NPASS Compound

Structure

NPC226708 OpenBabel07101719242D 27 31 0 0 1 0 0 0 0 0999 V2000 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3496 2.7737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7564 1.8601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3551 2.6691 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 21 1 0 0 0 0 2 3 2 0 0 0 0 2 12 1 0 0 0 0 3 15 1 0 0 0 0 4 5 1 0 0 0 0 4 11 1 0 0 0 0 5 21 1 0 0 0 0 6 12 1 0 0 0 0 7 11 2 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 17 1 0 0 0 0 9 25 1 0 0 0 0 9 26 1 0 0 0 0 10 24 1 0 0 0 0 10 27 1 0 0 0 0 11 13 1 0 0 0 0 12 18 2 0 0 0 0 13 14 1 0 0 0 0 14 6 1 1 0 0 0 14 21 1 0 0 0 0 15 19 2 0 0 0 0 15 24 1 0 0 0 0 16 17 2 0 0 0 0 16 25 1 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 27 1 0 0 0 0 20 22 2 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	369.12
Volume:	356.977
LogP:	2.536
LogD:	1.763
LogS:	-3.386
# Rotatable Bonds:	3
TPSA:	77.46
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.891
Synthetic Accessibility Score:	3.243
Fsp3:	0.35
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:	-5.094
MDCK Permeability:	2.8409185688360594e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.038
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.895
Plasma Protein Binding (PPB):	89.62745666503906%
Volume Distribution (VD):	1.846
Pgp-substrate:	6.973113059997559%

ADMET: Metabolism

CYP1A2-inhibitor:	0.657
CYP1A2-substrate:	0.355
CYP2C19-inhibitor:	0.208
CYP2C19-substrate:	0.314
CYP2C9-inhibitor:	0.072
CYP2C9-substrate:	0.086
CYP2D6-inhibitor:	0.932
CYP2D6-substrate:	0.358
CYP3A4-inhibitor:	0.708
CYP3A4-substrate:	0.355

ADMET: Excretion

Clearance (CL):	15.851
Half-life (T1/2):	0.295

ADMET: Toxicity

hERG Blockers:	0.141
Human Hepatotoxicity (H-HT):	0.432
Drug-inuced Liver Injury (DILI):	0.961
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.347
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.092
Carcinogencity:	0.919
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC226708

Natural Product ID:	NPC226708
*Common Name:**	Epi-Coryximine
IUPAC Name:	5-[[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]methyl]-1,3-benzodioxole-4-carboxylic acid
Synonyms:	Epi-Coryximine
Standard InCHIKey:	MVXPONFJJHYSIL-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C20H19NO6/c1-21-5-4-11-7-16-17(26-9-25-16)8-13(11)14(21)6-12-2-3-15-19(27-10-24-15)18(12)20(22)23/h2-3,7-8,14H,4-6,9-10H2,1H3,(H,22,23)/t14-/m0/s1
SMILES:	CN1CCc2cc3c(cc2[C@@H]1Cc1ccc2c(c1C(=O)O)OCO2)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1209456
PubChem CID:	49862477
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002955] Tetrahydroisoquinolines

*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
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	tubers	n.a.	n.a.	PMID[20594848]
NPO25345	Corydalis ternata	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[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	30000.0	nM	PMID[501232]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	30000.0	nM	PMID[501232]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	>	30000.0	nM	PMID[501232]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	27750.0	nM	PMID[501232]

☑ 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 NPC226708 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	278
0.1-0.2	1283
0.2-0.3	4605
0.3-0.4	11935
0.4-0.5	5038
0.5-0.6	8311
0.6-0.7	10191
0.7-0.8	975
0.8-0.85	48
0.85-0.9	9
0.9-0.95	22
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.96	High Similarity	NPC125924
0.9543	High Similarity	NPC469815
0.9543	High Similarity	NPC469816
0.9274	High Similarity	NPC70290
0.9274	High Similarity	NPC124302
0.9274	High Similarity	NPC14622
0.9274	High Similarity	NPC46744
0.9274	High Similarity	NPC73020
0.9274	High Similarity	NPC215098
0.9191	High Similarity	NPC27887
0.9171	High Similarity	NPC72788
0.9171	High Similarity	NPC314100
0.9171	High Similarity	NPC226652
0.9171	High Similarity	NPC120671
0.9071	High Similarity	NPC328700
0.9071	High Similarity	NPC202771
0.9071	High Similarity	NPC2173
0.9071	High Similarity	NPC119818
0.9006	High Similarity	NPC24228
0.8933	High Similarity	NPC477259
0.8933	High Similarity	NPC169387
0.8907	High Similarity	NPC207239
0.8846	High Similarity	NPC477258
0.8624	High Similarity	NPC80472
0.8571	High Similarity	NPC166979
0.8539	High Similarity	NPC222524
0.8508	High Similarity	NPC83511
0.8508	High Similarity	NPC116007
0.849	Intermediate Similarity	NPC46990
0.8483	Intermediate Similarity	NPC308267
0.8462	Intermediate Similarity	NPC18306
0.8371	Intermediate Similarity	NPC67978
0.8371	Intermediate Similarity	NPC303581
0.837	Intermediate Similarity	NPC208890
0.8362	Intermediate Similarity	NPC86469
0.8342	Intermediate Similarity	NPC33256
0.8207	Intermediate Similarity	NPC475981
0.8207	Intermediate Similarity	NPC474746
0.8192	Intermediate Similarity	NPC276944
0.8192	Intermediate Similarity	NPC238530
0.8192	Intermediate Similarity	NPC232514
0.8182	Intermediate Similarity	NPC63152
0.8177	Intermediate Similarity	NPC286135
0.8176	Intermediate Similarity	NPC475959
0.8161	Intermediate Similarity	NPC31311
0.8161	Intermediate Similarity	NPC234392
0.8118	Intermediate Similarity	NPC230098
0.8103	Intermediate Similarity	NPC41178
0.8103	Intermediate Similarity	NPC138487
0.8103	Intermediate Similarity	NPC216459
0.8092	Intermediate Similarity	NPC223124
0.8092	Intermediate Similarity	NPC210148
0.8092	Intermediate Similarity	NPC233029
0.8087	Intermediate Similarity	NPC121400
0.8075	Intermediate Similarity	NPC141440
0.8068	Intermediate Similarity	NPC111485
0.8057	Intermediate Similarity	NPC146288
0.8043	Intermediate Similarity	NPC474745
0.8022	Intermediate Similarity	NPC2314
0.8	Intermediate Similarity	NPC298979
0.7989	Intermediate Similarity	NPC474325
0.7978	Intermediate Similarity	NPC153631
0.7977	Intermediate Similarity	NPC223125
0.7949	Intermediate Similarity	NPC207971
0.7947	Intermediate Similarity	NPC94499
0.7935	Intermediate Similarity	NPC237044
0.7935	Intermediate Similarity	NPC474470
0.7933	Intermediate Similarity	NPC59567
0.7926	Intermediate Similarity	NPC162694
0.7921	Intermediate Similarity	NPC97072
0.7921	Intermediate Similarity	NPC215829
0.7912	Intermediate Similarity	NPC474708
0.7908	Intermediate Similarity	NPC268077
0.7907	Intermediate Similarity	NPC476151
0.7895	Intermediate Similarity	NPC185838
0.7892	Intermediate Similarity	NPC114364
0.7892	Intermediate Similarity	NPC320223
0.7892	Intermediate Similarity	NPC118633
0.7892	Intermediate Similarity	NPC294790
0.7892	Intermediate Similarity	NPC148693
0.788	Intermediate Similarity	NPC304675
0.7876	Intermediate Similarity	NPC71124
0.7869	Intermediate Similarity	NPC477640
0.7869	Intermediate Similarity	NPC470739
0.7869	Intermediate Similarity	NPC225597
0.7861	Intermediate Similarity	NPC246587
0.7861	Intermediate Similarity	NPC476571
0.7861	Intermediate Similarity	NPC24233
0.7861	Intermediate Similarity	NPC147390
0.7861	Intermediate Similarity	NPC135538
0.7861	Intermediate Similarity	NPC428
0.7857	Intermediate Similarity	NPC475845
0.7849	Intermediate Similarity	NPC244554
0.7838	Intermediate Similarity	NPC35680
0.7838	Intermediate Similarity	NPC241704
0.7821	Intermediate Similarity	NPC477559
0.7821	Intermediate Similarity	NPC266753
0.7821	Intermediate Similarity	NPC232924
0.7821	Intermediate Similarity	NPC306902
0.7821	Intermediate Similarity	NPC160298
0.7816	Intermediate Similarity	NPC103379
0.7816	Intermediate Similarity	NPC477565
0.7814	Intermediate Similarity	NPC474475
0.7814	Intermediate Similarity	NPC75958
0.7803	Intermediate Similarity	NPC321505
0.7803	Intermediate Similarity	NPC179825
0.7803	Intermediate Similarity	NPC191376
0.7802	Intermediate Similarity	NPC57812
0.7802	Intermediate Similarity	NPC474324
0.7802	Intermediate Similarity	NPC210918
0.7802	Intermediate Similarity	NPC247389
0.7802	Intermediate Similarity	NPC100566
0.7797	Intermediate Similarity	NPC184026
0.7797	Intermediate Similarity	NPC193949
0.7797	Intermediate Similarity	NPC207757
0.7797	Intermediate Similarity	NPC172765
0.7797	Intermediate Similarity	NPC110416
0.7797	Intermediate Similarity	NPC127674
0.7797	Intermediate Similarity	NPC276588
0.7797	Intermediate Similarity	NPC54379
0.7797	Intermediate Similarity	NPC2413
0.7797	Intermediate Similarity	NPC295691
0.7797	Intermediate Similarity	NPC469817
0.7797	Intermediate Similarity	NPC5238
0.7797	Intermediate Similarity	NPC93593
0.7797	Intermediate Similarity	NPC249797
0.7797	Intermediate Similarity	NPC39701
0.7797	Intermediate Similarity	NPC278799
0.7797	Intermediate Similarity	NPC78733
0.7797	Intermediate Similarity	NPC189266
0.7797	Intermediate Similarity	NPC204828
0.779	Intermediate Similarity	NPC231198
0.7784	Intermediate Similarity	NPC128560
0.7784	Intermediate Similarity	NPC199465
0.7784	Intermediate Similarity	NPC229166
0.7784	Intermediate Similarity	NPC187678
0.7778	Intermediate Similarity	NPC9867
0.7772	Intermediate Similarity	NPC470646
0.7766	Intermediate Similarity	NPC102760
0.7766	Intermediate Similarity	NPC248642
0.7766	Intermediate Similarity	NPC116284
0.7765	Intermediate Similarity	NPC106786
0.7765	Intermediate Similarity	NPC213206
0.7765	Intermediate Similarity	NPC328750
0.7765	Intermediate Similarity	NPC477080
0.7765	Intermediate Similarity	NPC474915
0.7765	Intermediate Similarity	NPC188163
0.776	Intermediate Similarity	NPC475686
0.776	Intermediate Similarity	NPC158148
0.776	Intermediate Similarity	NPC82533
0.776	Intermediate Similarity	NPC290759
0.776	Intermediate Similarity	NPC58766
0.776	Intermediate Similarity	NPC266176
0.776	Intermediate Similarity	NPC254957
0.776	Intermediate Similarity	NPC241055
0.7754	Intermediate Similarity	NPC32154
0.7749	Intermediate Similarity	NPC82763
0.7747	Intermediate Similarity	NPC476432
0.7747	Intermediate Similarity	NPC219341
0.7747	Intermediate Similarity	NPC24264
0.7744	Intermediate Similarity	NPC267414
0.7744	Intermediate Similarity	NPC5374
0.7735	Intermediate Similarity	NPC476569
0.7725	Intermediate Similarity	NPC156576
0.7722	Intermediate Similarity	NPC135006
0.7717	Intermediate Similarity	NPC311991
0.7706	Intermediate Similarity	NPC314682
0.7705	Intermediate Similarity	NPC181653
0.7705	Intermediate Similarity	NPC190332
0.7701	Intermediate Similarity	NPC210437
0.7701	Intermediate Similarity	NPC106295
0.7701	Intermediate Similarity	NPC476144
0.7701	Intermediate Similarity	NPC16107
0.7701	Intermediate Similarity	NPC51957
0.7692	Intermediate Similarity	NPC225774
0.7692	Intermediate Similarity	NPC16805
0.7692	Intermediate Similarity	NPC302527
0.7692	Intermediate Similarity	NPC83019
0.7692	Intermediate Similarity	NPC167546
0.7684	Intermediate Similarity	NPC148898
0.7676	Intermediate Similarity	NPC149090
0.7676	Intermediate Similarity	NPC19520
0.7676	Intermediate Similarity	NPC227683
0.767	Intermediate Similarity	NPC151895
0.767	Intermediate Similarity	NPC88249
0.767	Intermediate Similarity	NPC192768
0.767	Intermediate Similarity	NPC97221
0.767	Intermediate Similarity	NPC220858
0.766	Intermediate Similarity	NPC126284
0.7657	Intermediate Similarity	NPC7467
0.765	Intermediate Similarity	NPC264850
0.765	Intermediate Similarity	NPC22130
0.765	Intermediate Similarity	NPC116838
0.765	Intermediate Similarity	NPC13916
0.7644	Intermediate Similarity	NPC57036
0.7644	Intermediate Similarity	NPC214116
0.7641	Intermediate Similarity	NPC204580
0.7637	Intermediate Similarity	NPC78944
0.7637	Intermediate Similarity	NPC320104
0.7632	Intermediate Similarity	NPC135772

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 NPC226708 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	616
0.2-0.3	1116
0.3-0.4	1964
0.4-0.5	2504
0.5-0.6	1831
0.6-0.7	809
0.7-0.8	115
0.8-0.85	0
0.85-0.9	0
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9274	High Similarity	NPD4420	Approved
0.9071	High Similarity	NPD5005	Approved
0.9071	High Similarity	NPD5006	Approved
0.8	Intermediate Similarity	NPD7280	Phase 3
0.8	Intermediate Similarity	NPD7281	Phase 3
0.7809	Intermediate Similarity	NPD5978	Approved
0.7809	Intermediate Similarity	NPD5977	Approved
0.7765	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6297	Approved
0.773	Intermediate Similarity	NPD5313	Approved
0.773	Intermediate Similarity	NPD5312	Approved
0.7714	Intermediate Similarity	NPD3639	Approved
0.7714	Intermediate Similarity	NPD3641	Approved
0.7714	Intermediate Similarity	NPD3640	Phase 3
0.7701	Intermediate Similarity	NPD4584	Approved
0.7672	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD7296	Approved
0.7614	Intermediate Similarity	NPD5457	Discontinued
0.759	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD6853	Approved
0.7579	Intermediate Similarity	NPD6851	Approved
0.757	Intermediate Similarity	NPD6625	Approved
0.7568	Intermediate Similarity	NPD2898	Approved
0.7565	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD6386	Approved
0.7542	Intermediate Similarity	NPD6385	Approved
0.7529	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD5242	Approved
0.7512	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD2975	Approved
0.7374	Intermediate Similarity	NPD2974	Approved
0.7374	Intermediate Similarity	NPD2973	Approved
0.7363	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD824	Approved
0.7313	Intermediate Similarity	NPD2494	Approved
0.7313	Intermediate Similarity	NPD2493	Approved
0.7313	Intermediate Similarity	NPD3452	Approved
0.7313	Intermediate Similarity	NPD3450	Approved
0.7312	Intermediate Similarity	NPD6107	Approved
0.7311	Intermediate Similarity	NPD6997	Phase 2
0.7306	Intermediate Similarity	NPD6618	Phase 2
0.73	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2488	Approved
0.7296	Intermediate Similarity	NPD2490	Approved
0.7295	Intermediate Similarity	NPD7827	Phase 1
0.7292	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7291	Discontinued
0.7268	Intermediate Similarity	NPD4859	Phase 1
0.7264	Intermediate Similarity	NPD7907	Approved
0.7264	Intermediate Similarity	NPD4580	Approved
0.7264	Intermediate Similarity	NPD4107	Approved
0.7263	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6873	Phase 2
0.7249	Intermediate Similarity	NPD3446	Phase 1
0.7238	Intermediate Similarity	NPD4017	Approved
0.7225	Intermediate Similarity	NPD5441	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7930	Approved
0.7222	Intermediate Similarity	NPD1670	Discontinued
0.7216	Intermediate Similarity	NPD8054	Approved
0.7216	Intermediate Similarity	NPD8053	Approved
0.7208	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD4583	Approved
0.7206	Intermediate Similarity	NPD4582	Approved
0.72	Intermediate Similarity	NPD5564	Approved
0.7198	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD4481	Phase 3
0.7192	Intermediate Similarity	NPD3057	Approved
0.7189	Intermediate Similarity	NPD4966	Approved
0.7189	Intermediate Similarity	NPD4967	Phase 2
0.7189	Intermediate Similarity	NPD4965	Approved
0.7183	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6232	Discontinued
0.7181	Intermediate Similarity	NPD5711	Approved
0.7181	Intermediate Similarity	NPD5710	Approved
0.7181	Intermediate Similarity	NPD4010	Discontinued
0.7181	Intermediate Similarity	NPD6071	Discontinued
0.717	Intermediate Similarity	NPD4111	Phase 1
0.717	Intermediate Similarity	NPD4665	Approved
0.7166	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD2971	Approved
0.7165	Intermediate Similarity	NPD2968	Approved
0.7158	Intermediate Similarity	NPD4773	Phase 2
0.7158	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7110	Phase 1
0.7158	Intermediate Similarity	NPD4772	Phase 2
0.7157	Intermediate Similarity	NPD4004	Approved
0.7157	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD4002	Approved
0.7151	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7039	Approved
0.715	Intermediate Similarity	NPD7038	Approved
0.7149	Intermediate Similarity	NPD7048	Phase 3
0.7143	Intermediate Similarity	NPD4482	Phase 3
0.7135	Intermediate Similarity	NPD5241	Discontinued
0.7135	Intermediate Similarity	NPD2563	Approved
0.7135	Intermediate Similarity	NPD2560	Approved
0.712	Intermediate Similarity	NPD8099	Discontinued
0.712	Intermediate Similarity	NPD37	Approved
0.712	Intermediate Similarity	NPD8252	Approved
0.712	Intermediate Similarity	NPD7298	Approved
0.712	Intermediate Similarity	NPD6844	Discontinued
0.712	Intermediate Similarity	NPD8251	Approved
0.7119	Intermediate Similarity	NPD5177	Phase 3
0.7112	Intermediate Similarity	NPD6234	Discontinued
0.7109	Intermediate Similarity	NPD7047	Phase 3
0.7108	Intermediate Similarity	NPD2972	Approved
0.7108	Intermediate Similarity	NPD2491	Approved
0.7108	Intermediate Similarity	NPD3533	Approved
0.7108	Intermediate Similarity	NPD3448	Approved
0.7101	Intermediate Similarity	NPD7701	Phase 2
0.7095	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD4166	Phase 2
0.709	Intermediate Similarity	NPD6747	Phase 1
0.7089	Intermediate Similarity	NPD2899	Discontinued
0.7083	Intermediate Similarity	NPD8156	Discontinued
0.7081	Intermediate Similarity	NPD2977	Approved
0.7081	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD2978	Approved
0.7077	Intermediate Similarity	NPD6146	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7473	Discontinued
0.7065	Intermediate Similarity	NPD5582	Discontinued
0.7053	Intermediate Similarity	NPD2970	Approved
0.7053	Intermediate Similarity	NPD2969	Approved
0.7045	Intermediate Similarity	NPD2935	Discontinued
0.7044	Intermediate Similarity	NPD6874	Approved
0.7033	Intermediate Similarity	NPD7427	Discontinued
0.7033	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6030	Approved
0.7033	Intermediate Similarity	NPD6031	Approved
0.7031	Intermediate Similarity	NPD3818	Discontinued
0.7016	Intermediate Similarity	NPD6894	Phase 1
0.7016	Intermediate Similarity	NPD2489	Approved
0.7016	Intermediate Similarity	NPD27	Approved
0.7011	Intermediate Similarity	NPD1933	Approved
0.7005	Intermediate Similarity	NPD6788	Approved
0.7	Intermediate Similarity	NPD7315	Approved
0.7	Intermediate Similarity	NPD3051	Approved
0.6995	Remote Similarity	NPD6020	Phase 2
0.6985	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7584	Approved
0.6971	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD2492	Phase 1
0.6968	Remote Similarity	NPD5604	Discontinued
0.6968	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7833	Phase 2
0.6968	Remote Similarity	NPD7831	Phase 2
0.6963	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3455	Phase 2
0.6952	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7228	Approved
0.694	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7549	Discontinued
0.6937	Remote Similarity	NPD6723	Discontinued
0.6935	Remote Similarity	NPD7906	Approved
0.6923	Remote Similarity	NPD7999	Approved
0.6923	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6876	Approved
0.6919	Remote Similarity	NPD5676	Approved
0.6919	Remote Similarity	NPD7783	Phase 2
0.6919	Remote Similarity	NPD6875	Approved
0.6919	Remote Similarity	NPD683	Approved
0.6919	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD447	Suspended
0.6908	Remote Similarity	NPD7497	Discontinued
0.6904	Remote Similarity	NPD7313	Approved
0.6904	Remote Similarity	NPD7312	Approved
0.6904	Remote Similarity	NPD7310	Approved
0.6904	Remote Similarity	NPD7311	Approved
0.6897	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4361	Phase 2
0.6895	Remote Similarity	NPD5677	Discontinued
0.6893	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5890	Approved
0.6882	Remote Similarity	NPD5889	Approved
0.6879	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7565	Approved
0.6875	Remote Similarity	NPD8320	Phase 1
0.6875	Remote Similarity	NPD8319	Approved
0.6872	Remote Similarity	NPD7074	Phase 3
0.6869	Remote Similarity	NPD7309	Approved
0.6868	Remote Similarity	NPD2421	Approved
0.6868	Remote Similarity	NPD2420	Approved
0.6863	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD5353	Approved
0.6862	Remote Similarity	NPD5967	Approved
0.6859	Remote Similarity	NPD2821	Approved
0.6859	Remote Similarity	NPD7199	Phase 2
0.6856	Remote Similarity	NPD7177	Discontinued
0.6854	Remote Similarity	NPD4476	Approved
0.6854	Remote Similarity	NPD4477	Approved
0.6853	Remote Similarity	NPD4338	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data