NPASS Compound

Structure

NPC472320 OpenBabel07101719522D 40 43 0 0 1 0 0 0 0 0999 V2000 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 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 -0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 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 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 2 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 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 1 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 0.8660 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 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 -4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 O 0 0 0 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 -0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 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 3 1 0 0 0 0 1 8 2 0 0 0 0 2 4 2 0 0 0 0 2 8 1 0 0 0 0 3 9 2 0 0 0 0 4 9 1 0 0 0 0 5 10 2 0 0 0 0 5 11 1 0 0 0 0 6 26 1 0 0 0 0 7 27 1 0 0 0 0 8 16 1 0 0 0 0 9 28 1 0 0 0 0 10 14 1 0 0 0 0 10 29 1 0 0 0 0 11 15 2 0 0 0 0 11 39 1 0 0 0 0 12 6 1 6 0 0 0 12 17 1 0 0 0 0 12 38 1 0 0 0 0 13 7 1 6 0 0 0 13 18 1 0 0 0 0 13 40 1 0 0 0 0 14 16 1 0 0 0 0 14 19 2 0 0 0 0 15 19 1 0 0 0 0 16 30 2 0 0 0 0 17 20 1 0 0 0 0 17 31 1 1 0 0 0 18 21 1 0 0 0 0 18 32 1 1 0 0 0 19 33 1 0 0 0 0 20 22 1 0 0 0 0 20 34 1 6 0 0 0 21 23 1 0 0 0 0 21 35 1 6 0 0 0 22 24 1 0 0 0 0 22 36 1 1 0 0 0 23 25 1 0 0 0 0 23 37 1 1 0 0 0 24 15 1 6 0 0 0 24 38 1 0 0 0 0 25 39 1 6 0 0 0 25 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	570.16
Volume:	520.128
LogP:	-0.683
LogD:	-0.504
LogS:	-1.703
# Rotatable Bonds:	7
TPSA:	267.29
# H-Bond Aceptor:	15
# H-Bond Donor:	11
# Rings:	4
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.146
Synthetic Accessibility Score:	4.64
Fsp3:	0.48
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.64
MDCK Permeability:	1.2536780559457839e-05
Pgp-inhibitor:	0.041
Pgp-substrate:	0.978
Human Intestinal Absorption (HIA):	0.969
20% Bioavailability (F20%):	0.113
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.15
Plasma Protein Binding (PPB):	84.25934600830078%
Volume Distribution (VD):	0.459
Pgp-substrate:	16.728206634521484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.062
CYP1A2-substrate:	0.007
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.129
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.004

ADMET: Excretion

Clearance (CL):	1.241
Half-life (T1/2):	0.731

ADMET: Toxicity

hERG Blockers:	0.307
Human Hepatotoxicity (H-HT):	0.063
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.458
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.321
Carcinogencity:	0.066
Eye Corrosion:	0.003
Eye Irritation:	0.038
Respiratory Toxicity:	0.012

Download Data

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

Natural Product: NPC472320

Natural Product ID:	NPC472320
*Common Name:**	OLDTXCJYQJNUPS-IRXABLMPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OLDTXCJYQJNUPS-IRXABLMPSA-N
Standard InCHI:	InChI=1S/C25H30O15/c26-6-12-17(31)20(34)22(36)24(38-12)15-11(39-25-23(37)21(35)18(32)13(7-27)40-25)5-10(29)14(19(15)33)16(30)8-1-3-9(28)4-2-8/h1-5,12-13,17-18,20-29,31-37H,6-7H2/t12-,13-,17-,18-,20+,21+,22-,23-,24+,25-/m1/s1
SMILES:	OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)c1c(O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)cc(c(c1O)C(=O)c1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3358630
PubChem CID:	n.a.
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
NPO30586	Cyclopia genistoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s00217-002-0644-5]
NPO30586	Cyclopia genistoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25419864]

☑ 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
Others	3

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	Activity	=	22.0	%	PMID[542192]
NPT839	Cell Line	L6	Rattus norvegicus	Activity	=	27.0	%	PMID[542192]
NPT2	Others	Unspecified		Inhibition	=	43.0	%	PMID[542192]

☑ 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 NPC472320 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	420
0.1-0.2	1610
0.2-0.3	3537
0.3-0.4	8629
0.4-0.5	9591
0.5-0.6	4652
0.6-0.7	5410
0.7-0.8	5832
0.8-0.85	1957
0.85-0.9	837
0.9-0.95	207
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9804	High Similarity	NPC47923
0.9801	High Similarity	NPC170475
0.974	High Similarity	NPC44947
0.974	High Similarity	NPC259834
0.9739	High Similarity	NPC271479
0.9737	High Similarity	NPC23817
0.9737	High Similarity	NPC161749
0.9737	High Similarity	NPC197896
0.9737	High Similarity	NPC258035
0.9737	High Similarity	NPC313163
0.9737	High Similarity	NPC156457
0.9735	High Similarity	NPC39351
0.9735	High Similarity	NPC26195
0.9735	High Similarity	NPC169248
0.9735	High Similarity	NPC72649
0.9735	High Similarity	NPC97052
0.9677	High Similarity	NPC124155
0.9677	High Similarity	NPC257566
0.9675	High Similarity	NPC303913
0.9673	High Similarity	NPC73511
0.9673	High Similarity	NPC308265
0.9671	High Similarity	NPC206378
0.9613	High Similarity	NPC131745
0.9613	High Similarity	NPC190450
0.961	High Similarity	NPC200708
0.9605	High Similarity	NPC99233
0.9603	High Similarity	NPC259767
0.9603	High Similarity	NPC259182
0.9603	High Similarity	NPC121001
0.9603	High Similarity	NPC88484
0.9551	High Similarity	NPC66087
0.9551	High Similarity	NPC179198
0.9551	High Similarity	NPC278419
0.9551	High Similarity	NPC183672
0.9542	High Similarity	NPC45165
0.9539	High Similarity	NPC210003
0.9539	High Similarity	NPC83283
0.9539	High Similarity	NPC106625
0.9539	High Similarity	NPC29763
0.9539	High Similarity	NPC39360
0.9539	High Similarity	NPC143851
0.9487	High Similarity	NPC472876
0.9484	High Similarity	NPC246469
0.9484	High Similarity	NPC142860
0.9484	High Similarity	NPC97285
0.9484	High Similarity	NPC271270
0.9484	High Similarity	NPC153342
0.9481	High Similarity	NPC44931
0.9481	High Similarity	NPC473512
0.9481	High Similarity	NPC129827
0.9481	High Similarity	NPC43638
0.9481	High Similarity	NPC65003
0.9477	High Similarity	NPC95090
0.9477	High Similarity	NPC470604
0.9477	High Similarity	NPC27408
0.9477	High Similarity	NPC470605
0.9477	High Similarity	NPC470603
0.9434	High Similarity	NPC5319
0.9427	High Similarity	NPC29830
0.9419	High Similarity	NPC138811
0.9419	High Similarity	NPC43761
0.9419	High Similarity	NPC473634
0.9419	High Similarity	NPC22062
0.9416	High Similarity	NPC203500
0.9416	High Similarity	NPC323593
0.9416	High Similarity	NPC261866
0.9416	High Similarity	NPC149368
0.9416	High Similarity	NPC127406
0.9416	High Similarity	NPC307938
0.9416	High Similarity	NPC265480
0.9412	High Similarity	NPC108706
0.9412	High Similarity	NPC109594
0.9412	High Similarity	NPC78021
0.9412	High Similarity	NPC87304
0.9412	High Similarity	NPC268950
0.9412	High Similarity	NPC112701
0.9412	High Similarity	NPC326592
0.9412	High Similarity	NPC211158
0.9408	High Similarity	NPC477897
0.9408	High Similarity	NPC289774
0.9408	High Similarity	NPC209846
0.9408	High Similarity	NPC328740
0.9375	High Similarity	NPC150767
0.9375	High Similarity	NPC78734
0.9375	High Similarity	NPC218488
0.9375	High Similarity	NPC76047
0.9371	High Similarity	NPC477502
0.9371	High Similarity	NPC45400
0.9359	High Similarity	NPC470405
0.9359	High Similarity	NPC187379
0.9359	High Similarity	NPC473623
0.9359	High Similarity	NPC306978
0.9359	High Similarity	NPC471079
0.9359	High Similarity	NPC304741
0.9359	High Similarity	NPC136761
0.9355	High Similarity	NPC135391
0.9355	High Similarity	NPC6985
0.9355	High Similarity	NPC182634
0.9355	High Similarity	NPC470606
0.9355	High Similarity	NPC77672
0.9355	High Similarity	NPC60966
0.9355	High Similarity	NPC197304
0.9355	High Similarity	NPC78263
0.9355	High Similarity	NPC54802
0.9355	High Similarity	NPC133671
0.9355	High Similarity	NPC122809
0.9355	High Similarity	NPC108831
0.9351	High Similarity	NPC477958
0.9346	High Similarity	NPC161881
0.9346	High Similarity	NPC10807
0.9346	High Similarity	NPC244583
0.9346	High Similarity	NPC56232
0.9346	High Similarity	NPC150123
0.9346	High Similarity	NPC475790
0.9342	High Similarity	NPC177308
0.9342	High Similarity	NPC124478
0.9342	High Similarity	NPC213723
0.9321	High Similarity	NPC3718
0.9317	High Similarity	NPC256760
0.9313	High Similarity	NPC229687
0.9313	High Similarity	NPC222455
0.9308	High Similarity	NPC70441
0.9308	High Similarity	NPC236934
0.9308	High Similarity	NPC5778
0.9304	High Similarity	NPC168822
0.9299	High Similarity	NPC265885
0.9299	High Similarity	NPC477629
0.9299	High Similarity	NPC249281
0.9299	High Similarity	NPC116458
0.9299	High Similarity	NPC270675
0.9299	High Similarity	NPC246943
0.9299	High Similarity	NPC215710
0.9299	High Similarity	NPC101636
0.9299	High Similarity	NPC64305
0.9299	High Similarity	NPC139320
0.9299	High Similarity	NPC170052
0.9299	High Similarity	NPC253788
0.9299	High Similarity	NPC173582
0.9299	High Similarity	NPC476215
0.9299	High Similarity	NPC195685
0.9299	High Similarity	NPC473438
0.9299	High Similarity	NPC163242
0.9299	High Similarity	NPC181465
0.9299	High Similarity	NPC276377
0.9299	High Similarity	NPC210961
0.9299	High Similarity	NPC135846
0.9299	High Similarity	NPC472994
0.9299	High Similarity	NPC477628
0.9299	High Similarity	NPC297987
0.9295	High Similarity	NPC320283
0.9295	High Similarity	NPC111929
0.9295	High Similarity	NPC470607
0.9295	High Similarity	NPC472459
0.9295	High Similarity	NPC41121
0.929	High Similarity	NPC473657
0.929	High Similarity	NPC295613
0.9286	High Similarity	NPC7989
0.9286	High Similarity	NPC223701
0.9286	High Similarity	NPC472583
0.9286	High Similarity	NPC268193
0.9281	High Similarity	NPC474023
0.9281	High Similarity	NPC472422
0.9281	High Similarity	NPC472420
0.9281	High Similarity	NPC474021
0.9281	High Similarity	NPC190217
0.9281	High Similarity	NPC263384
0.9281	High Similarity	NPC244577
0.9281	High Similarity	NPC471676
0.9276	High Similarity	NPC89442
0.9264	High Similarity	NPC475246
0.9259	High Similarity	NPC208668
0.9259	High Similarity	NPC168789
0.9255	High Similarity	NPC51326
0.9255	High Similarity	NPC44558
0.9255	High Similarity	NPC34287
0.9255	High Similarity	NPC471416
0.9255	High Similarity	NPC231194
0.925	High Similarity	NPC160156
0.925	High Similarity	NPC92565
0.925	High Similarity	NPC229729
0.9245	High Similarity	NPC165720
0.9241	High Similarity	NPC475382
0.9241	High Similarity	NPC127782
0.9241	High Similarity	NPC189142
0.9241	High Similarity	NPC240306
0.9241	High Similarity	NPC300537
0.9241	High Similarity	NPC298171
0.9241	High Similarity	NPC93215
0.9241	High Similarity	NPC77660
0.9226	High Similarity	NPC304745
0.9226	High Similarity	NPC92395
0.9226	High Similarity	NPC111341
0.9226	High Similarity	NPC470681
0.9226	High Similarity	NPC87404
0.9221	High Similarity	NPC171651
0.9221	High Similarity	NPC243171
0.9221	High Similarity	NPC166067
0.9221	High Similarity	NPC35567
0.9216	High Similarity	NPC106025
0.9216	High Similarity	NPC38775

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 NPC472320 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	373
0.1-0.2	880
0.2-0.3	1740
0.3-0.4	2648
0.4-0.5	1985
0.5-0.6	1029
0.6-0.7	313
0.7-0.8	140
0.8-0.85	30
0.85-0.9	9
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9737	High Similarity	NPD4381	Clinical (unspecified phase)
0.9434	High Similarity	NPD7804	Clinical (unspecified phase)
0.9342	High Similarity	NPD4380	Phase 2
0.9136	High Similarity	NPD7074	Phase 3
0.9074	High Similarity	NPD7054	Approved
0.9018	High Similarity	NPD7472	Approved
0.9012	High Similarity	NPD3818	Discontinued
0.8987	High Similarity	NPD7075	Discontinued
0.8963	High Similarity	NPD6797	Phase 2
0.8909	High Similarity	NPD7251	Discontinued
0.8909	High Similarity	NPD6559	Discontinued
0.8855	High Similarity	NPD7808	Phase 3
0.8797	High Similarity	NPD7096	Clinical (unspecified phase)
0.8797	High Similarity	NPD2393	Clinical (unspecified phase)
0.8743	High Similarity	NPD4338	Clinical (unspecified phase)
0.8742	High Similarity	NPD1549	Phase 2
0.8734	High Similarity	NPD6801	Discontinued
0.8675	High Similarity	NPD1552	Clinical (unspecified phase)
0.8675	High Similarity	NPD1550	Clinical (unspecified phase)
0.8671	High Similarity	NPD7411	Suspended
0.8659	High Similarity	NPD6166	Phase 2
0.8659	High Similarity	NPD6168	Clinical (unspecified phase)
0.8659	High Similarity	NPD6167	Clinical (unspecified phase)
0.8645	High Similarity	NPD4378	Clinical (unspecified phase)
0.8625	High Similarity	NPD8443	Clinical (unspecified phase)
0.8616	High Similarity	NPD1934	Approved
0.8526	High Similarity	NPD7410	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD7819	Suspended
0.8421	Intermediate Similarity	NPD1510	Phase 2
0.8418	Intermediate Similarity	NPD5403	Approved
0.8366	Intermediate Similarity	NPD2796	Approved
0.8364	Intermediate Similarity	NPD6959	Discontinued
0.8363	Intermediate Similarity	NPD8312	Approved
0.8363	Intermediate Similarity	NPD8313	Approved
0.8344	Intermediate Similarity	NPD6799	Approved
0.8323	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD5494	Approved
0.8291	Intermediate Similarity	NPD5401	Approved
0.8282	Intermediate Similarity	NPD5402	Approved
0.8239	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD1511	Approved
0.8221	Intermediate Similarity	NPD8455	Phase 2
0.8221	Intermediate Similarity	NPD2801	Approved
0.8187	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD3817	Phase 2
0.8158	Intermediate Similarity	NPD1240	Approved
0.8152	Intermediate Similarity	NPD7584	Approved
0.8148	Intermediate Similarity	NPD6599	Discontinued
0.8125	Intermediate Similarity	NPD1512	Approved
0.8121	Intermediate Similarity	NPD7768	Phase 2
0.8121	Intermediate Similarity	NPD3882	Suspended
0.807	Intermediate Similarity	NPD5844	Phase 1
0.8052	Intermediate Similarity	NPD1607	Approved
0.8038	Intermediate Similarity	NPD3750	Approved
0.7975	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD3749	Approved
0.7925	Intermediate Similarity	NPD4628	Phase 3
0.7925	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD6782	Approved
0.7923	Intermediate Similarity	NPD6780	Approved
0.7923	Intermediate Similarity	NPD6777	Approved
0.7923	Intermediate Similarity	NPD6778	Approved
0.7923	Intermediate Similarity	NPD6779	Approved
0.7923	Intermediate Similarity	NPD6781	Approved
0.7923	Intermediate Similarity	NPD6776	Approved
0.7907	Intermediate Similarity	NPD3751	Discontinued
0.7898	Intermediate Similarity	NPD1551	Phase 2
0.7892	Intermediate Similarity	NPD1465	Phase 2
0.7882	Intermediate Similarity	NPD6232	Discontinued
0.7872	Intermediate Similarity	NPD8151	Discontinued
0.7849	Intermediate Similarity	NPD7473	Discontinued
0.7805	Intermediate Similarity	NPD1653	Approved
0.7796	Intermediate Similarity	NPD7435	Discontinued
0.7796	Intermediate Similarity	NPD7697	Approved
0.7796	Intermediate Similarity	NPD7696	Phase 3
0.7796	Intermediate Similarity	NPD7698	Approved
0.7785	Intermediate Similarity	NPD2935	Discontinued
0.7778	Intermediate Similarity	NPD3787	Discontinued
0.7771	Intermediate Similarity	NPD5953	Discontinued
0.776	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7458	Discontinued
0.775	Intermediate Similarity	NPD2800	Approved
0.7744	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD920	Approved
0.773	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7585	Approved
0.7725	Intermediate Similarity	NPD7701	Phase 2
0.7722	Intermediate Similarity	NPD3748	Approved
0.7716	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7228	Approved
0.7696	Intermediate Similarity	NPD7783	Phase 2
0.7696	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2313	Discontinued
0.7672	Intermediate Similarity	NPD7583	Approved
0.766	Intermediate Similarity	NPD7870	Phase 2
0.766	Intermediate Similarity	NPD7871	Phase 2
0.7657	Intermediate Similarity	NPD7286	Phase 2
0.765	Intermediate Similarity	NPD6534	Approved
0.765	Intermediate Similarity	NPD6535	Approved
0.7647	Intermediate Similarity	NPD6823	Phase 2
0.764	Intermediate Similarity	NPD1243	Approved
0.7624	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7700	Phase 2
0.7622	Intermediate Similarity	NPD2534	Approved
0.7622	Intermediate Similarity	NPD7699	Phase 2
0.7622	Intermediate Similarity	NPD2532	Approved
0.7622	Intermediate Similarity	NPD2533	Approved
0.7616	Intermediate Similarity	NPD7199	Phase 2
0.761	Intermediate Similarity	NPD2799	Discontinued
0.7595	Intermediate Similarity	NPD6651	Approved
0.7584	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD1613	Approved
0.758	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD4360	Phase 2
0.7554	Intermediate Similarity	NPD4363	Phase 3
0.7552	Intermediate Similarity	NPD7874	Approved
0.7552	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1091	Approved
0.755	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD3226	Approved
0.7532	Intermediate Similarity	NPD1933	Approved
0.7528	Intermediate Similarity	NPD7685	Pre-registration
0.7516	Intermediate Similarity	NPD7266	Discontinued
0.7515	Intermediate Similarity	NPD37	Approved
0.7513	Intermediate Similarity	NPD7801	Approved
0.75	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD919	Approved
0.7485	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD4966	Approved
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7474	Intermediate Similarity	NPD8320	Phase 1
0.7474	Intermediate Similarity	NPD8319	Approved
0.7468	Intermediate Similarity	NPD943	Approved
0.7468	Intermediate Similarity	NPD1203	Approved
0.7459	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6832	Phase 2
0.7436	Intermediate Similarity	NPD4908	Phase 1
0.7429	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD5124	Phase 1
0.7421	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2798	Approved
0.7414	Intermediate Similarity	NPD1247	Approved
0.741	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2346	Discontinued
0.7407	Intermediate Similarity	NPD2344	Approved
0.7405	Intermediate Similarity	NPD6213	Phase 3
0.7405	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6212	Phase 3
0.7391	Intermediate Similarity	NPD7033	Discontinued
0.7353	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7390	Discontinued
0.7349	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7240	Approved
0.733	Intermediate Similarity	NPD3926	Phase 2
0.7325	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD8150	Discontinued
0.7322	Intermediate Similarity	NPD8434	Phase 2
0.732	Intermediate Similarity	NPD1610	Phase 2
0.7284	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2424	Discontinued
0.7239	Intermediate Similarity	NPD6099	Approved
0.7239	Intermediate Similarity	NPD6100	Approved
0.7233	Intermediate Similarity	NPD6798	Discontinued
0.7229	Intermediate Similarity	NPD2309	Approved
0.7229	Intermediate Similarity	NPD6190	Approved
0.7212	Intermediate Similarity	NPD1652	Phase 2
0.7205	Intermediate Similarity	NPD230	Phase 1
0.7191	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD3823	Discontinued
0.7178	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD5711	Approved
0.7175	Intermediate Similarity	NPD5710	Approved
0.7171	Intermediate Similarity	NPD1548	Phase 1
0.717	Intermediate Similarity	NPD3027	Phase 3
0.7161	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4361	Phase 2
0.7136	Intermediate Similarity	NPD7930	Approved
0.7126	Intermediate Similarity	NPD4288	Approved
0.7125	Intermediate Similarity	NPD3268	Approved
0.7117	Intermediate Similarity	NPD7097	Phase 1
0.711	Intermediate Similarity	NPD6844	Discontinued
0.7108	Intermediate Similarity	NPD6674	Discontinued
0.7101	Intermediate Similarity	NPD4662	Approved
0.7101	Intermediate Similarity	NPD4661	Approved
0.7099	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6355	Discontinued
0.7099	Intermediate Similarity	NPD447	Suspended
0.7083	Intermediate Similarity	NPD5058	Phase 3
0.7081	Intermediate Similarity	NPD6233	Phase 2
0.7077	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4308	Phase 3

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