NPASS Compound

Structure

CID290193 OpenBabel06191716092D 22 24 0 0 1 0 0 0 0 0999 V2000 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 -1.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 9 1 0 0 0 0 5 10 1 0 0 0 0 6 7 2 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 12 17 1 0 0 0 0 13 15 2 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 16 20 1 1 0 0 0 17 18 1 0 0 0 0 17 21 1 1 0 0 0 18 19 1 0 0 0 0 18 20 1 1 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.21
Volume:	335.841
LogP:	4.57
LogD:	4.432
LogS:	-4.985
# Rotatable Bonds:	2
TPSA:	33.37
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.774
Synthetic Accessibility Score:	4.451
Fsp3:	0.6
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:	-4.447
MDCK Permeability:	1.7553444195073098e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.029
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.164
30% Bioavailability (F30%):	0.041

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.744
Plasma Protein Binding (PPB):	91.4586181640625%
Volume Distribution (VD):	1.518
Pgp-substrate:	8.40396499633789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.631
CYP1A2-substrate:	0.217
CYP2C19-inhibitor:	0.681
CYP2C19-substrate:	0.35
CYP2C9-inhibitor:	0.767
CYP2C9-substrate:	0.649
CYP2D6-inhibitor:	0.241
CYP2D6-substrate:	0.541
CYP3A4-inhibitor:	0.585
CYP3A4-substrate:	0.276

ADMET: Excretion

Clearance (CL):	10.021
Half-life (T1/2):	0.071

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.142
Drug-inuced Liver Injury (DILI):	0.167
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.943
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.053
Carcinogencity:	0.632
Eye Corrosion:	0.022
Eye Irritation:	0.524
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC290193

Natural Product ID:	NPC290193
*Common Name:**	Yunnacoronarin A
IUPAC Name:	(1R,4S,4aR,8aS)-4-[(E)-2-(furan-3-yl)ethenyl]-4a,8,8-trimethyl-3-methylidene-2,4,5,6,7,8a-hexahydro-1H-naphthalen-1-ol
Synonyms:
Standard InCHIKey:	UTIGHTZWXIGRIJ-JEQJTPLUSA-N
Standard InCHI:	InChI=1S/C20H28O2/c1-14-12-17(21)18-19(2,3)9-5-10-20(18,4)16(14)7-6-15-8-11-22-13-15/h6-8,11,13,16-18,21H,1,5,9-10,12H2,2-4H3/b7-6+/t16-,17+,18-,20+/m0/s1
SMILES:	C=C1C[C@@H](O)[C@@H]2[C@]([C@H]1/C=C/c1cocc1)(C)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462050
PubChem CID:	12187319
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO32565	hedychium longipetalum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351042]
NPO17266	Hedychium yunnanense	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15125.2	Taxus wallichiana var. wallichiana	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15125.2	Taxus wallichiana var. wallichiana	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17266	Hedychium yunnanense	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	8

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1161	Cell Line	CHO	Cricetulus griseus	IC50	=	17.89	ug.mL-1	PMID[496112]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	27.14	ug.mL-1	PMID[496112]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	28.05	ug.mL-1	PMID[496112]
NPT762	Cell Line	A-431	Homo sapiens	IC50	=	29.02	ug.mL-1	PMID[496112]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	46.56	ug.mL-1	PMID[496112]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	6.58	ug.mL-1	PMID[496113]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	0.56	ug.mL-1	PMID[496113]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6.21	ug.mL-1	PMID[496113]

☑ 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 NPC290193 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	257
0.1-0.2	1284
0.2-0.3	2715
0.3-0.4	6617
0.4-0.5	12251
0.5-0.6	11938
0.6-0.7	7000
0.7-0.8	558
0.8-0.85	58
0.85-0.9	17
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9831	High Similarity	NPC300098
0.9032	High Similarity	NPC290955
0.8898	High Similarity	NPC61788
0.888	High Similarity	NPC246392
0.881	High Similarity	NPC26532
0.881	High Similarity	NPC279877
0.8803	High Similarity	NPC277525
0.8769	High Similarity	NPC476947
0.876	High Similarity	NPC218838
0.8731	High Similarity	NPC475519
0.8647	High Similarity	NPC202260
0.8538	High Similarity	NPC473982
0.8504	High Similarity	NPC46536
0.8504	High Similarity	NPC138139
0.8504	High Similarity	NPC23086
0.8456	Intermediate Similarity	NPC263337
0.8455	Intermediate Similarity	NPC87466
0.845	Intermediate Similarity	NPC59502
0.8444	Intermediate Similarity	NPC67003
0.8372	Intermediate Similarity	NPC329707
0.8358	Intermediate Similarity	NPC307401
0.8333	Intermediate Similarity	NPC477967
0.8321	Intermediate Similarity	NPC89133
0.8321	Intermediate Similarity	NPC52412
0.8308	Intermediate Similarity	NPC208389
0.8284	Intermediate Similarity	NPC46896
0.8268	Intermediate Similarity	NPC16922
0.8261	Intermediate Similarity	NPC476946
0.8261	Intermediate Similarity	NPC243577
0.8231	Intermediate Similarity	NPC207294
0.8231	Intermediate Similarity	NPC112706
0.8203	Intermediate Similarity	NPC178382
0.8188	Intermediate Similarity	NPC121158
0.8154	Intermediate Similarity	NPC83178
0.8143	Intermediate Similarity	NPC5676
0.8143	Intermediate Similarity	NPC185456
0.814	Intermediate Similarity	NPC179354
0.8125	Intermediate Similarity	NPC272899
0.8125	Intermediate Similarity	NPC294511
0.8125	Intermediate Similarity	NPC121615
0.8112	Intermediate Similarity	NPC212257
0.8102	Intermediate Similarity	NPC474722
0.8099	Intermediate Similarity	NPC93666
0.8092	Intermediate Similarity	NPC477040
0.8077	Intermediate Similarity	NPC74612
0.8074	Intermediate Similarity	NPC158525
0.8071	Intermediate Similarity	NPC476944
0.8071	Intermediate Similarity	NPC251865
0.8065	Intermediate Similarity	NPC150895
0.8062	Intermediate Similarity	NPC118853
0.8045	Intermediate Similarity	NPC298190
0.8043	Intermediate Similarity	NPC473983
0.8043	Intermediate Similarity	NPC201370
0.8029	Intermediate Similarity	NPC472376
0.8028	Intermediate Similarity	NPC471174
0.8028	Intermediate Similarity	NPC302987
0.8028	Intermediate Similarity	NPC216755
0.8016	Intermediate Similarity	NPC243704
0.8	Intermediate Similarity	NPC246164
0.8	Intermediate Similarity	NPC303010
0.8	Intermediate Similarity	NPC473885
0.8	Intermediate Similarity	NPC471074
0.7986	Intermediate Similarity	NPC228842
0.7986	Intermediate Similarity	NPC205765
0.7972	Intermediate Similarity	NPC471007
0.7971	Intermediate Similarity	NPC90953
0.797	Intermediate Similarity	NPC476925
0.7969	Intermediate Similarity	NPC97566
0.7956	Intermediate Similarity	NPC4764
0.7955	Intermediate Similarity	NPC477123
0.7955	Intermediate Similarity	NPC476917
0.7955	Intermediate Similarity	NPC327527
0.7955	Intermediate Similarity	NPC477966
0.7945	Intermediate Similarity	NPC44606
0.7943	Intermediate Similarity	NPC158871
0.7926	Intermediate Similarity	NPC293253
0.7923	Intermediate Similarity	NPC243269
0.7923	Intermediate Similarity	NPC130275
0.7917	Intermediate Similarity	NPC470998
0.7917	Intermediate Similarity	NPC69647
0.7917	Intermediate Similarity	NPC234494
0.7917	Intermediate Similarity	NPC472654
0.7917	Intermediate Similarity	NPC195325
0.7917	Intermediate Similarity	NPC125182
0.7914	Intermediate Similarity	NPC148374
0.7914	Intermediate Similarity	NPC56197
0.7905	Intermediate Similarity	NPC304692
0.7905	Intermediate Similarity	NPC194499
0.7902	Intermediate Similarity	NPC255414
0.7902	Intermediate Similarity	NPC71821
0.7902	Intermediate Similarity	NPC286038
0.7895	Intermediate Similarity	NPC198904
0.7887	Intermediate Similarity	NPC56731
0.7872	Intermediate Similarity	NPC64568
0.7862	Intermediate Similarity	NPC196846
0.7862	Intermediate Similarity	NPC470997
0.7852	Intermediate Similarity	NPC474611
0.7847	Intermediate Similarity	NPC66991
0.7838	Intermediate Similarity	NPC104736
0.7838	Intermediate Similarity	NPC41880
0.7826	Intermediate Similarity	NPC170604
0.7826	Intermediate Similarity	NPC215109
0.782	Intermediate Similarity	NPC477039
0.7795	Intermediate Similarity	NPC212918
0.7793	Intermediate Similarity	NPC211625
0.7786	Intermediate Similarity	NPC90296
0.7786	Intermediate Similarity	NPC477038
0.7786	Intermediate Similarity	NPC477965
0.7785	Intermediate Similarity	NPC195954
0.7785	Intermediate Similarity	NPC7059
0.7785	Intermediate Similarity	NPC88007
0.777	Intermediate Similarity	NPC179170
0.777	Intermediate Similarity	NPC471996
0.7769	Intermediate Similarity	NPC317217
0.7769	Intermediate Similarity	NPC471549
0.7769	Intermediate Similarity	NPC473379
0.7762	Intermediate Similarity	NPC290038
0.7761	Intermediate Similarity	NPC223063
0.7761	Intermediate Similarity	NPC120836
0.7755	Intermediate Similarity	NPC470996
0.7755	Intermediate Similarity	NPC469503
0.7755	Intermediate Similarity	NPC33938
0.7755	Intermediate Similarity	NPC472672
0.7748	Intermediate Similarity	NPC79571
0.7748	Intermediate Similarity	NPC18986
0.7746	Intermediate Similarity	NPC267632
0.7733	Intermediate Similarity	NPC140952
0.7733	Intermediate Similarity	NPC84349
0.7733	Intermediate Similarity	NPC472823
0.7727	Intermediate Similarity	NPC474829
0.7721	Intermediate Similarity	NPC471995
0.7714	Intermediate Similarity	NPC233707
0.7708	Intermediate Similarity	NPC97904
0.7708	Intermediate Similarity	NPC346
0.7708	Intermediate Similarity	NPC233763
0.7703	Intermediate Similarity	NPC114880
0.7703	Intermediate Similarity	NPC253201
0.7703	Intermediate Similarity	NPC98206
0.7703	Intermediate Similarity	NPC34421
0.7703	Intermediate Similarity	NPC237259
0.7703	Intermediate Similarity	NPC302054
0.7703	Intermediate Similarity	NPC178932
0.7698	Intermediate Similarity	NPC470742
0.7697	Intermediate Similarity	NPC283209
0.7692	Intermediate Similarity	NPC199044
0.7692	Intermediate Similarity	NPC238843
0.7687	Intermediate Similarity	NPC272590
0.7682	Intermediate Similarity	NPC8389
0.7682	Intermediate Similarity	NPC287559
0.7682	Intermediate Similarity	NPC472299
0.7681	Intermediate Similarity	NPC209858
0.7681	Intermediate Similarity	NPC324117
0.7676	Intermediate Similarity	NPC20578
0.7676	Intermediate Similarity	NPC62103
0.7671	Intermediate Similarity	NPC95526
0.7667	Intermediate Similarity	NPC81405
0.7664	Intermediate Similarity	NPC471006
0.766	Intermediate Similarity	NPC18904
0.7656	Intermediate Similarity	NPC144745
0.7656	Intermediate Similarity	NPC208906
0.7652	Intermediate Similarity	NPC188377
0.7652	Intermediate Similarity	NPC65735
0.7651	Intermediate Similarity	NPC469336
0.7651	Intermediate Similarity	NPC35000
0.7651	Intermediate Similarity	NPC155939
0.7651	Intermediate Similarity	NPC141538
0.7651	Intermediate Similarity	NPC92979
0.7651	Intermediate Similarity	NPC75310
0.7651	Intermediate Similarity	NPC296807
0.7651	Intermediate Similarity	NPC88958
0.7643	Intermediate Similarity	NPC236532
0.7643	Intermediate Similarity	NPC476943
0.7635	Intermediate Similarity	NPC476940
0.7635	Intermediate Similarity	NPC476939
0.7635	Intermediate Similarity	NPC75906
0.7635	Intermediate Similarity	NPC268905
0.7635	Intermediate Similarity	NPC145830
0.7634	Intermediate Similarity	NPC36255
0.7632	Intermediate Similarity	NPC68848
0.7626	Intermediate Similarity	NPC146872
0.7622	Intermediate Similarity	NPC103134
0.7612	Intermediate Similarity	NPC474830
0.7609	Intermediate Similarity	NPC106247
0.7606	Intermediate Similarity	NPC20500
0.7597	Intermediate Similarity	NPC121995
0.7591	Intermediate Similarity	NPC471817
0.7586	Intermediate Similarity	NPC470999
0.7586	Intermediate Similarity	NPC62799
0.7586	Intermediate Similarity	NPC471292
0.7586	Intermediate Similarity	NPC478166
0.7584	Intermediate Similarity	NPC30222
0.7584	Intermediate Similarity	NPC57998
0.7584	Intermediate Similarity	NPC282445
0.7582	Intermediate Similarity	NPC285567
0.7581	Intermediate Similarity	NPC177331
0.7578	Intermediate Similarity	NPC79202
0.7578	Intermediate Similarity	NPC59035
0.7574	Intermediate Similarity	NPC939
0.7571	Intermediate Similarity	NPC310830
0.7571	Intermediate Similarity	NPC473268

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 NPC290193 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	921
0.2-0.3	1780
0.3-0.4	2808
0.4-0.5	2016
0.5-0.6	1122
0.6-0.7	240
0.7-0.8	8
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
0.7714	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD6273	Approved
0.7651	Intermediate Similarity	NPD5761	Phase 2
0.7651	Intermediate Similarity	NPD5760	Phase 2
0.741	Intermediate Similarity	NPD4140	Approved
0.731	Intermediate Similarity	NPD4628	Phase 3
0.7222	Intermediate Similarity	NPD2344	Approved
0.7203	Intermediate Similarity	NPD2799	Discontinued
0.716	Intermediate Similarity	NPD6764	Approved
0.716	Intermediate Similarity	NPD6765	Approved
0.7132	Intermediate Similarity	NPD5327	Phase 3
0.7113	Intermediate Similarity	NPD5735	Approved
0.7103	Intermediate Similarity	NPD1471	Phase 3
0.708	Intermediate Similarity	NPD1876	Approved
0.7075	Intermediate Similarity	NPD7003	Approved
0.7059	Intermediate Similarity	NPD3972	Approved
0.7048	Intermediate Similarity	NPD8434	Phase 2
0.7039	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2309	Approved
0.7015	Intermediate Similarity	NPD5585	Approved
0.6993	Remote Similarity	NPD6355	Discontinued
0.6988	Remote Similarity	NPD6785	Approved
0.6988	Remote Similarity	NPD6784	Approved
0.6985	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD2798	Approved
0.697	Remote Similarity	NPD7157	Approved
0.6947	Remote Similarity	NPD1241	Discontinued
0.6944	Remote Similarity	NPD6353	Approved
0.6923	Remote Similarity	NPD4060	Phase 1
0.6906	Remote Similarity	NPD2797	Approved
0.6892	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5691	Approved
0.6871	Remote Similarity	NPD5762	Approved
0.6871	Remote Similarity	NPD2346	Discontinued
0.6871	Remote Similarity	NPD5763	Approved
0.6853	Remote Similarity	NPD8032	Phase 2
0.6846	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4110	Phase 3
0.6838	Remote Similarity	NPD1778	Approved
0.6838	Remote Similarity	NPD4626	Approved
0.6835	Remote Similarity	NPD1283	Approved
0.6831	Remote Similarity	NPD7095	Approved
0.6824	Remote Similarity	NPD2424	Discontinued
0.6822	Remote Similarity	NPD2684	Approved
0.6813	Remote Similarity	NPD8127	Discontinued
0.6812	Remote Similarity	NPD1608	Approved
0.6809	Remote Similarity	NPD2861	Phase 2
0.6803	Remote Similarity	NPD2796	Approved
0.6803	Remote Similarity	NPD2935	Discontinued
0.6803	Remote Similarity	NPD4477	Approved
0.6803	Remote Similarity	NPD4476	Approved
0.6788	Remote Similarity	NPD3496	Discontinued
0.6783	Remote Similarity	NPD2313	Discontinued
0.6776	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4359	Approved
0.6761	Remote Similarity	NPD6832	Phase 2
0.6752	Remote Similarity	NPD7819	Suspended
0.6747	Remote Similarity	NPD6559	Discontinued
0.6738	Remote Similarity	NPD4624	Approved
0.6715	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.671	Remote Similarity	NPD7458	Discontinued
0.671	Remote Similarity	NPD2651	Approved
0.671	Remote Similarity	NPD2649	Approved
0.669	Remote Similarity	NPD3620	Phase 2
0.669	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.669	Remote Similarity	NPD5736	Approved
0.6667	Remote Similarity	NPD3134	Approved
0.6667	Remote Similarity	NPD7097	Phase 1
0.6667	Remote Similarity	NPD3268	Approved
0.6667	Remote Similarity	NPD6798	Discontinued
0.6667	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6002	Phase 3
0.6644	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6005	Phase 3
0.6644	Remote Similarity	NPD6004	Phase 3
0.6644	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD1651	Approved
0.6623	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3750	Approved
0.6622	Remote Similarity	NPD4308	Phase 3
0.6621	Remote Similarity	NPD4870	Approved
0.662	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD1281	Approved
0.6617	Remote Similarity	NPD7843	Approved
0.6615	Remote Similarity	NPD290	Approved
0.6604	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.66	Remote Similarity	NPD1549	Phase 2
0.66	Remote Similarity	NPD4534	Discontinued
0.6599	Remote Similarity	NPD6653	Approved
0.6599	Remote Similarity	NPD2157	Approved
0.6597	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6696	Suspended
0.6596	Remote Similarity	NPD8651	Approved
0.6594	Remote Similarity	NPD17	Approved
0.6593	Remote Similarity	NPD6671	Approved
0.6591	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6279	Approved
0.6582	Remote Similarity	NPD6280	Approved
0.6581	Remote Similarity	NPD920	Approved
0.6577	Remote Similarity	NPD6099	Approved
0.6577	Remote Similarity	NPD6100	Approved
0.6577	Remote Similarity	NPD1551	Phase 2
0.6575	Remote Similarity	NPD2979	Phase 3
0.6573	Remote Similarity	NPD9494	Approved
0.6573	Remote Similarity	NPD1712	Approved
0.6571	Remote Similarity	NPD2235	Phase 2
0.6571	Remote Similarity	NPD9717	Approved
0.6571	Remote Similarity	NPD2231	Phase 2
0.6569	Remote Similarity	NPD3091	Approved
0.6569	Remote Similarity	NPD1894	Discontinued
0.6561	Remote Similarity	NPD6599	Discontinued
0.6558	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD4662	Approved
0.6558	Remote Similarity	NPD4661	Approved
0.6558	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3764	Approved
0.6552	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6362	Approved
0.6549	Remote Similarity	NPD1203	Approved
0.6549	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5494	Approved
0.6541	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD7236	Approved
0.6533	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD4908	Phase 1
0.6525	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.651	Remote Similarity	NPD7033	Discontinued
0.651	Remote Similarity	NPD3748	Approved
0.6507	Remote Similarity	NPD6663	Approved
0.65	Remote Similarity	NPD2296	Approved
0.65	Remote Similarity	NPD1610	Phase 2
0.6497	Remote Similarity	NPD3226	Approved
0.6496	Remote Similarity	NPD5536	Phase 2
0.6493	Remote Similarity	NPD5535	Approved
0.649	Remote Similarity	NPD5958	Discontinued
0.6486	Remote Similarity	NPD4097	Suspended
0.6478	Remote Similarity	NPD6844	Discontinued
0.6475	Remote Similarity	NPD3095	Discontinued
0.6475	Remote Similarity	NPD3019	Approved
0.6475	Remote Similarity	NPD2932	Approved
0.6467	Remote Similarity	NPD6032	Approved
0.6467	Remote Similarity	NPD5844	Phase 1
0.6467	Remote Similarity	NPD2438	Suspended
0.6463	Remote Similarity	NPD4307	Phase 2
0.6463	Remote Similarity	NPD2238	Phase 2
0.6463	Remote Similarity	NPD3140	Approved
0.6463	Remote Similarity	NPD1240	Approved
0.6463	Remote Similarity	NPD3142	Approved
0.646	Remote Similarity	NPD7768	Phase 2
0.646	Remote Similarity	NPD3882	Suspended
0.6456	Remote Similarity	NPD7028	Phase 2
0.6456	Remote Similarity	NPD4380	Phase 2
0.6454	Remote Similarity	NPD2230	Approved
0.6454	Remote Similarity	NPD2232	Approved
0.6454	Remote Similarity	NPD2233	Approved
0.6447	Remote Similarity	NPD1243	Approved
0.6447	Remote Similarity	NPD2800	Approved
0.6447	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5283	Phase 1
0.6438	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD3267	Approved
0.6434	Remote Similarity	NPD3266	Approved
0.6429	Remote Similarity	NPD3847	Discontinued
0.6429	Remote Similarity	NPD6667	Approved
0.6429	Remote Similarity	NPD6666	Approved
0.642	Remote Similarity	NPD3749	Approved
0.642	Remote Similarity	NPD7075	Discontinued
0.6419	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD5124	Phase 1
0.6415	Remote Similarity	NPD7411	Suspended
0.6412	Remote Similarity	NPD968	Approved
0.6408	Remote Similarity	NPD3685	Discontinued
0.6405	Remote Similarity	NPD8166	Discontinued
0.6403	Remote Similarity	NPD3444	Approved
0.6403	Remote Similarity	NPD3445	Approved
0.6403	Remote Similarity	NPD3443	Approved
0.6403	Remote Similarity	NPD1357	Approved
0.64	Remote Similarity	NPD1510	Phase 2
0.6397	Remote Similarity	NPD2629	Approved
0.6395	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4062	Phase 3
0.6395	Remote Similarity	NPD6233	Phase 2
0.6389	Remote Similarity	NPD5647	Approved
0.6389	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD3690	Phase 2
0.6389	Remote Similarity	NPD3691	Phase 2
0.6389	Remote Similarity	NPD6584	Phase 3
0.6387	Remote Similarity	NPD6799	Approved
0.6383	Remote Similarity	NPD1611	Approved
0.6383	Remote Similarity	NPD3092	Approved
0.6382	Remote Similarity	NPD7037	Approved
0.6382	Remote Similarity	NPD970	Clinical (unspecified phase)

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