NPASS Compound

Structure

NPC472026 OpenBabel07101718222D 28 29 0 0 1 0 0 0 0 0999 V2000 -2.6456 5.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 6.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 5.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 4.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0646 -2.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 3.0933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5116 0.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3776 -0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2437 0.0933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2437 1.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3776 1.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9135 -0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8736 -3.1915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 -1.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 -0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 1.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5522 -2.0704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -2.1970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 0.0933 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 -4.3776 2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 10 1 0 0 0 0 7 25 1 0 0 0 0 8 18 1 0 0 0 0 8 19 1 0 0 0 0 9 18 1 0 0 0 0 9 26 1 0 0 0 0 10 2 1 1 0 0 0 10 27 1 0 0 0 0 11 7 1 6 0 0 0 11 12 1 0 0 0 0 11 28 1 0 0 0 0 12 13 1 0 0 0 0 12 20 1 1 0 0 0 13 14 1 0 0 0 0 13 21 1 6 0 0 0 14 16 1 0 0 0 0 14 22 1 1 0 0 0 15 17 1 0 0 0 0 15 18 1 1 0 0 0 15 23 1 0 0 0 0 16 27 1 6 0 0 0 16 28 1 0 0 0 0 17 25 1 6 0 0 0 17 26 1 0 0 0 0 18 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.22
Volume:	390.674
LogP:	0.661
LogD:	-0.055
LogS:	-2.09
# Rotatable Bonds:	10
TPSA:	158.3
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.228
Synthetic Accessibility Score:	4.565
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.683
MDCK Permeability:	7.086727418936789e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.766
Human Intestinal Absorption (HIA):	0.899
20% Bioavailability (F20%):	0.88
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.116
Plasma Protein Binding (PPB):	49.3262939453125%
Volume Distribution (VD):	0.42
Pgp-substrate:	39.302711486816406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.077
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.275
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.085
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.033

ADMET: Excretion

Clearance (CL):	1.342
Half-life (T1/2):	0.794

ADMET: Toxicity

hERG Blockers:	0.102
Human Hepatotoxicity (H-HT):	0.078
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.568
Rat Oral Acute Toxicity:	0.173
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.886
Carcinogencity:	0.098
Eye Corrosion:	0.003
Eye Irritation:	0.096
Respiratory Toxicity:	0.18

Download Data

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

Natural Product: NPC472026

Natural Product ID:	NPC472026
*Common Name:**	GPAACNGMYVWROH-GXMCXPELSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GPAACNGMYVWROH-GXMCXPELSA-N
Standard InCHI:	InChI=1S/C18H34O10/c1-3-4-5-6-10(2)27-16-14(22)13(21)12(20)11(28-16)7-25-17-15(23)18(24,8-19)9-26-17/h10-17,19-24H,3-9H2,1-2H3/t10-,11+,12+,13-,14+,15-,16+,17+,18+/m0/s1
SMILES:	CCCCCC(C)OC1C(C(C(C(O1)COC2C(C(CO2)(CO)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3326718
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[23506561]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	leaves	n.a.	n.a.	PMID[25127165]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6648	Piper retrofractum	Species	Piperaceae	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
Others	6

Activity Type	# Activity
Individual Protein	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	Inhibition	=	8.62	%	PMID[554081]
NPT35	Others	n.a.		Activity	=	1.04	uM	PMID[554081]
NPT35	Others	n.a.		Activity	=	3.07	uM	PMID[554081]
NPT35	Others	n.a.		Activity	=	0.34	uM	PMID[554081]
NPT35	Others	n.a.		Activity	=	1.13	uM	PMID[554081]
NPT35	Others	n.a.		Activity	=	19.63	%	PMID[554081]

☑ 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 NPC472026 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	517
0.1-0.2	6635
0.2-0.3	16615
0.3-0.4	10337
0.4-0.5	6273
0.5-0.6	1974
0.6-0.7	253
0.7-0.8	75
0.8-0.85	13
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9464	High Similarity	NPC219040
0.8793	High Similarity	NPC472025
0.875	High Similarity	NPC130683
0.875	High Similarity	NPC323361
0.8644	High Similarity	NPC34877
0.8644	High Similarity	NPC290179
0.8621	High Similarity	NPC148424
0.8393	Intermediate Similarity	NPC124963
0.8393	Intermediate Similarity	NPC233726
0.8393	Intermediate Similarity	NPC326533
0.8393	Intermediate Similarity	NPC23134
0.8361	Intermediate Similarity	NPC477753
0.8361	Intermediate Similarity	NPC477755
0.8361	Intermediate Similarity	NPC477757
0.8361	Intermediate Similarity	NPC477763
0.8361	Intermediate Similarity	NPC477750
0.8361	Intermediate Similarity	NPC477762
0.8281	Intermediate Similarity	NPC477751
0.8281	Intermediate Similarity	NPC477752
0.8281	Intermediate Similarity	NPC477764
0.8281	Intermediate Similarity	NPC477756
0.8276	Intermediate Similarity	NPC303727
0.8214	Intermediate Similarity	NPC323574
0.8154	Intermediate Similarity	NPC477758
0.8154	Intermediate Similarity	NPC477761
0.8154	Intermediate Similarity	NPC477754
0.8154	Intermediate Similarity	NPC477760
0.8154	Intermediate Similarity	NPC477759
0.8103	Intermediate Similarity	NPC165198
0.8103	Intermediate Similarity	NPC242073
0.8103	Intermediate Similarity	NPC107914
0.8103	Intermediate Similarity	NPC67660
0.8103	Intermediate Similarity	NPC58629
0.8103	Intermediate Similarity	NPC89145
0.8103	Intermediate Similarity	NPC145112
0.8103	Intermediate Similarity	NPC246558
0.8103	Intermediate Similarity	NPC157514
0.8103	Intermediate Similarity	NPC269166
0.8036	Intermediate Similarity	NPC42503
0.8036	Intermediate Similarity	NPC282143
0.8036	Intermediate Similarity	NPC299781
0.8036	Intermediate Similarity	NPC82512
0.8036	Intermediate Similarity	NPC157193
0.8033	Intermediate Similarity	NPC317023
0.7941	Intermediate Similarity	NPC184550
0.7941	Intermediate Similarity	NPC185419
0.7903	Intermediate Similarity	NPC143326
0.7857	Intermediate Similarity	NPC14144
0.7846	Intermediate Similarity	NPC471761
0.7846	Intermediate Similarity	NPC190418
0.7846	Intermediate Similarity	NPC471760
0.7826	Intermediate Similarity	NPC308096
0.7826	Intermediate Similarity	NPC291228
0.7714	Intermediate Similarity	NPC138273
0.7679	Intermediate Similarity	NPC277475
0.7679	Intermediate Similarity	NPC230789
0.7679	Intermediate Similarity	NPC321087
0.7679	Intermediate Similarity	NPC252918
0.7612	Intermediate Similarity	NPC206601
0.7576	Intermediate Similarity	NPC76881
0.7576	Intermediate Similarity	NPC147292
0.7576	Intermediate Similarity	NPC12040
0.7538	Intermediate Similarity	NPC268243
0.75	Intermediate Similarity	NPC67099
0.75	Intermediate Similarity	NPC285364
0.75	Intermediate Similarity	NPC279575
0.75	Intermediate Similarity	NPC289758
0.75	Intermediate Similarity	NPC92246
0.75	Intermediate Similarity	NPC255377
0.75	Intermediate Similarity	NPC69445
0.75	Intermediate Similarity	NPC199857
0.75	Intermediate Similarity	NPC165846
0.75	Intermediate Similarity	NPC21209
0.75	Intermediate Similarity	NPC155457
0.75	Intermediate Similarity	NPC73906
0.75	Intermediate Similarity	NPC97736
0.75	Intermediate Similarity	NPC176017
0.75	Intermediate Similarity	NPC50228
0.7465	Intermediate Similarity	NPC166250
0.746	Intermediate Similarity	NPC320032
0.746	Intermediate Similarity	NPC322855
0.7424	Intermediate Similarity	NPC31496
0.7424	Intermediate Similarity	NPC6848
0.7397	Intermediate Similarity	NPC188793
0.7391	Intermediate Similarity	NPC211428
0.7391	Intermediate Similarity	NPC241265
0.7391	Intermediate Similarity	NPC285003
0.7297	Intermediate Similarity	NPC272841
0.7286	Intermediate Similarity	NPC474078
0.7286	Intermediate Similarity	NPC52268
0.7286	Intermediate Similarity	NPC53760
0.7286	Intermediate Similarity	NPC471879
0.7273	Intermediate Similarity	NPC325773
0.7273	Intermediate Similarity	NPC277570
0.7246	Intermediate Similarity	NPC250619
0.7222	Intermediate Similarity	NPC308489
0.72	Intermediate Similarity	NPC170595
0.7143	Intermediate Similarity	NPC320240
0.7143	Intermediate Similarity	NPC29721
0.7143	Intermediate Similarity	NPC70756
0.7083	Intermediate Similarity	NPC206823
0.7083	Intermediate Similarity	NPC470659
0.7083	Intermediate Similarity	NPC163812
0.7083	Intermediate Similarity	NPC9763
0.7083	Intermediate Similarity	NPC169085
0.7083	Intermediate Similarity	NPC225748
0.7083	Intermediate Similarity	NPC248427
0.7083	Intermediate Similarity	NPC39266
0.7083	Intermediate Similarity	NPC470660
0.7067	Intermediate Similarity	NPC177343
0.7013	Intermediate Similarity	NPC216941
0.6974	Remote Similarity	NPC146992
0.6974	Remote Similarity	NPC477344
0.6974	Remote Similarity	NPC158302
0.6974	Remote Similarity	NPC477346
0.6974	Remote Similarity	NPC22742
0.6974	Remote Similarity	NPC294748
0.6974	Remote Similarity	NPC85759
0.6964	Remote Similarity	NPC320189
0.6964	Remote Similarity	NPC298699
0.6964	Remote Similarity	NPC86191
0.6964	Remote Similarity	NPC134252
0.6964	Remote Similarity	NPC213159
0.6964	Remote Similarity	NPC291502
0.6964	Remote Similarity	NPC317182
0.6944	Remote Similarity	NPC470173
0.6935	Remote Similarity	NPC317626
0.6935	Remote Similarity	NPC314821
0.6935	Remote Similarity	NPC317501
0.6923	Remote Similarity	NPC475849
0.6923	Remote Similarity	NPC20072
0.6912	Remote Similarity	NPC294813
0.6912	Remote Similarity	NPC13143
0.6912	Remote Similarity	NPC476702
0.6883	Remote Similarity	NPC100697
0.6857	Remote Similarity	NPC179823
0.6849	Remote Similarity	NPC55652
0.6835	Remote Similarity	NPC241959
0.6835	Remote Similarity	NPC474266
0.68	Remote Similarity	NPC229655
0.68	Remote Similarity	NPC477350
0.6795	Remote Similarity	NPC224953
0.6795	Remote Similarity	NPC143421
0.6795	Remote Similarity	NPC475327
0.6795	Remote Similarity	NPC126685
0.6795	Remote Similarity	NPC477319
0.6795	Remote Similarity	NPC472201
0.6795	Remote Similarity	NPC183888
0.6795	Remote Similarity	NPC44782
0.6795	Remote Similarity	NPC477347
0.6795	Remote Similarity	NPC184915
0.6795	Remote Similarity	NPC472204
0.6795	Remote Similarity	NPC169345
0.6795	Remote Similarity	NPC307400
0.6795	Remote Similarity	NPC475667
0.6795	Remote Similarity	NPC186992
0.6795	Remote Similarity	NPC119583
0.6795	Remote Similarity	NPC290012
0.6795	Remote Similarity	NPC472203
0.6795	Remote Similarity	NPC89843
0.6795	Remote Similarity	NPC477331
0.6795	Remote Similarity	NPC476087
0.6795	Remote Similarity	NPC27289
0.6795	Remote Similarity	NPC173328
0.6795	Remote Similarity	NPC259294
0.6795	Remote Similarity	NPC477317
0.6795	Remote Similarity	NPC475270
0.6795	Remote Similarity	NPC123204
0.6795	Remote Similarity	NPC238056
0.6795	Remote Similarity	NPC472202
0.6795	Remote Similarity	NPC115013
0.6795	Remote Similarity	NPC297768
0.6795	Remote Similarity	NPC472200
0.6795	Remote Similarity	NPC477318
0.6795	Remote Similarity	NPC472205
0.6795	Remote Similarity	NPC269318
0.679	Remote Similarity	NPC107603
0.679	Remote Similarity	NPC268633
0.679	Remote Similarity	NPC471410
0.679	Remote Similarity	NPC471411
0.6769	Remote Similarity	NPC322148
0.675	Remote Similarity	NPC474156
0.675	Remote Similarity	NPC288471
0.6747	Remote Similarity	NPC82955
0.6719	Remote Similarity	NPC326557
0.6711	Remote Similarity	NPC476783
0.6711	Remote Similarity	NPC216883
0.6711	Remote Similarity	NPC476781
0.6711	Remote Similarity	NPC476782
0.6707	Remote Similarity	NPC43912
0.6707	Remote Similarity	NPC140446
0.6707	Remote Similarity	NPC472396
0.6667	Remote Similarity	NPC118078
0.6667	Remote Similarity	NPC267592
0.6667	Remote Similarity	NPC253123
0.6667	Remote Similarity	NPC290612
0.6627	Remote Similarity	NPC470009
0.6625	Remote Similarity	NPC472352
0.6625	Remote Similarity	NPC477332
0.6625	Remote Similarity	NPC60849

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 NPC472026 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	629
0.1-0.2	5181
0.2-0.3	2305
0.3-0.4	613
0.4-0.5	296
0.5-0.6	85
0.6-0.7	18
0.7-0.8	16
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD889	Approved
0.875	High Similarity	NPD894	Approved
0.875	High Similarity	NPD887	Approved
0.875	High Similarity	NPD895	Approved
0.8571	High Similarity	NPD2269	Approved
0.8393	Intermediate Similarity	NPD904	Phase 3
0.8393	Intermediate Similarity	NPD905	Approved
0.8305	Intermediate Similarity	NPD2267	Suspended
0.8103	Intermediate Similarity	NPD890	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD888	Phase 3
0.8103	Intermediate Similarity	NPD892	Phase 3
0.8103	Intermediate Similarity	NPD893	Approved
0.8103	Intermediate Similarity	NPD891	Phase 3
0.7778	Intermediate Similarity	NPD6123	Approved
0.7538	Intermediate Similarity	NPD847	Phase 1
0.75	Intermediate Similarity	NPD8997	Approved
0.75	Intermediate Similarity	NPD8993	Phase 1
0.75	Intermediate Similarity	NPD8998	Phase 2
0.75	Intermediate Similarity	NPD8999	Phase 3
0.75	Intermediate Similarity	NPD9000	Phase 3
0.7377	Intermediate Similarity	NPD7346	Approved
0.7241	Intermediate Similarity	NPD8965	Approved
0.7241	Intermediate Similarity	NPD8966	Approved
0.7143	Intermediate Similarity	NPD9006	Approved
0.7042	Intermediate Similarity	NPD7532	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD8788	Approved
0.6935	Remote Similarity	NPD9036	Phase 3
0.6935	Remote Similarity	NPD9035	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD1457	Discontinued
0.6769	Remote Similarity	NPD369	Approved
0.6719	Remote Similarity	NPD884	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD885	Approved
0.6622	Remote Similarity	NPD3181	Approved
0.662	Remote Similarity	NPD897	Approved
0.662	Remote Similarity	NPD898	Approved
0.662	Remote Similarity	NPD896	Approved
0.6508	Remote Similarity	NPD9049	Discontinued
0.6508	Remote Similarity	NPD9050	Approved
0.6379	Remote Similarity	NPD8957	Approved
0.6329	Remote Similarity	NPD7329	Approved
0.6322	Remote Similarity	NPD8171	Discontinued
0.6316	Remote Similarity	NPD1810	Approved
0.6316	Remote Similarity	NPD1811	Approved
0.6167	Remote Similarity	NPD9219	Approved
0.6167	Remote Similarity	NPD9218	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD8994	Approved
0.6034	Remote Similarity	NPD7536	Approved
0.5972	Remote Similarity	NPD371	Approved
0.5932	Remote Similarity	NPD8967	Approved
0.593	Remote Similarity	NPD2698	Approved
0.5921	Remote Similarity	NPD2687	Approved
0.5921	Remote Similarity	NPD2686	Approved
0.5921	Remote Similarity	NPD2254	Approved
0.5873	Remote Similarity	NPD9139	Approved
0.5846	Remote Similarity	NPD1400	Approved
0.5846	Remote Similarity	NPD1399	Approved
0.5833	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD3669	Approved
0.5833	Remote Similarity	NPD8958	Phase 2
0.5833	Remote Similarity	NPD8961	Approved
0.5821	Remote Similarity	NPD3730	Approved
0.5821	Remote Similarity	NPD3728	Approved
0.5795	Remote Similarity	NPD5796	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD5794	Approved
0.5795	Remote Similarity	NPD5795	Approved
0.5795	Remote Similarity	NPD5798	Approved
0.5795	Remote Similarity	NPD5797	Approved
0.5789	Remote Similarity	NPD9445	Approved
0.573	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD9053	Approved
0.5714	Remote Similarity	NPD9051	Approved
0.5714	Remote Similarity	NPD9052	Approved
0.567	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD6928	Phase 2
0.5632	Remote Similarity	NPD3200	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD8084	Approved
0.5625	Remote Similarity	NPD8083	Approved
0.5625	Remote Similarity	NPD8138	Approved
0.5625	Remote Similarity	NPD8082	Approved
0.5625	Remote Similarity	NPD8086	Approved
0.5625	Remote Similarity	NPD8085	Approved
0.5625	Remote Similarity	NPD8139	Approved
0.56	Remote Similarity	NPD9033	Approved
0.56	Remote Similarity	NPD9031	Approved
0.56	Remote Similarity	NPD9032	Approved
0.56	Remote Similarity	NPD9030	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