NPASS Compound

Structure

NPC472010 OpenBabel07101718332D 30 32 0 0 1 0 0 0 0 0999 V2000 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 6.0000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 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 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 2 0 0 0 0 5 18 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 15 2 0 0 0 0 8 17 1 0 0 0 0 9 16 1 0 0 0 0 9 23 1 0 0 0 0 10 18 2 0 0 0 0 11 21 1 0 0 0 0 12 16 2 0 0 0 0 13 19 2 0 0 0 0 13 25 1 0 0 0 0 14 19 1 0 0 0 0 14 26 1 0 0 0 0 17 24 1 0 0 0 0 18 21 1 0 0 0 0 19 20 1 0 0 0 0 20 11 1 1 0 0 0 20 22 1 0 0 0 0 21 27 2 0 0 0 0 22 10 1 1 0 0 0 22 29 1 0 0 0 0 23 24 1 6 0 0 0 23 30 1 0 0 0 0 24 28 1 6 0 0 0 25 12 1 1 0 0 0 25 29 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.24
Volume:	443.419
LogP:	3.729
LogD:	3.065
LogS:	-3.532
# Rotatable Bonds:	6
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.644
Synthetic Accessibility Score:	5.618
Fsp3:	0.56
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.678
MDCK Permeability:	1.0776870112749748e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.149
20% Bioavailability (F20%):	0.986
30% Bioavailability (F30%):	0.632

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.163
Plasma Protein Binding (PPB):	82.58150482177734%
Volume Distribution (VD):	1.828
Pgp-substrate:	10.731263160705566%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.147
CYP2C19-inhibitor:	0.115
CYP2C19-substrate:	0.674
CYP2C9-inhibitor:	0.128
CYP2C9-substrate:	0.069
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.146
CYP3A4-substrate:	0.317

ADMET: Excretion

Clearance (CL):	9.825
Half-life (T1/2):	0.371

ADMET: Toxicity

hERG Blockers:	0.08
Human Hepatotoxicity (H-HT):	0.898
Drug-inuced Liver Injury (DILI):	0.715
AMES Toxicity:	0.262
Rat Oral Acute Toxicity:	0.129
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.907
Carcinogencity:	0.9
Eye Corrosion:	0.003
Eye Irritation:	0.14
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC472010

Natural Product ID:	NPC472010
*Common Name:**	NXHLFRSMOKTBBP-VCXBPWIGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NXHLFRSMOKTBBP-VCXBPWIGSA-N
Standard InCHI:	InChI=1S/C25H34O5/c1-15(2)7-6-8-17(4)24(28)23-9-16(3)12-25(30-23)13-19(14-26)20-11-21(27)18(5)10-22(20)29-25/h7,10,12-13,20,22-24,26,28H,4,6,8-9,11,14H2,1-3,5H3/t20-,22-,23+,24+,25-/m1/s1
SMILES:	OCC1=C[C@@]2(O[C@@H](CC(=C2)C)[C@H](C(=C)CCC=C(C)C)O)O[C@H]2[C@@H]1CC(=O)C(=C2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3322967
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

*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
NPO32877	phorbas	Genus	Hymedesmiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[25124114]

☑ 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	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT369	Cell Line	ACHN	Homo sapiens	IC50	>	50000.0	nM	PMID[505301]
NPT376	Cell Line	A498	Homo sapiens	IC50	=	17300.0	nM	PMID[505301]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	50000.0	nM	PMID[505301]

☑ 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 NPC472010 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	207
0.1-0.2	1246
0.2-0.3	4701
0.3-0.4	9786
0.4-0.5	15352
0.5-0.6	7827
0.6-0.7	3292
0.7-0.8	279
0.8-0.85	1
0.85-0.9	1
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9529	High Similarity	NPC241054
0.9419	High Similarity	NPC106051
0.9419	High Similarity	NPC472011
0.931	High Similarity	NPC471054
0.8681	High Similarity	NPC471059
0.8632	High Similarity	NPC472012
0.8022	Intermediate Similarity	NPC471060
0.7957	Intermediate Similarity	NPC471058
0.7957	Intermediate Similarity	NPC471057
0.7789	Intermediate Similarity	NPC265856
0.7732	Intermediate Similarity	NPC256368
0.7723	Intermediate Similarity	NPC201191
0.7677	Intermediate Similarity	NPC266842
0.766	Intermediate Similarity	NPC471055
0.766	Intermediate Similarity	NPC471056
0.7629	Intermediate Similarity	NPC295204
0.7629	Intermediate Similarity	NPC238090
0.7629	Intermediate Similarity	NPC472195
0.7629	Intermediate Similarity	NPC273579
0.7629	Intermediate Similarity	NPC472196
0.7629	Intermediate Similarity	NPC288240
0.7629	Intermediate Similarity	NPC162205
0.7609	Intermediate Similarity	NPC286770
0.7609	Intermediate Similarity	NPC284472
0.7609	Intermediate Similarity	NPC229799
0.7604	Intermediate Similarity	NPC3952
0.7553	Intermediate Similarity	NPC311163
0.7551	Intermediate Similarity	NPC71589
0.7551	Intermediate Similarity	NPC159698
0.7547	Intermediate Similarity	NPC37116
0.7528	Intermediate Similarity	NPC471061
0.7527	Intermediate Similarity	NPC70424
0.7527	Intermediate Similarity	NPC243618
0.7526	Intermediate Similarity	NPC477749
0.75	Intermediate Similarity	NPC310450
0.75	Intermediate Similarity	NPC11383
0.75	Intermediate Similarity	NPC133450
0.75	Intermediate Similarity	NPC475046
0.75	Intermediate Similarity	NPC20066
0.75	Intermediate Similarity	NPC474959
0.7474	Intermediate Similarity	NPC300779
0.7473	Intermediate Similarity	NPC162741
0.7473	Intermediate Similarity	NPC91332
0.7449	Intermediate Similarity	NPC189651
0.7449	Intermediate Similarity	NPC475098
0.7449	Intermediate Similarity	NPC11456
0.7447	Intermediate Similarity	NPC471494
0.7447	Intermediate Similarity	NPC21469
0.7426	Intermediate Similarity	NPC198422
0.7426	Intermediate Similarity	NPC203627
0.7426	Intermediate Similarity	NPC40182
0.7423	Intermediate Similarity	NPC166554
0.7423	Intermediate Similarity	NPC202886
0.7423	Intermediate Similarity	NPC177668
0.7419	Intermediate Similarity	NPC44261
0.7407	Intermediate Similarity	NPC236217
0.7374	Intermediate Similarity	NPC2003
0.7374	Intermediate Similarity	NPC25701
0.7347	Intermediate Similarity	NPC141831
0.7347	Intermediate Similarity	NPC473321
0.7347	Intermediate Similarity	NPC472197
0.7347	Intermediate Similarity	NPC470373
0.7347	Intermediate Similarity	NPC30515
0.7347	Intermediate Similarity	NPC470379
0.734	Intermediate Similarity	NPC9868
0.7333	Intermediate Similarity	NPC469852
0.7321	Intermediate Similarity	NPC475834
0.7321	Intermediate Similarity	NPC474179
0.732	Intermediate Similarity	NPC139418
0.732	Intermediate Similarity	NPC477748
0.7308	Intermediate Similarity	NPC473624
0.7308	Intermediate Similarity	NPC99266
0.7308	Intermediate Similarity	NPC267869
0.7308	Intermediate Similarity	NPC234304
0.7308	Intermediate Similarity	NPC118761
0.7308	Intermediate Similarity	NPC197541
0.7308	Intermediate Similarity	NPC284929
0.7308	Intermediate Similarity	NPC151516
0.73	Intermediate Similarity	NPC469543
0.73	Intermediate Similarity	NPC170204
0.73	Intermediate Similarity	NPC36954
0.73	Intermediate Similarity	NPC227494
0.7292	Intermediate Similarity	NPC45409
0.7292	Intermediate Similarity	NPC316138
0.7292	Intermediate Similarity	NPC313658
0.7282	Intermediate Similarity	NPC298255
0.7282	Intermediate Similarity	NPC472637
0.7282	Intermediate Similarity	NPC28304
0.7273	Intermediate Similarity	NPC475912
0.7273	Intermediate Similarity	NPC469692
0.7273	Intermediate Similarity	NPC469645
0.7273	Intermediate Similarity	NPC320552
0.7273	Intermediate Similarity	NPC61201
0.7264	Intermediate Similarity	NPC469853
0.7263	Intermediate Similarity	NPC182383
0.7263	Intermediate Similarity	NPC11804
0.7263	Intermediate Similarity	NPC77971
0.7257	Intermediate Similarity	NPC48692
0.7255	Intermediate Similarity	NPC187761
0.7255	Intermediate Similarity	NPC307517
0.7255	Intermediate Similarity	NPC83895
0.7255	Intermediate Similarity	NPC306908
0.7255	Intermediate Similarity	NPC187268
0.7255	Intermediate Similarity	NPC81483
0.7255	Intermediate Similarity	NPC169468
0.7255	Intermediate Similarity	NPC61630
0.7253	Intermediate Similarity	NPC93763
0.7253	Intermediate Similarity	NPC108816
0.7253	Intermediate Similarity	NPC326753
0.7245	Intermediate Similarity	NPC281942
0.7245	Intermediate Similarity	NPC473904
0.7245	Intermediate Similarity	NPC6414
0.7245	Intermediate Similarity	NPC232426
0.7245	Intermediate Similarity	NPC303451
0.7245	Intermediate Similarity	NPC51004
0.7245	Intermediate Similarity	NPC253186
0.7245	Intermediate Similarity	NPC476004
0.7245	Intermediate Similarity	NPC473619
0.7245	Intermediate Similarity	NPC327253
0.7245	Intermediate Similarity	NPC471399
0.7245	Intermediate Similarity	NPC474761
0.7241	Intermediate Similarity	NPC202011
0.7234	Intermediate Similarity	NPC185256
0.7234	Intermediate Similarity	NPC169575
0.7234	Intermediate Similarity	NPC40746
0.7234	Intermediate Similarity	NPC161045
0.7234	Intermediate Similarity	NPC16488
0.7232	Intermediate Similarity	NPC475913
0.7228	Intermediate Similarity	NPC306041
0.7222	Intermediate Similarity	NPC29133
0.7222	Intermediate Similarity	NPC473627
0.7212	Intermediate Similarity	NPC223834
0.7212	Intermediate Similarity	NPC134077
0.7212	Intermediate Similarity	NPC222062
0.7212	Intermediate Similarity	NPC137430
0.7204	Intermediate Similarity	NPC112868
0.72	Intermediate Similarity	NPC104925
0.72	Intermediate Similarity	NPC81386
0.72	Intermediate Similarity	NPC298973
0.72	Intermediate Similarity	NPC476415
0.72	Intermediate Similarity	NPC121825
0.72	Intermediate Similarity	NPC474035
0.72	Intermediate Similarity	NPC477241
0.7191	Intermediate Similarity	NPC160540
0.7188	Intermediate Similarity	NPC134885
0.7188	Intermediate Similarity	NPC305475
0.7188	Intermediate Similarity	NPC186332
0.7188	Intermediate Similarity	NPC219498
0.7188	Intermediate Similarity	NPC473687
0.7188	Intermediate Similarity	NPC469483
0.7188	Intermediate Similarity	NPC210218
0.7188	Intermediate Similarity	NPC316426
0.7188	Intermediate Similarity	NPC134807
0.7188	Intermediate Similarity	NPC475461
0.7188	Intermediate Similarity	NPC47937
0.7188	Intermediate Similarity	NPC315395
0.7188	Intermediate Similarity	NPC469910
0.7188	Intermediate Similarity	NPC112685
0.7188	Intermediate Similarity	NPC204686
0.7188	Intermediate Similarity	NPC308412
0.7188	Intermediate Similarity	NPC47220
0.7184	Intermediate Similarity	NPC22149
0.7184	Intermediate Similarity	NPC306344
0.7184	Intermediate Similarity	NPC255677
0.7172	Intermediate Similarity	NPC472199
0.7172	Intermediate Similarity	NPC184463
0.7172	Intermediate Similarity	NPC303697
0.717	Intermediate Similarity	NPC472751
0.717	Intermediate Similarity	NPC472749
0.717	Intermediate Similarity	NPC476740
0.717	Intermediate Similarity	NPC476738
0.7168	Intermediate Similarity	NPC473274
0.7158	Intermediate Similarity	NPC96259
0.7158	Intermediate Similarity	NPC474251
0.7158	Intermediate Similarity	NPC141193
0.7158	Intermediate Similarity	NPC266718
0.7157	Intermediate Similarity	NPC475332
0.7157	Intermediate Similarity	NPC76266
0.7157	Intermediate Similarity	NPC278506
0.7157	Intermediate Similarity	NPC474194
0.7157	Intermediate Similarity	NPC40812
0.7156	Intermediate Similarity	NPC470961
0.7143	Intermediate Similarity	NPC8196
0.7143	Intermediate Similarity	NPC7563
0.7143	Intermediate Similarity	NPC116177
0.7143	Intermediate Similarity	NPC320630
0.7143	Intermediate Similarity	NPC475711
0.7143	Intermediate Similarity	NPC309398
0.7143	Intermediate Similarity	NPC473968
0.7143	Intermediate Similarity	NPC40049
0.7143	Intermediate Similarity	NPC206001
0.7143	Intermediate Similarity	NPC472747
0.7143	Intermediate Similarity	NPC218927
0.7143	Intermediate Similarity	NPC268298
0.7143	Intermediate Similarity	NPC472750
0.7143	Intermediate Similarity	NPC474032
0.7143	Intermediate Similarity	NPC307411
0.713	Intermediate Similarity	NPC137911
0.713	Intermediate Similarity	NPC315836
0.713	Intermediate Similarity	NPC313668

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 NPC472010 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1681
0.2-0.3	3766
0.3-0.4	2460
0.4-0.5	724
0.5-0.6	284
0.6-0.7	45
0.7-0.8	3
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
0.76	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD6698	Approved
0.7245	Intermediate Similarity	NPD46	Approved
0.7053	Intermediate Similarity	NPD6110	Phase 1
0.7037	Intermediate Similarity	NPD6686	Approved
0.7	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD7115	Discovery
0.6979	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4225	Approved
0.69	Remote Similarity	NPD7838	Discovery
0.6897	Remote Similarity	NPD8513	Phase 3
0.6789	Remote Similarity	NPD6412	Phase 2
0.6752	Remote Similarity	NPD8515	Approved
0.6752	Remote Similarity	NPD8516	Approved
0.6752	Remote Similarity	NPD8517	Approved
0.6733	Remote Similarity	NPD5785	Approved
0.6696	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7983	Approved
0.6637	Remote Similarity	NPD6053	Discontinued
0.6607	Remote Similarity	NPD6371	Approved
0.6566	Remote Similarity	NPD5363	Approved
0.6562	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7639	Approved
0.6542	Remote Similarity	NPD7640	Approved
0.6481	Remote Similarity	NPD5344	Discontinued
0.6476	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD8074	Phase 3
0.6449	Remote Similarity	NPD7638	Approved
0.6442	Remote Similarity	NPD5779	Approved
0.6442	Remote Similarity	NPD5778	Approved
0.6442	Remote Similarity	NPD6399	Phase 3
0.64	Remote Similarity	NPD1694	Approved
0.64	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7154	Phase 3
0.6355	Remote Similarity	NPD7902	Approved
0.6354	Remote Similarity	NPD4268	Approved
0.6354	Remote Similarity	NPD4271	Approved
0.6348	Remote Similarity	NPD6882	Approved
0.6339	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5786	Approved
0.6333	Remote Similarity	NPD7503	Approved
0.6311	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6101	Approved
0.6271	Remote Similarity	NPD7500	Approved
0.6263	Remote Similarity	NPD4270	Approved
0.6263	Remote Similarity	NPD4269	Approved
0.6262	Remote Similarity	NPD7839	Suspended
0.626	Remote Similarity	NPD7507	Approved
0.625	Remote Similarity	NPD6054	Approved
0.625	Remote Similarity	NPD4756	Discovery
0.623	Remote Similarity	NPD7829	Approved
0.623	Remote Similarity	NPD7642	Approved
0.623	Remote Similarity	NPD8328	Phase 3
0.623	Remote Similarity	NPD7830	Approved
0.6226	Remote Similarity	NPD7748	Approved
0.6224	Remote Similarity	NPD4822	Approved
0.6224	Remote Similarity	NPD4821	Approved
0.6224	Remote Similarity	NPD4820	Approved
0.6224	Remote Similarity	NPD4252	Approved
0.6224	Remote Similarity	NPD4819	Approved
0.6222	Remote Similarity	NPD7331	Phase 2
0.6218	Remote Similarity	NPD7641	Discontinued
0.6207	Remote Similarity	NPD8297	Approved
0.62	Remote Similarity	NPD5362	Discontinued
0.619	Remote Similarity	NPD6411	Approved
0.619	Remote Similarity	NPD7515	Phase 2
0.619	Remote Similarity	NPD6079	Approved
0.6176	Remote Similarity	NPD3618	Phase 1
0.6154	Remote Similarity	NPD5328	Approved
0.6148	Remote Similarity	NPD6370	Approved
0.6148	Remote Similarity	NPD7623	Phase 3
0.6148	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6881	Approved
0.614	Remote Similarity	NPD6899	Approved
0.6139	Remote Similarity	NPD3665	Phase 1
0.6139	Remote Similarity	NPD4786	Approved
0.6139	Remote Similarity	NPD3133	Approved
0.6139	Remote Similarity	NPD3666	Approved
0.6134	Remote Similarity	NPD6009	Approved
0.6126	Remote Similarity	NPD5211	Phase 2
0.6121	Remote Similarity	NPD6649	Approved
0.6121	Remote Similarity	NPD6650	Approved
0.6117	Remote Similarity	NPD4251	Approved
0.6117	Remote Similarity	NPD4250	Approved
0.6116	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD6059	Approved
0.6111	Remote Similarity	NPD7319	Approved
0.6106	Remote Similarity	NPD7128	Approved
0.6106	Remote Similarity	NPD6675	Approved
0.6106	Remote Similarity	NPD5739	Approved
0.6106	Remote Similarity	NPD6402	Approved
0.61	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.61	Remote Similarity	NPD6435	Approved
0.61	Remote Similarity	NPD5209	Approved
0.61	Remote Similarity	NPD3667	Approved
0.6091	Remote Similarity	NPD6648	Approved
0.6087	Remote Similarity	NPD6373	Approved
0.6087	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6372	Approved
0.6087	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7327	Approved
0.6083	Remote Similarity	NPD7328	Approved
0.6078	Remote Similarity	NPD1696	Phase 3
0.6078	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD7900	Approved
0.6075	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD8033	Approved
0.6066	Remote Similarity	NPD6016	Approved
0.6066	Remote Similarity	NPD6015	Approved
0.6061	Remote Similarity	NPD4695	Discontinued
0.6061	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6083	Phase 2
0.6055	Remote Similarity	NPD6084	Phase 2
0.6053	Remote Similarity	NPD5697	Approved
0.6048	Remote Similarity	NPD7492	Approved
0.604	Remote Similarity	NPD5332	Approved
0.604	Remote Similarity	NPD5331	Approved
0.6038	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD7102	Approved
0.6034	Remote Similarity	NPD6883	Approved
0.6034	Remote Similarity	NPD7290	Approved
0.6033	Remote Similarity	NPD7516	Approved
0.602	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4249	Approved
0.6019	Remote Similarity	NPD6409	Approved
0.6019	Remote Similarity	NPD7521	Approved
0.6019	Remote Similarity	NPD7334	Approved
0.6019	Remote Similarity	NPD6684	Approved
0.6019	Remote Similarity	NPD7146	Approved
0.6019	Remote Similarity	NPD5330	Approved
0.6018	Remote Similarity	NPD5141	Approved
0.6017	Remote Similarity	NPD4632	Approved
0.6016	Remote Similarity	NPD5988	Approved
0.6016	Remote Similarity	NPD7260	Phase 2
0.6	Remote Similarity	NPD5370	Suspended
0.6	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD4790	Discontinued
0.6	Remote Similarity	NPD5369	Approved
0.6	Remote Similarity	NPD7320	Approved
0.6	Remote Similarity	NPD6616	Approved
0.5984	Remote Similarity	NPD8377	Approved
0.5984	Remote Similarity	NPD8294	Approved
0.5983	Remote Similarity	NPD8130	Phase 1
0.5983	Remote Similarity	NPD6617	Approved
0.5983	Remote Similarity	NPD6847	Approved
0.5983	Remote Similarity	NPD6869	Approved
0.5982	Remote Similarity	NPD7632	Discontinued
0.5963	Remote Similarity	NPD5221	Approved
0.5963	Remote Similarity	NPD5222	Approved
0.5963	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD4697	Phase 3
0.5955	Remote Similarity	NPD368	Approved
0.5952	Remote Similarity	NPD7747	Phase 1
0.5952	Remote Similarity	NPD7746	Phase 1
0.5952	Remote Similarity	NPD7078	Approved
0.5948	Remote Similarity	NPD6012	Approved
0.5948	Remote Similarity	NPD6013	Approved
0.5948	Remote Similarity	NPD6014	Approved
0.5946	Remote Similarity	NPD5286	Approved
0.5946	Remote Similarity	NPD5285	Approved
0.5946	Remote Similarity	NPD4696	Approved
0.5935	Remote Similarity	NPD8380	Approved
0.5935	Remote Similarity	NPD8444	Approved
0.5935	Remote Similarity	NPD8379	Approved
0.5935	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD8296	Approved
0.5935	Remote Similarity	NPD8335	Approved
0.5935	Remote Similarity	NPD8378	Approved
0.5934	Remote Similarity	NPD7341	Phase 2
0.5934	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD6647	Phase 2
0.5913	Remote Similarity	NPD5701	Approved
0.5909	Remote Similarity	NPD4755	Approved
0.5909	Remote Similarity	NPD5173	Approved
0.5906	Remote Similarity	NPD7736	Approved
0.5905	Remote Similarity	NPD6903	Approved
0.5905	Remote Similarity	NPD6672	Approved
0.5905	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD5737	Approved
0.59	Remote Similarity	NPD5368	Approved
0.5897	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD5223	Approved
0.5889	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD7637	Suspended
0.5876	Remote Similarity	NPD8039	Approved
0.5873	Remote Similarity	NPD8451	Approved
0.5872	Remote Similarity	NPD4629	Approved
0.5872	Remote Similarity	NPD5210	Approved
0.5872	Remote Similarity	NPD5695	Phase 3
0.587	Remote Similarity	NPD3704	Approved
0.5868	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD4519	Discontinued
0.5865	Remote Similarity	NPD4623	Approved
0.5865	Remote Similarity	NPD5279	Phase 3
0.5865	Remote Similarity	NPD6422	Discontinued
0.5862	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD5696	Approved
0.5854	Remote Similarity	NPD6319	Approved
0.5849	Remote Similarity	NPD4753	Phase 2

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