NPASS Compound

Structure

NPC471817 OpenBabel07101718192D 27 28 0 0 1 0 0 0 0 0999 V2000 0.0000 -2.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3446 -2.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3534 -2.2844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3189 -2.2844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1260 0.9573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8362 -3.3793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6723 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5480 0.1829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6153 0.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1843 0.7146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6723 -0.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8362 0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6226 1.5749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0796 1.8193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3446 -1.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2307 0.8657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6723 -2.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9326 -0.2499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6723 -1.9310 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -0.9655 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8362 -1.4483 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 -4.1808 -1.4483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5085 -3.3793 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1825 -1.1825 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9399 2.2576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5085 -1.4483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 15 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 6 17 1 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 26 1 0 0 0 0 14 16 2 0 0 0 0 14 26 1 0 0 0 0 15 23 2 0 0 0 0 15 27 1 0 0 0 0 17 19 1 0 0 0 0 17 24 2 0 0 0 0 18 22 1 0 0 0 0 18 25 2 0 0 0 0 19 20 1 0 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 6 0 0 0 22 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.22
Volume:	402.724
LogP:	3.434
LogD:	3.281
LogS:	-4.266
# Rotatable Bonds:	9
TPSA:	73.58
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.624
Synthetic Accessibility Score:	4.187
Fsp3:	0.682
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.719
MDCK Permeability:	2.7266469260212034e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.186
30% Bioavailability (F30%):	0.94

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.446
Plasma Protein Binding (PPB):	89.7102279663086%
Volume Distribution (VD):	1.378
Pgp-substrate:	7.799282550811768%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.125
CYP2C19-inhibitor:	0.511
CYP2C19-substrate:	0.636
CYP2C9-inhibitor:	0.829
CYP2C9-substrate:	0.169
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.129
CYP3A4-inhibitor:	0.794
CYP3A4-substrate:	0.463

ADMET: Excretion

Clearance (CL):	11.936
Half-life (T1/2):	0.769

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.24
Drug-inuced Liver Injury (DILI):	0.307
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.955
Maximum Recommended Daily Dose:	0.23
Skin Sensitization:	0.07
Carcinogencity:	0.934
Eye Corrosion:	0.038
Eye Irritation:	0.036
Respiratory Toxicity:	0.944

Download Data

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

Natural Product: NPC471817

Natural Product ID:	NPC471817
*Common Name:**	Lagopsin F
IUPAC Name:	[1-[(1S,2S)-2-[3-(furan-3-yl)propanoyl]-2,6,6-trimethylcyclohexyl]-2-oxobutyl] acetate
Synonyms:
Standard InCHIKey:	WRGBXVVSPJQVPJ-VDZZXDNDSA-N
Standard InCHI:	InChI=1S/C22H32O5/c1-6-17(24)19(27-15(2)23)20-21(3,4)11-7-12-22(20,5)18(25)9-8-16-10-13-26-14-16/h10,13-14,19-20H,6-9,11-12H2,1-5H3/t19?,20-,22+/m0/s1
SMILES:	CCC(=O)C([C@H]1C(C)(C)CCC[C@]1(C)C(=O)CCc1cocc1)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3234604
PubChem CID:	90670466
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic 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
NPO17287	Lagopsis supina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24707938]
NPO17287	Lagopsis supina	Species	Lamiaceae	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
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	<	50.0	%	PMID[541908]

☑ 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 NPC471817 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	278
0.1-0.2	1393
0.2-0.3	3363
0.3-0.4	7593
0.4-0.5	12754
0.5-0.6	10363
0.6-0.7	5962
0.7-0.8	831
0.8-0.85	125
0.85-0.9	30
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8976	High Similarity	NPC179354
0.8881	High Similarity	NPC42400
0.8849	High Similarity	NPC262198
0.8819	High Similarity	NPC16922
0.876	High Similarity	NPC74612
0.8732	High Similarity	NPC46551
0.8705	High Similarity	NPC238843
0.8705	High Similarity	NPC199044
0.8705	High Similarity	NPC142113
0.8702	High Similarity	NPC208389
0.8676	High Similarity	NPC476943
0.8667	High Similarity	NPC146872
0.8633	High Similarity	NPC267632
0.8615	High Similarity	NPC138139
0.8615	High Similarity	NPC46536
0.8603	High Similarity	NPC310830
0.8594	High Similarity	NPC317217
0.8582	High Similarity	NPC471292
0.8571	High Similarity	NPC89133
0.8571	High Similarity	NPC243704
0.8571	High Similarity	NPC298190
0.8551	High Similarity	NPC56197
0.8542	High Similarity	NPC272590
0.854	High Similarity	NPC220094
0.8504	High Similarity	NPC473969
0.8485	Intermediate Similarity	NPC112706
0.8485	Intermediate Similarity	NPC207294
0.848	Intermediate Similarity	NPC150895
0.8462	Intermediate Similarity	NPC477965
0.8462	Intermediate Similarity	NPC477038
0.8456	Intermediate Similarity	NPC92941
0.845	Intermediate Similarity	NPC477967
0.8444	Intermediate Similarity	NPC470740
0.8429	Intermediate Similarity	NPC473152
0.8409	Intermediate Similarity	NPC474830
0.8409	Intermediate Similarity	NPC83178
0.8406	Intermediate Similarity	NPC236532
0.8397	Intermediate Similarity	NPC474829
0.8378	Intermediate Similarity	NPC472283
0.8372	Intermediate Similarity	NPC1848
0.837	Intermediate Similarity	NPC473982
0.8367	Intermediate Similarity	NPC281258
0.8358	Intermediate Similarity	NPC21460
0.8357	Intermediate Similarity	NPC20500
0.8346	Intermediate Similarity	NPC477123
0.8346	Intermediate Similarity	NPC477966
0.8346	Intermediate Similarity	NPC131801
0.8346	Intermediate Similarity	NPC477040
0.8346	Intermediate Similarity	NPC476917
0.8346	Intermediate Similarity	NPC208906
0.8346	Intermediate Similarity	NPC327527
0.8346	Intermediate Similarity	NPC144745
0.8345	Intermediate Similarity	NPC159927
0.8345	Intermediate Similarity	NPC196864
0.8345	Intermediate Similarity	NPC477404
0.8345	Intermediate Similarity	NPC469335
0.8345	Intermediate Similarity	NPC90953
0.8333	Intermediate Similarity	NPC470742
0.8322	Intermediate Similarity	NPC237155
0.8322	Intermediate Similarity	NPC477403
0.8311	Intermediate Similarity	NPC263265
0.8311	Intermediate Similarity	NPC60973
0.8309	Intermediate Similarity	NPC471006
0.8308	Intermediate Similarity	NPC36255
0.8298	Intermediate Similarity	NPC121158
0.8288	Intermediate Similarity	NPC291150
0.8288	Intermediate Similarity	NPC116717
0.8286	Intermediate Similarity	NPC148374
0.8284	Intermediate Similarity	NPC198904
0.8271	Intermediate Similarity	NPC95567
0.8271	Intermediate Similarity	NPC137570
0.8271	Intermediate Similarity	NPC319140
0.8267	Intermediate Similarity	NPC25255
0.8267	Intermediate Similarity	NPC191828
0.8258	Intermediate Similarity	NPC230979
0.8252	Intermediate Similarity	NPC185456
0.8252	Intermediate Similarity	NPC34056
0.8239	Intermediate Similarity	NPC243577
0.8239	Intermediate Similarity	NPC223415
0.8231	Intermediate Similarity	NPC246164
0.8222	Intermediate Similarity	NPC476925
0.8219	Intermediate Similarity	NPC5180
0.8212	Intermediate Similarity	NPC193798
0.8212	Intermediate Similarity	NPC197596
0.8212	Intermediate Similarity	NPC6326
0.8212	Intermediate Similarity	NPC470939
0.8209	Intermediate Similarity	NPC477039
0.8209	Intermediate Similarity	NPC26532
0.8201	Intermediate Similarity	NPC170604
0.8201	Intermediate Similarity	NPC215109
0.8201	Intermediate Similarity	NPC307401
0.8195	Intermediate Similarity	NPC474260
0.8195	Intermediate Similarity	NPC329922
0.8195	Intermediate Similarity	NPC23086
0.8195	Intermediate Similarity	NPC81912
0.8195	Intermediate Similarity	NPC329694
0.8194	Intermediate Similarity	NPC233763
0.8188	Intermediate Similarity	NPC209364
0.8188	Intermediate Similarity	NPC107646
0.8188	Intermediate Similarity	NPC469485
0.8182	Intermediate Similarity	NPC65735
0.8182	Intermediate Similarity	NPC476944
0.8182	Intermediate Similarity	NPC243269
0.8182	Intermediate Similarity	NPC188377
0.8182	Intermediate Similarity	NPC83115
0.8182	Intermediate Similarity	NPC86935
0.8182	Intermediate Similarity	NPC251865
0.8176	Intermediate Similarity	NPC178932
0.8175	Intermediate Similarity	NPC474425
0.8175	Intermediate Similarity	NPC474407
0.8175	Intermediate Similarity	NPC474426
0.8175	Intermediate Similarity	NPC293253
0.8162	Intermediate Similarity	NPC61788
0.8151	Intermediate Similarity	NPC329180
0.8151	Intermediate Similarity	NPC234494
0.8151	Intermediate Similarity	NPC471001
0.8146	Intermediate Similarity	NPC305016
0.8146	Intermediate Similarity	NPC477402
0.8143	Intermediate Similarity	NPC177262
0.8138	Intermediate Similarity	NPC10088
0.8138	Intermediate Similarity	NPC71821
0.8138	Intermediate Similarity	NPC216755
0.8138	Intermediate Similarity	NPC224418
0.8138	Intermediate Similarity	NPC471174
0.8138	Intermediate Similarity	NPC302987
0.8138	Intermediate Similarity	NPC470941
0.8134	Intermediate Similarity	NPC246392
0.8134	Intermediate Similarity	NPC476016
0.8133	Intermediate Similarity	NPC286722
0.8133	Intermediate Similarity	NPC173544
0.8125	Intermediate Similarity	NPC56731
0.8121	Intermediate Similarity	NPC264943
0.8121	Intermediate Similarity	NPC469336
0.8121	Intermediate Similarity	NPC25351
0.8121	Intermediate Similarity	NPC469850
0.8121	Intermediate Similarity	NPC92979
0.812	Intermediate Similarity	NPC471074
0.812	Intermediate Similarity	NPC71274
0.812	Intermediate Similarity	NPC471559
0.812	Intermediate Similarity	NPC473885
0.812	Intermediate Similarity	NPC75557
0.8112	Intermediate Similarity	NPC80635
0.8112	Intermediate Similarity	NPC470741
0.8108	Intermediate Similarity	NPC75906
0.8105	Intermediate Similarity	NPC476858
0.8105	Intermediate Similarity	NPC123088
0.8105	Intermediate Similarity	NPC476857
0.8105	Intermediate Similarity	NPC476856
0.8102	Intermediate Similarity	NPC471995
0.8095	Intermediate Similarity	NPC470997
0.8095	Intermediate Similarity	NPC156189
0.8092	Intermediate Similarity	NPC69028
0.8092	Intermediate Similarity	NPC263432
0.8092	Intermediate Similarity	NPC97566
0.8092	Intermediate Similarity	NPC329938
0.8085	Intermediate Similarity	NPC202260
0.8079	Intermediate Similarity	NPC475295
0.8079	Intermediate Similarity	NPC473473
0.8071	Intermediate Similarity	NPC310043
0.8069	Intermediate Similarity	NPC276676
0.8069	Intermediate Similarity	NPC346
0.8067	Intermediate Similarity	NPC204663
0.8067	Intermediate Similarity	NPC126723
0.8065	Intermediate Similarity	NPC473356
0.8065	Intermediate Similarity	NPC471521
0.8058	Intermediate Similarity	NPC158525
0.8058	Intermediate Similarity	NPC476947
0.8047	Intermediate Similarity	NPC28054
0.8045	Intermediate Similarity	NPC130275
0.8043	Intermediate Similarity	NPC218838
0.8039	Intermediate Similarity	NPC292389
0.8039	Intermediate Similarity	NPC663
0.8039	Intermediate Similarity	NPC477405
0.8039	Intermediate Similarity	NPC224394
0.8039	Intermediate Similarity	NPC469338
0.8029	Intermediate Similarity	NPC17681
0.8028	Intermediate Similarity	NPC90296
0.8028	Intermediate Similarity	NPC67003
0.8027	Intermediate Similarity	NPC472654
0.8026	Intermediate Similarity	NPC475381
0.8016	Intermediate Similarity	NPC105249
0.8015	Intermediate Similarity	NPC59502
0.8015	Intermediate Similarity	NPC223063
0.8015	Intermediate Similarity	NPC120836
0.8014	Intermediate Similarity	NPC255414
0.8014	Intermediate Similarity	NPC250228
0.8014	Intermediate Similarity	NPC221809
0.8013	Intermediate Similarity	NPC197137
0.8013	Intermediate Similarity	NPC167142
0.8013	Intermediate Similarity	NPC469847
0.8013	Intermediate Similarity	NPC249021
0.8013	Intermediate Similarity	NPC472772
0.8013	Intermediate Similarity	NPC195131
0.8	Intermediate Similarity	NPC471554
0.8	Intermediate Similarity	NPC87466
0.8	Intermediate Similarity	NPC476224
0.8	Intermediate Similarity	NPC75310
0.8	Intermediate Similarity	NPC476850
0.8	Intermediate Similarity	NPC471501
0.8	Intermediate Similarity	NPC46896

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 NPC471817 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	1003
0.2-0.3	1884
0.3-0.4	2781
0.4-0.5	2054
0.5-0.6	943
0.6-0.7	225
0.7-0.8	12
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
0.7586	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1471	Phase 3
0.7452	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5760	Phase 2
0.7419	Intermediate Similarity	NPD5761	Phase 2
0.7273	Intermediate Similarity	NPD6764	Approved
0.7273	Intermediate Similarity	NPD6765	Approved
0.7262	Intermediate Similarity	NPD8434	Phase 2
0.7252	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD3266	Approved
0.7163	Intermediate Similarity	NPD3267	Approved
0.7152	Intermediate Similarity	NPD3887	Approved
0.7133	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6832	Phase 2
0.7123	Intermediate Similarity	NPD6355	Discontinued
0.7101	Intermediate Similarity	NPD6785	Approved
0.7101	Intermediate Similarity	NPD6784	Approved
0.7095	Intermediate Similarity	NPD2799	Discontinued
0.7086	Intermediate Similarity	NPD4628	Phase 3
0.7078	Intermediate Similarity	NPD6273	Approved
0.7071	Intermediate Similarity	NPD3972	Approved
0.7042	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3268	Approved
0.7032	Intermediate Similarity	NPD920	Approved
0.7006	Intermediate Similarity	NPD6599	Discontinued
0.6986	Remote Similarity	NPD8032	Phase 2
0.6963	Remote Similarity	NPD1241	Discontinued
0.6928	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD919	Approved
0.6903	Remote Similarity	NPD642	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6808	Phase 2
0.6887	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2353	Approved
0.6883	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1876	Approved
0.6842	Remote Similarity	NPD2182	Approved
0.6839	Remote Similarity	NPD6799	Approved
0.6829	Remote Similarity	NPD1247	Approved
0.6803	Remote Similarity	NPD6798	Discontinued
0.6803	Remote Similarity	NPD2313	Discontinued
0.6791	Remote Similarity	NPD2067	Discontinued
0.6786	Remote Similarity	NPD5585	Approved
0.6776	Remote Similarity	NPD2344	Approved
0.6776	Remote Similarity	NPD2346	Discontinued
0.6759	Remote Similarity	NPD1019	Discontinued
0.6759	Remote Similarity	NPD5647	Approved
0.6748	Remote Similarity	NPD7075	Discontinued
0.6738	Remote Similarity	NPD17	Approved
0.673	Remote Similarity	NPD7458	Discontinued
0.673	Remote Similarity	NPD3226	Approved
0.6728	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD9717	Approved
0.671	Remote Similarity	NPD2354	Approved
0.6708	Remote Similarity	NPD6801	Discontinued
0.6692	Remote Similarity	NPD3134	Approved
0.669	Remote Similarity	NPD2797	Approved
0.6688	Remote Similarity	NPD1243	Approved
0.6667	Remote Similarity	NPD7236	Approved
0.6667	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7819	Suspended
0.6646	Remote Similarity	NPD7411	Suspended
0.6645	Remote Similarity	NPD3748	Approved
0.6645	Remote Similarity	NPD7003	Approved
0.6644	Remote Similarity	NPD6233	Phase 2
0.6644	Remote Similarity	NPD2798	Approved
0.6644	Remote Similarity	NPD4062	Phase 3
0.6643	Remote Similarity	NPD9092	Discovery
0.6625	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4534	Discontinued
0.6623	Remote Similarity	NPD2897	Discontinued
0.6622	Remote Similarity	NPD7095	Approved
0.6604	Remote Similarity	NPD5403	Approved
0.6603	Remote Similarity	NPD2309	Approved
0.6601	Remote Similarity	NPD2796	Approved
0.66	Remote Similarity	NPD3142	Approved
0.66	Remote Similarity	NPD2979	Phase 3
0.66	Remote Similarity	NPD4307	Phase 2
0.66	Remote Similarity	NPD3140	Approved
0.6597	Remote Similarity	NPD1608	Approved
0.6582	Remote Similarity	NPD5401	Approved
0.6575	Remote Similarity	NPD6362	Approved
0.6558	Remote Similarity	NPD5763	Approved
0.6558	Remote Similarity	NPD6005	Phase 3
0.6558	Remote Similarity	NPD5762	Approved
0.6558	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD6004	Phase 3
0.6558	Remote Similarity	NPD6002	Phase 3
0.6558	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4622	Approved
0.6556	Remote Similarity	NPD4618	Approved
0.6552	Remote Similarity	NPD4359	Approved
0.6549	Remote Similarity	NPD5691	Approved
0.6543	Remote Similarity	NPD5889	Approved
0.6543	Remote Similarity	NPD5890	Approved
0.6541	Remote Similarity	NPD5049	Phase 3
0.6541	Remote Similarity	NPD164	Approved
0.6538	Remote Similarity	NPD4110	Phase 3
0.6538	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD1281	Approved
0.6524	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD1358	Approved
0.6516	Remote Similarity	NPD5958	Discontinued
0.651	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1778	Approved
0.6503	Remote Similarity	NPD6280	Approved
0.6503	Remote Similarity	NPD6279	Approved
0.6494	Remote Similarity	NPD2438	Suspended
0.649	Remote Similarity	NPD4140	Approved
0.649	Remote Similarity	NPD4060	Phase 1
0.6479	Remote Similarity	NPD9545	Approved
0.6478	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5688	Approved
0.6471	Remote Similarity	NPD5689	Approved
0.6467	Remote Similarity	NPD5494	Approved
0.6467	Remote Similarity	NPD3764	Approved
0.6467	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD1203	Approved
0.646	Remote Similarity	NPD957	Approved
0.646	Remote Similarity	NPD7239	Suspended
0.6458	Remote Similarity	NPD3496	Discontinued
0.6449	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD4107	Approved
0.6447	Remote Similarity	NPD1933	Approved
0.6446	Remote Similarity	NPD3749	Approved
0.6438	Remote Similarity	NPD5327	Phase 3
0.6433	Remote Similarity	NPD2163	Approved
0.6433	Remote Similarity	NPD3750	Approved
0.6429	Remote Similarity	NPD8127	Discontinued
0.6429	Remote Similarity	NPD4308	Phase 3
0.6424	Remote Similarity	NPD4870	Approved
0.6424	Remote Similarity	NPD5402	Approved
0.6405	Remote Similarity	NPD6653	Approved
0.6403	Remote Similarity	NPD5535	Approved
0.64	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD1283	Approved
0.6387	Remote Similarity	NPD4476	Approved
0.6387	Remote Similarity	NPD4477	Approved
0.6387	Remote Similarity	NPD2531	Phase 2
0.6387	Remote Similarity	NPD1551	Phase 2
0.6387	Remote Similarity	NPD2935	Discontinued
0.6386	Remote Similarity	NPD3882	Suspended
0.6383	Remote Similarity	NPD7157	Approved
0.638	Remote Similarity	NPD6585	Discontinued
0.6375	Remote Similarity	NPD2534	Approved
0.6375	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD2532	Approved
0.6375	Remote Similarity	NPD2533	Approved
0.6364	Remote Similarity	NPD7097	Phase 1
0.6364	Remote Similarity	NPD1894	Discontinued
0.6353	Remote Similarity	NPD3926	Phase 2
0.6352	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD7440	Discontinued
0.635	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6873	Phase 2
0.6341	Remote Similarity	NPD958	Approved
0.634	Remote Similarity	NPD447	Suspended
0.6329	Remote Similarity	NPD8166	Discontinued
0.6325	Remote Similarity	NPD3817	Phase 2
0.6324	Remote Similarity	NPD4482	Phase 3
0.6323	Remote Similarity	NPD7033	Discontinued
0.6319	Remote Similarity	NPD1651	Approved
0.6316	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD1549	Phase 2
0.6301	Remote Similarity	NPD6287	Discontinued
0.6296	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD3873	Phase 3
0.6296	Remote Similarity	NPD3869	Phase 3
0.6287	Remote Similarity	NPD7768	Phase 2
0.6286	Remote Similarity	NPD6559	Discontinued
0.6276	Remote Similarity	NPD4626	Approved
0.6267	Remote Similarity	NPD9494	Approved
0.6266	Remote Similarity	NPD2800	Approved
0.625	Remote Similarity	NPD411	Approved
0.625	Remote Similarity	NPD9697	Approved
0.6242	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD6677	Suspended
0.6241	Remote Similarity	NPD1238	Approved
0.6236	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD2186	Approved
0.6233	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD9493	Approved
0.6221	Remote Similarity	NPD2403	Approved
0.6221	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.622	Remote Similarity	NPD2651	Approved
0.622	Remote Similarity	NPD2649	Approved
0.6209	Remote Similarity	NPD6663	Approved
0.6205	Remote Similarity	NPD7577	Discontinued
0.6205	Remote Similarity	NPD8404	Phase 2
0.6203	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD2629	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