NPASS Compound

Structure

NPC259042 OpenBabel07101719242D 24 26 0 0 1 0 0 0 0 0999 V2000 5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1472 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 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 9 1 0 0 0 0 2 9 1 0 0 0 0 3 10 2 0 0 0 0 4 11 2 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 7 16 1 0 0 0 0 8 19 1 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 14 1 0 0 0 0 12 6 1 1 0 0 0 12 15 1 0 0 0 0 13 19 1 1 0 0 0 14 23 1 6 0 0 0 15 8 1 1 0 0 0 15 24 1 0 0 0 0 16 19 1 6 0 0 0 16 20 1 0 0 0 0 17 21 2 0 0 0 0 17 23 1 0 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 19 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.18
Volume:	344.916
LogP:	2.21
LogD:	1.61
LogS:	-3.318
# Rotatable Bonds:	3
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.477
Synthetic Accessibility Score:	4.658
Fsp3:	0.684
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.756
MDCK Permeability:	4.878312392975204e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.198

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	77.59540557861328%
Volume Distribution (VD):	1.162
Pgp-substrate:	29.023256301879883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.091
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.533
CYP2C9-inhibitor:	0.269
CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.383
CYP3A4-substrate:	0.305

ADMET: Excretion

Clearance (CL):	6.698
Half-life (T1/2):	0.296

ADMET: Toxicity

hERG Blockers:	0.467
Human Hepatotoxicity (H-HT):	0.893
Drug-inuced Liver Injury (DILI):	0.892
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.933
Maximum Recommended Daily Dose:	0.982
Skin Sensitization:	0.302
Carcinogencity:	0.118
Eye Corrosion:	0.223
Eye Irritation:	0.258
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC259042

Natural Product ID:	NPC259042
*Common Name:**	1Alpha-Hydroxy-3Alpha-Isobutyryloxyisoalantolactone
IUPAC Name:	[(3aR,4aS,6R,8S,8aR,9aR)-8-hydroxy-8a-methyl-3,5-dimethylidene-2-oxo-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-6-yl] 2-methylpropanoate
Synonyms:
Standard InCHIKey:	DEXDLEUFCATLMY-XPYFFNBCSA-N
Standard InCHI:	InChI=1S/C19H26O5/c1-9(2)17(21)23-14-7-16(20)19(5)8-15-12(6-13(19)11(14)4)10(3)18(22)24-15/h9,12-16,20H,3-4,6-8H2,1-2,5H3/t12-,13+,14-,15-,16+,19-/m1/s1
SMILES:	CC(C)C(=O)O[C@@H]1C[C@@H]([C@]2(C)C[C@@H]3[C@H](C[C@H]2C1=C)C(=C)C(=O)O3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1912054
PubChem CID:	57399824
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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
NPO22238	Inula falconeri	Species	Asteraceae	Eukaryota	aerial parts	Tibet, China	n.a.	PMID[21924800]
NPO22238	Inula falconeri	Species	Asteraceae	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
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	9120.0	nM	PMID[480334]

☑ 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 NPC259042 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	204
0.1-0.2	1361
0.2-0.3	4542
0.3-0.4	8066
0.4-0.5	12950
0.5-0.6	5797
0.6-0.7	6681
0.7-0.8	2808
0.8-0.85	194
0.85-0.9	55
0.9-0.95	26
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC157686
0.9886	High Similarity	NPC225474
0.9886	High Similarity	NPC148000
0.9886	High Similarity	NPC469596
0.9778	High Similarity	NPC473963
0.9667	High Similarity	NPC473964
0.9667	High Similarity	NPC93245
0.9663	High Similarity	NPC24861
0.9565	High Similarity	NPC47024
0.9545	High Similarity	NPC475776
0.9457	High Similarity	NPC476806
0.9457	High Similarity	NPC476807
0.9451	High Similarity	NPC284518
0.9432	High Similarity	NPC116620
0.9348	High Similarity	NPC136781
0.9263	High Similarity	NPC61442
0.9255	High Similarity	NPC475958
0.9247	High Similarity	NPC216478
0.9239	High Similarity	NPC228766
0.9239	High Similarity	NPC165528
0.9213	High Similarity	NPC194642
0.9205	High Similarity	NPC175293
0.9205	High Similarity	NPC305029
0.9158	High Similarity	NPC164551
0.9091	High Similarity	NPC85698
0.9091	High Similarity	NPC185638
0.9053	High Similarity	NPC308824
0.9053	High Similarity	NPC242666
0.9022	High Similarity	NPC474841
0.9022	High Similarity	NPC473434
0.9022	High Similarity	NPC471446
0.8989	High Similarity	NPC181103
0.898	High Similarity	NPC78966
0.898	High Similarity	NPC284732
0.8936	High Similarity	NPC474921
0.8936	High Similarity	NPC474395
0.8925	High Similarity	NPC90014
0.8901	High Similarity	NPC153853
0.8889	High Similarity	NPC37628
0.8876	High Similarity	NPC9231
0.8866	High Similarity	NPC156681
0.8866	High Similarity	NPC72842
0.8866	High Similarity	NPC99510
0.8864	High Similarity	NPC97505
0.8854	High Similarity	NPC111292
0.88	High Similarity	NPC474243
0.8778	High Similarity	NPC470012
0.8763	High Similarity	NPC476081
0.8723	High Similarity	NPC56369
0.871	High Similarity	NPC147272
0.8667	High Similarity	NPC477920
0.8646	High Similarity	NPC38471
0.8646	High Similarity	NPC98837
0.8646	High Similarity	NPC20479
0.8646	High Similarity	NPC89099
0.8646	High Similarity	NPC162459
0.8646	High Similarity	NPC38296
0.8646	High Similarity	NPC28864
0.8636	High Similarity	NPC226988
0.8602	High Similarity	NPC233345
0.8602	High Similarity	NPC186363
0.8586	High Similarity	NPC283850
0.8571	High Similarity	NPC170615
0.8557	High Similarity	NPC293866
0.8542	High Similarity	NPC10864
0.8523	High Similarity	NPC209318
0.8523	High Similarity	NPC223330
0.8515	High Similarity	NPC275539
0.8515	High Similarity	NPC189075
0.8511	High Similarity	NPC199543
0.8495	Intermediate Similarity	NPC158488
0.8485	Intermediate Similarity	NPC120321
0.8478	Intermediate Similarity	NPC277771
0.8469	Intermediate Similarity	NPC46848
0.8454	Intermediate Similarity	NPC473155
0.8454	Intermediate Similarity	NPC16911
0.8454	Intermediate Similarity	NPC78427
0.8444	Intermediate Similarity	NPC470011
0.8438	Intermediate Similarity	NPC256227
0.8438	Intermediate Similarity	NPC29410
0.8438	Intermediate Similarity	NPC200054
0.8438	Intermediate Similarity	NPC134072
0.8438	Intermediate Similarity	NPC234993
0.8421	Intermediate Similarity	NPC57117
0.8416	Intermediate Similarity	NPC110496
0.8416	Intermediate Similarity	NPC187435
0.8416	Intermediate Similarity	NPC67321
0.8404	Intermediate Similarity	NPC72845
0.84	Intermediate Similarity	NPC477127
0.8384	Intermediate Similarity	NPC275990
0.8384	Intermediate Similarity	NPC304832
0.8384	Intermediate Similarity	NPC273005
0.8384	Intermediate Similarity	NPC76866
0.8384	Intermediate Similarity	NPC165250
0.8384	Intermediate Similarity	NPC214946
0.8384	Intermediate Similarity	NPC31058
0.8384	Intermediate Similarity	NPC286519
0.8384	Intermediate Similarity	NPC88203
0.8384	Intermediate Similarity	NPC246736
0.8384	Intermediate Similarity	NPC469606
0.8384	Intermediate Similarity	NPC148628
0.8367	Intermediate Similarity	NPC287676
0.8351	Intermediate Similarity	NPC111348
0.8351	Intermediate Similarity	NPC91695
0.8351	Intermediate Similarity	NPC70145
0.8333	Intermediate Similarity	NPC183012
0.8333	Intermediate Similarity	NPC98639
0.8317	Intermediate Similarity	NPC28791
0.8317	Intermediate Similarity	NPC295366
0.8317	Intermediate Similarity	NPC469607
0.8317	Intermediate Similarity	NPC34768
0.8316	Intermediate Similarity	NPC139692
0.83	Intermediate Similarity	NPC87927
0.83	Intermediate Similarity	NPC221421
0.8286	Intermediate Similarity	NPC477126
0.8283	Intermediate Similarity	NPC253886
0.8283	Intermediate Similarity	NPC121218
0.8283	Intermediate Similarity	NPC289148
0.8283	Intermediate Similarity	NPC52899
0.8283	Intermediate Similarity	NPC163963
0.8283	Intermediate Similarity	NPC471412
0.828	Intermediate Similarity	NPC477302
0.8269	Intermediate Similarity	NPC474846
0.8269	Intermediate Similarity	NPC469655
0.8269	Intermediate Similarity	NPC469656
0.8265	Intermediate Similarity	NPC474793
0.8265	Intermediate Similarity	NPC471038
0.8247	Intermediate Similarity	NPC202833
0.8242	Intermediate Similarity	NPC219011
0.8235	Intermediate Similarity	NPC251824
0.8235	Intermediate Similarity	NPC143609
0.8235	Intermediate Similarity	NPC86852
0.8235	Intermediate Similarity	NPC302788
0.8229	Intermediate Similarity	NPC250075
0.8229	Intermediate Similarity	NPC47853
0.8229	Intermediate Similarity	NPC3359
0.8229	Intermediate Similarity	NPC66581
0.8218	Intermediate Similarity	NPC301787
0.8218	Intermediate Similarity	NPC84928
0.8211	Intermediate Similarity	NPC130840
0.8211	Intermediate Similarity	NPC198054
0.82	Intermediate Similarity	NPC162973
0.82	Intermediate Similarity	NPC58329
0.8191	Intermediate Similarity	NPC206001
0.8191	Intermediate Similarity	NPC253618
0.8191	Intermediate Similarity	NPC218927
0.8191	Intermediate Similarity	NPC77001
0.819	Intermediate Similarity	NPC194951
0.819	Intermediate Similarity	NPC12046
0.8182	Intermediate Similarity	NPC476303
0.8182	Intermediate Similarity	NPC293890
0.8182	Intermediate Similarity	NPC471413
0.8182	Intermediate Similarity	NPC477656
0.8182	Intermediate Similarity	NPC267921
0.8182	Intermediate Similarity	NPC477655
0.8173	Intermediate Similarity	NPC124053
0.8173	Intermediate Similarity	NPC478209
0.8163	Intermediate Similarity	NPC474343
0.8163	Intermediate Similarity	NPC253586
0.8155	Intermediate Similarity	NPC218123
0.8155	Intermediate Similarity	NPC112895
0.8155	Intermediate Similarity	NPC273155
0.8155	Intermediate Similarity	NPC231278
0.8155	Intermediate Similarity	NPC306265
0.8155	Intermediate Similarity	NPC255082
0.8144	Intermediate Similarity	NPC210214
0.8144	Intermediate Similarity	NPC470232
0.8144	Intermediate Similarity	NPC276110
0.8137	Intermediate Similarity	NPC200957
0.8137	Intermediate Similarity	NPC37600
0.8137	Intermediate Similarity	NPC138908
0.8137	Intermediate Similarity	NPC222833
0.8137	Intermediate Similarity	NPC111952
0.8137	Intermediate Similarity	NPC478208
0.8132	Intermediate Similarity	NPC194637
0.8132	Intermediate Similarity	NPC243347
0.8125	Intermediate Similarity	NPC294263
0.8119	Intermediate Similarity	NPC254202
0.8119	Intermediate Similarity	NPC159533
0.8119	Intermediate Similarity	NPC476237
0.8119	Intermediate Similarity	NPC36688
0.8119	Intermediate Similarity	NPC96217
0.8119	Intermediate Similarity	NPC216114
0.8119	Intermediate Similarity	NPC139347
0.8113	Intermediate Similarity	NPC25909
0.8113	Intermediate Similarity	NPC157441
0.8111	Intermediate Similarity	NPC38642
0.8111	Intermediate Similarity	NPC475743
0.8111	Intermediate Similarity	NPC475951
0.8105	Intermediate Similarity	NPC54065
0.8105	Intermediate Similarity	NPC297474
0.81	Intermediate Similarity	NPC39683
0.81	Intermediate Similarity	NPC471790
0.81	Intermediate Similarity	NPC252614
0.81	Intermediate Similarity	NPC148279
0.81	Intermediate Similarity	NPC295276
0.81	Intermediate Similarity	NPC236585
0.8095	Intermediate Similarity	NPC94650
0.809	Intermediate Similarity	NPC263951
0.8085	Intermediate Similarity	NPC136879

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 NPC259042 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	1753
0.2-0.3	3782
0.3-0.4	2222
0.4-0.5	683
0.5-0.6	255
0.6-0.7	204
0.7-0.8	66
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
0.79	Intermediate Similarity	NPD4225	Approved
0.79	Intermediate Similarity	NPD7638	Approved
0.7822	Intermediate Similarity	NPD7640	Approved
0.7822	Intermediate Similarity	NPD7639	Approved
0.7736	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD8035	Phase 2
0.7653	Intermediate Similarity	NPD8034	Phase 2
0.7642	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD6686	Approved
0.74	Intermediate Similarity	NPD6399	Phase 3
0.7396	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7632	Discontinued
0.7297	Intermediate Similarity	NPD8133	Approved
0.729	Intermediate Similarity	NPD6008	Approved
0.7282	Intermediate Similarity	NPD7902	Approved
0.7263	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7115	Discovery
0.7222	Intermediate Similarity	NPD5697	Approved
0.7216	Intermediate Similarity	NPD1694	Approved
0.7157	Intermediate Similarity	NPD7748	Approved
0.7156	Intermediate Similarity	NPD6881	Approved
0.7156	Intermediate Similarity	NPD6899	Approved
0.7143	Intermediate Similarity	NPD3618	Phase 1
0.713	Intermediate Similarity	NPD7128	Approved
0.713	Intermediate Similarity	NPD6402	Approved
0.713	Intermediate Similarity	NPD6675	Approved
0.713	Intermediate Similarity	NPD5739	Approved
0.7129	Intermediate Similarity	NPD7515	Phase 2
0.7117	Intermediate Similarity	NPD6649	Approved
0.7117	Intermediate Similarity	NPD6650	Approved
0.7091	Intermediate Similarity	NPD6373	Approved
0.7091	Intermediate Similarity	NPD6013	Approved
0.7091	Intermediate Similarity	NPD6012	Approved
0.7091	Intermediate Similarity	NPD6372	Approved
0.7091	Intermediate Similarity	NPD6014	Approved
0.7087	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5701	Approved
0.7027	Intermediate Similarity	NPD7290	Approved
0.7027	Intermediate Similarity	NPD6883	Approved
0.7027	Intermediate Similarity	NPD7102	Approved
0.7021	Intermediate Similarity	NPD6115	Approved
0.7021	Intermediate Similarity	NPD6114	Approved
0.7021	Intermediate Similarity	NPD6697	Approved
0.7021	Intermediate Similarity	NPD6118	Approved
0.7	Intermediate Similarity	NPD6011	Approved
0.7	Intermediate Similarity	NPD7320	Approved
0.6991	Remote Similarity	NPD4632	Approved
0.699	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7900	Approved
0.6964	Remote Similarity	NPD6869	Approved
0.6964	Remote Similarity	NPD6847	Approved
0.6964	Remote Similarity	NPD8130	Phase 1
0.6964	Remote Similarity	NPD6617	Approved
0.6937	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6319	Approved
0.6917	Remote Similarity	NPD7507	Approved
0.6916	Remote Similarity	NPD5344	Discontinued
0.6915	Remote Similarity	NPD6116	Phase 1
0.6907	Remote Similarity	NPD3667	Approved
0.6903	Remote Similarity	NPD8297	Approved
0.6903	Remote Similarity	NPD6882	Approved
0.6885	Remote Similarity	NPD7319	Approved
0.6864	Remote Similarity	NPD6921	Approved
0.6863	Remote Similarity	NPD46	Approved
0.6863	Remote Similarity	NPD6698	Approved
0.6852	Remote Similarity	NPD5211	Phase 2
0.6833	Remote Similarity	NPD7492	Approved
0.6822	Remote Similarity	NPD5285	Approved
0.6822	Remote Similarity	NPD5286	Approved
0.6822	Remote Similarity	NPD4696	Approved
0.681	Remote Similarity	NPD6009	Approved
0.6809	Remote Similarity	NPD6117	Approved
0.6796	Remote Similarity	NPD7637	Suspended
0.6796	Remote Similarity	NPD6079	Approved
0.6792	Remote Similarity	NPD6084	Phase 2
0.6792	Remote Similarity	NPD4755	Approved
0.6792	Remote Similarity	NPD6083	Phase 2
0.678	Remote Similarity	NPD6054	Approved
0.6777	Remote Similarity	NPD6616	Approved
0.6768	Remote Similarity	NPD4786	Approved
0.6765	Remote Similarity	NPD1695	Approved
0.6765	Remote Similarity	NPD5328	Approved
0.6757	Remote Similarity	NPD6412	Phase 2
0.6754	Remote Similarity	NPD6053	Discontinued
0.6752	Remote Similarity	NPD7327	Approved
0.6752	Remote Similarity	NPD7328	Approved
0.6731	Remote Similarity	NPD5778	Approved
0.6731	Remote Similarity	NPD5779	Approved
0.6731	Remote Similarity	NPD4202	Approved
0.6729	Remote Similarity	NPD5696	Approved
0.6727	Remote Similarity	NPD5141	Approved
0.6726	Remote Similarity	NPD6371	Approved
0.6724	Remote Similarity	NPD6274	Approved
0.6723	Remote Similarity	NPD5983	Phase 2
0.6723	Remote Similarity	NPD6015	Approved
0.6723	Remote Similarity	NPD6016	Approved
0.6721	Remote Similarity	NPD7078	Approved
0.6698	Remote Similarity	NPD5222	Approved
0.6698	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5221	Approved
0.6698	Remote Similarity	NPD4697	Phase 3
0.6697	Remote Similarity	NPD5225	Approved
0.6697	Remote Similarity	NPD5224	Approved
0.6697	Remote Similarity	NPD5226	Approved
0.6697	Remote Similarity	NPD4633	Approved
0.6695	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7736	Approved
0.6639	Remote Similarity	NPD6059	Approved
0.6636	Remote Similarity	NPD5175	Approved
0.6636	Remote Similarity	NPD5174	Approved
0.6636	Remote Similarity	NPD5173	Approved
0.6635	Remote Similarity	NPD6411	Approved
0.6634	Remote Similarity	NPD5330	Approved
0.6634	Remote Similarity	NPD7146	Approved
0.6634	Remote Similarity	NPD6684	Approved
0.6634	Remote Similarity	NPD7521	Approved
0.6634	Remote Similarity	NPD6409	Approved
0.6634	Remote Similarity	NPD7334	Approved
0.6612	Remote Similarity	NPD8328	Phase 3
0.6612	Remote Similarity	NPD7604	Phase 2
0.6607	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5223	Approved
0.6604	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5695	Phase 3
0.66	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.66	Remote Similarity	NPD3666	Approved
0.66	Remote Similarity	NPD3665	Phase 1
0.66	Remote Similarity	NPD3133	Approved
0.6596	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD8293	Discontinued
0.6583	Remote Similarity	NPD8033	Approved
0.6583	Remote Similarity	NPD8379	Approved
0.6583	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD8335	Approved
0.6583	Remote Similarity	NPD8380	Approved
0.6583	Remote Similarity	NPD8378	Approved
0.6583	Remote Similarity	NPD8296	Approved
0.6579	Remote Similarity	NPD4634	Approved
0.6569	Remote Similarity	NPD3573	Approved
0.6555	Remote Similarity	NPD7101	Approved
0.6555	Remote Similarity	NPD7100	Approved
0.6538	Remote Similarity	NPD5785	Approved
0.6535	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD3703	Phase 2
0.6525	Remote Similarity	NPD6317	Approved
0.6505	Remote Similarity	NPD6672	Approved
0.6505	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6903	Approved
0.6505	Remote Similarity	NPD5737	Approved
0.6504	Remote Similarity	NPD6336	Discontinued
0.65	Remote Similarity	NPD8294	Approved
0.65	Remote Similarity	NPD6695	Phase 3
0.65	Remote Similarity	NPD8377	Approved
0.6476	Remote Similarity	NPD5693	Phase 1
0.6471	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6314	Approved
0.6471	Remote Similarity	NPD6335	Approved
0.6471	Remote Similarity	NPD6313	Approved
0.6449	Remote Similarity	NPD4629	Approved
0.6449	Remote Similarity	NPD5210	Approved
0.6446	Remote Similarity	NPD7503	Approved
0.6446	Remote Similarity	NPD8513	Phase 3
0.6446	Remote Similarity	NPD8515	Approved
0.6446	Remote Similarity	NPD8517	Approved
0.6446	Remote Similarity	NPD8516	Approved
0.6442	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD4753	Phase 2
0.6442	Remote Similarity	NPD6101	Approved
0.6441	Remote Similarity	NPD6868	Approved
0.6436	Remote Similarity	NPD3668	Phase 3
0.6404	Remote Similarity	NPD4729	Approved
0.6404	Remote Similarity	NPD4730	Approved
0.6404	Remote Similarity	NPD5128	Approved
0.6381	Remote Similarity	NPD7838	Discovery
0.6379	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD4768	Approved
0.6372	Remote Similarity	NPD4767	Approved
0.6364	Remote Similarity	NPD4695	Discontinued
0.6364	Remote Similarity	NPD7525	Registered
0.6355	Remote Similarity	NPD6001	Approved
0.6344	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6067	Discontinued
0.6339	Remote Similarity	NPD4754	Approved
0.6321	Remote Similarity	NPD5284	Approved
0.6321	Remote Similarity	NPD5281	Approved
0.6311	Remote Similarity	NPD6909	Approved
0.6311	Remote Similarity	NPD4249	Approved
0.6311	Remote Similarity	NPD6908	Approved
0.6306	Remote Similarity	NPD1700	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