NPASS Compound

Structure

NPC470572 OpenBabel07101718332D 30 32 0 0 1 0 0 0 0 0999 V2000 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 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 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5411 1.5878 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 -5.1962 1.0000 0.0000 C 0 0 0 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 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 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 2 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 1.2321 2.5388 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 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 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 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6443 3.3479 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 2.2321 2.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 9 1 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 11 1 0 0 0 0 4 14 1 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 10 1 0 0 0 0 6 15 1 0 0 0 0 7 10 1 0 0 0 0 7 27 1 0 0 0 0 8 28 1 0 0 0 0 10 29 1 1 0 0 0 11 12 2 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 8 1 1 0 0 0 13 16 1 0 0 0 0 13 30 1 0 0 0 0 14 22 2 0 0 0 0 14 28 1 0 0 0 0 15 23 2 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 16 24 1 6 0 0 0 17 18 1 0 0 0 0 17 25 1 1 0 0 0 18 19 1 0 0 0 0 18 26 1 6 0 0 0 19 29 1 1 0 0 0 19 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.12
Volume:	392.385
LogP:	0.57
LogD:	-0.03
LogS:	-1.591
# Rotatable Bonds:	7
TPSA:	172.21
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.21
Synthetic Accessibility Score:	4.167
Fsp3:	0.474
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.213
MDCK Permeability:	3.70517373085022e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.931
20% Bioavailability (F20%):	0.939
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.372
Plasma Protein Binding (PPB):	71.65348052978516%
Volume Distribution (VD):	0.272
Pgp-substrate:	30.10325813293457%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.032
CYP2C19-inhibitor:	0.083
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.048
CYP2C9-substrate:	0.26
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.149
CYP3A4-inhibitor:	0.12
CYP3A4-substrate:	0.069

ADMET: Excretion

Clearance (CL):	4.346
Half-life (T1/2):	0.954

ADMET: Toxicity

hERG Blockers:	0.135
Human Hepatotoxicity (H-HT):	0.046
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.803
Rat Oral Acute Toxicity:	0.278
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.945
Carcinogencity:	0.484
Eye Corrosion:	0.003
Eye Irritation:	0.409
Respiratory Toxicity:	0.044

Download Data

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

Natural Product: NPC470572

Natural Product ID:	NPC470572
*Common Name:**	6'-Ocaffeoylgoodyeroside
IUPAC Name:	[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(3S)-5-oxooxolan-3-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:	6'-Ocaffeoylgoodyeroside
Standard InCHIKey:	CYEFUTNNSBRMEB-ICCSCHITSA-N
Standard InCHI:	InChI=1S/C19H22O11/c20-11-3-1-9(5-12(11)21)2-4-14(22)28-8-13-16(24)17(25)18(26)19(30-13)29-10-6-15(23)27-7-10/h1-5,10,13,16-21,24-26H,6-8H2/b4-2+/t10-,13+,16+,17-,18+,19+/m0/s1
SMILES:	O=C1OC[C@H](C1)O[C@@H]1O[C@H](COC(=O)/C=C/c2ccc(c(c2)O)O)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071306
PubChem CID:	70693126
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids 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
NPO33136	sarracenia purpurea	Species	Sarraceniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22738356]

☑ 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	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6482	Individual Protein	Glucose-6-phosphatase	Rattus norvegicus	IC50	=	13900.0	nM	PMID[536924]
NPT6482	Individual Protein	Glucose-6-phosphatase	Rattus norvegicus	Inhibition	=	44.0	%	PMID[536924]

☑ 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 NPC470572 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	305
0.1-0.2	1210
0.2-0.3	3201
0.3-0.4	7722
0.4-0.5	10307
0.5-0.6	7195
0.6-0.7	9672
0.7-0.8	2644
0.8-0.85	337
0.85-0.9	90
0.9-0.95	10
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9847	High Similarity	NPC220942
0.9612	High Similarity	NPC219677
0.9538	High Similarity	NPC473924
0.9466	High Similarity	NPC254398
0.9457	High Similarity	NPC477294
0.9457	High Similarity	NPC477293
0.9457	High Similarity	NPC229784
0.9394	High Similarity	NPC471883
0.938	High Similarity	NPC232880
0.9313	High Similarity	NPC281798
0.9302	High Similarity	NPC476873
0.9242	High Similarity	NPC473285
0.9118	High Similarity	NPC171134
0.9118	High Similarity	NPC321184
0.9118	High Similarity	NPC321638
0.9118	High Similarity	NPC226005
0.9118	High Similarity	NPC328273
0.9104	High Similarity	NPC287597
0.9104	High Similarity	NPC34293
0.9104	High Similarity	NPC886
0.9071	High Similarity	NPC473867
0.9037	High Similarity	NPC476870
0.8971	High Similarity	NPC157554
0.8963	High Similarity	NPC474895
0.8915	High Similarity	NPC52097
0.8905	High Similarity	NPC260425
0.8905	High Similarity	NPC476376
0.8905	High Similarity	NPC78363
0.8864	High Similarity	NPC45224
0.8864	High Similarity	NPC35288
0.8864	High Similarity	NPC173150
0.8864	High Similarity	NPC156692
0.8864	High Similarity	NPC471882
0.8864	High Similarity	NPC471881
0.8857	High Similarity	NPC105005
0.8857	High Similarity	NPC40305
0.8855	High Similarity	NPC126991
0.8855	High Similarity	NPC83218
0.8841	High Similarity	NPC197316
0.8841	High Similarity	NPC205195
0.8841	High Similarity	NPC64141
0.8841	High Similarity	NPC68092
0.8841	High Similarity	NPC89105
0.8841	High Similarity	NPC472350
0.8841	High Similarity	NPC476383
0.8841	High Similarity	NPC81515
0.8841	High Similarity	NPC100389
0.8837	High Similarity	NPC11724
0.8832	High Similarity	NPC186418
0.8797	High Similarity	NPC225307
0.8794	High Similarity	NPC296954
0.8794	High Similarity	NPC300894
0.8794	High Similarity	NPC110063
0.8794	High Similarity	NPC297342
0.8794	High Similarity	NPC141455
0.8794	High Similarity	NPC196063
0.8788	High Similarity	NPC475695
0.8788	High Similarity	NPC471157
0.8786	High Similarity	NPC296643
0.8777	High Similarity	NPC202700
0.876	High Similarity	NPC476872
0.8732	High Similarity	NPC83743
0.8732	High Similarity	NPC262182
0.8732	High Similarity	NPC287615
0.8732	High Similarity	NPC216819
0.8714	High Similarity	NPC186406
0.8714	High Similarity	NPC476385
0.8714	High Similarity	NPC134405
0.8714	High Similarity	NPC476377
0.8714	High Similarity	NPC47471
0.8712	High Similarity	NPC90318
0.8696	High Similarity	NPC37468
0.869	High Similarity	NPC12006
0.8681	High Similarity	NPC28776
0.8681	High Similarity	NPC473138
0.8671	High Similarity	NPC229505
0.8667	High Similarity	NPC329344
0.8667	High Similarity	NPC32626
0.8667	High Similarity	NPC237506
0.8667	High Similarity	NPC217052
0.8652	High Similarity	NPC140502
0.8652	High Similarity	NPC222433
0.8652	High Similarity	NPC157816
0.8652	High Similarity	NPC265648
0.8647	High Similarity	NPC61181
0.8647	High Similarity	NPC168653
0.8647	High Similarity	NPC252114
0.8647	High Similarity	NPC147192
0.8647	High Similarity	NPC251407
0.8643	High Similarity	NPC475530
0.8643	High Similarity	NPC473799
0.8639	High Similarity	NPC87403
0.8623	High Similarity	NPC123988
0.8621	High Similarity	NPC478242
0.8603	High Similarity	NPC478255
0.8601	High Similarity	NPC108455
0.8592	High Similarity	NPC476378
0.8592	High Similarity	NPC119537
0.8592	High Similarity	NPC476384
0.8592	High Similarity	NPC269141
0.8592	High Similarity	NPC205864
0.8592	High Similarity	NPC476380
0.8592	High Similarity	NPC247032
0.8592	High Similarity	NPC264632
0.8592	High Similarity	NPC478239
0.8592	High Similarity	NPC476397
0.8592	High Similarity	NPC476375
0.8592	High Similarity	NPC76406
0.8592	High Similarity	NPC476381
0.8592	High Similarity	NPC112
0.8592	High Similarity	NPC96795
0.8592	High Similarity	NPC298257
0.8592	High Similarity	NPC175214
0.8582	High Similarity	NPC103533
0.8582	High Similarity	NPC288416
0.8582	High Similarity	NPC106677
0.8571	High Similarity	NPC132921
0.8571	High Similarity	NPC106818
0.8571	High Similarity	NPC203664
0.8562	High Similarity	NPC69367
0.8561	High Similarity	NPC154485
0.8561	High Similarity	NPC471872
0.8561	High Similarity	NPC472132
0.8561	High Similarity	NPC474275
0.8561	High Similarity	NPC224208
0.8552	High Similarity	NPC201148
0.8552	High Similarity	NPC199311
0.8552	High Similarity	NPC80732
0.8552	High Similarity	NPC215095
0.8552	High Similarity	NPC261122
0.8552	High Similarity	NPC300262
0.8552	High Similarity	NPC3460
0.8552	High Similarity	NPC192763
0.8552	High Similarity	NPC28651
0.8552	High Similarity	NPC210611
0.8551	High Similarity	NPC106406
0.855	High Similarity	NPC266045
0.854	High Similarity	NPC252833
0.8531	High Similarity	NPC229036
0.8531	High Similarity	NPC64195
0.8531	High Similarity	NPC292443
0.8531	High Similarity	NPC476867
0.8531	High Similarity	NPC232228
0.8503	High Similarity	NPC140151
0.85	High Similarity	NPC310252
0.85	High Similarity	NPC84789
0.85	High Similarity	NPC302583
0.85	High Similarity	NPC100558
0.8493	Intermediate Similarity	NPC75945
0.8493	Intermediate Similarity	NPC283839
0.8493	Intermediate Similarity	NPC90896
0.8493	Intermediate Similarity	NPC92117
0.8489	Intermediate Similarity	NPC158325
0.8489	Intermediate Similarity	NPC103398
0.8489	Intermediate Similarity	NPC180171
0.8483	Intermediate Similarity	NPC18789
0.8478	Intermediate Similarity	NPC6836
0.8478	Intermediate Similarity	NPC28637
0.8472	Intermediate Similarity	NPC252292
0.8472	Intermediate Similarity	NPC476869
0.8472	Intermediate Similarity	NPC476866
0.8472	Intermediate Similarity	NPC476382
0.8472	Intermediate Similarity	NPC476864
0.8472	Intermediate Similarity	NPC34587
0.8472	Intermediate Similarity	NPC100998
0.8472	Intermediate Similarity	NPC476868
0.8472	Intermediate Similarity	NPC34927
0.8467	Intermediate Similarity	NPC318799
0.8467	Intermediate Similarity	NPC254819
0.8456	Intermediate Similarity	NPC307110
0.8456	Intermediate Similarity	NPC253595
0.8446	Intermediate Similarity	NPC289438
0.844	Intermediate Similarity	NPC219428
0.844	Intermediate Similarity	NPC220936
0.844	Intermediate Similarity	NPC302857
0.844	Intermediate Similarity	NPC37250
0.844	Intermediate Similarity	NPC278068
0.844	Intermediate Similarity	NPC142703
0.844	Intermediate Similarity	NPC152942
0.844	Intermediate Similarity	NPC31745
0.8435	Intermediate Similarity	NPC470934
0.8435	Intermediate Similarity	NPC188393
0.8425	Intermediate Similarity	NPC120621
0.8425	Intermediate Similarity	NPC248257
0.8425	Intermediate Similarity	NPC23677
0.8417	Intermediate Similarity	NPC470881
0.8414	Intermediate Similarity	NPC476865
0.8414	Intermediate Similarity	NPC199928
0.8411	Intermediate Similarity	NPC286919
0.8411	Intermediate Similarity	NPC475663
0.8411	Intermediate Similarity	NPC226759
0.8403	Intermediate Similarity	NPC63304
0.84	Intermediate Similarity	NPC475484
0.8389	Intermediate Similarity	NPC44730
0.8389	Intermediate Similarity	NPC471874
0.838	Intermediate Similarity	NPC205751
0.838	Intermediate Similarity	NPC476819
0.838	Intermediate Similarity	NPC274891
0.838	Intermediate Similarity	NPC156709
0.838	Intermediate Similarity	NPC474875

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 NPC470572 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	720
0.2-0.3	1718
0.3-0.4	2999
0.4-0.5	2000
0.5-0.6	1108
0.6-0.7	337
0.7-0.8	28
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8841	High Similarity	NPD7266	Discontinued
0.8207	Intermediate Similarity	NPD6190	Approved
0.8121	Intermediate Similarity	NPD1653	Approved
0.7875	Intermediate Similarity	NPD3818	Discontinued
0.7708	Intermediate Similarity	NPD230	Phase 1
0.7683	Intermediate Similarity	NPD7685	Pre-registration
0.7636	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6234	Discontinued
0.7546	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7054	Approved
0.7455	Intermediate Similarity	NPD7472	Approved
0.7455	Intermediate Similarity	NPD7074	Phase 3
0.7452	Intermediate Similarity	NPD37	Approved
0.7421	Intermediate Similarity	NPD4965	Approved
0.7421	Intermediate Similarity	NPD4967	Phase 2
0.7421	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4966	Approved
0.741	Intermediate Similarity	NPD6797	Phase 2
0.7391	Intermediate Similarity	NPD1357	Approved
0.7375	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7251	Discontinued
0.7365	Intermediate Similarity	NPD6559	Discontinued
0.7357	Intermediate Similarity	NPD1091	Approved
0.731	Intermediate Similarity	NPD3027	Phase 3
0.7294	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD3705	Approved
0.7219	Intermediate Similarity	NPD7808	Phase 3
0.7205	Intermediate Similarity	NPD3882	Suspended
0.7185	Intermediate Similarity	NPD969	Suspended
0.7183	Intermediate Similarity	NPD9269	Phase 2
0.7162	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1613	Approved
0.7162	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1934	Approved
0.7081	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD8166	Discontinued
0.7076	Intermediate Similarity	NPD8312	Approved
0.7076	Intermediate Similarity	NPD8313	Approved
0.7071	Intermediate Similarity	NPD9545	Approved
0.7059	Intermediate Similarity	NPD7240	Approved
0.7055	Intermediate Similarity	NPD9494	Approved
0.7039	Intermediate Similarity	NPD9570	Approved
0.703	Intermediate Similarity	NPD7199	Phase 2
0.7027	Intermediate Similarity	NPD3764	Approved
0.702	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6166	Phase 2
0.7006	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4380	Phase 2
0.7	Intermediate Similarity	NPD447	Suspended
0.7	Intermediate Similarity	NPD5536	Phase 2
0.7	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2801	Approved
0.6975	Remote Similarity	NPD8455	Phase 2
0.6971	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4628	Phase 3
0.6968	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3455	Phase 2
0.6933	Remote Similarity	NPD5402	Approved
0.6933	Remote Similarity	NPD3817	Phase 2
0.6933	Remote Similarity	NPD943	Approved
0.6901	Remote Similarity	NPD9268	Approved
0.6893	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1358	Approved
0.6882	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7075	Discontinued
0.6845	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6653	Approved
0.6835	Remote Similarity	NPD1511	Approved
0.6835	Remote Similarity	NPD4357	Discontinued
0.6824	Remote Similarity	NPD3751	Discontinued
0.6824	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2935	Discontinued
0.6812	Remote Similarity	NPD228	Approved
0.6797	Remote Similarity	NPD7097	Phase 1
0.6795	Remote Similarity	NPD6674	Discontinued
0.6788	Remote Similarity	NPD3021	Approved
0.6788	Remote Similarity	NPD3022	Approved
0.6786	Remote Similarity	NPD6232	Discontinued
0.6776	Remote Similarity	NPD1933	Approved
0.6768	Remote Similarity	NPD1465	Phase 2
0.6768	Remote Similarity	NPD2978	Approved
0.6768	Remote Similarity	NPD2977	Approved
0.6758	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5647	Approved
0.6753	Remote Similarity	NPD651	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1512	Approved
0.6736	Remote Similarity	NPD5126	Approved
0.6736	Remote Similarity	NPD5125	Phase 3
0.6732	Remote Similarity	NPD2492	Phase 1
0.6731	Remote Similarity	NPD2424	Discontinued
0.6726	Remote Similarity	NPD8127	Discontinued
0.6711	Remote Similarity	NPD826	Approved
0.6711	Remote Similarity	NPD825	Approved
0.6708	Remote Similarity	NPD5403	Approved
0.6703	Remote Similarity	NPD7680	Approved
0.6691	Remote Similarity	NPD3134	Approved
0.669	Remote Similarity	NPD9493	Approved
0.6688	Remote Similarity	NPD1652	Phase 2
0.6687	Remote Similarity	NPD2534	Approved
0.6687	Remote Similarity	NPD2532	Approved
0.6687	Remote Similarity	NPD2533	Approved
0.6686	Remote Similarity	NPD3787	Discontinued
0.6686	Remote Similarity	NPD5844	Phase 1
0.6667	Remote Similarity	NPD5494	Approved
0.6667	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5058	Phase 3
0.6667	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7473	Discontinued
0.6667	Remote Similarity	NPD3687	Approved
0.6667	Remote Similarity	NPD3686	Approved
0.6648	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4110	Phase 3
0.6645	Remote Similarity	NPD6233	Phase 2
0.6645	Remote Similarity	NPD7033	Discontinued
0.6627	Remote Similarity	NPD5353	Approved
0.6625	Remote Similarity	NPD6799	Approved
0.6624	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD9384	Approved
0.6621	Remote Similarity	NPD9381	Approved
0.6606	Remote Similarity	NPD6801	Discontinued
0.6603	Remote Similarity	NPD1551	Phase 2
0.6601	Remote Similarity	NPD4060	Phase 1
0.66	Remote Similarity	NPD2861	Phase 2
0.66	Remote Similarity	NPD5736	Approved
0.6584	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD5401	Approved
0.6584	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD3496	Discontinued
0.6573	Remote Similarity	NPD8150	Discontinued
0.6566	Remote Similarity	NPD7819	Suspended
0.6558	Remote Similarity	NPD6355	Discontinued
0.6558	Remote Similarity	NPD555	Phase 2
0.6558	Remote Similarity	NPD4340	Discontinued
0.6554	Remote Similarity	NPD2982	Phase 2
0.6554	Remote Similarity	NPD2983	Phase 2
0.6545	Remote Similarity	NPD6385	Approved
0.6545	Remote Similarity	NPD6386	Approved
0.6538	Remote Similarity	NPD6535	Approved
0.6538	Remote Similarity	NPD6534	Approved
0.6533	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD422	Phase 1
0.6524	Remote Similarity	NPD7435	Discontinued
0.6522	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD1549	Phase 2
0.6519	Remote Similarity	NPD7296	Approved
0.6513	Remote Similarity	NPD7095	Approved
0.6507	Remote Similarity	NPD1778	Approved
0.65	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD3059	Approved
0.6494	Remote Similarity	NPD3061	Approved
0.6494	Remote Similarity	NPD3620	Phase 2
0.6494	Remote Similarity	NPD3062	Approved
0.6494	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD8320	Phase 1
0.6489	Remote Similarity	NPD8319	Approved
0.6486	Remote Similarity	NPD2981	Phase 2
0.6485	Remote Similarity	NPD7028	Phase 2
0.6481	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.648	Remote Similarity	NPD8434	Phase 2
0.6478	Remote Similarity	NPD4236	Phase 3
0.6478	Remote Similarity	NPD4237	Approved
0.6471	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6798	Discontinued
0.6467	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD3094	Phase 2
0.6467	Remote Similarity	NPD1203	Approved
0.6456	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD5762	Approved
0.6456	Remote Similarity	NPD6004	Phase 3
0.6456	Remote Similarity	NPD6005	Phase 3
0.6456	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD5763	Approved
0.6456	Remote Similarity	NPD6002	Phase 3
0.6452	Remote Similarity	NPD6776	Approved
0.6452	Remote Similarity	NPD6779	Approved
0.6452	Remote Similarity	NPD6778	Approved
0.6452	Remote Similarity	NPD6782	Approved
0.6452	Remote Similarity	NPD5124	Phase 1
0.6452	Remote Similarity	NPD6781	Approved
0.6452	Remote Similarity	NPD6780	Approved
0.6452	Remote Similarity	NPD6777	Approved
0.6452	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7411	Suspended
0.6444	Remote Similarity	NPD6842	Approved
0.6444	Remote Similarity	NPD6843	Phase 3
0.6444	Remote Similarity	NPD1242	Phase 1
0.6444	Remote Similarity	NPD6841	Approved
0.6443	Remote Similarity	NPD9622	Approved
0.644	Remote Similarity	NPD8151	Discontinued
0.6438	Remote Similarity	NPD3400	Discontinued
0.6438	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD1510	Phase 2

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