NPASS Compound

Structure

NPC123395 OpenBabel07101719512D 23 26 0 0 1 0 0 0 0 0999 V2000 1.0705 4.2946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1590 2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4158 2.9563 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 -1.5388 0.5000 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 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 1.6691 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 1.7321 1.0000 0.0000 C 0 0 0 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 0.5352 2.6473 0.0000 C 0 0 1 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2784 3.3164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 7 1 0 0 0 0 5 12 1 0 0 0 0 6 8 1 0 0 0 0 6 13 2 0 0 0 0 7 20 1 0 0 0 0 8 20 1 0 0 0 0 9 15 2 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 18 1 0 0 0 0 11 12 2 0 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 13 18 1 0 0 0 0 14 22 1 6 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 16 19 2 0 0 0 0 17 21 2 0 0 0 0 17 23 1 0 0 0 0 18 20 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.15
Volume:	318.204
LogP:	1.73
LogD:	1.356
LogS:	-2.26
# Rotatable Bonds:	3
TPSA:	51.66
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.78
Synthetic Accessibility Score:	4.666
Fsp3:	0.444
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:	-4.757
MDCK Permeability:	2.830302037182264e-05
Pgp-inhibitor:	0.597
Pgp-substrate:	0.036
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.095

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.987
Plasma Protein Binding (PPB):	55.07304382324219%
Volume Distribution (VD):	2.384
Pgp-substrate:	40.112457275390625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.067
CYP1A2-substrate:	0.577
CYP2C19-inhibitor:	0.126
CYP2C19-substrate:	0.877
CYP2C9-inhibitor:	0.369
CYP2C9-substrate:	0.31
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.431
CYP3A4-inhibitor:	0.586
CYP3A4-substrate:	0.931

ADMET: Excretion

Clearance (CL):	14.946
Half-life (T1/2):	0.528

ADMET: Toxicity

hERG Blockers:	0.273
Human Hepatotoxicity (H-HT):	0.873
Drug-inuced Liver Injury (DILI):	0.202
AMES Toxicity:	0.363
Rat Oral Acute Toxicity:	0.087
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.854
Carcinogencity:	0.888
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.865

Download Data

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

Natural Product: NPC123395

Natural Product ID:	NPC123395
*Common Name:**	Erymelanthine
IUPAC Name:	methyl (2R,13bS)-2-methoxy-2,6,8,9-tetrahydro-1H-indolo[7a,1-a][2,6]naphthyridine-12-carboxylate
Synonyms:	Erymelanthine
Standard InCHIKey:	KCJQBANVNQOQJT-KSSFIOAISA-N
Standard InCHI:	InChI=1S/C18H20N2O3/c1-22-14-4-3-13-6-8-20-7-5-12-11-19-16(17(21)23-2)9-15(12)18(13,20)10-14/h3-4,6,9,11,14H,5,7-8,10H2,1-2H3/t14-,18-/m0/s1
SMILES:	CO[C@H]1C=CC2=CCN3CCc4cnc(cc4[C@]23C1)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450858
PubChem CID:	44570488
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001782] Erythrina alkaloids [CHEMONTID:0002780] Erythrinanes

*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
NPO20031	Erythrina velutina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19026536]
NPO20031	Erythrina velutina	Species	Fabaceae	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	2
Others	2

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[567555]
NPT15	Cell Line	Jurkat	Homo sapiens	Inhibition	=	1.1	%	PMID[567555]
NPT15	Cell Line	Jurkat	Homo sapiens	Inhibition	=	24.2	%	PMID[567555]

☑ 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 NPC123395 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	315
0.1-0.2	2076
0.2-0.3	9298
0.3-0.4	14972
0.4-0.5	10726
0.5-0.6	3162
0.6-0.7	1809
0.7-0.8	323
0.8-0.85	15
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8424	Intermediate Similarity	NPC207851
0.8298	Intermediate Similarity	NPC469489
0.8238	Intermediate Similarity	NPC103361
0.8232	Intermediate Similarity	NPC249614
0.822	Intermediate Similarity	NPC135950
0.8122	Intermediate Similarity	NPC327592
0.8109	Intermediate Similarity	NPC118940
0.8109	Intermediate Similarity	NPC318299
0.8081	Intermediate Similarity	NPC317373
0.8069	Intermediate Similarity	NPC317752
0.8066	Intermediate Similarity	NPC41717
0.7929	Intermediate Similarity	NPC57398
0.7923	Intermediate Similarity	NPC470894
0.785	Intermediate Similarity	NPC289086
0.7839	Intermediate Similarity	NPC328318
0.7839	Intermediate Similarity	NPC328596
0.7816	Intermediate Similarity	NPC36405
0.7745	Intermediate Similarity	NPC123839
0.7734	Intermediate Similarity	NPC266249
0.7681	Intermediate Similarity	NPC477979
0.7668	Intermediate Similarity	NPC118084
0.7626	Intermediate Similarity	NPC109922
0.7619	Intermediate Similarity	NPC84347
0.7614	Intermediate Similarity	NPC192306
0.761	Intermediate Similarity	NPC472070
0.7606	Intermediate Similarity	NPC191310
0.7594	Intermediate Similarity	NPC477788
0.7569	Intermediate Similarity	NPC107287
0.7561	Intermediate Similarity	NPC63041
0.7559	Intermediate Similarity	NPC57797
0.7559	Intermediate Similarity	NPC250807
0.7553	Intermediate Similarity	NPC273532
0.7549	Intermediate Similarity	NPC238457
0.7548	Intermediate Similarity	NPC165837
0.7538	Intermediate Similarity	NPC472116
0.7526	Intermediate Similarity	NPC282103
0.7525	Intermediate Similarity	NPC103230
0.7524	Intermediate Similarity	NPC304179
0.7524	Intermediate Similarity	NPC312645
0.7524	Intermediate Similarity	NPC477908
0.7524	Intermediate Similarity	NPC206343
0.7524	Intermediate Similarity	NPC48042
0.7524	Intermediate Similarity	NPC472550
0.7523	Intermediate Similarity	NPC473850
0.7512	Intermediate Similarity	NPC264674
0.75	Intermediate Similarity	NPC106824
0.75	Intermediate Similarity	NPC280473
0.75	Intermediate Similarity	NPC323551
0.75	Intermediate Similarity	NPC132539
0.75	Intermediate Similarity	NPC477901
0.7488	Intermediate Similarity	NPC472069
0.7488	Intermediate Similarity	NPC472063
0.7488	Intermediate Similarity	NPC472062
0.7476	Intermediate Similarity	NPC477909
0.7476	Intermediate Similarity	NPC42678
0.7476	Intermediate Similarity	NPC477907
0.7476	Intermediate Similarity	NPC207531
0.7475	Intermediate Similarity	NPC470279
0.7474	Intermediate Similarity	NPC284559
0.7464	Intermediate Similarity	NPC41724
0.7464	Intermediate Similarity	NPC89508
0.7464	Intermediate Similarity	NPC51008
0.7463	Intermediate Similarity	NPC472064
0.7463	Intermediate Similarity	NPC472065
0.7463	Intermediate Similarity	NPC472286
0.7463	Intermediate Similarity	NPC472287
0.7454	Intermediate Similarity	NPC146824
0.7454	Intermediate Similarity	NPC228377
0.7454	Intermediate Similarity	NPC477787
0.7454	Intermediate Similarity	NPC122968
0.7454	Intermediate Similarity	NPC328186
0.7453	Intermediate Similarity	NPC472555
0.745	Intermediate Similarity	NPC245916
0.7444	Intermediate Similarity	NPC112741
0.744	Intermediate Similarity	NPC472752
0.743	Intermediate Similarity	NPC235364
0.7426	Intermediate Similarity	NPC284338
0.7423	Intermediate Similarity	NPC143533
0.7419	Intermediate Similarity	NPC475362
0.7416	Intermediate Similarity	NPC472553
0.7406	Intermediate Similarity	NPC62367
0.7406	Intermediate Similarity	NPC319556
0.7395	Intermediate Similarity	NPC76565
0.7391	Intermediate Similarity	NPC470190
0.7381	Intermediate Similarity	NPC236668
0.7371	Intermediate Similarity	NPC216428
0.7366	Intermediate Similarity	NPC317572
0.7366	Intermediate Similarity	NPC165599
0.7361	Intermediate Similarity	NPC477900
0.7361	Intermediate Similarity	NPC475137
0.7361	Intermediate Similarity	NPC26881
0.7361	Intermediate Similarity	NPC477899
0.7361	Intermediate Similarity	NPC475498
0.7358	Intermediate Similarity	NPC472285
0.7352	Intermediate Similarity	NPC473689
0.7352	Intermediate Similarity	NPC267853
0.7352	Intermediate Similarity	NPC260434
0.7352	Intermediate Similarity	NPC292416
0.7352	Intermediate Similarity	NPC316841
0.7349	Intermediate Similarity	NPC477911
0.7349	Intermediate Similarity	NPC216612
0.7346	Intermediate Similarity	NPC319128
0.7346	Intermediate Similarity	NPC4421
0.7346	Intermediate Similarity	NPC228331
0.7346	Intermediate Similarity	NPC146976
0.7343	Intermediate Similarity	NPC475835
0.7337	Intermediate Similarity	NPC263455
0.7337	Intermediate Similarity	NPC138370
0.7333	Intermediate Similarity	NPC476467
0.733	Intermediate Similarity	NPC473239
0.733	Intermediate Similarity	NPC327769
0.733	Intermediate Similarity	NPC316411
0.7327	Intermediate Similarity	NPC473506
0.7318	Intermediate Similarity	NPC244839
0.7318	Intermediate Similarity	NPC244897
0.7318	Intermediate Similarity	NPC320324
0.7318	Intermediate Similarity	NPC319880
0.7315	Intermediate Similarity	NPC322482
0.7315	Intermediate Similarity	NPC229893
0.7311	Intermediate Similarity	NPC62844
0.7311	Intermediate Similarity	NPC477910
0.7311	Intermediate Similarity	NPC193361
0.7308	Intermediate Similarity	NPC470280
0.7302	Intermediate Similarity	NPC477912
0.7302	Intermediate Similarity	NPC477903
0.7299	Intermediate Similarity	NPC234078
0.7299	Intermediate Similarity	NPC221100
0.7294	Intermediate Similarity	NPC475631
0.7294	Intermediate Similarity	NPC87152
0.7294	Intermediate Similarity	NPC475600
0.7294	Intermediate Similarity	NPC476110
0.7293	Intermediate Similarity	NPC302159
0.7286	Intermediate Similarity	NPC82370
0.7286	Intermediate Similarity	NPC470189
0.7286	Intermediate Similarity	NPC40919
0.7285	Intermediate Similarity	NPC237702
0.7283	Intermediate Similarity	NPC312860
0.7277	Intermediate Similarity	NPC471016
0.7273	Intermediate Similarity	NPC315062
0.7265	Intermediate Similarity	NPC15801
0.7264	Intermediate Similarity	NPC198673
0.726	Intermediate Similarity	NPC475644
0.726	Intermediate Similarity	NPC471977
0.726	Intermediate Similarity	NPC314297
0.726	Intermediate Similarity	NPC315545
0.726	Intermediate Similarity	NPC471190
0.726	Intermediate Similarity	NPC470486
0.7252	Intermediate Similarity	NPC170751
0.7252	Intermediate Similarity	NPC475406
0.7251	Intermediate Similarity	NPC292517
0.7245	Intermediate Similarity	NPC159125
0.7243	Intermediate Similarity	NPC158020
0.7243	Intermediate Similarity	NPC473089
0.7243	Intermediate Similarity	NPC212768
0.7243	Intermediate Similarity	NPC6576
0.7243	Intermediate Similarity	NPC75600
0.7243	Intermediate Similarity	NPC314270
0.7243	Intermediate Similarity	NPC473115
0.7236	Intermediate Similarity	NPC44354
0.7236	Intermediate Similarity	NPC75544
0.7236	Intermediate Similarity	NPC111602
0.7236	Intermediate Similarity	NPC102338
0.7236	Intermediate Similarity	NPC196251
0.7236	Intermediate Similarity	NPC63199
0.723	Intermediate Similarity	NPC470306
0.7227	Intermediate Similarity	NPC91125
0.722	Intermediate Similarity	NPC38959
0.722	Intermediate Similarity	NPC327904
0.7215	Intermediate Similarity	NPC192712
0.7212	Intermediate Similarity	NPC313796
0.7212	Intermediate Similarity	NPC315638
0.7212	Intermediate Similarity	NPC313345
0.7212	Intermediate Similarity	NPC314855
0.7212	Intermediate Similarity	NPC309498
0.7209	Intermediate Similarity	NPC301368
0.7209	Intermediate Similarity	NPC84815
0.7208	Intermediate Similarity	NPC258480
0.7208	Intermediate Similarity	NPC472119
0.7208	Intermediate Similarity	NPC46895
0.7206	Intermediate Similarity	NPC168911
0.7206	Intermediate Similarity	NPC474916
0.7206	Intermediate Similarity	NPC472284
0.7202	Intermediate Similarity	NPC477902
0.7196	Intermediate Similarity	NPC471014
0.7196	Intermediate Similarity	NPC475408
0.7195	Intermediate Similarity	NPC475303
0.7195	Intermediate Similarity	NPC475596
0.7195	Intermediate Similarity	NPC477906
0.7192	Intermediate Similarity	NPC77061
0.7182	Intermediate Similarity	NPC230085
0.7182	Intermediate Similarity	NPC159630
0.7181	Intermediate Similarity	NPC322644
0.7178	Intermediate Similarity	NPC269886
0.7178	Intermediate Similarity	NPC472295
0.7178	Intermediate Similarity	NPC81802
0.7178	Intermediate Similarity	NPC247735
0.7178	Intermediate Similarity	NPC472210
0.7177	Intermediate Similarity	NPC156044
0.7177	Intermediate Similarity	NPC244741
0.7176	Intermediate Similarity	NPC472099

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 NPC123395 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	564
0.2-0.3	762
0.3-0.4	1402
0.4-0.5	2875
0.5-0.6	2369
0.6-0.7	897
0.7-0.8	82
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7914	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD3393	Approved
0.7816	Intermediate Similarity	NPD3389	Approved
0.7816	Intermediate Similarity	NPD3394	Approved
0.78	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD2582	Approved
0.7735	Intermediate Similarity	NPD2581	Approved
0.7704	Intermediate Similarity	NPD4526	Approved
0.7704	Intermediate Similarity	NPD4529	Approved
0.7704	Intermediate Similarity	NPD4528	Approved
0.7673	Intermediate Similarity	NPD3947	Discontinued
0.7665	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2510	Approved
0.7647	Intermediate Similarity	NPD2509	Approved
0.7644	Intermediate Similarity	NPD3178	Discontinued
0.7591	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD1996	Discontinued
0.7551	Intermediate Similarity	NPD8063	Discontinued
0.7541	Intermediate Similarity	NPD820	Phase 3
0.7536	Intermediate Similarity	NPD4417	Approved
0.7536	Intermediate Similarity	NPD5475	Discontinued
0.7463	Intermediate Similarity	NPD7001	Phase 3
0.7463	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5891	Approved
0.7453	Intermediate Similarity	NPD6770	Approved
0.7444	Intermediate Similarity	NPD9271	Approved
0.7385	Intermediate Similarity	NPD1096	Discontinued
0.7379	Intermediate Similarity	NPD7010	Phase 3
0.7371	Intermediate Similarity	NPD7404	Approved
0.7363	Intermediate Similarity	NPD7061	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD3371	Approved
0.733	Intermediate Similarity	NPD5901	Discontinued
0.733	Intermediate Similarity	NPD2077	Approved
0.733	Intermediate Similarity	NPD2076	Approved
0.7327	Intermediate Similarity	NPD8289	Discontinued
0.7325	Intermediate Similarity	NPD5482	Discontinued
0.7312	Intermediate Similarity	NPD5255	Approved
0.7312	Intermediate Similarity	NPD1630	Approved
0.7302	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD5088	Discontinued
0.7283	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2336	Approved
0.722	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD3794	Approved
0.7217	Intermediate Similarity	NPD3795	Approved
0.7217	Intermediate Similarity	NPD2823	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD6665	Discontinued
0.7214	Intermediate Similarity	NPD4376	Phase 3
0.7204	Intermediate Similarity	NPD7470	Discontinued
0.7198	Intermediate Similarity	NPD5513	Phase 2
0.7196	Intermediate Similarity	NPD1631	Approved
0.7196	Intermediate Similarity	NPD2787	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7688	Phase 1
0.7186	Intermediate Similarity	NPD1034	Phase 3
0.7186	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD8479	Phase 2
0.7171	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6999	Discontinued
0.717	Intermediate Similarity	NPD5866	Approved
0.7163	Intermediate Similarity	NPD6568	Discontinued
0.7163	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD4429	Discontinued
0.715	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD1659	Phase 1
0.7136	Intermediate Similarity	NPD4500	Approved
0.7136	Intermediate Similarity	NPD4501	Approved
0.7129	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6569	Phase 2
0.7124	Intermediate Similarity	NPD7885	Phase 2
0.7124	Intermediate Similarity	NPD7886	Phase 2
0.7111	Intermediate Similarity	NPD107	Approved
0.711	Intermediate Similarity	NPD8356	Approved
0.711	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD4506	Discontinued
0.7109	Intermediate Similarity	NPD6529	Discontinued
0.7108	Intermediate Similarity	NPD2307	Discontinued
0.7083	Intermediate Similarity	NPD1623	Approved
0.7081	Intermediate Similarity	NPD7396	Approved
0.7067	Intermediate Similarity	NPD3006	Discontinued
0.7062	Intermediate Similarity	NPD7467	Discontinued
0.7062	Intermediate Similarity	NPD7666	Phase 3
0.7062	Intermediate Similarity	NPD7665	Phase 2
0.7059	Intermediate Similarity	NPD4602	Approved
0.7059	Intermediate Similarity	NPD4427	Phase 2
0.7056	Intermediate Similarity	NPD4804	Approved
0.705	Intermediate Similarity	NPD3315	Phase 3
0.7047	Intermediate Similarity	NPD1573	Approved
0.7047	Intermediate Similarity	NPD1575	Approved
0.7043	Intermediate Similarity	NPD8468	Phase 2
0.7041	Intermediate Similarity	NPD1032	Phase 2
0.7037	Intermediate Similarity	NPD8326	Phase 3
0.7037	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8325	Phase 3
0.703	Intermediate Similarity	NPD3321	Discontinued
0.7029	Intermediate Similarity	NPD5450	Discontinued
0.7026	Intermediate Similarity	NPD1586	Approved
0.7024	Intermediate Similarity	NPD3477	Phase 2
0.7024	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6790	Phase 1
0.7014	Intermediate Similarity	NPD5640	Discontinued
0.7005	Intermediate Similarity	NPD6578	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4889	Approved
0.7	Intermediate Similarity	NPD6987	Phase 1
0.7	Intermediate Similarity	NPD6323	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2511	Approved
0.7	Intermediate Similarity	NPD3247	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5862	Discovery
0.699	Remote Similarity	NPD5104	Approved
0.699	Remote Similarity	NPD5003	Discontinued
0.6982	Remote Similarity	NPD8430	Approved
0.698	Remote Similarity	NPD7234	Approved
0.698	Remote Similarity	NPD7233	Approved
0.6979	Remote Similarity	NPD2915	Discontinued
0.6978	Remote Similarity	NPD4805	Approved
0.6974	Remote Similarity	NPD750	Phase 2
0.697	Remote Similarity	NPD1643	Phase 3
0.696	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD9075	Approved
0.6957	Remote Similarity	NPD9074	Approved
0.6954	Remote Similarity	NPD6642	Approved
0.6954	Remote Similarity	NPD6641	Approved
0.6953	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6242	Discontinued
0.6941	Remote Similarity	NPD3280	Approved
0.6937	Remote Similarity	NPD7426	Phase 1
0.6933	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD4948	Discontinued
0.693	Remote Similarity	NPD7069	Discontinued
0.693	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6635	Approved
0.6927	Remote Similarity	NPD5632	Approved
0.692	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.692	Remote Similarity	NPD5022	Discontinued
0.6919	Remote Similarity	NPD1587	Approved
0.6916	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD687	Clinical (unspecified phase)
0.691	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4923	Phase 1
0.6909	Remote Similarity	NPD4301	Approved
0.6904	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7168	Phase 3
0.689	Remote Similarity	NPD6479	Discontinued
0.6882	Remote Similarity	NPD1270	Approved
0.6872	Remote Similarity	NPD6176	Phase 1
0.6869	Remote Similarity	NPD2753	Discontinued
0.6866	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7180	Phase 3
0.6863	Remote Similarity	NPD2564	Approved
0.6863	Remote Similarity	NPD2565	Phase 2
0.686	Remote Similarity	NPD5512	Phase 3
0.6838	Remote Similarity	NPD4558	Phase 2
0.6837	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.683	Remote Similarity	NPD3259	Approved
0.6828	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1802	Approved
0.6828	Remote Similarity	NPD1801	Approved
0.6824	Remote Similarity	NPD8100	Phase 3
0.6818	Remote Similarity	NPD3238	Discontinued
0.6816	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6068	Discontinued
0.6813	Remote Similarity	NPD2896	Discontinued
0.6812	Remote Similarity	NPD946	Discontinued
0.6806	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6995	Phase 1
0.68	Remote Similarity	NPD9510	Approved
0.6796	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5505	Discontinued
0.6794	Remote Similarity	NPD53	Approved
0.6794	Remote Similarity	NPD7778	Approved
0.6794	Remote Similarity	NPD7777	Approved
0.6793	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6281	Approved
0.678	Remote Similarity	NPD4499	Approved
0.6773	Remote Similarity	NPD7395	Discontinued
0.6771	Remote Similarity	NPD6173	Approved
0.6768	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD482	Approved
0.6767	Remote Similarity	NPD6716	Phase 1
0.6766	Remote Similarity	NPD9362	Approved
0.6765	Remote Similarity	NPD8020	Approved
0.6765	Remote Similarity	NPD8021	Approved
0.6762	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD8114	Approved
0.6761	Remote Similarity	NPD4037	Approved
0.6761	Remote Similarity	NPD4039	Approved
0.6761	Remote Similarity	NPD4122	Approved
0.6761	Remote Similarity	NPD4034	Approved
0.6761	Remote Similarity	NPD7712	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