NPASS Compound

Structure

NPC471214 OpenBabel07101718292D 31 33 0 0 1 0 0 0 0 0999 V2000 6.1962 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6962 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6962 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6962 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 6 1 0 0 0 0 2 7 2 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 13 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 29 1 0 0 0 0 10 17 2 0 0 0 0 11 17 1 0 0 0 0 11 22 1 0 0 0 0 12 8 1 6 0 0 0 12 14 1 0 0 0 0 12 30 1 0 0 0 0 13 20 1 0 0 0 0 13 23 2 0 0 0 0 14 15 1 0 0 0 0 14 24 1 1 0 0 0 15 16 1 0 0 0 0 15 25 1 6 0 0 0 16 18 1 0 0 0 0 16 26 1 1 0 0 0 17 31 1 0 0 0 0 18 30 1 0 0 0 0 18 31 1 6 0 0 0 19 20 1 0 0 0 0 19 27 2 0 0 0 0 19 29 1 0 0 0 0 20 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.13
Volume:	409.681
LogP:	0.282
LogD:	-0.003
LogS:	-1.655
# Rotatable Bonds:	7
TPSA:	183.21
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.168
Synthetic Accessibility Score:	4.416
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.181
MDCK Permeability:	6.395926175173372e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.662
Human Intestinal Absorption (HIA):	0.123
20% Bioavailability (F20%):	0.37
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.204
Plasma Protein Binding (PPB):	54.37779998779297%
Volume Distribution (VD):	0.328
Pgp-substrate:	38.26926803588867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.222
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.191
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.108

ADMET: Excretion

Clearance (CL):	1.495
Half-life (T1/2):	0.95

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.081
Drug-inuced Liver Injury (DILI):	0.765
AMES Toxicity:	0.607
Rat Oral Acute Toxicity:	0.107
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.042
Carcinogencity:	0.487
Eye Corrosion:	0.003
Eye Irritation:	0.08
Respiratory Toxicity:	0.016

Download Data

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

Natural Product: NPC471214

Natural Product ID:	NPC471214
*Common Name:**	Idescarpin
IUPAC Name:	[3-hydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl 1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate
Synonyms:
Standard InCHIKey:	LNCXAOPUEFHMOC-ZTWYEDEXSA-N
Standard InCHI:	InChI=1S/C20H24O11/c21-8-12-14(24)15(25)16(26)18(30-12)31-17-10(4-3-5-11(17)22)9-29-19(27)20(28)7-2-1-6-13(20)23/h2-5,7,12,14-16,18,21-22,24-26,28H,1,6,8-9H2/t12-,14-,15+,16-,18+,20?/m1/s1
SMILES:	C1CC(=O)C(C=C1)(C(=O)OCC2=C(C(=CC=C2)O)OC3C(C(C(C(O3)CO)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2387741
PubChem CID:	21591971
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO27632	Idesia polycarpa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23628332]
NPO27632	Idesia polycarpa	Species	Salicaceae	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
NPT520	Cell Line	3T3-L1	Mus musculus	IC50	=	23200.0	nM	PMID[503779]

☑ 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 NPC471214 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	349
0.1-0.2	1521
0.2-0.3	3951
0.3-0.4	9154
0.4-0.5	9248
0.5-0.6	5075
0.6-0.7	7387
0.7-0.8	5573
0.8-0.85	413
0.85-0.9	23
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9514	High Similarity	NPC474422
0.9342	High Similarity	NPC71780
0.8896	High Similarity	NPC476026
0.8896	High Similarity	NPC474441
0.8896	High Similarity	NPC474398
0.8896	High Similarity	NPC474401
0.8811	High Similarity	NPC87696
0.875	High Similarity	NPC131874
0.8732	High Similarity	NPC166168
0.8718	High Similarity	NPC231475
0.8718	High Similarity	NPC57072
0.8667	High Similarity	NPC199928
0.8662	High Similarity	NPC44507
0.8658	High Similarity	NPC232228
0.8658	High Similarity	NPC292443
0.8654	High Similarity	NPC223335
0.8654	High Similarity	NPC40920
0.8618	High Similarity	NPC22137
0.8618	High Similarity	NPC478242
0.8616	High Similarity	NPC475183
0.8608	High Similarity	NPC217950
0.8599	High Similarity	NPC469654
0.859	High Similarity	NPC163635
0.8553	High Similarity	NPC116229
0.8528	High Similarity	NPC153755
0.8519	High Similarity	NPC67424
0.8514	High Similarity	NPC202700
0.8509	High Similarity	NPC197285
0.8509	High Similarity	NPC21100
0.8509	High Similarity	NPC475174
0.8487	Intermediate Similarity	NPC41844
0.8476	Intermediate Similarity	NPC4390
0.8471	Intermediate Similarity	NPC478055
0.8467	Intermediate Similarity	NPC478239
0.8466	Intermediate Similarity	NPC20505
0.8466	Intermediate Similarity	NPC265214
0.8466	Intermediate Similarity	NPC116864
0.8466	Intermediate Similarity	NPC244776
0.8466	Intermediate Similarity	NPC155763
0.8466	Intermediate Similarity	NPC235260
0.8457	Intermediate Similarity	NPC116745
0.8457	Intermediate Similarity	NPC128403
0.8456	Intermediate Similarity	NPC186406
0.8447	Intermediate Similarity	NPC472131
0.8447	Intermediate Similarity	NPC280923
0.8447	Intermediate Similarity	NPC277205
0.8447	Intermediate Similarity	NPC472130
0.8446	Intermediate Similarity	NPC100389
0.8438	Intermediate Similarity	NPC22324
0.8435	Intermediate Similarity	NPC186418
0.8431	Intermediate Similarity	NPC83975
0.8431	Intermediate Similarity	NPC140722
0.8431	Intermediate Similarity	NPC92054
0.8431	Intermediate Similarity	NPC4958
0.8424	Intermediate Similarity	NPC115760
0.8424	Intermediate Similarity	NPC237435
0.8424	Intermediate Similarity	NPC477848
0.8424	Intermediate Similarity	NPC101191
0.8424	Intermediate Similarity	NPC49344
0.8424	Intermediate Similarity	NPC210094
0.8424	Intermediate Similarity	NPC135277
0.8424	Intermediate Similarity	NPC43211
0.8415	Intermediate Similarity	NPC175107
0.8415	Intermediate Similarity	NPC190003
0.8408	Intermediate Similarity	NPC38699
0.8405	Intermediate Similarity	NPC138927
0.8405	Intermediate Similarity	NPC225434
0.8405	Intermediate Similarity	NPC219904
0.8405	Intermediate Similarity	NPC203050
0.8405	Intermediate Similarity	NPC120099
0.8405	Intermediate Similarity	NPC223747
0.84	Intermediate Similarity	NPC475084
0.84	Intermediate Similarity	NPC164599
0.84	Intermediate Similarity	NPC157816
0.8397	Intermediate Similarity	NPC299706
0.8397	Intermediate Similarity	NPC115466
0.8397	Intermediate Similarity	NPC61604
0.8397	Intermediate Similarity	NPC183536
0.8397	Intermediate Similarity	NPC245615
0.8397	Intermediate Similarity	NPC34965
0.8395	Intermediate Similarity	NPC145038
0.8395	Intermediate Similarity	NPC88789
0.8395	Intermediate Similarity	NPC253662
0.8395	Intermediate Similarity	NPC179950
0.8395	Intermediate Similarity	NPC254306
0.8395	Intermediate Similarity	NPC118284
0.8395	Intermediate Similarity	NPC276222
0.8395	Intermediate Similarity	NPC308404
0.8395	Intermediate Similarity	NPC274618
0.8395	Intermediate Similarity	NPC56077
0.8395	Intermediate Similarity	NPC281131
0.8387	Intermediate Similarity	NPC213197
0.8385	Intermediate Similarity	NPC191306
0.8385	Intermediate Similarity	NPC270335
0.8385	Intermediate Similarity	NPC88043
0.8377	Intermediate Similarity	NPC313334
0.8377	Intermediate Similarity	NPC111785
0.8377	Intermediate Similarity	NPC212670
0.8377	Intermediate Similarity	NPC206264
0.8373	Intermediate Similarity	NPC198324
0.8373	Intermediate Similarity	NPC268533
0.8373	Intermediate Similarity	NPC472385
0.8373	Intermediate Similarity	NPC211532
0.8373	Intermediate Similarity	NPC233994
0.8367	Intermediate Similarity	NPC320259
0.8354	Intermediate Similarity	NPC206123
0.8354	Intermediate Similarity	NPC282987
0.8354	Intermediate Similarity	NPC471405
0.8354	Intermediate Similarity	NPC72249
0.8354	Intermediate Similarity	NPC149011
0.8354	Intermediate Similarity	NPC204937
0.8354	Intermediate Similarity	NPC285197
0.8354	Intermediate Similarity	NPC84265
0.8354	Intermediate Similarity	NPC245014
0.8344	Intermediate Similarity	NPC226304
0.8344	Intermediate Similarity	NPC325555
0.8344	Intermediate Similarity	NPC299435
0.8344	Intermediate Similarity	NPC317489
0.8344	Intermediate Similarity	NPC191046
0.8344	Intermediate Similarity	NPC48640
0.8344	Intermediate Similarity	NPC160156
0.8344	Intermediate Similarity	NPC149244
0.8344	Intermediate Similarity	NPC223424
0.8344	Intermediate Similarity	NPC173637
0.8344	Intermediate Similarity	NPC127546
0.8344	Intermediate Similarity	NPC252169
0.8344	Intermediate Similarity	NPC299761
0.8344	Intermediate Similarity	NPC279281
0.8344	Intermediate Similarity	NPC92565
0.8344	Intermediate Similarity	NPC194095
0.8344	Intermediate Similarity	NPC230439
0.8344	Intermediate Similarity	NPC185103
0.8344	Intermediate Similarity	NPC265530
0.8344	Intermediate Similarity	NPC327032
0.8344	Intermediate Similarity	NPC84362
0.8344	Intermediate Similarity	NPC260604
0.8344	Intermediate Similarity	NPC92153
0.8344	Intermediate Similarity	NPC52550
0.8344	Intermediate Similarity	NPC298847
0.8333	Intermediate Similarity	NPC240431
0.8333	Intermediate Similarity	NPC311830
0.8333	Intermediate Similarity	NPC165720
0.8333	Intermediate Similarity	NPC22832
0.8333	Intermediate Similarity	NPC19388
0.8333	Intermediate Similarity	NPC55786
0.8323	Intermediate Similarity	NPC189142
0.8323	Intermediate Similarity	NPC217520
0.8323	Intermediate Similarity	NPC259576
0.8323	Intermediate Similarity	NPC77660
0.8323	Intermediate Similarity	NPC300537
0.8323	Intermediate Similarity	NPC127782
0.8323	Intermediate Similarity	NPC139571
0.8323	Intermediate Similarity	NPC221091
0.8323	Intermediate Similarity	NPC173837
0.8313	Intermediate Similarity	NPC81042
0.8313	Intermediate Similarity	NPC34267
0.8313	Intermediate Similarity	NPC214621
0.8313	Intermediate Similarity	NPC223426
0.8313	Intermediate Similarity	NPC264735
0.8313	Intermediate Similarity	NPC253685
0.8312	Intermediate Similarity	NPC302989
0.8311	Intermediate Similarity	NPC104167
0.8311	Intermediate Similarity	NPC157554
0.8311	Intermediate Similarity	NPC37468
0.8303	Intermediate Similarity	NPC26230
0.8303	Intermediate Similarity	NPC254540
0.8303	Intermediate Similarity	NPC245452
0.8303	Intermediate Similarity	NPC476405
0.8303	Intermediate Similarity	NPC117260
0.8303	Intermediate Similarity	NPC172807
0.8303	Intermediate Similarity	NPC211594
0.8303	Intermediate Similarity	NPC60735
0.8302	Intermediate Similarity	NPC286919
0.8302	Intermediate Similarity	NPC475663
0.8299	Intermediate Similarity	NPC471029
0.8299	Intermediate Similarity	NPC34456
0.8293	Intermediate Similarity	NPC472133
0.8293	Intermediate Similarity	NPC270578
0.8293	Intermediate Similarity	NPC52382
0.8291	Intermediate Similarity	NPC10205
0.8291	Intermediate Similarity	NPC131532
0.8288	Intermediate Similarity	NPC269421
0.8282	Intermediate Similarity	NPC5778
0.8282	Intermediate Similarity	NPC255615
0.8282	Intermediate Similarity	NPC328940
0.8282	Intermediate Similarity	NPC113968
0.8282	Intermediate Similarity	NPC135599
0.8282	Intermediate Similarity	NPC277174
0.8282	Intermediate Similarity	NPC73855
0.8282	Intermediate Similarity	NPC236934
0.8282	Intermediate Similarity	NPC67037
0.828	Intermediate Similarity	NPC157898
0.828	Intermediate Similarity	NPC150442
0.828	Intermediate Similarity	NPC215811
0.8278	Intermediate Similarity	NPC145319
0.8278	Intermediate Similarity	NPC140502
0.8278	Intermediate Similarity	NPC31081
0.8278	Intermediate Similarity	NPC245219
0.8272	Intermediate Similarity	NPC227297
0.8272	Intermediate Similarity	NPC94777

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 NPC471214 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	297
0.1-0.2	862
0.2-0.3	2036
0.3-0.4	2667
0.4-0.5	1791
0.5-0.6	979
0.6-0.7	437
0.7-0.8	77
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8424	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD1653	Approved
0.8193	Intermediate Similarity	NPD6797	Phase 2
0.8182	Intermediate Similarity	NPD7054	Approved
0.8144	Intermediate Similarity	NPD7251	Discontinued
0.8133	Intermediate Similarity	NPD7074	Phase 3
0.8133	Intermediate Similarity	NPD7472	Approved
0.8121	Intermediate Similarity	NPD3818	Discontinued
0.8095	Intermediate Similarity	NPD7808	Phase 3
0.8028	Intermediate Similarity	NPD1091	Approved
0.7892	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD6166	Phase 2
0.7853	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD3817	Phase 2
0.7826	Intermediate Similarity	NPD1934	Approved
0.7771	Intermediate Similarity	NPD3787	Discontinued
0.773	Intermediate Similarity	NPD5402	Approved
0.7727	Intermediate Similarity	NPD7266	Discontinued
0.7697	Intermediate Similarity	NPD6234	Discontinued
0.7692	Intermediate Similarity	NPD3751	Discontinued
0.7692	Intermediate Similarity	NPD7228	Approved
0.7683	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1613	Approved
0.7669	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6190	Approved
0.7625	Intermediate Similarity	NPD5403	Approved
0.7619	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6559	Discontinued
0.7607	Intermediate Similarity	NPD37	Approved
0.7605	Intermediate Similarity	NPD7199	Phase 2
0.7576	Intermediate Similarity	NPD4966	Approved
0.7576	Intermediate Similarity	NPD4967	Phase 2
0.7576	Intermediate Similarity	NPD3882	Suspended
0.7576	Intermediate Similarity	NPD4965	Approved
0.7562	Intermediate Similarity	NPD1512	Approved
0.7561	Intermediate Similarity	NPD8455	Phase 2
0.7561	Intermediate Similarity	NPD2801	Approved
0.7558	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7075	Discontinued
0.7529	Intermediate Similarity	NPD8313	Approved
0.7529	Intermediate Similarity	NPD8312	Approved
0.7516	Intermediate Similarity	NPD1933	Approved
0.7516	Intermediate Similarity	NPD447	Suspended
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD5401	Approved
0.7484	Intermediate Similarity	NPD7033	Discontinued
0.7443	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1511	Approved
0.743	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3027	Phase 3
0.7351	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6798	Discontinued
0.7296	Intermediate Similarity	NPD6674	Discontinued
0.7289	Intermediate Similarity	NPD6801	Discontinued
0.7284	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4380	Phase 2
0.7273	Intermediate Similarity	NPD6233	Phase 2
0.725	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6799	Approved
0.7222	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7240	Approved
0.72	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6355	Discontinued
0.7162	Intermediate Similarity	NPD1778	Approved
0.7143	Intermediate Similarity	NPD1465	Phase 2
0.7143	Intermediate Similarity	NPD5844	Phase 1
0.7134	Intermediate Similarity	NPD6653	Approved
0.7115	Intermediate Similarity	NPD4060	Phase 1
0.7107	Intermediate Similarity	NPD1551	Phase 2
0.7097	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7097	Phase 1
0.7089	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5763	Approved
0.7063	Intermediate Similarity	NPD5762	Approved
0.7063	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5647	Approved
0.7052	Intermediate Similarity	NPD6232	Discontinued
0.7041	Intermediate Similarity	NPD7819	Suspended
0.7039	Intermediate Similarity	NPD3225	Approved
0.7037	Intermediate Similarity	NPD7435	Discontinued
0.7032	Intermediate Similarity	NPD7095	Approved
0.7029	Intermediate Similarity	NPD7473	Discontinued
0.7019	Intermediate Similarity	NPD1549	Phase 2
0.7	Intermediate Similarity	NPD6099	Approved
0.7	Intermediate Similarity	NPD6100	Approved
0.6993	Remote Similarity	NPD1203	Approved
0.6987	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1357	Approved
0.6975	Remote Similarity	NPD1652	Phase 2
0.6974	Remote Similarity	NPD4749	Approved
0.6968	Remote Similarity	NPD6782	Approved
0.6968	Remote Similarity	NPD6776	Approved
0.6968	Remote Similarity	NPD6781	Approved
0.6968	Remote Similarity	NPD6777	Approved
0.6968	Remote Similarity	NPD6779	Approved
0.6968	Remote Similarity	NPD6778	Approved
0.6968	Remote Similarity	NPD6780	Approved
0.6964	Remote Similarity	NPD6599	Discontinued
0.6962	Remote Similarity	NPD230	Phase 1
0.6957	Remote Similarity	NPD6004	Phase 3
0.6957	Remote Similarity	NPD6002	Phase 3
0.6957	Remote Similarity	NPD6005	Phase 3
0.6957	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3705	Approved
0.6943	Remote Similarity	NPD4062	Phase 3
0.6936	Remote Similarity	NPD5494	Approved
0.6933	Remote Similarity	NPD3750	Approved
0.6933	Remote Similarity	NPD4628	Phase 3
0.6933	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4110	Phase 3
0.6923	Remote Similarity	NPD7411	Suspended
0.6923	Remote Similarity	NPD8434	Phase 2
0.6923	Remote Similarity	NPD8150	Discontinued
0.6915	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2424	Discontinued
0.6908	Remote Similarity	NPD9717	Approved
0.6903	Remote Similarity	NPD2861	Phase 2
0.6897	Remote Similarity	NPD8127	Discontinued
0.6894	Remote Similarity	NPD2935	Discontinued
0.6887	Remote Similarity	NPD3496	Discontinued
0.6883	Remote Similarity	NPD2797	Approved
0.6879	Remote Similarity	NPD919	Approved
0.6879	Remote Similarity	NPD3268	Approved
0.6859	Remote Similarity	NPD6832	Phase 2
0.6859	Remote Similarity	NPD7680	Approved
0.6855	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5124	Phase 1
0.6855	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD290	Approved
0.6845	Remote Similarity	NPD3686	Approved
0.6845	Remote Similarity	NPD3687	Approved
0.6824	Remote Similarity	NPD6671	Approved
0.6821	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7874	Approved
0.681	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD3226	Approved
0.6802	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1608	Approved
0.679	Remote Similarity	NPD6032	Approved
0.6781	Remote Similarity	NPD228	Approved
0.6772	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2313	Discontinued
0.6772	Remote Similarity	NPD1048	Approved
0.6772	Remote Similarity	NPD411	Approved
0.6771	Remote Similarity	NPD7698	Approved
0.6771	Remote Similarity	NPD7696	Phase 3
0.6771	Remote Similarity	NPD7697	Approved
0.6768	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD3146	Approved
0.6766	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD5585	Approved
0.6752	Remote Similarity	NPD4908	Phase 1
0.675	Remote Similarity	NPD4340	Discontinued
0.6749	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD2346	Discontinued
0.6747	Remote Similarity	NPD5058	Phase 3
0.6736	Remote Similarity	NPD7870	Phase 2
0.6736	Remote Similarity	NPD7871	Phase 2
0.6733	Remote Similarity	NPD5536	Phase 2
0.6732	Remote Similarity	NPD422	Phase 1
0.6732	Remote Similarity	NPD1610	Phase 2
0.6728	Remote Similarity	NPD1510	Phase 2
0.6725	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD3926	Phase 2
0.6721	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6823	Phase 2
0.6718	Remote Similarity	NPD7701	Phase 2
0.6709	Remote Similarity	NPD4625	Phase 3
0.6706	Remote Similarity	NPD3111	Phase 1
0.6705	Remote Similarity	NPD6959	Discontinued
0.6703	Remote Similarity	NPD6841	Approved
0.6703	Remote Similarity	NPD6843	Phase 3
0.6703	Remote Similarity	NPD6842	Approved
0.6702	Remote Similarity	NPD6534	Approved
0.6702	Remote Similarity	NPD6535	Approved
0.6701	Remote Similarity	NPD7783	Phase 2
0.6701	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1548	Phase 1
0.6688	Remote Similarity	NPD3018	Phase 2
0.6688	Remote Similarity	NPD9494	Approved
0.6687	Remote Similarity	NPD2796	Approved
0.6687	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7296	Approved
0.6667	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7028	Phase 2
0.6667	Remote Similarity	NPD8389	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