NPASS Compound

Structure

CID301666 OpenBabel06191716112D 33 38 0 0 1 0 0 0 0 0999 V2000 -0.0649 -2.7440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7148 -1.7077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7355 -4.0561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9736 -0.9994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6977 -2.3022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6880 -3.1041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0071 -1.9690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2118 -3.1876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2118 -0.5484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4499 -2.7477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3592 -1.5347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4499 -0.1085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0004 -1.9768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8573 -1.7811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7355 -1.4281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4480 -1.9645 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1029 -1.5246 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7355 -3.1876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9736 -2.7477 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4974 -1.8680 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2118 -1.4281 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4974 -2.7477 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2009 -1.0958 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8577 -0.1959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9736 -1.8680 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4499 -1.8680 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6880 -1.4281 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2392 -0.9886 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6880 -0.5484 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2496 -1.4337 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2496 -3.1820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3803 0.4591 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 3 18 2 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 11 1 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 12 2 0 0 0 0 9 21 1 0 0 0 0 10 26 1 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 15 20 1 0 0 0 0 15 25 1 0 0 0 0 16 1 1 6 0 0 0 16 17 1 0 0 0 0 17 2 1 1 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 25 1 6 0 0 0 20 22 1 0 0 0 0 20 30 1 1 0 0 0 21 25 1 6 0 0 0 21 26 1 0 0 0 0 22 31 1 6 0 0 0 23 28 1 6 0 0 0 23 29 1 0 0 0 0 24 28 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 25 4 1 6 0 0 0 26 27 1 1 0 0 0 27 29 1 1 0 0 0 28 11 1 1 0 0 0 29 12 1 1 0 0 0 29 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.31
Volume:	486.053
LogP:	4.451
LogD:	4.082
LogS:	-5.346
# Rotatable Bonds:	0
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.397
Synthetic Accessibility Score:	6.786
Fsp3:	0.828
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.289
MDCK Permeability:	1.3774814760836307e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.978
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.732

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.078
Plasma Protein Binding (PPB):	88.87257385253906%
Volume Distribution (VD):	1.148
Pgp-substrate:	7.069113731384277%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.706
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.824
CYP2C9-inhibitor:	0.115
CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.938
CYP3A4-substrate:	0.543

ADMET: Excretion

Clearance (CL):	4.674
Half-life (T1/2):	0.066

ADMET: Toxicity

hERG Blockers:	0.381
Human Hepatotoxicity (H-HT):	0.548
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.853
Maximum Recommended Daily Dose:	0.264
Skin Sensitization:	0.076
Carcinogencity:	0.082
Eye Corrosion:	0.012
Eye Irritation:	0.012
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC301666

Natural Product ID:	NPC301666
*Common Name:**	Ilekudinol A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ATPPQNYORHPCJE-OUZPOPPESA-N
Standard InCHI:	InChI=1S/C29H42O4/c1-16-7-11-28-14-13-27(6)26(5)10-8-19-18(3)22(31)20(30)15-25(19,4)21(26)9-12-29(27,33-24(28)32)23(28)17(16)2/h9,12,16-17,19-23,30-31H,3,7-8,10-11,13-15H2,1-2,4-6H3/t16-,17+,19+,20-,21-,22-,23-,25+,26-,27+,28+,29+/m1/s1
SMILES:	C[C@@H]1CC[C@@]23[C@@H]([C@H]1C)[C@]1(C=C[C@H]4[C@@]([C@@]1(CC2)C)(C)CC[C@@H]1[C@]4(C)C[C@@H](O)[C@@H](C1=C)O)OC3=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL492155
PubChem CID:	10718549
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO33035	ilex kudincha	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425145]
NPO33035	ilex kudincha	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479318]
NPO20508	Ilex kaushue	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20508	Ilex kaushue	Species	Aquifoliaceae	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
Others	2

Activity Type	# Activity
CELL-LINE	2
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3065	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase 1	Rattus norvegicus	IC50	=	154000.0	nM	PMID[475942]
NPT20950	CELL-LINE	Erythrocyte	n.a.	Activity	=	0.248	mg/ml	PMID[475943]
NPT20950	CELL-LINE	Erythrocyte	n.a.	Activity	=	0.658	mg/ml	PMID[475943]

☑ 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 NPC301666 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	1209
0.2-0.3	3805
0.3-0.4	8751
0.4-0.5	13002
0.5-0.6	6312
0.6-0.7	5510
0.7-0.8	3477
0.8-0.85	363
0.85-0.9	57
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9293	High Similarity	NPC235142
0.9286	High Similarity	NPC234617
0.9286	High Similarity	NPC124703
0.899	High Similarity	NPC255589
0.899	High Similarity	NPC259788
0.8911	High Similarity	NPC233012
0.8911	High Similarity	NPC54909
0.8889	High Similarity	NPC158371
0.8889	High Similarity	NPC207922
0.8889	High Similarity	NPC259733
0.8878	High Similarity	NPC87095
0.8878	High Similarity	NPC91010
0.88	High Similarity	NPC9613
0.88	High Similarity	NPC247139
0.88	High Similarity	NPC10057
0.8788	High Similarity	NPC290481
0.8788	High Similarity	NPC53565
0.8788	High Similarity	NPC96916
0.8776	High Similarity	NPC63118
0.8776	High Similarity	NPC49776
0.8776	High Similarity	NPC474436
0.8776	High Similarity	NPC307335
0.8776	High Similarity	NPC74855
0.8776	High Similarity	NPC275809
0.8776	High Similarity	NPC136313
0.87	High Similarity	NPC230151
0.87	High Similarity	NPC327179
0.87	High Similarity	NPC116457
0.87	High Similarity	NPC73004
0.87	High Similarity	NPC173744
0.87	High Similarity	NPC204961
0.8673	High Similarity	NPC472149
0.8673	High Similarity	NPC300351
0.8673	High Similarity	NPC25299
0.8673	High Similarity	NPC52021
0.8673	High Similarity	NPC306541
0.8673	High Similarity	NPC84319
0.8673	High Similarity	NPC71074
0.8673	High Similarity	NPC235884
0.8627	High Similarity	NPC35239
0.8624	High Similarity	NPC67259
0.8624	High Similarity	NPC147912
0.8614	High Similarity	NPC43686
0.8614	High Similarity	NPC312075
0.8614	High Similarity	NPC203343
0.86	High Similarity	NPC198245
0.8586	High Similarity	NPC474806
0.8586	High Similarity	NPC118519
0.8586	High Similarity	NPC158059
0.8586	High Similarity	NPC133579
0.8586	High Similarity	NPC202728
0.8571	High Similarity	NPC80566
0.8571	High Similarity	NPC474728
0.8571	High Similarity	NPC49320
0.8544	High Similarity	NPC256247
0.8529	High Similarity	NPC271614
0.8529	High Similarity	NPC29765
0.8529	High Similarity	NPC111214
0.8529	High Similarity	NPC174663
0.8529	High Similarity	NPC188833
0.8529	High Similarity	NPC164349
0.85	High Similarity	NPC299996
0.85	High Similarity	NPC88116
0.85	High Similarity	NPC263548
0.85	High Similarity	NPC188102
0.85	High Similarity	NPC191412
0.85	High Similarity	NPC282395
0.85	High Similarity	NPC231063
0.85	High Similarity	NPC20235
0.85	High Similarity	NPC145667
0.85	High Similarity	NPC296164
0.85	High Similarity	NPC32407
0.85	High Similarity	NPC6818
0.85	High Similarity	NPC114159
0.8491	Intermediate Similarity	NPC255387
0.8491	Intermediate Similarity	NPC131665
0.8485	Intermediate Similarity	NPC285184
0.8485	Intermediate Similarity	NPC77099
0.8485	Intermediate Similarity	NPC60755
0.8485	Intermediate Similarity	NPC470590
0.8485	Intermediate Similarity	NPC187722
0.8469	Intermediate Similarity	NPC143232
0.8469	Intermediate Similarity	NPC198664
0.8469	Intermediate Similarity	NPC274330
0.8469	Intermediate Similarity	NPC470588
0.8462	Intermediate Similarity	NPC273668
0.8447	Intermediate Similarity	NPC474190
0.8431	Intermediate Similarity	NPC106112
0.8431	Intermediate Similarity	NPC175351
0.8431	Intermediate Similarity	NPC121402
0.8431	Intermediate Similarity	NPC151681
0.8431	Intermediate Similarity	NPC132753
0.8431	Intermediate Similarity	NPC261935
0.8431	Intermediate Similarity	NPC224356
0.8416	Intermediate Similarity	NPC32118
0.8411	Intermediate Similarity	NPC275539
0.8411	Intermediate Similarity	NPC189075
0.84	Intermediate Similarity	NPC229281
0.84	Intermediate Similarity	NPC86368
0.84	Intermediate Similarity	NPC169343
0.8384	Intermediate Similarity	NPC7260
0.8384	Intermediate Similarity	NPC198818
0.8384	Intermediate Similarity	NPC18872
0.8384	Intermediate Similarity	NPC120968
0.8384	Intermediate Similarity	NPC113989
0.8384	Intermediate Similarity	NPC120840
0.8384	Intermediate Similarity	NPC227467
0.8384	Intermediate Similarity	NPC470589
0.8384	Intermediate Similarity	NPC290614
0.8384	Intermediate Similarity	NPC291028
0.8384	Intermediate Similarity	NPC111110
0.8384	Intermediate Similarity	NPC126369
0.8384	Intermediate Similarity	NPC273621
0.8384	Intermediate Similarity	NPC76286
0.8384	Intermediate Similarity	NPC210037
0.8384	Intermediate Similarity	NPC477872
0.8381	Intermediate Similarity	NPC36688
0.8378	Intermediate Similarity	NPC64318
0.8367	Intermediate Similarity	NPC246708
0.8367	Intermediate Similarity	NPC474512
0.8367	Intermediate Similarity	NPC290690
0.8367	Intermediate Similarity	NPC470629
0.8367	Intermediate Similarity	NPC182797
0.8367	Intermediate Similarity	NPC17733
0.8367	Intermediate Similarity	NPC473242
0.8367	Intermediate Similarity	NPC40552
0.8367	Intermediate Similarity	NPC52169
0.8367	Intermediate Similarity	NPC181225
0.8365	Intermediate Similarity	NPC303559
0.835	Intermediate Similarity	NPC478056
0.8333	Intermediate Similarity	NPC472216
0.8333	Intermediate Similarity	NPC25848
0.8333	Intermediate Similarity	NPC201657
0.8333	Intermediate Similarity	NPC305464
0.8333	Intermediate Similarity	NPC154526
0.8333	Intermediate Similarity	NPC284828
0.8333	Intermediate Similarity	NPC157113
0.8333	Intermediate Similarity	NPC62516
0.8333	Intermediate Similarity	NPC173905
0.8333	Intermediate Similarity	NPC472362
0.8333	Intermediate Similarity	NPC132824
0.8333	Intermediate Similarity	NPC5475
0.8333	Intermediate Similarity	NPC307282
0.8333	Intermediate Similarity	NPC19376
0.8333	Intermediate Similarity	NPC472363
0.8333	Intermediate Similarity	NPC235053
0.8318	Intermediate Similarity	NPC110496
0.8318	Intermediate Similarity	NPC67321
0.8318	Intermediate Similarity	NPC187435
0.8318	Intermediate Similarity	NPC230541
0.8318	Intermediate Similarity	NPC475176
0.8317	Intermediate Similarity	NPC60692
0.8304	Intermediate Similarity	NPC470493
0.8304	Intermediate Similarity	NPC470492
0.8304	Intermediate Similarity	NPC476965
0.8304	Intermediate Similarity	NPC473590
0.8304	Intermediate Similarity	NPC167606
0.8304	Intermediate Similarity	NPC286528
0.8304	Intermediate Similarity	NPC20302
0.8304	Intermediate Similarity	NPC183580
0.8304	Intermediate Similarity	NPC312824
0.8304	Intermediate Similarity	NPC470959
0.8304	Intermediate Similarity	NPC140055
0.8302	Intermediate Similarity	NPC284865
0.83	Intermediate Similarity	NPC38754
0.83	Intermediate Similarity	NPC49420
0.83	Intermediate Similarity	NPC105189
0.8288	Intermediate Similarity	NPC110861
0.8286	Intermediate Similarity	NPC283343
0.8286	Intermediate Similarity	NPC258547
0.8286	Intermediate Similarity	NPC476890
0.8283	Intermediate Similarity	NPC290972
0.8283	Intermediate Similarity	NPC64872
0.8283	Intermediate Similarity	NPC25906
0.8283	Intermediate Similarity	NPC293048
0.8283	Intermediate Similarity	NPC59263
0.8283	Intermediate Similarity	NPC130520
0.8283	Intermediate Similarity	NPC270768
0.8283	Intermediate Similarity	NPC30522
0.8283	Intermediate Similarity	NPC281524
0.8283	Intermediate Similarity	NPC121798
0.8283	Intermediate Similarity	NPC61543
0.8283	Intermediate Similarity	NPC263393
0.8283	Intermediate Similarity	NPC225585
0.8283	Intermediate Similarity	NPC127689
0.8283	Intermediate Similarity	NPC234346
0.8269	Intermediate Similarity	NPC473176
0.8265	Intermediate Similarity	NPC171203
0.8265	Intermediate Similarity	NPC130577
0.8265	Intermediate Similarity	NPC68160
0.8265	Intermediate Similarity	NPC98442
0.8265	Intermediate Similarity	NPC142415
0.8265	Intermediate Similarity	NPC88716
0.8265	Intermediate Similarity	NPC51700
0.8265	Intermediate Similarity	NPC18064
0.8265	Intermediate Similarity	NPC102683
0.8265	Intermediate Similarity	NPC242468
0.8265	Intermediate Similarity	NPC307426
0.8265	Intermediate Similarity	NPC293564
0.8252	Intermediate Similarity	NPC187933

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 NPC301666 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1361
0.2-0.3	3522
0.3-0.4	2650
0.4-0.5	900
0.5-0.6	263
0.6-0.7	204
0.7-0.8	71
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8304	Intermediate Similarity	NPD7115	Discovery
0.8137	Intermediate Similarity	NPD7748	Approved
0.8119	Intermediate Similarity	NPD7515	Phase 2
0.8077	Intermediate Similarity	NPD7902	Approved
0.8	Intermediate Similarity	NPD4225	Approved
0.7925	Intermediate Similarity	NPD7640	Approved
0.7925	Intermediate Similarity	NPD7639	Approved
0.783	Intermediate Similarity	NPD7638	Approved
0.7788	Intermediate Similarity	NPD7900	Approved
0.7788	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6399	Phase 3
0.7596	Intermediate Similarity	NPD8034	Phase 2
0.7596	Intermediate Similarity	NPD8035	Phase 2
0.7525	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1694	Approved
0.7304	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7632	Discontinued
0.7282	Intermediate Similarity	NPD3618	Phase 1
0.7281	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD6899	Approved
0.7281	Intermediate Similarity	NPD6881	Approved
0.7273	Intermediate Similarity	NPD8513	Phase 3
0.7273	Intermediate Similarity	NPD8515	Approved
0.7273	Intermediate Similarity	NPD8516	Approved
0.7273	Intermediate Similarity	NPD7645	Phase 2
0.7273	Intermediate Similarity	NPD8517	Approved
0.7257	Intermediate Similarity	NPD7128	Approved
0.7257	Intermediate Similarity	NPD6675	Approved
0.7257	Intermediate Similarity	NPD6402	Approved
0.7257	Intermediate Similarity	NPD5739	Approved
0.7255	Intermediate Similarity	NPD4786	Approved
0.7241	Intermediate Similarity	NPD6649	Approved
0.7241	Intermediate Similarity	NPD6650	Approved
0.7228	Intermediate Similarity	NPD3667	Approved
0.7217	Intermediate Similarity	NPD6372	Approved
0.7217	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD6373	Approved
0.7193	Intermediate Similarity	NPD5697	Approved
0.7179	Intermediate Similarity	NPD8297	Approved
0.7177	Intermediate Similarity	NPD7507	Approved
0.7155	Intermediate Similarity	NPD7290	Approved
0.7155	Intermediate Similarity	NPD6883	Approved
0.7155	Intermediate Similarity	NPD7102	Approved
0.7143	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7320	Approved
0.713	Intermediate Similarity	NPD6686	Approved
0.713	Intermediate Similarity	NPD6011	Approved
0.7119	Intermediate Similarity	NPD8133	Approved
0.7103	Intermediate Similarity	NPD6411	Approved
0.7103	Intermediate Similarity	NPD6079	Approved
0.7094	Intermediate Similarity	NPD8130	Phase 1
0.7094	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6869	Approved
0.7094	Intermediate Similarity	NPD6847	Approved
0.7094	Intermediate Similarity	NPD6617	Approved
0.7091	Intermediate Similarity	NPD6084	Phase 2
0.7091	Intermediate Similarity	NPD6083	Phase 2
0.7083	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5328	Approved
0.7069	Intermediate Similarity	NPD6012	Approved
0.7069	Intermediate Similarity	NPD6014	Approved
0.7069	Intermediate Similarity	NPD6013	Approved
0.7064	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3573	Approved
0.7043	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5701	Approved
0.7037	Intermediate Similarity	NPD5779	Approved
0.7037	Intermediate Similarity	NPD5778	Approved
0.7034	Intermediate Similarity	NPD6882	Approved
0.7016	Intermediate Similarity	NPD8328	Phase 3
0.7008	Intermediate Similarity	NPD7319	Approved
0.6992	Remote Similarity	NPD8033	Approved
0.6991	Remote Similarity	NPD5211	Phase 2
0.6975	Remote Similarity	NPD4632	Approved
0.6967	Remote Similarity	NPD7516	Approved
0.6957	Remote Similarity	NPD6008	Approved
0.6952	Remote Similarity	NPD6409	Approved
0.6952	Remote Similarity	NPD7146	Approved
0.6952	Remote Similarity	NPD7521	Approved
0.6952	Remote Similarity	NPD5330	Approved
0.6952	Remote Similarity	NPD6684	Approved
0.6952	Remote Similarity	NPD7334	Approved
0.6949	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6051	Approved
0.6916	Remote Similarity	NPD6101	Approved
0.6916	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD8294	Approved
0.6911	Remote Similarity	NPD8377	Approved
0.6903	Remote Similarity	NPD5344	Discontinued
0.6885	Remote Similarity	NPD7327	Approved
0.6885	Remote Similarity	NPD7328	Approved
0.6881	Remote Similarity	NPD4202	Approved
0.6875	Remote Similarity	NPD5696	Approved
0.687	Remote Similarity	NPD5141	Approved
0.6863	Remote Similarity	NPD7525	Registered
0.6855	Remote Similarity	NPD7503	Approved
0.6855	Remote Similarity	NPD8379	Approved
0.6855	Remote Similarity	NPD8296	Approved
0.6855	Remote Similarity	NPD8335	Approved
0.6855	Remote Similarity	NPD8378	Approved
0.6855	Remote Similarity	NPD8380	Approved
0.6852	Remote Similarity	NPD5785	Approved
0.6847	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5222	Approved
0.6847	Remote Similarity	NPD5221	Approved
0.6847	Remote Similarity	NPD4697	Phase 3
0.6822	Remote Similarity	NPD5737	Approved
0.6822	Remote Similarity	NPD6903	Approved
0.6822	Remote Similarity	NPD6672	Approved
0.6814	Remote Similarity	NPD5285	Approved
0.6814	Remote Similarity	NPD5286	Approved
0.6814	Remote Similarity	NPD4696	Approved
0.6797	Remote Similarity	NPD7736	Approved
0.6792	Remote Similarity	NPD4519	Discontinued
0.6792	Remote Similarity	NPD4623	Approved
0.6789	Remote Similarity	NPD7637	Suspended
0.6789	Remote Similarity	NPD5693	Phase 1
0.6786	Remote Similarity	NPD4755	Approved
0.6786	Remote Similarity	NPD5173	Approved
0.6774	Remote Similarity	NPD6319	Approved
0.6762	Remote Similarity	NPD3665	Phase 1
0.6762	Remote Similarity	NPD3666	Approved
0.6762	Remote Similarity	NPD3668	Phase 3
0.6762	Remote Similarity	NPD3133	Approved
0.6757	Remote Similarity	NPD5695	Phase 3
0.6754	Remote Similarity	NPD5223	Approved
0.6752	Remote Similarity	NPD6412	Phase 2
0.6748	Remote Similarity	NPD6335	Approved
0.6721	Remote Similarity	NPD6868	Approved
0.672	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD8074	Phase 3
0.6696	Remote Similarity	NPD5225	Approved
0.6696	Remote Similarity	NPD5224	Approved
0.6696	Remote Similarity	NPD5226	Approved
0.6696	Remote Similarity	NPD4633	Approved
0.6694	Remote Similarity	NPD7100	Approved
0.6694	Remote Similarity	NPD7101	Approved
0.6693	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD7154	Phase 3
0.6641	Remote Similarity	NPD6616	Approved
0.664	Remote Similarity	NPD6054	Approved
0.6638	Remote Similarity	NPD5174	Approved
0.6638	Remote Similarity	NPD5175	Approved
0.6636	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6098	Approved
0.6636	Remote Similarity	NPD5284	Approved
0.6636	Remote Similarity	NPD5281	Approved
0.6634	Remote Similarity	NPD6117	Approved
0.6614	Remote Similarity	NPD7604	Phase 2
0.6613	Remote Similarity	NPD6313	Approved
0.6613	Remote Similarity	NPD6314	Approved
0.6612	Remote Similarity	NPD6053	Discontinued
0.6607	Remote Similarity	NPD5210	Approved
0.6607	Remote Similarity	NPD4629	Approved
0.6607	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4753	Phase 2
0.6606	Remote Similarity	NPD6904	Approved
0.6606	Remote Similarity	NPD6673	Approved
0.6606	Remote Similarity	NPD6080	Approved
0.6589	Remote Similarity	NPD7078	Approved
0.6587	Remote Similarity	NPD5983	Phase 2
0.6587	Remote Similarity	NPD6921	Approved
0.6585	Remote Similarity	NPD6274	Approved
0.6583	Remote Similarity	NPD4634	Approved
0.6583	Remote Similarity	NPD6371	Approved
0.6574	Remote Similarity	NPD7524	Approved
0.6571	Remote Similarity	NPD4269	Approved
0.6571	Remote Similarity	NPD4270	Approved
0.6569	Remote Similarity	NPD6116	Phase 1
0.6545	Remote Similarity	NPD46	Approved
0.6545	Remote Similarity	NPD6698	Approved
0.6545	Remote Similarity	NPD5207	Approved
0.6535	Remote Similarity	NPD8039	Approved
0.6535	Remote Similarity	NPD6942	Approved
0.6535	Remote Similarity	NPD7339	Approved
0.6535	Remote Similarity	NPD6370	Approved
0.6522	Remote Similarity	NPD6648	Approved
0.6512	Remote Similarity	NPD6336	Discontinued
0.6508	Remote Similarity	NPD6059	Approved
0.6505	Remote Similarity	NPD6697	Approved
0.6505	Remote Similarity	NPD6115	Approved
0.6505	Remote Similarity	NPD6118	Approved
0.6505	Remote Similarity	NPD6114	Approved
0.6496	Remote Similarity	NPD4754	Approved
0.6481	Remote Similarity	NPD5786	Approved
0.6476	Remote Similarity	NPD5369	Approved
0.6471	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD4159	Approved
0.6462	Remote Similarity	NPD8293	Discontinued
0.6457	Remote Similarity	NPD6908	Approved
0.6457	Remote Similarity	NPD6015	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