NPASS Compound

Structure

CID136860 OpenBabel06191715492D 26 29 0 0 1 0 0 0 0 0999 V2000 7.7942 2.5000 0.0000 C 0 0 0 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 6.0622 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 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 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 3.4641 0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 6.9282 3.0000 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 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 22 1 0 0 0 0 7 14 1 0 0 0 0 7 17 1 0 0 0 0 8 13 2 0 0 0 0 8 18 1 0 0 0 0 9 14 2 0 0 0 0 9 19 1 0 0 0 0 10 15 2 0 0 0 0 10 20 1 0 0 0 0 11 16 2 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 22 1 0 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 16 17 1 0 0 0 0 17 22 1 1 0 0 0 18 21 2 0 0 0 0 18 23 1 0 0 0 0 19 20 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	355.18
Volume:	367.885
LogP:	2.719
LogD:	3.142
LogS:	-2.784
# Rotatable Bonds:	4
TPSA:	40.16
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.841
Synthetic Accessibility Score:	2.715
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.151
MDCK Permeability:	3.391175050637685e-05
Pgp-inhibitor:	0.772
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.785
30% Bioavailability (F30%):	0.703

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.979
Plasma Protein Binding (PPB):	67.68148040771484%
Volume Distribution (VD):	1.401
Pgp-substrate:	17.916494369506836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.108
CYP1A2-substrate:	0.958
CYP2C19-inhibitor:	0.175
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.7
CYP2D6-inhibitor:	0.448
CYP2D6-substrate:	0.942
CYP3A4-inhibitor:	0.056
CYP3A4-substrate:	0.926

ADMET: Excretion

Clearance (CL):	11.61
Half-life (T1/2):	0.761

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.141
Drug-inuced Liver Injury (DILI):	0.869
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.283
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.204
Carcinogencity:	0.052
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC136860

Natural Product ID:	NPC136860
*Common Name:**	Xylopinine
IUPAC Name:	(13aS)-2,3,10,11-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline
Synonyms:	(-)-Xylopinine; Xylopinine
Standard InCHIKey:	YOAUKNYXWBTMMF-KRWDZBQOSA-N
Standard InCHI:	InChI=1S/C21H25NO4/c1-23-18-8-13-5-6-22-12-15-10-20(25-3)19(24-2)9-14(15)7-17(22)16(13)11-21(18)26-4/h8-11,17H,5-7,12H2,1-4H3/p+1/t17-/m0/s1
SMILES:	COc1cc2CC[NH+]3Cc4cc(c(cc4C[C@H]3c2cc1OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465824
PubChem CID:	226520
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001909] Protoberberine alkaloids 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
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1021/np50053a043]
NPO26006	Stephania rotunda	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	tubers	n.a.	n.a.	PMID[20594848]
NPO10548	Stephania viridiflavens	Species	Menispermaceae	Eukaryota	n.a.	root	n.a.	PMID[20645211]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22737858]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23194502]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[25277281]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	tuber	n.a.	PMID[25670016]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32058719]
NPO22151	Stephania pierrei	Species	Menispermaceae	Eukaryota	tubers	n.a.	n.a.	PMID[8254346]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277309]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10548	Stephania viridiflavens	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10548	Stephania viridiflavens	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10548	Stephania viridiflavens	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26006	Stephania rotunda	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10548	Stephania viridiflavens	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19863	Micromelum ceylanicum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22151	Stephania pierrei	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20570	Esperiopsis digitata	Species	Esperiopsidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16408	Grevillea hilliana	Species	Proteaceae	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
ED50	2
IC50	1

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	>	10000.0	ng/ml	PMID[522258]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	52300.0	nM	PMID[522259]

☑ 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 NPC136860 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	304
0.1-0.2	1667
0.2-0.3	9686
0.3-0.4	8210
0.4-0.5	7347
0.5-0.6	11447
0.6-0.7	3087
0.7-0.8	560
0.8-0.85	219
0.85-0.9	102
0.9-0.95	54
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476567
1.0	High Similarity	NPC128019
0.971	High Similarity	NPC16107
0.971	High Similarity	NPC476144
0.971	High Similarity	NPC210437
0.971	High Similarity	NPC106295
0.971	High Similarity	NPC51957
0.9704	High Similarity	NPC188163
0.9704	High Similarity	NPC213206
0.9704	High Similarity	NPC474915
0.9704	High Similarity	NPC328750
0.964	High Similarity	NPC7467
0.963	High Similarity	NPC314682
0.9504	High Similarity	NPC151895
0.9504	High Similarity	NPC192768
0.9504	High Similarity	NPC88249
0.9504	High Similarity	NPC97221
0.9504	High Similarity	NPC220858
0.9371	High Similarity	NPC233029
0.9371	High Similarity	NPC210148
0.9286	High Similarity	NPC185838
0.9241	High Similarity	NPC5238
0.9241	High Similarity	NPC193949
0.9241	High Similarity	NPC80129
0.9241	High Similarity	NPC127674
0.9241	High Similarity	NPC39701
0.9241	High Similarity	NPC276588
0.9241	High Similarity	NPC172765
0.9241	High Similarity	NPC54379
0.9241	High Similarity	NPC295691
0.9241	High Similarity	NPC469817
0.9241	High Similarity	NPC184026
0.9241	High Similarity	NPC41178
0.9241	High Similarity	NPC189266
0.9241	High Similarity	NPC204828
0.9241	High Similarity	NPC187022
0.9241	High Similarity	NPC138487
0.9241	High Similarity	NPC278799
0.9241	High Similarity	NPC207757
0.9241	High Similarity	NPC216459
0.9241	High Similarity	NPC2413
0.9241	High Similarity	NPC110416
0.9241	High Similarity	NPC249797
0.9225	High Similarity	NPC476571
0.9225	High Similarity	NPC475959
0.9225	High Similarity	NPC147390
0.9225	High Similarity	NPC246587
0.9225	High Similarity	NPC135538
0.9225	High Similarity	NPC428
0.9225	High Similarity	NPC24233
0.9178	High Similarity	NPC146288
0.9178	High Similarity	NPC25084
0.9178	High Similarity	NPC247639
0.9167	High Similarity	NPC476568
0.9161	High Similarity	NPC92541
0.9155	High Similarity	NPC179825
0.9155	High Similarity	NPC321505
0.9155	High Similarity	NPC191376
0.9104	High Similarity	NPC160193
0.9054	High Similarity	NPC111485
0.9054	High Similarity	NPC216816
0.9048	High Similarity	NPC234392
0.9048	High Similarity	NPC31311
0.9034	High Similarity	NPC81733
0.9034	High Similarity	NPC326316
0.9034	High Similarity	NPC476579
0.9021	High Similarity	NPC476151
0.9021	High Similarity	NPC144863
0.898	High Similarity	NPC99659
0.898	High Similarity	NPC325871
0.8958	High Similarity	NPC130941
0.8926	High Similarity	NPC477080
0.8921	High Similarity	NPC253429
0.8897	High Similarity	NPC60538
0.8897	High Similarity	NPC103379
0.8897	High Similarity	NPC477565
0.8897	High Similarity	NPC219162
0.8897	High Similarity	NPC207824
0.8881	High Similarity	NPC130926
0.8874	High Similarity	NPC475393
0.8859	High Similarity	NPC476572
0.8844	High Similarity	NPC37272
0.8816	High Similarity	NPC232514
0.8816	High Similarity	NPC238530
0.8816	High Similarity	NPC24465
0.8816	High Similarity	NPC276944
0.8816	High Similarity	NPC121275
0.8816	High Similarity	NPC284183
0.8816	High Similarity	NPC4138
0.8815	High Similarity	NPC172403
0.8776	High Similarity	NPC277669
0.8776	High Similarity	NPC76213
0.8759	High Similarity	NPC253883
0.8759	High Similarity	NPC95075
0.8759	High Similarity	NPC90844
0.8758	High Similarity	NPC13916
0.8758	High Similarity	NPC240841
0.8758	High Similarity	NPC317272
0.8758	High Similarity	NPC42549
0.8758	High Similarity	NPC250846
0.8758	High Similarity	NPC264850
0.8758	High Similarity	NPC256012
0.8758	High Similarity	NPC268503
0.8667	High Similarity	NPC170503
0.8667	High Similarity	NPC126519
0.8667	High Similarity	NPC203784
0.8645	High Similarity	NPC66573
0.8643	High Similarity	NPC11147
0.8633	High Similarity	NPC160692
0.8627	High Similarity	NPC324144
0.8618	High Similarity	NPC266753
0.8618	High Similarity	NPC306902
0.8618	High Similarity	NPC232924
0.8618	High Similarity	NPC27410
0.8618	High Similarity	NPC166014
0.8618	High Similarity	NPC160298
0.8618	High Similarity	NPC477559
0.8601	High Similarity	NPC470925
0.86	High Similarity	NPC93593
0.86	High Similarity	NPC244112
0.859	High Similarity	NPC109925
0.8582	High Similarity	NPC7018
0.8582	High Similarity	NPC301050
0.8582	High Similarity	NPC131204
0.8581	High Similarity	NPC274026
0.8571	High Similarity	NPC477563
0.8571	High Similarity	NPC196447
0.8571	High Similarity	NPC302527
0.8571	High Similarity	NPC212794
0.8571	High Similarity	NPC306843
0.8571	High Similarity	NPC16805
0.8571	High Similarity	NPC78222
0.8571	High Similarity	NPC136508
0.8571	High Similarity	NPC13504
0.8571	High Similarity	NPC96603
0.8571	High Similarity	NPC167546
0.8571	High Similarity	NPC253043
0.8553	High Similarity	NPC106786
0.8543	High Similarity	NPC186063
0.8535	High Similarity	NPC198498
0.8535	High Similarity	NPC115284
0.8535	High Similarity	NPC76682
0.8535	High Similarity	NPC276890
0.8535	High Similarity	NPC10908
0.8535	High Similarity	NPC63646
0.8535	High Similarity	NPC317439
0.8535	High Similarity	NPC227060
0.8535	High Similarity	NPC317145
0.8533	High Similarity	NPC2295
0.8533	High Similarity	NPC477564
0.8523	High Similarity	NPC8337
0.8523	High Similarity	NPC85747
0.8516	High Similarity	NPC476432
0.8516	High Similarity	NPC24264
0.8506	High Similarity	NPC233650
0.8506	High Similarity	NPC59567
0.8481	Intermediate Similarity	NPC12424
0.8481	Intermediate Similarity	NPC2314
0.8481	Intermediate Similarity	NPC251580
0.8481	Intermediate Similarity	NPC41376
0.8481	Intermediate Similarity	NPC129518
0.8477	Intermediate Similarity	NPC78733
0.8467	Intermediate Similarity	NPC476580
0.8467	Intermediate Similarity	NPC82285
0.8467	Intermediate Similarity	NPC26601
0.8467	Intermediate Similarity	NPC470924
0.8467	Intermediate Similarity	NPC148898
0.8467	Intermediate Similarity	NPC133011
0.8462	Intermediate Similarity	NPC306555
0.8462	Intermediate Similarity	NPC247389
0.8462	Intermediate Similarity	NPC158376
0.8462	Intermediate Similarity	NPC210918
0.8462	Intermediate Similarity	NPC117188
0.8462	Intermediate Similarity	NPC81218
0.8462	Intermediate Similarity	NPC205421
0.8462	Intermediate Similarity	NPC12053
0.8462	Intermediate Similarity	NPC474931
0.8462	Intermediate Similarity	NPC145832
0.8452	Intermediate Similarity	NPC134858
0.8452	Intermediate Similarity	NPC169743
0.8452	Intermediate Similarity	NPC225774
0.8429	Intermediate Similarity	NPC118419
0.8425	Intermediate Similarity	NPC294249
0.8421	Intermediate Similarity	NPC147091
0.8418	Intermediate Similarity	NPC108434
0.8418	Intermediate Similarity	NPC475215
0.8397	Intermediate Similarity	NPC219341
0.8387	Intermediate Similarity	NPC476569
0.8377	Intermediate Similarity	NPC205167
0.8375	Intermediate Similarity	NPC222524
0.8375	Intermediate Similarity	NPC241704
0.8375	Intermediate Similarity	NPC293093
0.8355	Intermediate Similarity	NPC76079
0.8344	Intermediate Similarity	NPC210140
0.8344	Intermediate Similarity	NPC150879
0.8344	Intermediate Similarity	NPC204947
0.8344	Intermediate Similarity	NPC298979
0.8333	Intermediate Similarity	NPC223125
0.8323	Intermediate Similarity	NPC60186
0.8312	Intermediate Similarity	NPC118804

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 NPC136860 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	766
0.2-0.3	1064
0.3-0.4	1716
0.4-0.5	2740
0.5-0.6	1782
0.6-0.7	682
0.7-0.8	175
0.8-0.85	22
0.85-0.9	9
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.971	High Similarity	NPD4584	Approved
0.9704	High Similarity	NPD4664	Clinical (unspecified phase)
0.9241	High Similarity	NPD7298	Approved
0.9028	High Similarity	NPD3641	Approved
0.9028	High Similarity	NPD3640	Phase 3
0.9028	High Similarity	NPD3639	Approved
0.8904	High Similarity	NPD4017	Approved
0.8784	High Similarity	NPD4772	Phase 2
0.8784	High Similarity	NPD4773	Phase 2
0.8639	High Similarity	NPD6031	Approved
0.8639	High Similarity	NPD6030	Approved
0.8551	High Similarity	NPD2669	Clinical (unspecified phase)
0.8535	High Similarity	NPD8099	Discontinued
0.8535	High Similarity	NPD8251	Approved
0.8535	High Similarity	NPD8252	Approved
0.8521	High Similarity	NPD6028	Clinical (unspecified phase)
0.8521	High Similarity	NPD6029	Clinical (unspecified phase)
0.8506	High Similarity	NPD7201	Clinical (unspecified phase)
0.8489	Intermediate Similarity	NPD5718	Phase 2
0.8481	Intermediate Similarity	NPD8156	Discontinued
0.8452	Intermediate Similarity	NPD6107	Approved
0.8435	Intermediate Similarity	NPD3124	Discontinued
0.8397	Intermediate Similarity	NPD4010	Discontinued
0.8299	Intermediate Similarity	NPD5241	Discontinued
0.828	Intermediate Similarity	NPD4166	Phase 2
0.8217	Intermediate Similarity	NPD7802	Discontinued
0.8214	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD6896	Approved
0.8194	Intermediate Similarity	NPD6788	Approved
0.8194	Intermediate Similarity	NPD6895	Approved
0.8182	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD8053	Approved
0.8171	Intermediate Similarity	NPD8054	Approved
0.8137	Intermediate Similarity	NPD5313	Approved
0.8137	Intermediate Similarity	NPD5312	Approved
0.8025	Intermediate Similarity	NPD7831	Phase 2
0.8025	Intermediate Similarity	NPD7833	Phase 2
0.8025	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD3109	Approved
0.7986	Intermediate Similarity	NPD3110	Approved
0.795	Intermediate Similarity	NPD2898	Approved
0.7933	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD6297	Approved
0.7922	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD5978	Approved
0.7898	Intermediate Similarity	NPD5977	Approved
0.7895	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD4481	Phase 3
0.7829	Intermediate Similarity	NPD2421	Approved
0.7829	Intermediate Similarity	NPD2420	Approved
0.7826	Intermediate Similarity	NPD3051	Approved
0.7821	Intermediate Similarity	NPD7110	Phase 1
0.7821	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD4474	Approved
0.7793	Intermediate Similarity	NPD4475	Approved
0.7778	Intermediate Similarity	NPD2970	Approved
0.7778	Intermediate Similarity	NPD6687	Approved
0.7778	Intermediate Similarity	NPD2969	Approved
0.7778	Intermediate Similarity	NPD6688	Approved
0.7763	Intermediate Similarity	NPD7124	Phase 2
0.7763	Intermediate Similarity	NPD3845	Phase 1
0.7748	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6853	Approved
0.7738	Intermediate Similarity	NPD6851	Approved
0.7738	Intermediate Similarity	NPD6618	Phase 2
0.773	Intermediate Similarity	NPD27	Approved
0.773	Intermediate Similarity	NPD2489	Approved
0.7716	Intermediate Similarity	NPD6071	Discontinued
0.7712	Intermediate Similarity	NPD7598	Phase 2
0.7682	Intermediate Similarity	NPD5177	Phase 3
0.7679	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD2563	Approved
0.7673	Intermediate Similarity	NPD2560	Approved
0.7662	Intermediate Similarity	NPD1424	Approved
0.7647	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6875	Approved
0.7643	Intermediate Similarity	NPD6876	Approved
0.7632	Intermediate Similarity	NPD6748	Discontinued
0.7616	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD8095	Phase 1
0.7613	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7291	Discontinued
0.758	Intermediate Similarity	NPD4005	Discontinued
0.7578	Intermediate Similarity	NPD4055	Discovery
0.7574	Intermediate Similarity	NPD5283	Phase 1
0.7569	Intermediate Similarity	NPD7905	Discontinued
0.7566	Intermediate Similarity	NPD3060	Approved
0.7566	Intermediate Similarity	NPD4162	Approved
0.7551	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD2674	Phase 3
0.7543	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4098	Discontinued
0.7485	Intermediate Similarity	NPD5677	Discontinued
0.7485	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4236	Phase 3
0.7451	Intermediate Similarity	NPD4237	Approved
0.7447	Intermediate Similarity	NPD2667	Approved
0.7447	Intermediate Similarity	NPD2668	Approved
0.744	Intermediate Similarity	NPD3920	Phase 2
0.7438	Intermediate Similarity	NPD5720	Discontinued
0.7425	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1753	Discontinued
0.7412	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7906	Approved
0.7371	Intermediate Similarity	NPD3924	Approved
0.7371	Intermediate Similarity	NPD3921	Approved
0.7371	Intermediate Similarity	NPD3922	Approved
0.7371	Intermediate Similarity	NPD3923	Approved
0.7368	Intermediate Similarity	NPD2971	Approved
0.7368	Intermediate Similarity	NPD7280	Phase 3
0.7368	Intermediate Similarity	NPD7311	Approved
0.7368	Intermediate Similarity	NPD7310	Approved
0.7368	Intermediate Similarity	NPD7312	Approved
0.7368	Intermediate Similarity	NPD7313	Approved
0.7368	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2968	Approved
0.7368	Intermediate Similarity	NPD7281	Phase 3
0.7365	Intermediate Similarity	NPD5110	Phase 2
0.7365	Intermediate Similarity	NPD3145	Approved
0.7365	Intermediate Similarity	NPD5111	Phase 2
0.7365	Intermediate Similarity	NPD3144	Approved
0.7365	Intermediate Similarity	NPD5109	Approved
0.7361	Intermediate Similarity	NPD1421	Approved
0.7361	Intermediate Similarity	NPD1669	Approved
0.7361	Intermediate Similarity	NPD1420	Approved
0.736	Intermediate Similarity	NPD4420	Approved
0.7351	Intermediate Similarity	NPD6111	Discontinued
0.7342	Intermediate Similarity	NPD2122	Discontinued
0.7342	Intermediate Similarity	NPD4727	Phase 1
0.7329	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7309	Approved
0.7325	Intermediate Similarity	NPD4123	Phase 3
0.7321	Intermediate Similarity	NPD4498	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3530	Approved
0.7315	Intermediate Similarity	NPD3531	Approved
0.7315	Intermediate Similarity	NPD3532	Approved
0.7303	Intermediate Similarity	NPD7034	Discontinued
0.7294	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD2230	Approved
0.7292	Intermediate Similarity	NPD2232	Approved
0.7292	Intermediate Similarity	NPD2233	Approved
0.729	Intermediate Similarity	NPD6331	Phase 2
0.729	Intermediate Similarity	NPD5754	Discontinued
0.7285	Intermediate Similarity	NPD2653	Approved
0.7285	Intermediate Similarity	NPD2492	Phase 1
0.7285	Intermediate Similarity	NPD2989	Phase 2
0.7285	Intermediate Similarity	NPD2986	Phase 2
0.7284	Intermediate Similarity	NPD2978	Approved
0.7284	Intermediate Similarity	NPD2977	Approved
0.7284	Intermediate Similarity	NPD4585	Approved
0.7278	Intermediate Similarity	NPD6090	Discontinued
0.7267	Intermediate Similarity	NPD4577	Approved
0.7267	Intermediate Similarity	NPD6385	Approved
0.7267	Intermediate Similarity	NPD6386	Approved
0.7267	Intermediate Similarity	NPD4578	Approved
0.7254	Intermediate Similarity	NPD2595	Approved
0.7254	Intermediate Similarity	NPD2594	Approved
0.7244	Intermediate Similarity	NPD3692	Discontinued
0.7241	Intermediate Similarity	NPD4663	Approved
0.7233	Intermediate Similarity	NPD5976	Discontinued
0.7226	Intermediate Similarity	NPD44	Approved
0.7226	Intermediate Similarity	NPD6364	Approved
0.7216	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3656	Approved
0.7198	Intermediate Similarity	NPD5006	Approved
0.7198	Intermediate Similarity	NPD5005	Approved
0.7197	Intermediate Similarity	NPD2120	Phase 2
0.7188	Intermediate Similarity	NPD4210	Discontinued
0.7182	Intermediate Similarity	NPD6612	Phase 2
0.7181	Intermediate Similarity	NPD5156	Approved
0.7181	Intermediate Similarity	NPD5155	Approved
0.7178	Intermediate Similarity	NPD5772	Approved
0.7178	Intermediate Similarity	NPD5773	Approved
0.7162	Intermediate Similarity	NPD3635	Approved
0.7162	Intermediate Similarity	NPD3637	Approved
0.7162	Intermediate Similarity	NPD3636	Approved
0.7161	Intermediate Similarity	NPD7153	Discontinued
0.716	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6873	Phase 2
0.7152	Intermediate Similarity	NPD5604	Discontinued
0.7152	Intermediate Similarity	NPD2238	Phase 2
0.7143	Intermediate Similarity	NPD3055	Approved
0.7143	Intermediate Similarity	NPD6357	Discontinued
0.7143	Intermediate Similarity	NPD4083	Discontinued
0.7143	Intermediate Similarity	NPD3053	Approved
0.7143	Intermediate Similarity	NPD2161	Phase 2
0.7134	Intermediate Similarity	NPD3301	Approved
0.7134	Intermediate Similarity	NPD5160	Discontinued

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