NPASS Compound

Structure

NPC474777 OpenBabel07101719522D 30 31 0 0 1 0 0 0 0 0999 V2000 -1.9375 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4844 -2.5169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5643 -2.7875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3089 3.2640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7131 2.7454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4844 2.5169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2401 -0.5930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4531 -0.8390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2842 -2.1393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8814 1.3233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8814 0.3546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9688 1.6779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6607 2.5440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9600 1.6227 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4531 0.8390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9688 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3906 0.8390 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4844 0.8390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4531 -0.8390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1615 -0.8924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9600 0.0552 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4531 0.8390 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.4219 -0.8390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4415 -1.5406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4844 -0.8390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9687 -1.6779 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0828 -1.1917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 14 1 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 8 28 1 0 0 0 0 9 29 1 0 0 0 0 10 30 1 0 0 0 0 11 12 1 0 0 0 0 11 16 1 0 0 0 0 12 24 1 0 0 0 0 13 15 2 0 0 0 0 13 17 1 0 0 0 0 15 20 1 0 0 0 0 16 14 1 1 0 0 0 16 19 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 19 24 1 1 0 0 0 20 21 2 0 0 0 0 20 25 1 0 0 0 0 21 28 1 0 0 0 0 22 26 2 0 0 0 0 22 29 1 0 0 0 0 23 24 1 0 0 0 0 23 27 2 0 0 0 0 23 30 1 0 0 0 0 24 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	482.17
Volume:	456.6
LogP:	5.773
LogD:	5.43
LogS:	-6.669
# Rotatable Bonds:	10
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.421
Synthetic Accessibility Score:	3.919
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.761
MDCK Permeability:	2.340679020562675e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.3

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	100.297607421875%
Volume Distribution (VD):	1.28
Pgp-substrate:	2.160275459289551%

ADMET: Metabolism

CYP1A2-inhibitor:	0.218
CYP1A2-substrate:	0.831
CYP2C19-inhibitor:	0.866
CYP2C19-substrate:	0.757
CYP2C9-inhibitor:	0.951
CYP2C9-substrate:	0.552
CYP2D6-inhibitor:	0.427
CYP2D6-substrate:	0.287
CYP3A4-inhibitor:	0.608
CYP3A4-substrate:	0.759

ADMET: Excretion

Clearance (CL):	1.646
Half-life (T1/2):	0.029

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.027
Drug-inuced Liver Injury (DILI):	0.611
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.172
Carcinogencity:	0.045
Eye Corrosion:	0.003
Eye Irritation:	0.838
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC474777

Natural Product ID:	NPC474777
*Common Name:**	Tryethylhamigeran E
IUPAC Name:	ethyl 3-bromo-2-ethoxy-6-[(1R,2R,5R)-2-ethoxycarbonyl-2-methyl-5-propan-2-ylcyclopentyl]-4-methylbenzoate
Synonyms:	Tryethylhamigeran E
Standard InCHIKey:	RVBGQZLCMIXENV-SWWFSWNPSA-N
Standard InCHI:	InChI=1S/C24H35BrO5/c1-8-28-21-18(22(26)29-9-2)17(13-15(6)20(21)25)19-16(14(4)5)11-12-24(19,7)23(27)30-10-3/h13-14,16,19H,8-12H2,1-7H3/t16-,19-,24-/m1/s1
SMILES:	CCOC(=O)c1c(OCC)c(Br)c(cc1[C@H]1[C@H](CC[C@@]1(C)C(=O)OCC)C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482248
PubChem CID:	10457985
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
NPO2050	Hamigera tarangaensis	Species	Hymedesmiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650083]
NPO2050	Hamigera tarangaensis	Species	Hymedesmiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29373034]
NPO2050	Hamigera tarangaensis	Species	Hymedesmiidae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	54200.0	nM	PMID[519500]

☑ 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 NPC474777 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	440
0.1-0.2	1786
0.2-0.3	3997
0.3-0.4	11472
0.4-0.5	9211
0.5-0.6	9335
0.6-0.7	6340
0.7-0.8	111
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8323	Intermediate Similarity	NPC475976
0.8293	Intermediate Similarity	NPC200331
0.8153	Intermediate Similarity	NPC160839
0.7929	Intermediate Similarity	NPC90245
0.7882	Intermediate Similarity	NPC293312
0.7738	Intermediate Similarity	NPC471541
0.7667	Intermediate Similarity	NPC470163
0.7667	Intermediate Similarity	NPC470162
0.7593	Intermediate Similarity	NPC84426
0.7529	Intermediate Similarity	NPC470566
0.75	Intermediate Similarity	NPC470160
0.7486	Intermediate Similarity	NPC470567
0.747	Intermediate Similarity	NPC472298
0.7468	Intermediate Similarity	NPC217914
0.7396	Intermediate Similarity	NPC472799
0.7396	Intermediate Similarity	NPC477669
0.7394	Intermediate Similarity	NPC211565
0.7394	Intermediate Similarity	NPC60389
0.7394	Intermediate Similarity	NPC471346
0.7394	Intermediate Similarity	NPC473927
0.7375	Intermediate Similarity	NPC471542
0.7365	Intermediate Similarity	NPC228906
0.7365	Intermediate Similarity	NPC469416
0.7365	Intermediate Similarity	NPC471348
0.7355	Intermediate Similarity	NPC281499
0.7321	Intermediate Similarity	NPC477676
0.731	Intermediate Similarity	NPC477674
0.7305	Intermediate Similarity	NPC219560
0.7278	Intermediate Similarity	NPC477673
0.7278	Intermediate Similarity	NPC477672
0.7273	Intermediate Similarity	NPC290038
0.7273	Intermediate Similarity	NPC469385
0.7262	Intermediate Similarity	NPC291049
0.7262	Intermediate Similarity	NPC233267
0.725	Intermediate Similarity	NPC470844
0.7235	Intermediate Similarity	NPC273483
0.7229	Intermediate Similarity	NPC75694
0.7226	Intermediate Similarity	NPC475361
0.7219	Intermediate Similarity	NPC150928
0.7219	Intermediate Similarity	NPC144010
0.7219	Intermediate Similarity	NPC158866
0.7219	Intermediate Similarity	NPC474660
0.7215	Intermediate Similarity	NPC279596
0.7215	Intermediate Similarity	NPC196979
0.7215	Intermediate Similarity	NPC470977
0.7215	Intermediate Similarity	NPC470976
0.7215	Intermediate Similarity	NPC15083
0.7212	Intermediate Similarity	NPC471643
0.7212	Intermediate Similarity	NPC471639
0.7209	Intermediate Similarity	NPC4547
0.7202	Intermediate Similarity	NPC37139
0.7202	Intermediate Similarity	NPC95526
0.7202	Intermediate Similarity	NPC105415
0.72	Intermediate Similarity	NPC472206
0.7188	Intermediate Similarity	NPC209858
0.7186	Intermediate Similarity	NPC470357
0.7186	Intermediate Similarity	NPC224418
0.7182	Intermediate Similarity	NPC295914
0.7178	Intermediate Similarity	NPC476191
0.7176	Intermediate Similarity	NPC133856
0.7175	Intermediate Similarity	NPC125465
0.7169	Intermediate Similarity	NPC189650
0.7169	Intermediate Similarity	NPC56731
0.7152	Intermediate Similarity	NPC471640
0.7152	Intermediate Similarity	NPC183348
0.7152	Intermediate Similarity	NPC473271
0.7152	Intermediate Similarity	NPC471644
0.7152	Intermediate Similarity	NPC329493
0.7152	Intermediate Similarity	NPC282230
0.7151	Intermediate Similarity	NPC149618
0.7151	Intermediate Similarity	NPC477687
0.7151	Intermediate Similarity	NPC477671
0.7151	Intermediate Similarity	NPC3898
0.7151	Intermediate Similarity	NPC89625
0.7143	Intermediate Similarity	NPC125801
0.7143	Intermediate Similarity	NPC469425
0.7143	Intermediate Similarity	NPC137296
0.7143	Intermediate Similarity	NPC8817
0.7135	Intermediate Similarity	NPC24232
0.7135	Intermediate Similarity	NPC271681
0.7135	Intermediate Similarity	NPC471347
0.7135	Intermediate Similarity	NPC471349
0.7134	Intermediate Similarity	NPC125861
0.7134	Intermediate Similarity	NPC196034
0.7134	Intermediate Similarity	NPC165172
0.7134	Intermediate Similarity	NPC477535
0.7126	Intermediate Similarity	NPC239118
0.7126	Intermediate Similarity	NPC477692
0.7118	Intermediate Similarity	NPC473466
0.711	Intermediate Similarity	NPC477675
0.7108	Intermediate Similarity	NPC163948
0.7107	Intermediate Similarity	NPC7012
0.7107	Intermediate Similarity	NPC164295
0.7107	Intermediate Similarity	NPC239134
0.7107	Intermediate Similarity	NPC477412
0.7105	Intermediate Similarity	NPC230951
0.7093	Intermediate Similarity	NPC470102
0.7093	Intermediate Similarity	NPC477691
0.7091	Intermediate Similarity	NPC149780
0.7091	Intermediate Similarity	NPC1704
0.7091	Intermediate Similarity	NPC149533
0.7091	Intermediate Similarity	NPC67650
0.7089	Intermediate Similarity	NPC170546
0.7089	Intermediate Similarity	NPC66246
0.7089	Intermediate Similarity	NPC57552
0.7086	Intermediate Similarity	NPC47623
0.7083	Intermediate Similarity	NPC225173
0.7083	Intermediate Similarity	NPC163846
0.7083	Intermediate Similarity	NPC237208
0.7083	Intermediate Similarity	NPC286038
0.7081	Intermediate Similarity	NPC27394
0.7081	Intermediate Similarity	NPC324117
0.7079	Intermediate Similarity	NPC165460
0.7076	Intermediate Similarity	NPC175617
0.7076	Intermediate Similarity	NPC478148
0.7069	Intermediate Similarity	NPC67197
0.7069	Intermediate Similarity	NPC158542
0.7069	Intermediate Similarity	NPC272196
0.7066	Intermediate Similarity	NPC470932
0.7063	Intermediate Similarity	NPC293253
0.7059	Intermediate Similarity	NPC474305
0.7059	Intermediate Similarity	NPC322569
0.7048	Intermediate Similarity	NPC469579
0.7048	Intermediate Similarity	NPC24075
0.7048	Intermediate Similarity	NPC96692
0.7048	Intermediate Similarity	NPC470273
0.7041	Intermediate Similarity	NPC93666
0.7041	Intermediate Similarity	NPC66991
0.7037	Intermediate Similarity	NPC298900
0.7035	Intermediate Similarity	NPC87708
0.7035	Intermediate Similarity	NPC44606
0.7035	Intermediate Similarity	NPC477690
0.7035	Intermediate Similarity	NPC217447
0.703	Intermediate Similarity	NPC168471
0.703	Intermediate Similarity	NPC477537
0.7029	Intermediate Similarity	NPC4950
0.7029	Intermediate Similarity	NPC474373
0.7029	Intermediate Similarity	NPC218818
0.7024	Intermediate Similarity	NPC62799
0.7024	Intermediate Similarity	NPC134621
0.7024	Intermediate Similarity	NPC29577
0.7022	Intermediate Similarity	NPC316262
0.7022	Intermediate Similarity	NPC314653
0.702	Intermediate Similarity	NPC217423
0.7019	Intermediate Similarity	NPC477536
0.7018	Intermediate Similarity	NPC119929
0.7012	Intermediate Similarity	NPC307883
0.7012	Intermediate Similarity	NPC233707
0.7012	Intermediate Similarity	NPC233780
0.7011	Intermediate Similarity	NPC305490
0.7011	Intermediate Similarity	NPC146211
0.7011	Intermediate Similarity	NPC469507
0.7006	Intermediate Similarity	NPC472006
0.7006	Intermediate Similarity	NPC51106
0.7006	Intermediate Similarity	NPC159721
0.7006	Intermediate Similarity	NPC473022
0.7006	Intermediate Similarity	NPC474737
0.7006	Intermediate Similarity	NPC144843
0.7006	Intermediate Similarity	NPC471731
0.7	Intermediate Similarity	NPC475848
0.7	Intermediate Similarity	NPC474306
0.6994	Remote Similarity	NPC232996
0.6994	Remote Similarity	NPC210942
0.6994	Remote Similarity	NPC307401
0.6994	Remote Similarity	NPC169990
0.6994	Remote Similarity	NPC21797
0.6994	Remote Similarity	NPC194847
0.6989	Remote Similarity	NPC143050
0.6989	Remote Similarity	NPC313368
0.6988	Remote Similarity	NPC470856
0.6987	Remote Similarity	NPC56332
0.6983	Remote Similarity	NPC472621
0.6982	Remote Similarity	NPC281398
0.6981	Remote Similarity	NPC131684
0.6977	Remote Similarity	NPC72958
0.6977	Remote Similarity	NPC232645
0.6977	Remote Similarity	NPC39819
0.6977	Remote Similarity	NPC149526
0.6977	Remote Similarity	NPC474417
0.6977	Remote Similarity	NPC473732
0.6975	Remote Similarity	NPC1249
0.6974	Remote Similarity	NPC171023
0.697	Remote Similarity	NPC36414
0.6966	Remote Similarity	NPC100849
0.6966	Remote Similarity	NPC17432
0.6964	Remote Similarity	NPC260152
0.6964	Remote Similarity	NPC42540
0.6964	Remote Similarity	NPC66404
0.6964	Remote Similarity	NPC95123
0.6964	Remote Similarity	NPC151607
0.6964	Remote Similarity	NPC184702
0.6964	Remote Similarity	NPC89664
0.6964	Remote Similarity	NPC274085
0.6962	Remote Similarity	NPC293387
0.6959	Remote Similarity	NPC97028
0.6959	Remote Similarity	NPC100985
0.6959	Remote Similarity	NPC288036
0.6959	Remote Similarity	NPC70764
0.6959	Remote Similarity	NPC65589
0.6959	Remote Similarity	NPC97029

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 NPC474777 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	374
0.1-0.2	1070
0.2-0.3	1907
0.3-0.4	2931
0.4-0.5	1878
0.5-0.6	802
0.6-0.7	180
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
0.7329	Intermediate Similarity	NPD2346	Discontinued
0.7244	Intermediate Similarity	NPD6832	Phase 2
0.7229	Intermediate Similarity	NPD2533	Approved
0.7229	Intermediate Similarity	NPD2534	Approved
0.7229	Intermediate Similarity	NPD2532	Approved
0.7151	Intermediate Similarity	NPD4288	Approved
0.7107	Intermediate Similarity	NPD8032	Phase 2
0.7093	Intermediate Similarity	NPD7819	Suspended
0.7083	Intermediate Similarity	NPD6273	Approved
0.7059	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5691	Approved
0.7019	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2799	Discontinued
0.6988	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2935	Discontinued
0.6937	Remote Similarity	NPD411	Approved
0.6937	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1019	Discontinued
0.6867	Remote Similarity	NPD970	Clinical (unspecified phase)
0.686	Remote Similarity	NPD3226	Approved
0.6859	Remote Similarity	NPD9717	Approved
0.6857	Remote Similarity	NPD2296	Approved
0.6852	Remote Similarity	NPD2979	Phase 3
0.6832	Remote Similarity	NPD2313	Discontinued
0.6824	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6599	Discontinued
0.6795	Remote Similarity	NPD1281	Approved
0.6786	Remote Similarity	NPD7003	Approved
0.6774	Remote Similarity	NPD4626	Approved
0.6748	Remote Similarity	NPD4307	Phase 2
0.6747	Remote Similarity	NPD2438	Suspended
0.672	Remote Similarity	NPD4287	Approved
0.6707	Remote Similarity	NPD6002	Phase 3
0.6707	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5763	Approved
0.6707	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6004	Phase 3
0.6707	Remote Similarity	NPD5762	Approved
0.6707	Remote Similarity	NPD6005	Phase 3
0.6707	Remote Similarity	NPD447	Suspended
0.6707	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1283	Approved
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD1876	Approved
0.6647	Remote Similarity	NPD1551	Phase 2
0.6647	Remote Similarity	NPD2531	Phase 2
0.6646	Remote Similarity	NPD4140	Approved
0.663	Remote Similarity	NPD5710	Approved
0.663	Remote Similarity	NPD5711	Approved
0.6629	Remote Similarity	NPD7768	Phase 2
0.6627	Remote Similarity	NPD1243	Approved
0.6625	Remote Similarity	NPD3267	Approved
0.6625	Remote Similarity	NPD2797	Approved
0.6625	Remote Similarity	NPD3266	Approved
0.6625	Remote Similarity	NPD1203	Approved
0.6612	Remote Similarity	NPD7473	Discontinued
0.661	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6355	Discontinued
0.6606	Remote Similarity	NPD1933	Approved
0.6604	Remote Similarity	NPD5327	Phase 3
0.6603	Remote Similarity	NPD5585	Approved
0.6588	Remote Similarity	NPD4628	Phase 3
0.6587	Remote Similarity	NPD3748	Approved
0.6587	Remote Similarity	NPD4308	Phase 3
0.6584	Remote Similarity	NPD2798	Approved
0.6582	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD1611	Approved
0.6581	Remote Similarity	NPD7644	Approved
0.6575	Remote Similarity	NPD6959	Discontinued
0.6575	Remote Similarity	NPD8127	Discontinued
0.6571	Remote Similarity	NPD7458	Discontinued
0.6561	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD920	Approved
0.6548	Remote Similarity	NPD6099	Approved
0.6548	Remote Similarity	NPD6100	Approved
0.6548	Remote Similarity	NPD2796	Approved
0.6543	Remote Similarity	NPD8313	Approved
0.6543	Remote Similarity	NPD8312	Approved
0.6538	Remote Similarity	NPD6232	Discontinued
0.6529	Remote Similarity	NPD2800	Approved
0.6524	Remote Similarity	NPD3268	Approved
0.6524	Remote Similarity	NPD7985	Registered
0.6519	Remote Similarity	NPD5494	Approved
0.6519	Remote Similarity	NPD3496	Discontinued
0.6512	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD1471	Phase 3
0.65	Remote Similarity	NPD7075	Discontinued
0.6497	Remote Similarity	NPD1651	Approved
0.6497	Remote Similarity	NPD5889	Approved
0.6497	Remote Similarity	NPD7411	Suspended
0.6497	Remote Similarity	NPD5890	Approved
0.6495	Remote Similarity	NPD7539	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4110	Phase 3
0.6491	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD4870	Approved
0.648	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6799	Approved
0.6467	Remote Similarity	NPD6653	Approved
0.6464	Remote Similarity	NPD919	Approved
0.6457	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD17	Approved
0.6452	Remote Similarity	NPD5844	Phase 1
0.645	Remote Similarity	NPD5408	Approved
0.645	Remote Similarity	NPD4477	Approved
0.645	Remote Similarity	NPD5404	Approved
0.645	Remote Similarity	NPD4476	Approved
0.645	Remote Similarity	NPD5406	Approved
0.645	Remote Similarity	NPD5405	Approved
0.6446	Remote Similarity	NPD4060	Phase 1
0.6438	Remote Similarity	NPD3972	Approved
0.6437	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD5761	Phase 2
0.6425	Remote Similarity	NPD5760	Phase 2
0.6425	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.641	Remote Similarity	NPD9493	Approved
0.6398	Remote Similarity	NPD4359	Approved
0.6398	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD3750	Approved
0.6389	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD3817	Phase 2
0.6386	Remote Similarity	NPD6663	Approved
0.638	Remote Similarity	NPD5647	Approved
0.6369	Remote Similarity	NPD6801	Discontinued
0.6369	Remote Similarity	NPD6651	Approved
0.6364	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD7315	Approved
0.6358	Remote Similarity	NPD6696	Suspended
0.6349	Remote Similarity	NPD1298	Discontinued
0.6349	Remote Similarity	NPD6559	Discontinued
0.6348	Remote Similarity	NPD6585	Discontinued
0.6341	Remote Similarity	NPD5736	Approved
0.6341	Remote Similarity	NPD2237	Approved
0.634	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD1608	Approved
0.6325	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD7236	Approved
0.6319	Remote Similarity	NPD6362	Approved
0.631	Remote Similarity	NPD7177	Discontinued
0.6304	Remote Similarity	NPD7199	Phase 2
0.6301	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD5402	Approved
0.6294	Remote Similarity	NPD7033	Discontinued
0.629	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.628	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD6353	Approved
0.6271	Remote Similarity	NPD5403	Approved
0.627	Remote Similarity	NPD7229	Phase 3
0.625	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1578	Phase 2
0.625	Remote Similarity	NPD5401	Approved
0.6237	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD7239	Suspended
0.623	Remote Similarity	NPD3749	Approved
0.6224	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4302	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD6620	Discovery
0.6222	Remote Similarity	NPD6873	Phase 2
0.6221	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD2344	Approved
0.6221	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD1241	Discontinued
0.6213	Remote Similarity	NPD5735	Approved
0.6213	Remote Similarity	NPD4622	Approved
0.6213	Remote Similarity	NPD4618	Approved
0.6209	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD2182	Approved
0.62	Remote Similarity	NPD8285	Discontinued
0.6188	Remote Similarity	NPD3025	Approved
0.6188	Remote Similarity	NPD1934	Approved
0.6188	Remote Similarity	NPD3024	Approved
0.6186	Remote Similarity	NPD8434	Phase 2
0.6185	Remote Similarity	NPD2897	Discontinued
0.6185	Remote Similarity	NPD1549	Phase 2
0.6183	Remote Similarity	NPD6808	Phase 2
0.6176	Remote Similarity	NPD2157	Approved
0.6176	Remote Similarity	NPD1607	Approved
0.6175	Remote Similarity	NPD3882	Suspended
0.6168	Remote Similarity	NPD7095	Approved
0.6167	Remote Similarity	NPD7028	Phase 2
0.614	Remote Similarity	NPD5689	Approved
0.614	Remote Similarity	NPD5688	Approved
0.6131	Remote Similarity	NPD6798	Discontinued
0.6129	Remote Similarity	NPD1247	Approved
0.6122	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD8166	Discontinued
0.6111	Remote Similarity	NPD3026	Approved
0.6111	Remote Similarity	NPD3023	Approved
0.6111	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD1510	Phase 2
0.6103	Remote Similarity	NPD8150	Discontinued
0.6102	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6101	Remote Similarity	NPD7340	Approved
0.6099	Remote Similarity	NPD37	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