NPASS Compound

Structure

NPC469401 OpenBabel07101718292D 34 37 0 0 1 0 0 0 0 0999 V2000 2.1335 -1.8472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8387 -1.6339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7801 2.0376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2984 5.1690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2984 5.1690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6644 2.8030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2593 2.3547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6644 3.8030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7984 2.3030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9664 3.0618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9324 3.8030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8406 -1.1401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0523 -2.0879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9868 1.4288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2934 2.6135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5163 1.9842 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2574 1.0183 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6158 0.0847 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9350 3.5471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6776 2.5288 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2588 0.9659 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8387 -0.5446 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7984 4.3030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9324 2.8030 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.8065 -1.3989 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1047 -3.0865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1173 0.4374 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4797 4.3858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5817 -0.1741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8910 -1.5433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9364 3.4948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0995 1.8995 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 5.0629 1.8115 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 15 2 0 0 0 0 8 23 1 0 0 0 0 9 24 1 0 0 0 0 10 24 1 0 0 0 0 11 23 1 0 0 0 0 11 24 1 0 0 0 0 12 25 2 0 0 0 0 12 29 1 0 0 0 0 13 26 2 0 0 0 0 13 30 1 0 0 0 0 14 27 2 0 0 0 0 14 34 1 0 0 0 0 15 19 1 0 0 0 0 16 15 1 1 0 0 0 16 17 1 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 18 29 1 0 0 0 0 19 28 2 0 0 0 0 19 31 1 0 0 0 0 20 31 1 0 0 0 0 20 32 1 0 0 0 0 21 32 1 0 0 0 0 21 33 1 0 0 0 0 22 30 1 0 0 0 0 22 33 1 0 0 0 0 24 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.18
Volume:	397.322
LogP:	3.245
LogD:	2.747
LogS:	-4.05
# Rotatable Bonds:	5
TPSA:	97.36
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.399
Synthetic Accessibility Score:	4.966
Fsp3:	0.762
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:	-4.882
MDCK Permeability:	6.897204730194062e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.241
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.176
Plasma Protein Binding (PPB):	78.72185516357422%
Volume Distribution (VD):	2.325
Pgp-substrate:	28.458877563476562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.08
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.198
CYP2C9-inhibitor:	0.125
CYP2C9-substrate:	0.077
CYP2D6-inhibitor:	0.822
CYP2D6-substrate:	0.158
CYP3A4-inhibitor:	0.501
CYP3A4-substrate:	0.281

ADMET: Excretion

Clearance (CL):	1.085
Half-life (T1/2):	0.254

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.773
Drug-inuced Liver Injury (DILI):	0.849
AMES Toxicity:	0.705
Rat Oral Acute Toxicity:	0.129
Maximum Recommended Daily Dose:	0.473
Skin Sensitization:	0.945
Carcinogencity:	0.296
Eye Corrosion:	0.441
Eye Irritation:	0.632
Respiratory Toxicity:	0.802

Download Data

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

Natural Product: NPC469401

Natural Product ID:	NPC469401
*Common Name:**	Gracilin J
IUPAC Name:	[(2R,3S,3aS,3bR,4Z,6aS,7aR)-2-acetyloxy-4-[2-(1-acetyloxy-3,3-dimethylcyclohexyl)ethylidene]-5-oxo-2,3,3a,3b,6a,7a-hexahydrodifuro[5,3-a:5',4'-d]furan-3-yl] acetate
Synonyms:	Gracilin J
Standard InCHIKey:	NMUUJHGEYJKFAT-CARDQYAASA-N
Standard InCHI:	InChI=1S/C24H32O10/c1-12(25)29-18-17-16-15(7-10-24(34-14(3)27)9-6-8-23(4,5)11-24)19(28)31-20(16)32-21(17)33-22(18)30-13(2)26/h7,16-18,20-22H,6,8-11H2,1-5H3/b15-7-/t16-,17-,18-,20+,21+,22-,24?/m0/s1
SMILES:	CC(=O)OC1C2C3C(OC2OC1OC(=O)C)OC(=O)C3=CCC4(CCCC(C4)(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077759
PubChem CID:	46882976
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO33347	spongionella sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19601607]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	15000.0	nM	PMID[465279]
NPT927	Cell Line	PBMC	Homo sapiens	IC50	=	30000.0	nM	PMID[465279]

☑ 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 NPC469401 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	261
0.1-0.2	1490
0.2-0.3	5527
0.3-0.4	10856
0.4-0.5	11760
0.5-0.6	7525
0.6-0.7	4771
0.7-0.8	499
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9485	High Similarity	NPC469402
0.8208	Intermediate Similarity	NPC305157
0.8208	Intermediate Similarity	NPC307846
0.8158	Intermediate Similarity	NPC151616
0.8148	Intermediate Similarity	NPC475960
0.8087	Intermediate Similarity	NPC204731
0.8077	Intermediate Similarity	NPC279561
0.8073	Intermediate Similarity	NPC112457
0.8018	Intermediate Similarity	NPC222834
0.7946	Intermediate Similarity	NPC470120
0.7921	Intermediate Similarity	NPC475748
0.7895	Intermediate Similarity	NPC23046
0.7881	Intermediate Similarity	NPC469379
0.7881	Intermediate Similarity	NPC86346
0.7881	Intermediate Similarity	NPC75856
0.787	Intermediate Similarity	NPC474917
0.7845	Intermediate Similarity	NPC48692
0.783	Intermediate Similarity	NPC470761
0.783	Intermediate Similarity	NPC473219
0.7818	Intermediate Similarity	NPC219900
0.7818	Intermediate Similarity	NPC392
0.7818	Intermediate Similarity	NPC177524
0.7807	Intermediate Similarity	NPC471816
0.7798	Intermediate Similarity	NPC239961
0.7797	Intermediate Similarity	NPC469382
0.7788	Intermediate Similarity	NPC473535
0.7788	Intermediate Similarity	NPC264153
0.7788	Intermediate Similarity	NPC157441
0.7778	Intermediate Similarity	NPC473250
0.7778	Intermediate Similarity	NPC132395
0.7778	Intermediate Similarity	NPC471365
0.7778	Intermediate Similarity	NPC471364
0.7769	Intermediate Similarity	NPC470851
0.7768	Intermediate Similarity	NPC474750
0.7767	Intermediate Similarity	NPC476300
0.775	Intermediate Similarity	NPC298841
0.775	Intermediate Similarity	NPC42399
0.7745	Intermediate Similarity	NPC80875
0.7736	Intermediate Similarity	NPC476800
0.7736	Intermediate Similarity	NPC471366
0.7736	Intermediate Similarity	NPC472186
0.7736	Intermediate Similarity	NPC318917
0.7719	Intermediate Similarity	NPC90472
0.7714	Intermediate Similarity	NPC311166
0.7712	Intermediate Similarity	NPC473231
0.7699	Intermediate Similarity	NPC12046
0.7699	Intermediate Similarity	NPC194951
0.7692	Intermediate Similarity	NPC473316
0.7692	Intermediate Similarity	NPC4548
0.7692	Intermediate Similarity	NPC147635
0.7692	Intermediate Similarity	NPC473330
0.7692	Intermediate Similarity	NPC163693
0.7679	Intermediate Similarity	NPC235014
0.7679	Intermediate Similarity	NPC253906
0.7679	Intermediate Similarity	NPC83005
0.767	Intermediate Similarity	NPC65513
0.7664	Intermediate Similarity	NPC473204
0.7664	Intermediate Similarity	NPC473545
0.7664	Intermediate Similarity	NPC472187
0.7652	Intermediate Similarity	NPC277583
0.7652	Intermediate Similarity	NPC243981
0.7642	Intermediate Similarity	NPC472188
0.7636	Intermediate Similarity	NPC127609
0.7632	Intermediate Similarity	NPC311592
0.7632	Intermediate Similarity	NPC75167
0.7632	Intermediate Similarity	NPC293658
0.7632	Intermediate Similarity	NPC474410
0.7624	Intermediate Similarity	NPC231889
0.7619	Intermediate Similarity	NPC167893
0.7619	Intermediate Similarity	NPC473369
0.7619	Intermediate Similarity	NPC36954
0.7615	Intermediate Similarity	NPC254202
0.7615	Intermediate Similarity	NPC120009
0.7607	Intermediate Similarity	NPC475834
0.7607	Intermediate Similarity	NPC474179
0.7596	Intermediate Similarity	NPC475657
0.7596	Intermediate Similarity	NPC179746
0.7596	Intermediate Similarity	NPC81419
0.7593	Intermediate Similarity	NPC473384
0.7589	Intermediate Similarity	NPC469370
0.7589	Intermediate Similarity	NPC206618
0.7586	Intermediate Similarity	NPC13713
0.7586	Intermediate Similarity	NPC473656
0.7586	Intermediate Similarity	NPC473968
0.7573	Intermediate Similarity	NPC51004
0.757	Intermediate Similarity	NPC473154
0.757	Intermediate Similarity	NPC187268
0.7568	Intermediate Similarity	NPC184512
0.7568	Intermediate Similarity	NPC180744
0.7565	Intermediate Similarity	NPC181145
0.7547	Intermediate Similarity	NPC171598
0.7547	Intermediate Similarity	NPC476315
0.7545	Intermediate Similarity	NPC472748
0.7544	Intermediate Similarity	NPC471570
0.7544	Intermediate Similarity	NPC269530
0.7541	Intermediate Similarity	NPC473620
0.7541	Intermediate Similarity	NPC470850
0.7524	Intermediate Similarity	NPC474338
0.7524	Intermediate Similarity	NPC88507
0.7522	Intermediate Similarity	NPC5103
0.7522	Intermediate Similarity	NPC46407
0.7522	Intermediate Similarity	NPC119550
0.7521	Intermediate Similarity	NPC222307
0.7521	Intermediate Similarity	NPC475372
0.7521	Intermediate Similarity	NPC475913
0.75	Intermediate Similarity	NPC217921
0.75	Intermediate Similarity	NPC12172
0.75	Intermediate Similarity	NPC27363
0.75	Intermediate Similarity	NPC10150
0.75	Intermediate Similarity	NPC38948
0.75	Intermediate Similarity	NPC128795
0.75	Intermediate Similarity	NPC30515
0.75	Intermediate Similarity	NPC184463
0.75	Intermediate Similarity	NPC473069
0.75	Intermediate Similarity	NPC42747
0.75	Intermediate Similarity	NPC135015
0.75	Intermediate Similarity	NPC48548
0.75	Intermediate Similarity	NPC129992
0.75	Intermediate Similarity	NPC208886
0.748	Intermediate Similarity	NPC472770
0.7479	Intermediate Similarity	NPC473228
0.7479	Intermediate Similarity	NPC470829
0.7478	Intermediate Similarity	NPC469454
0.7478	Intermediate Similarity	NPC469496
0.7478	Intermediate Similarity	NPC469463
0.7477	Intermediate Similarity	NPC476762
0.7477	Intermediate Similarity	NPC476761
0.7477	Intermediate Similarity	NPC252296
0.7477	Intermediate Similarity	NPC257726
0.7477	Intermediate Similarity	NPC470975
0.7477	Intermediate Similarity	NPC218158
0.7477	Intermediate Similarity	NPC472751
0.7477	Intermediate Similarity	NPC103088
0.7477	Intermediate Similarity	NPC476760
0.7477	Intermediate Similarity	NPC470979
0.7477	Intermediate Similarity	NPC472749
0.7477	Intermediate Similarity	NPC204054
0.7476	Intermediate Similarity	NPC151770
0.7476	Intermediate Similarity	NPC307411
0.7476	Intermediate Similarity	NPC166919
0.7459	Intermediate Similarity	NPC11732
0.7458	Intermediate Similarity	NPC476529
0.7458	Intermediate Similarity	NPC475520
0.7458	Intermediate Similarity	NPC475775
0.7458	Intermediate Similarity	NPC477071
0.7458	Intermediate Similarity	NPC469380
0.7458	Intermediate Similarity	NPC122971
0.7458	Intermediate Similarity	NPC312536
0.7456	Intermediate Similarity	NPC179798
0.7456	Intermediate Similarity	NPC17791
0.7456	Intermediate Similarity	NPC304180
0.7455	Intermediate Similarity	NPC474775
0.7455	Intermediate Similarity	NPC7613
0.7455	Intermediate Similarity	NPC475889
0.7455	Intermediate Similarity	NPC472750
0.7455	Intermediate Similarity	NPC127933
0.7455	Intermediate Similarity	NPC7644
0.7455	Intermediate Similarity	NPC472747
0.7453	Intermediate Similarity	NPC471362
0.7453	Intermediate Similarity	NPC471372
0.7453	Intermediate Similarity	NPC472189
0.7451	Intermediate Similarity	NPC475703
0.744	Intermediate Similarity	NPC478151
0.744	Intermediate Similarity	NPC88668
0.7436	Intermediate Similarity	NPC475323
0.7436	Intermediate Similarity	NPC474483
0.7434	Intermediate Similarity	NPC187876
0.7434	Intermediate Similarity	NPC273433
0.7434	Intermediate Similarity	NPC471934
0.7434	Intermediate Similarity	NPC316974
0.7434	Intermediate Similarity	NPC40728
0.7431	Intermediate Similarity	NPC198992
0.7429	Intermediate Similarity	NPC475912
0.7429	Intermediate Similarity	NPC471571
0.7419	Intermediate Similarity	NPC476852
0.7417	Intermediate Similarity	NPC287236
0.7417	Intermediate Similarity	NPC192309
0.7411	Intermediate Similarity	NPC475510
0.7411	Intermediate Similarity	NPC88013
0.7411	Intermediate Similarity	NPC475587
0.7411	Intermediate Similarity	NPC125423
0.7411	Intermediate Similarity	NPC109376
0.7411	Intermediate Similarity	NPC293512
0.7407	Intermediate Similarity	NPC208233
0.7404	Intermediate Similarity	NPC312042
0.74	Intermediate Similarity	NPC469
0.74	Intermediate Similarity	NPC170286
0.7398	Intermediate Similarity	NPC270109
0.7398	Intermediate Similarity	NPC172823
0.7398	Intermediate Similarity	NPC311534
0.7395	Intermediate Similarity	NPC241192
0.7395	Intermediate Similarity	NPC109607
0.7395	Intermediate Similarity	NPC107338
0.7395	Intermediate Similarity	NPC470312
0.7395	Intermediate Similarity	NPC143755
0.7391	Intermediate Similarity	NPC470025
0.7391	Intermediate Similarity	NPC317460
0.7391	Intermediate Similarity	NPC328074
0.7391	Intermediate Similarity	NPC321272
0.7391	Intermediate Similarity	NPC174836

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 NPC469401 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	1925
0.2-0.3	4109
0.3-0.4	1997
0.4-0.5	562
0.5-0.6	254
0.6-0.7	78
0.7-0.8	2
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
0.7818	Intermediate Similarity	NPD6686	Approved
0.7377	Intermediate Similarity	NPD7507	Approved
0.72	Intermediate Similarity	NPD7319	Approved
0.7105	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD7327	Approved
0.6942	Remote Similarity	NPD7328	Approved
0.6937	Remote Similarity	NPD4225	Approved
0.6937	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6698	Approved
0.6916	Remote Similarity	NPD46	Approved
0.6911	Remote Similarity	NPD8515	Approved
0.6911	Remote Similarity	NPD8033	Approved
0.6911	Remote Similarity	NPD8516	Approved
0.6911	Remote Similarity	NPD8517	Approved
0.6911	Remote Similarity	NPD8513	Phase 3
0.6885	Remote Similarity	NPD7516	Approved
0.687	Remote Similarity	NPD6008	Approved
0.6855	Remote Similarity	NPD6370	Approved
0.685	Remote Similarity	NPD7736	Approved
0.6829	Remote Similarity	NPD8294	Approved
0.6829	Remote Similarity	NPD8377	Approved
0.6822	Remote Similarity	NPD1695	Approved
0.6818	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6371	Approved
0.6774	Remote Similarity	NPD8296	Approved
0.6774	Remote Similarity	NPD8380	Approved
0.6774	Remote Similarity	NPD8335	Approved
0.6774	Remote Similarity	NPD8379	Approved
0.6774	Remote Similarity	NPD7503	Approved
0.6774	Remote Similarity	NPD8378	Approved
0.6772	Remote Similarity	NPD8293	Discontinued
0.6772	Remote Similarity	NPD7078	Approved
0.6762	Remote Similarity	NPD1694	Approved
0.6746	Remote Similarity	NPD7492	Approved
0.6723	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6054	Approved
0.6693	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD8328	Phase 3
0.6639	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7638	Approved
0.6612	Remote Similarity	NPD8133	Approved
0.6606	Remote Similarity	NPD7838	Discovery
0.6579	Remote Similarity	NPD6648	Approved
0.6579	Remote Similarity	NPD7639	Approved
0.6579	Remote Similarity	NPD7640	Approved
0.656	Remote Similarity	NPD6059	Approved
0.6529	Remote Similarity	NPD6882	Approved
0.6529	Remote Similarity	NPD6053	Discontinued
0.6522	Remote Similarity	NPD5344	Discontinued
0.6508	Remote Similarity	NPD6015	Approved
0.6508	Remote Similarity	NPD6016	Approved
0.6457	Remote Similarity	NPD5988	Approved
0.6452	Remote Similarity	NPD6009	Approved
0.6452	Remote Similarity	NPD7115	Discovery
0.6452	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5282	Discontinued
0.6417	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD7642	Approved
0.6396	Remote Similarity	NPD7983	Approved
0.6393	Remote Similarity	NPD8297	Approved
0.6385	Remote Similarity	NPD8074	Phase 3
0.6355	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6649	Approved
0.6311	Remote Similarity	NPD6650	Approved
0.6299	Remote Similarity	NPD6319	Approved
0.6281	Remote Similarity	NPD6372	Approved
0.6281	Remote Similarity	NPD6373	Approved
0.6279	Remote Similarity	NPD7829	Approved
0.6279	Remote Similarity	NPD7830	Approved
0.627	Remote Similarity	NPD7641	Discontinued
0.6228	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.621	Remote Similarity	NPD4632	Approved
0.6198	Remote Similarity	NPD6881	Approved
0.6198	Remote Similarity	NPD7320	Approved
0.6198	Remote Similarity	NPD6899	Approved
0.6198	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5778	Approved
0.6195	Remote Similarity	NPD5779	Approved
0.6194	Remote Similarity	NPD7260	Phase 2
0.6183	Remote Similarity	NPD8451	Approved
0.6168	Remote Similarity	NPD5209	Approved
0.6167	Remote Similarity	NPD5739	Approved
0.6167	Remote Similarity	NPD7128	Approved
0.6167	Remote Similarity	NPD6402	Approved
0.6167	Remote Similarity	NPD6675	Approved
0.6161	Remote Similarity	NPD5785	Approved
0.6154	Remote Similarity	NPD6067	Discontinued
0.6148	Remote Similarity	NPD6845	Suspended
0.614	Remote Similarity	NPD7900	Approved
0.614	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD8448	Approved
0.6126	Remote Similarity	NPD6903	Approved
0.6116	Remote Similarity	NPD5697	Approved
0.6098	Remote Similarity	NPD7102	Approved
0.6098	Remote Similarity	NPD6883	Approved
0.6098	Remote Similarity	NPD7290	Approved
0.6091	Remote Similarity	NPD6684	Approved
0.6091	Remote Similarity	NPD7334	Approved
0.6091	Remote Similarity	NPD7521	Approved
0.6091	Remote Similarity	NPD6409	Approved
0.6091	Remote Similarity	NPD5330	Approved
0.6091	Remote Similarity	NPD7146	Approved
0.609	Remote Similarity	NPD8336	Approved
0.609	Remote Similarity	NPD6033	Approved
0.609	Remote Similarity	NPD8337	Approved
0.6053	Remote Similarity	NPD6399	Phase 3
0.605	Remote Similarity	NPD7632	Discontinued
0.6048	Remote Similarity	NPD6869	Approved
0.6048	Remote Similarity	NPD6847	Approved
0.6048	Remote Similarity	NPD6617	Approved
0.6048	Remote Similarity	NPD8130	Phase 1
0.6036	Remote Similarity	NPD3573	Approved
0.6036	Remote Similarity	NPD4250	Approved
0.6036	Remote Similarity	NPD4251	Approved
0.6034	Remote Similarity	NPD7839	Suspended
0.6031	Remote Similarity	NPD7604	Phase 2
0.6029	Remote Similarity	NPD8338	Approved
0.6016	Remote Similarity	NPD6012	Approved
0.6016	Remote Similarity	NPD6014	Approved
0.6016	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD8266	Approved
0.6	Remote Similarity	NPD8267	Approved
0.6	Remote Similarity	NPD8268	Approved
0.6	Remote Similarity	NPD8444	Approved
0.6	Remote Similarity	NPD8392	Approved
0.6	Remote Similarity	NPD8391	Approved
0.6	Remote Similarity	NPD8390	Approved
0.6	Remote Similarity	NPD8269	Approved
0.6	Remote Similarity	NPD5983	Phase 2
0.5985	Remote Similarity	NPD8341	Approved
0.5985	Remote Similarity	NPD8340	Approved
0.5985	Remote Similarity	NPD8299	Approved
0.5985	Remote Similarity	NPD8342	Approved
0.5984	Remote Similarity	NPD5701	Approved
0.5983	Remote Similarity	NPD7902	Approved
0.5982	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6672	Approved
0.5982	Remote Similarity	NPD5737	Approved
0.5965	Remote Similarity	NPD5693	Phase 1
0.5965	Remote Similarity	NPD6411	Approved
0.5965	Remote Similarity	NPD7637	Suspended
0.595	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.595	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD4249	Approved
0.594	Remote Similarity	NPD6336	Discontinued
0.5935	Remote Similarity	NPD6011	Approved
0.5929	Remote Similarity	NPD6051	Approved
0.5877	Remote Similarity	NPD5207	Approved
0.5862	Remote Similarity	NPD6001	Approved
0.5862	Remote Similarity	NPD7748	Approved
0.5859	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD6084	Phase 2
0.5847	Remote Similarity	NPD6083	Phase 2
0.5833	Remote Similarity	NPD8080	Discontinued
0.5814	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD5695	Phase 3
0.581	Remote Similarity	NPD8039	Approved
0.5798	Remote Similarity	NPD5696	Approved
0.5794	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6080	Approved
0.5789	Remote Similarity	NPD6673	Approved
0.5789	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6101	Approved
0.5789	Remote Similarity	NPD7122	Discontinued
0.5789	Remote Similarity	NPD6904	Approved
0.5785	Remote Similarity	NPD5211	Phase 2
0.578	Remote Similarity	NPD1780	Approved
0.578	Remote Similarity	NPD1779	Approved
0.5776	Remote Similarity	NPD7799	Discontinued
0.5766	Remote Similarity	NPD5956	Approved
0.5758	Remote Similarity	NPD6921	Approved
0.5758	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.575	Remote Similarity	NPD4696	Approved
0.575	Remote Similarity	NPD5285	Approved
0.575	Remote Similarity	NPD5286	Approved
0.5736	Remote Similarity	NPD6274	Approved
0.5727	Remote Similarity	NPD6435	Approved
0.5725	Remote Similarity	NPD7101	Approved
0.5725	Remote Similarity	NPD7100	Approved
0.5714	Remote Similarity	NPD5363	Approved
0.5714	Remote Similarity	NPD7625	Phase 1
0.5714	Remote Similarity	NPD4755	Approved
0.5714	Remote Similarity	NPD4634	Approved
0.5691	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD5141	Approved
0.569	Remote Similarity	NPD7515	Phase 2
0.569	Remote Similarity	NPD6079	Approved
0.569	Remote Similarity	NPD6050	Approved
0.5688	Remote Similarity	NPD4820	Approved
0.5688	Remote Similarity	NPD4821	Approved
0.5688	Remote Similarity	NPD4819	Approved
0.5688	Remote Similarity	NPD4822	Approved
0.5688	Remote Similarity	NPD5790	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