similarity	NPD7008	Discontinued
0.6369	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2354	Approved
0.6364	Remote Similarity	NPD6696	Suspended
0.6364	Remote Similarity	NPD290	Approved
0.6358	Remote Similarity	NPD7768	Phase 2
0.6358	Remote Similarity	NPD3882	Suspended
0.6353	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD4060	Phase 1
0.635	Remote Similarity	NPD2557	Approved
0.6346	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD2534	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