NPASS Compound

Structure

NPC125924 OpenBabel07101718322D 26 30 0 0 1 0 0 0 0 0999 V2000 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 2 2 0 0 0 0 1 11 1 0 0 0 0 2 14 1 0 0 0 0 3 4 1 0 0 0 0 3 10 1 0 0 0 0 4 20 1 0 0 0 0 5 11 1 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 24 1 0 0 0 0 8 25 1 0 0 0 0 9 23 1 0 0 0 0 9 26 1 0 0 0 0 10 12 1 0 0 0 0 11 17 2 0 0 0 0 12 13 1 0 0 0 0 13 5 1 1 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 14 23 1 0 0 0 0 15 16 2 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 26 1 0 0 0 0 19 21 2 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	355.11
Volume:	339.681
LogP:	0.486
LogD:	1.255
LogS:	-2.769
# Rotatable Bonds:	3
TPSA:	86.25
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.873
Synthetic Accessibility Score:	3.258
Fsp3:	0.316
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:	-5.365
MDCK Permeability:	1.6023193893488497e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.252
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.178
Plasma Protein Binding (PPB):	92.63895416259766%
Volume Distribution (VD):	1.693
Pgp-substrate:	7.604820251464844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.65
CYP1A2-substrate:	0.205
CYP2C19-inhibitor:	0.205
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.071
CYP2D6-inhibitor:	0.934
CYP2D6-substrate:	0.249
CYP3A4-inhibitor:	0.546
CYP3A4-substrate:	0.211

ADMET: Excretion

Clearance (CL):	11.973
Half-life (T1/2):	0.296

ADMET: Toxicity

hERG Blockers:	0.142
Human Hepatotoxicity (H-HT):	0.763
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.157
Rat Oral Acute Toxicity:	0.288
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.131
Carcinogencity:	0.908
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.928

Download Data

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

Natural Product: NPC125924

Natural Product ID:	NPC125924
*Common Name:**	Coryternatine A
IUPAC Name:	5-[[(5S)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]methyl]-1,3-benzodioxole-4-carboxylic acid
Synonyms:
Standard InCHIKey:	UZOSDBREZDOHGU-ZDUSSCGKSA-N
Standard InCHI:	InChI=1S/C19H17NO6/c21-19(22)17-11(1-2-14-18(17)26-9-23-14)5-13-12-7-16-15(24-8-25-16)6-10(12)3-4-20-13/h1-2,6-7,13,20H,3-5,8-9H2,(H,21,22)/t13-/m0/s1
SMILES:	c1cc2c(c(c1C[C@H]1c3cc4c(cc3CCN1)OCO4)C(=O)O)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1209457
PubChem CID:	46911013
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[541683]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	30000.0	nM	PMID[541683]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	>	30000.0	nM	PMID[541683]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	23290.0	nM	PMID[541683]

☑ 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 NPC125924 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	295
0.1-0.2	1466
0.2-0.3	5440
0.3-0.4	11898
0.4-0.5	4666
0.5-0.6	10175
0.6-0.7	8118
0.7-0.8	596
0.8-0.85	17
0.85-0.9	22
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9828	High Similarity	NPC469815
0.9828	High Similarity	NPC469816
0.96	High Similarity	NPC226708
0.8913	High Similarity	NPC46744
0.8913	High Similarity	NPC124302
0.8913	High Similarity	NPC14622
0.8913	High Similarity	NPC73020
0.8913	High Similarity	NPC70290
0.8913	High Similarity	NPC215098
0.882	High Similarity	NPC27887
0.8817	High Similarity	NPC226652
0.8817	High Similarity	NPC120671
0.8817	High Similarity	NPC314100
0.8817	High Similarity	NPC72788
0.8743	High Similarity	NPC46990
0.8723	High Similarity	NPC328700
0.8723	High Similarity	NPC2173
0.8723	High Similarity	NPC119818
0.8723	High Similarity	NPC202771
0.8656	High Similarity	NPC24228
0.8579	High Similarity	NPC169387
0.8579	High Similarity	NPC477259
0.8564	High Similarity	NPC207239
0.8503	High Similarity	NPC477258
0.8352	Intermediate Similarity	NPC121400
0.8299	Intermediate Similarity	NPC80472
0.827	Intermediate Similarity	NPC83511
0.8235	Intermediate Similarity	NPC166979
0.8197	Intermediate Similarity	NPC222524
0.8172	Intermediate Similarity	NPC116007
0.8142	Intermediate Similarity	NPC308267
0.8128	Intermediate Similarity	NPC18306
0.8042	Intermediate Similarity	NPC208890
0.8033	Intermediate Similarity	NPC67978
0.8033	Intermediate Similarity	NPC303581
0.8022	Intermediate Similarity	NPC86469
0.8021	Intermediate Similarity	NPC33256
0.7978	Intermediate Similarity	NPC152212
0.7926	Intermediate Similarity	NPC275132
0.7921	Intermediate Similarity	NPC234392
0.7921	Intermediate Similarity	NPC31311
0.7895	Intermediate Similarity	NPC57036
0.7886	Intermediate Similarity	NPC207824
0.7886	Intermediate Similarity	NPC60538
0.7884	Intermediate Similarity	NPC474746
0.7884	Intermediate Similarity	NPC135772
0.7884	Intermediate Similarity	NPC475981
0.7868	Intermediate Similarity	NPC286135
0.7865	Intermediate Similarity	NPC63152
0.7857	Intermediate Similarity	NPC232514
0.7857	Intermediate Similarity	NPC238530
0.7857	Intermediate Similarity	NPC276944
0.7853	Intermediate Similarity	NPC223124
0.7849	Intermediate Similarity	NPC477558
0.7829	Intermediate Similarity	NPC475959
0.7814	Intermediate Similarity	NPC86144
0.7814	Intermediate Similarity	NPC304659
0.7809	Intermediate Similarity	NPC477564
0.7809	Intermediate Similarity	NPC2295
0.7802	Intermediate Similarity	NPC189470
0.7801	Intermediate Similarity	NPC230098
0.7797	Intermediate Similarity	NPC277669
0.7797	Intermediate Similarity	NPC76213
0.7778	Intermediate Similarity	NPC312918
0.7778	Intermediate Similarity	NPC155442
0.7778	Intermediate Similarity	NPC477561
0.7778	Intermediate Similarity	NPC32413
0.7778	Intermediate Similarity	NPC474506
0.7778	Intermediate Similarity	NPC476574
0.7765	Intermediate Similarity	NPC216459
0.7765	Intermediate Similarity	NPC138487
0.7765	Intermediate Similarity	NPC41178
0.776	Intermediate Similarity	NPC186546
0.776	Intermediate Similarity	NPC476576
0.776	Intermediate Similarity	NPC141440
0.7753	Intermediate Similarity	NPC233029
0.7753	Intermediate Similarity	NPC210148
0.774	Intermediate Similarity	NPC223125
0.7735	Intermediate Similarity	NPC111485
0.7725	Intermediate Similarity	NPC470879
0.7725	Intermediate Similarity	NPC474745
0.7725	Intermediate Similarity	NPC258695
0.7722	Intermediate Similarity	NPC146288
0.7701	Intermediate Similarity	NPC2314
0.7692	Intermediate Similarity	NPC97072
0.7692	Intermediate Similarity	NPC215829
0.7688	Intermediate Similarity	NPC6152
0.7676	Intermediate Similarity	NPC298979
0.7672	Intermediate Similarity	NPC23219
0.7672	Intermediate Similarity	NPC474325
0.765	Intermediate Similarity	NPC207971
0.765	Intermediate Similarity	NPC153631
0.7644	Intermediate Similarity	NPC476575
0.7641	Intermediate Similarity	NPC117717
0.7641	Intermediate Similarity	NPC94499
0.7619	Intermediate Similarity	NPC474470
0.7619	Intermediate Similarity	NPC112575
0.7619	Intermediate Similarity	NPC237044
0.7617	Intermediate Similarity	NPC162694
0.7612	Intermediate Similarity	NPC268077
0.7609	Intermediate Similarity	NPC59567
0.7594	Intermediate Similarity	NPC474475
0.7594	Intermediate Similarity	NPC474708
0.7579	Intermediate Similarity	NPC118633
0.7579	Intermediate Similarity	NPC148693
0.7579	Intermediate Similarity	NPC320223
0.7579	Intermediate Similarity	NPC114364
0.7579	Intermediate Similarity	NPC294790
0.7576	Intermediate Similarity	NPC71124
0.7571	Intermediate Similarity	NPC476151
0.7566	Intermediate Similarity	NPC304675
0.7557	Intermediate Similarity	NPC185838
0.7553	Intermediate Similarity	NPC225597
0.7553	Intermediate Similarity	NPC470739
0.7553	Intermediate Similarity	NPC477640
0.754	Intermediate Similarity	NPC475686
0.754	Intermediate Similarity	NPC58766
0.754	Intermediate Similarity	NPC475845
0.7539	Intermediate Similarity	NPC244554
0.7538	Intermediate Similarity	NPC5374
0.7528	Intermediate Similarity	NPC476571
0.7528	Intermediate Similarity	NPC24233
0.7528	Intermediate Similarity	NPC246587
0.7528	Intermediate Similarity	NPC428
0.7528	Intermediate Similarity	NPC135538
0.7528	Intermediate Similarity	NPC147390
0.7527	Intermediate Similarity	NPC81247
0.7527	Intermediate Similarity	NPC35627
0.7527	Intermediate Similarity	NPC476573
0.7526	Intermediate Similarity	NPC35680
0.7526	Intermediate Similarity	NPC241704
0.7513	Intermediate Similarity	NPC4669
0.7513	Intermediate Similarity	NPC66341
0.7513	Intermediate Similarity	NPC192135
0.7513	Intermediate Similarity	NPC477020
0.75	Intermediate Similarity	NPC311991
0.75	Intermediate Similarity	NPC75958
0.75	Intermediate Similarity	NPC266753
0.75	Intermediate Similarity	NPC232924
0.75	Intermediate Similarity	NPC475754
0.75	Intermediate Similarity	NPC160298
0.75	Intermediate Similarity	NPC306902
0.75	Intermediate Similarity	NPC477559
0.7487	Intermediate Similarity	NPC210918
0.7487	Intermediate Similarity	NPC190332
0.7487	Intermediate Similarity	NPC474324
0.7487	Intermediate Similarity	NPC181653
0.7487	Intermediate Similarity	NPC100566
0.7487	Intermediate Similarity	NPC247389
0.7487	Intermediate Similarity	NPC57812
0.7486	Intermediate Similarity	NPC477565
0.7486	Intermediate Similarity	NPC103379
0.7475	Intermediate Similarity	NPC470646
0.7474	Intermediate Similarity	NPC9867
0.7474	Intermediate Similarity	NPC229166
0.7474	Intermediate Similarity	NPC187678
0.7474	Intermediate Similarity	NPC199465
0.7474	Intermediate Similarity	NPC128560
0.7473	Intermediate Similarity	NPC249797
0.7473	Intermediate Similarity	NPC189266
0.7473	Intermediate Similarity	NPC172765
0.7473	Intermediate Similarity	NPC127674
0.7473	Intermediate Similarity	NPC5238
0.7473	Intermediate Similarity	NPC469817
0.7473	Intermediate Similarity	NPC93593
0.7473	Intermediate Similarity	NPC2413
0.7473	Intermediate Similarity	NPC276588
0.7473	Intermediate Similarity	NPC54379
0.7473	Intermediate Similarity	NPC295691
0.7473	Intermediate Similarity	NPC204828
0.7473	Intermediate Similarity	NPC193949
0.7473	Intermediate Similarity	NPC184026
0.7473	Intermediate Similarity	NPC2770
0.7473	Intermediate Similarity	NPC278799
0.7473	Intermediate Similarity	NPC207757
0.7473	Intermediate Similarity	NPC110416
0.7473	Intermediate Similarity	NPC78733
0.7473	Intermediate Similarity	NPC231198
0.7473	Intermediate Similarity	NPC39103
0.7473	Intermediate Similarity	NPC39701
0.7472	Intermediate Similarity	NPC321505
0.7472	Intermediate Similarity	NPC179825
0.7472	Intermediate Similarity	NPC191376
0.7462	Intermediate Similarity	NPC254957
0.7461	Intermediate Similarity	NPC102760
0.7461	Intermediate Similarity	NPC116284
0.7461	Intermediate Similarity	NPC248642
0.745	Intermediate Similarity	NPC267414
0.7449	Intermediate Similarity	NPC281581
0.7449	Intermediate Similarity	NPC82763
0.7448	Intermediate Similarity	NPC267408
0.7448	Intermediate Similarity	NPC474507
0.7448	Intermediate Similarity	NPC32154
0.7447	Intermediate Similarity	NPC266176
0.7447	Intermediate Similarity	NPC158148
0.7447	Intermediate Similarity	NPC241055
0.7447	Intermediate Similarity	NPC82533
0.7447	Intermediate Similarity	NPC290759
0.7446	Intermediate Similarity	NPC477080
0.7446	Intermediate Similarity	NPC106786

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 NPC125924 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	645
0.2-0.3	1101
0.3-0.4	2029
0.4-0.5	2597
0.5-0.6	1753
0.6-0.7	766
0.7-0.8	65
0.8-0.85	0
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8913	High Similarity	NPD4420	Approved
0.8723	High Similarity	NPD5006	Approved
0.8723	High Similarity	NPD5005	Approved
0.7903	Intermediate Similarity	NPD6297	Approved
0.7857	Intermediate Similarity	NPD5457	Discontinued
0.7737	Intermediate Similarity	NPD6853	Approved
0.7737	Intermediate Similarity	NPD6851	Approved
0.7684	Intermediate Similarity	NPD7280	Phase 3
0.7684	Intermediate Similarity	NPD7281	Phase 3
0.7524	Intermediate Similarity	NPD7827	Phase 1
0.7486	Intermediate Similarity	NPD5978	Approved
0.7486	Intermediate Similarity	NPD5977	Approved
0.7465	Intermediate Similarity	NPD6625	Approved
0.7461	Intermediate Similarity	NPD6618	Phase 2
0.7452	Intermediate Similarity	NPD7930	Approved
0.745	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD5312	Approved
0.7421	Intermediate Similarity	NPD5313	Approved
0.7415	Intermediate Similarity	NPD4859	Phase 1
0.7406	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7038	Approved
0.7396	Intermediate Similarity	NPD7039	Approved
0.7389	Intermediate Similarity	NPD3641	Approved
0.7389	Intermediate Similarity	NPD3640	Phase 3
0.7389	Intermediate Similarity	NPD3639	Approved
0.738	Intermediate Similarity	NPD6107	Approved
0.7374	Intermediate Similarity	NPD4584	Approved
0.7371	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD2978	Approved
0.7337	Intermediate Similarity	NPD2977	Approved
0.7323	Intermediate Similarity	NPD7296	Approved
0.7303	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6031	Approved
0.7293	Intermediate Similarity	NPD6030	Approved
0.7283	Intermediate Similarity	NPD7298	Approved
0.7282	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD2898	Approved
0.7256	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6386	Approved
0.7228	Intermediate Similarity	NPD6385	Approved
0.7222	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD5242	Approved
0.7158	Intermediate Similarity	NPD4166	Phase 2
0.715	Intermediate Similarity	NPD7999	Approved
0.7149	Intermediate Similarity	NPD6723	Discontinued
0.7143	Intermediate Similarity	NPD6146	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6997	Phase 2
0.7128	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD3450	Approved
0.7122	Intermediate Similarity	NPD3452	Approved
0.7121	Intermediate Similarity	NPD3857	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD3863	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD3455	Phase 2
0.7094	Intermediate Similarity	NPD2973	Approved
0.7094	Intermediate Similarity	NPD2974	Approved
0.7094	Intermediate Similarity	NPD2975	Approved
0.7087	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7783	Phase 2
0.7062	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2493	Approved
0.7039	Intermediate Similarity	NPD2494	Approved
0.7033	Intermediate Similarity	NPD7584	Approved
0.7027	Intermediate Similarity	NPD824	Approved
0.7022	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD2488	Approved
0.7015	Intermediate Similarity	NPD2490	Approved
0.7005	Intermediate Similarity	NPD3936	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7907	Approved
0.7	Intermediate Similarity	NPD7291	Discontinued
0.6991	Remote Similarity	NPD4665	Approved
0.6991	Remote Similarity	NPD4111	Phase 1
0.699	Remote Similarity	NPD6780	Approved
0.699	Remote Similarity	NPD4107	Approved
0.699	Remote Similarity	NPD6778	Approved
0.699	Remote Similarity	NPD6776	Approved
0.699	Remote Similarity	NPD6782	Approved
0.699	Remote Similarity	NPD4580	Approved
0.699	Remote Similarity	NPD6779	Approved
0.699	Remote Similarity	NPD6777	Approved
0.699	Remote Similarity	NPD6781	Approved
0.6989	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4967	Phase 2
0.6984	Remote Similarity	NPD4965	Approved
0.6984	Remote Similarity	NPD4966	Approved
0.6979	Remote Similarity	NPD6232	Discontinued
0.6978	Remote Similarity	NPD3845	Phase 1
0.6976	Remote Similarity	NPD4668	Phase 2
0.6974	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD4002	Approved
0.6971	Remote Similarity	NPD4004	Approved
0.6965	Remote Similarity	NPD5928	Phase 1
0.6959	Remote Similarity	NPD3446	Phase 1
0.6959	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6873	Phase 2
0.695	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD4583	Approved
0.6938	Remote Similarity	NPD4582	Approved
0.6935	Remote Similarity	NPD8054	Approved
0.6935	Remote Similarity	NPD8053	Approved
0.6935	Remote Similarity	NPD4017	Approved
0.6931	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5564	Approved
0.6923	Remote Similarity	NPD3448	Approved
0.6923	Remote Similarity	NPD3818	Discontinued
0.6923	Remote Similarity	NPD3057	Approved
0.6923	Remote Similarity	NPD6823	Phase 2
0.6919	Remote Similarity	NPD1670	Discontinued
0.6916	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD37	Approved
0.6915	Remote Similarity	NPD7693	Approved
0.6912	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6234	Discontinued
0.6907	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4481	Phase 3
0.6903	Remote Similarity	NPD7048	Phase 3
0.6897	Remote Similarity	NPD8152	Approved
0.6897	Remote Similarity	NPD8153	Approved
0.6895	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5071	Phase 2
0.6891	Remote Similarity	NPD5710	Approved
0.6891	Remote Similarity	NPD4010	Discontinued
0.6891	Remote Similarity	NPD5711	Approved
0.6891	Remote Similarity	NPD6071	Discontinued
0.689	Remote Similarity	NPD7697	Approved
0.689	Remote Similarity	NPD7696	Phase 3
0.689	Remote Similarity	NPD7698	Approved
0.6885	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2968	Approved
0.6884	Remote Similarity	NPD2971	Approved
0.6881	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4585	Approved
0.6875	Remote Similarity	NPD4482	Phase 3
0.6875	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7583	Approved
0.6872	Remote Similarity	NPD7473	Discontinued
0.6869	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD7110	Phase 1
0.6862	Remote Similarity	NPD4772	Phase 2
0.6862	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD4773	Phase 2
0.6859	Remote Similarity	NPD1307	Phase 2
0.6859	Remote Similarity	NPD1309	Phase 2
0.6857	Remote Similarity	NPD7871	Phase 2
0.6857	Remote Similarity	NPD7870	Phase 2
0.6857	Remote Similarity	NPD4040	Phase 1
0.6852	Remote Similarity	NPD7047	Phase 3
0.6845	Remote Similarity	NPD2651	Approved
0.6845	Remote Similarity	NPD2649	Approved
0.6842	Remote Similarity	NPD3533	Approved
0.6842	Remote Similarity	NPD2560	Approved
0.6842	Remote Similarity	NPD2972	Approved
0.6842	Remote Similarity	NPD2491	Approved
0.6842	Remote Similarity	NPD2563	Approved
0.684	Remote Similarity	NPD7585	Approved
0.684	Remote Similarity	NPD7701	Phase 2
0.6837	Remote Similarity	NPD8252	Approved
0.6837	Remote Similarity	NPD8099	Discontinued
0.6837	Remote Similarity	NPD8251	Approved
0.6835	Remote Similarity	NPD2899	Discontinued
0.6834	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD2935	Discontinued
0.6831	Remote Similarity	NPD5241	Discontinued
0.6828	Remote Similarity	NPD7427	Discontinued
0.6828	Remote Similarity	NPD4727	Phase 1
0.6825	Remote Similarity	NPD6844	Discontinued
0.6823	Remote Similarity	NPD5709	Phase 3
0.6821	Remote Similarity	NPD6894	Phase 1
0.6813	Remote Similarity	NPD3060	Approved
0.6813	Remote Similarity	NPD5177	Phase 3
0.6813	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD1424	Approved
0.681	Remote Similarity	NPD7435	Discontinued
0.6804	Remote Similarity	NPD7315	Approved
0.6804	Remote Similarity	NPD6747	Phase 1
0.6802	Remote Similarity	NPD8156	Discontinued
0.6798	Remote Similarity	NPD1933	Approved
0.6796	Remote Similarity	NPD5582	Discontinued
0.6791	Remote Similarity	NPD3686	Approved
0.6791	Remote Similarity	NPD3687	Approved
0.6789	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4666	Phase 3
0.678	Remote Similarity	NPD6212	Phase 3
0.678	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6213	Phase 3
0.6779	Remote Similarity	NPD6874	Approved
0.6774	Remote Similarity	NPD8149	Discontinued
0.6771	Remote Similarity	NPD8469	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