NPASS Compound

Structure

NPC475326 OpenBabel07101718282D 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 -4.5000 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 2.5981 -1.5000 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 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 2.5981 -2.5000 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 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 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 1.7321 -4.0000 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 19 1 0 0 0 0 8 19 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 18 1 0 0 0 0 14 22 1 1 0 0 0 15 18 1 0 0 0 0 16 17 2 0 0 0 0 16 20 1 0 0 0 0 17 23 1 0 0 0 0 18 11 1 1 0 0 0 18 19 1 0 0 0 0 19 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	315.15
Volume:	318.634
LogP:	0.158
LogD:	1.093
LogS:	-1.212
# Rotatable Bonds:	2
TPSA:	61.75
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.672
Synthetic Accessibility Score:	5.218
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.572
MDCK Permeability:	1.8342267139814794e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.949
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.432
Plasma Protein Binding (PPB):	34.60954284667969%
Volume Distribution (VD):	3.364
Pgp-substrate:	61.58174133300781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.166
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.716
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.629
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.388
CYP3A4-inhibitor:	0.041
CYP3A4-substrate:	0.93

ADMET: Excretion

Clearance (CL):	15.614
Half-life (T1/2):	0.949

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.881
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.811
Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.377
Carcinogencity:	0.93
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.77

Download Data

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

Natural Product: NPC475326

Natural Product ID:	NPC475326
*Common Name:**	Erysodine N-Oxide
IUPAC Name:	(2R,13bS)-2,12-dimethoxy-7-oxido-2,6,8,9-tetrahydro-1H-indolo[7a,1-a]isoquinolin-7-ium-11-ol
Synonyms:	Erysodine N-Oxide
Standard InCHIKey:	KJUGMBCUNNTOMY-ZWSMLAFMSA-N
Standard InCHI:	InChI=1S/C18H21NO4/c1-22-14-4-3-13-6-8-19(21)7-5-12-9-16(20)17(23-2)10-15(12)18(13,19)11-14/h3-4,6,9-10,14,20H,5,7-8,11H2,1-2H3/t14-,18-,19?/m0/s1
SMILES:	CO[C@H]1C=CC2=CCN3(=O)[C@]2(C1)c1cc(OC)c(cc1CC3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503526
PubChem CID:	44570448
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[456550]
NPT15	Cell Line	Jurkat	Homo sapiens	Inhibition	=	2.4	%	PMID[456550]
NPT15	Cell Line	Jurkat	Homo sapiens	Inhibition	=	18.9	%	PMID[456550]

☑ 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 NPC475326 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	264
0.1-0.2	1429
0.2-0.3	6616
0.3-0.4	11543
0.4-0.5	6901
0.5-0.6	11633
0.6-0.7	3431
0.7-0.8	656
0.8-0.85	154
0.85-0.9	58
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9463	High Similarity	NPC82285
0.9463	High Similarity	NPC133011
0.9205	High Similarity	NPC37272
0.92	High Similarity	NPC274026
0.8993	High Similarity	NPC130926
0.891	High Similarity	NPC59028
0.891	High Similarity	NPC92191
0.8903	High Similarity	NPC147091
0.8816	High Similarity	NPC476571
0.8816	High Similarity	NPC246587
0.8816	High Similarity	NPC147390
0.8816	High Similarity	NPC135538
0.8816	High Similarity	NPC428
0.8816	High Similarity	NPC24233
0.875	High Similarity	NPC191376
0.875	High Similarity	NPC321505
0.875	High Similarity	NPC179825
0.8734	High Similarity	NPC205167
0.8642	High Similarity	NPC164429
0.8636	High Similarity	NPC477565
0.8636	High Similarity	NPC103379
0.8618	High Similarity	NPC185838
0.8616	High Similarity	NPC249274
0.8599	High Similarity	NPC5238
0.8599	High Similarity	NPC204828
0.8599	High Similarity	NPC110416
0.8599	High Similarity	NPC469817
0.8599	High Similarity	NPC249797
0.8599	High Similarity	NPC127674
0.8599	High Similarity	NPC54379
0.8599	High Similarity	NPC207757
0.8599	High Similarity	NPC295691
0.8599	High Similarity	NPC276588
0.8599	High Similarity	NPC39701
0.8599	High Similarity	NPC184026
0.8599	High Similarity	NPC193949
0.8599	High Similarity	NPC189266
0.8599	High Similarity	NPC172765
0.8599	High Similarity	NPC2413
0.8599	High Similarity	NPC278799
0.859	High Similarity	NPC148898
0.8581	High Similarity	NPC220858
0.8581	High Similarity	NPC151895
0.8581	High Similarity	NPC192768
0.8581	High Similarity	NPC97221
0.8581	High Similarity	NPC88249
0.8506	High Similarity	NPC476151
0.8457	Intermediate Similarity	NPC76116
0.8456	Intermediate Similarity	NPC131204
0.8456	Intermediate Similarity	NPC301050
0.8408	Intermediate Similarity	NPC76213
0.8408	Intermediate Similarity	NPC277669
0.8355	Intermediate Similarity	NPC474915
0.8355	Intermediate Similarity	NPC213206
0.8355	Intermediate Similarity	NPC188163
0.8355	Intermediate Similarity	NPC328750
0.8354	Intermediate Similarity	NPC470924
0.8344	Intermediate Similarity	NPC232514
0.8344	Intermediate Similarity	NPC276944
0.8344	Intermediate Similarity	NPC238530
0.8323	Intermediate Similarity	NPC111485
0.8323	Intermediate Similarity	NPC49353
0.8303	Intermediate Similarity	NPC160570
0.8302	Intermediate Similarity	NPC2295
0.8302	Intermediate Similarity	NPC477564
0.8294	Intermediate Similarity	NPC233718
0.8289	Intermediate Similarity	NPC314682
0.828	Intermediate Similarity	NPC207824
0.828	Intermediate Similarity	NPC60538
0.8272	Intermediate Similarity	NPC97072
0.8272	Intermediate Similarity	NPC215829
0.8242	Intermediate Similarity	NPC210140
0.8242	Intermediate Similarity	NPC100566
0.8232	Intermediate Similarity	NPC231198
0.8194	Intermediate Similarity	NPC294249
0.8182	Intermediate Similarity	NPC264850
0.8182	Intermediate Similarity	NPC13916
0.816	Intermediate Similarity	NPC27410
0.816	Intermediate Similarity	NPC166014
0.8153	Intermediate Similarity	NPC476144
0.8153	Intermediate Similarity	NPC210437
0.8153	Intermediate Similarity	NPC51957
0.8153	Intermediate Similarity	NPC16107
0.8153	Intermediate Similarity	NPC106295
0.8144	Intermediate Similarity	NPC329911
0.8137	Intermediate Similarity	NPC78733
0.8133	Intermediate Similarity	NPC301189
0.8133	Intermediate Similarity	NPC181653
0.8133	Intermediate Similarity	NPC190332
0.8133	Intermediate Similarity	NPC298186
0.8129	Intermediate Similarity	NPC476567
0.8129	Intermediate Similarity	NPC128019
0.8129	Intermediate Similarity	NPC136860
0.8121	Intermediate Similarity	NPC134858
0.8121	Intermediate Similarity	NPC24465
0.811	Intermediate Similarity	NPC60186
0.8107	Intermediate Similarity	NPC187678
0.8101	Intermediate Similarity	NPC475959
0.8101	Intermediate Similarity	NPC7467
0.8095	Intermediate Similarity	NPC470739
0.8095	Intermediate Similarity	NPC476331
0.8095	Intermediate Similarity	NPC225597
0.8095	Intermediate Similarity	NPC477640
0.8086	Intermediate Similarity	NPC186063
0.8084	Intermediate Similarity	NPC158148
0.8084	Intermediate Similarity	NPC266176
0.8084	Intermediate Similarity	NPC83198
0.8084	Intermediate Similarity	NPC204908
0.8084	Intermediate Similarity	NPC58766
0.8084	Intermediate Similarity	NPC470324
0.8084	Intermediate Similarity	NPC290759
0.8084	Intermediate Similarity	NPC82533
0.8084	Intermediate Similarity	NPC475686
0.8072	Intermediate Similarity	NPC317272
0.8072	Intermediate Similarity	NPC240841
0.8072	Intermediate Similarity	NPC250846
0.8072	Intermediate Similarity	NPC42549
0.8072	Intermediate Similarity	NPC268503
0.8072	Intermediate Similarity	NPC124657
0.8072	Intermediate Similarity	NPC256012
0.8061	Intermediate Similarity	NPC233650
0.8061	Intermediate Similarity	NPC324144
0.8054	Intermediate Similarity	NPC160193
0.805	Intermediate Similarity	NPC44869
0.8049	Intermediate Similarity	NPC18402
0.8036	Intermediate Similarity	NPC474475
0.8026	Intermediate Similarity	NPC475828
0.8024	Intermediate Similarity	NPC145832
0.8024	Intermediate Similarity	NPC117188
0.8024	Intermediate Similarity	NPC205421
0.8024	Intermediate Similarity	NPC158376
0.8024	Intermediate Similarity	NPC306555
0.8024	Intermediate Similarity	NPC81218
0.8024	Intermediate Similarity	NPC12053
0.8024	Intermediate Similarity	NPC474931
0.8012	Intermediate Similarity	NPC4138
0.8012	Intermediate Similarity	NPC477560
0.8012	Intermediate Similarity	NPC121275
0.8012	Intermediate Similarity	NPC13504
0.8012	Intermediate Similarity	NPC136508
0.8012	Intermediate Similarity	NPC284183
0.8012	Intermediate Similarity	NPC253043
0.8012	Intermediate Similarity	NPC96603
0.8012	Intermediate Similarity	NPC78222
0.8012	Intermediate Similarity	NPC196447
0.8012	Intermediate Similarity	NPC477563
0.8012	Intermediate Similarity	NPC306843
0.8012	Intermediate Similarity	NPC212794
0.7988	Intermediate Similarity	NPC57272
0.7965	Intermediate Similarity	NPC32154
0.7964	Intermediate Similarity	NPC476002
0.7953	Intermediate Similarity	NPC237044
0.7952	Intermediate Similarity	NPC320104
0.795	Intermediate Similarity	NPC476579
0.7941	Intermediate Similarity	NPC232386
0.7941	Intermediate Similarity	NPC2314
0.7941	Intermediate Similarity	NPC152680
0.7941	Intermediate Similarity	NPC190783
0.7917	Intermediate Similarity	NPC150879
0.7914	Intermediate Similarity	NPC216459
0.7914	Intermediate Similarity	NPC41178
0.7914	Intermediate Similarity	NPC138487
0.7907	Intermediate Similarity	NPC474325
0.7901	Intermediate Similarity	NPC26601
0.7895	Intermediate Similarity	NPC304675
0.7882	Intermediate Similarity	NPC10871
0.7871	Intermediate Similarity	NPC210086
0.787	Intermediate Similarity	NPC66573
0.7866	Intermediate Similarity	NPC477132
0.7866	Intermediate Similarity	NPC477133
0.7866	Intermediate Similarity	NPC37205
0.7866	Intermediate Similarity	NPC160931
0.7866	Intermediate Similarity	NPC146288
0.7861	Intermediate Similarity	NPC474745
0.7857	Intermediate Similarity	NPC81247
0.7857	Intermediate Similarity	NPC35627
0.7857	Intermediate Similarity	NPC476573
0.7849	Intermediate Similarity	NPC474470
0.7849	Intermediate Similarity	NPC241704
0.7844	Intermediate Similarity	NPC59567
0.7844	Intermediate Similarity	NPC1229
0.7831	Intermediate Similarity	NPC4304
0.7831	Intermediate Similarity	NPC226428
0.7824	Intermediate Similarity	NPC311991
0.7824	Intermediate Similarity	NPC109925
0.7818	Intermediate Similarity	NPC40389
0.7818	Intermediate Similarity	NPC148014
0.7818	Intermediate Similarity	NPC78359
0.7818	Intermediate Similarity	NPC65490
0.7818	Intermediate Similarity	NPC315707
0.7811	Intermediate Similarity	NPC298979
0.7806	Intermediate Similarity	NPC253429
0.7803	Intermediate Similarity	NPC114364
0.7803	Intermediate Similarity	NPC320223
0.7798	Intermediate Similarity	NPC3375
0.7798	Intermediate Similarity	NPC255607
0.7791	Intermediate Similarity	NPC223124
0.7791	Intermediate Similarity	NPC233029
0.7791	Intermediate Similarity	NPC210148
0.7791	Intermediate Similarity	NPC128560

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 NPC475326 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	709
0.2-0.3	1026
0.3-0.4	2083
0.4-0.5	2683
0.5-0.6	1709
0.6-0.7	623
0.7-0.8	135
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8355	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD4772	Phase 2
0.8187	Intermediate Similarity	NPD4773	Phase 2
0.8153	Intermediate Similarity	NPD4584	Approved
0.8084	Intermediate Similarity	NPD2898	Approved
0.7964	Intermediate Similarity	NPD4010	Discontinued
0.787	Intermediate Similarity	NPD2489	Approved
0.787	Intermediate Similarity	NPD27	Approved
0.7857	Intermediate Similarity	NPD6071	Discontinued
0.7848	Intermediate Similarity	NPD5241	Discontinued
0.7818	Intermediate Similarity	NPD2563	Approved
0.7818	Intermediate Similarity	NPD2560	Approved
0.7812	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD4017	Approved
0.7725	Intermediate Similarity	NPD7831	Phase 2
0.7725	Intermediate Similarity	NPD7833	Phase 2
0.7725	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD3639	Approved
0.7716	Intermediate Similarity	NPD3641	Approved
0.7716	Intermediate Similarity	NPD6030	Approved
0.7716	Intermediate Similarity	NPD6031	Approved
0.7716	Intermediate Similarity	NPD3640	Phase 3
0.7714	Intermediate Similarity	NPD7313	Approved
0.7714	Intermediate Similarity	NPD7312	Approved
0.7714	Intermediate Similarity	NPD7311	Approved
0.7714	Intermediate Similarity	NPD7310	Approved
0.7706	Intermediate Similarity	NPD2969	Approved
0.7706	Intermediate Similarity	NPD2970	Approved
0.767	Intermediate Similarity	NPD7309	Approved
0.767	Intermediate Similarity	NPD8054	Approved
0.767	Intermediate Similarity	NPD8053	Approved
0.7651	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2674	Phase 3
0.759	Intermediate Similarity	NPD7298	Approved
0.7588	Intermediate Similarity	NPD6107	Approved
0.7582	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD3051	Approved
0.7444	Intermediate Similarity	NPD7906	Approved
0.7423	Intermediate Similarity	NPD2421	Approved
0.7423	Intermediate Similarity	NPD2420	Approved
0.7421	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3144	Approved
0.7419	Intermediate Similarity	NPD5718	Phase 2
0.7419	Intermediate Similarity	NPD3145	Approved
0.7391	Intermediate Similarity	NPD5177	Phase 3
0.7391	Intermediate Similarity	NPD3060	Approved
0.7362	Intermediate Similarity	NPD3845	Phase 1
0.7358	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD2977	Approved
0.7337	Intermediate Similarity	NPD2978	Approved
0.733	Intermediate Similarity	NPD8156	Discontinued
0.733	Intermediate Similarity	NPD5312	Approved
0.733	Intermediate Similarity	NPD5313	Approved
0.7318	Intermediate Similarity	NPD4577	Approved
0.7318	Intermediate Similarity	NPD4578	Approved
0.7312	Intermediate Similarity	NPD2161	Phase 2
0.7293	Intermediate Similarity	NPD4663	Approved
0.729	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4236	Phase 3
0.7284	Intermediate Similarity	NPD4162	Approved
0.7284	Intermediate Similarity	NPD4237	Approved
0.7273	Intermediate Similarity	NPD8252	Approved
0.7273	Intermediate Similarity	NPD8099	Discontinued
0.7273	Intermediate Similarity	NPD8251	Approved
0.7257	Intermediate Similarity	NPD4481	Phase 3
0.7256	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1753	Discontinued
0.7247	Intermediate Similarity	NPD6297	Approved
0.7241	Intermediate Similarity	NPD4166	Phase 2
0.7235	Intermediate Similarity	NPD5772	Approved
0.7235	Intermediate Similarity	NPD5773	Approved
0.7222	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3124	Discontinued
0.7195	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6896	Approved
0.7188	Intermediate Similarity	NPD6895	Approved
0.7184	Intermediate Similarity	NPD7802	Discontinued
0.7182	Intermediate Similarity	NPD6853	Approved
0.7182	Intermediate Similarity	NPD6851	Approved
0.7174	Intermediate Similarity	NPD2488	Approved
0.7174	Intermediate Similarity	NPD2490	Approved
0.7151	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6788	Approved
0.7119	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2238	Phase 2
0.7101	Intermediate Similarity	NPD824	Approved
0.7093	Intermediate Similarity	NPD5978	Approved
0.7093	Intermediate Similarity	NPD5977	Approved
0.7091	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1424	Approved
0.7055	Intermediate Similarity	NPD3656	Approved
0.7039	Intermediate Similarity	NPD2668	Approved
0.7039	Intermediate Similarity	NPD2667	Approved
0.703	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6331	Phase 2
0.7024	Intermediate Similarity	NPD6090	Discontinued
0.7019	Intermediate Similarity	NPD817	Approved
0.7019	Intermediate Similarity	NPD823	Approved
0.7013	Intermediate Similarity	NPD2233	Approved
0.7013	Intermediate Similarity	NPD2232	Approved
0.7013	Intermediate Similarity	NPD2230	Approved
0.7006	Intermediate Similarity	NPD6688	Approved
0.7006	Intermediate Similarity	NPD6687	Approved
0.7	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3692	Discontinued
0.6979	Remote Similarity	NPD3448	Approved
0.6979	Remote Similarity	NPD2491	Approved
0.6977	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4123	Phase 3
0.6951	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD1375	Discontinued
0.6941	Remote Similarity	NPD4210	Discontinued
0.694	Remote Similarity	NPD7281	Phase 3
0.694	Remote Similarity	NPD7280	Phase 3
0.6937	Remote Similarity	NPD4475	Approved
0.6937	Remote Similarity	NPD4474	Approved
0.6931	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD3452	Approved
0.6927	Remote Similarity	NPD2493	Approved
0.6927	Remote Similarity	NPD2494	Approved
0.6927	Remote Similarity	NPD3450	Approved
0.6919	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7110	Phase 1
0.6909	Remote Similarity	NPD7153	Discontinued
0.6901	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4005	Discontinued
0.6897	Remote Similarity	NPD5967	Approved
0.6894	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3109	Approved
0.6894	Remote Similarity	NPD3110	Approved
0.6894	Remote Similarity	NPD3620	Phase 2
0.6886	Remote Similarity	NPD2677	Approved
0.6885	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3053	Approved
0.6879	Remote Similarity	NPD3055	Approved
0.6875	Remote Similarity	NPD1039	Discontinued
0.6875	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD4873	Discontinued
0.6845	Remote Similarity	NPD7124	Phase 2
0.6842	Remote Similarity	NPD5582	Discontinued
0.6839	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD1136	Approved
0.6832	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD1130	Approved
0.6832	Remote Similarity	NPD1132	Approved
0.6824	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7526	Approved
0.6824	Remote Similarity	NPD52	Approved
0.6821	Remote Similarity	NPD4582	Approved
0.6821	Remote Similarity	NPD4040	Phase 1
0.6821	Remote Similarity	NPD4583	Approved
0.6818	Remote Similarity	NPD4055	Discovery
0.6818	Remote Similarity	NPD5604	Discontinued
0.6815	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7037	Approved
0.6804	Remote Similarity	NPD3057	Approved
0.6804	Remote Similarity	NPD3533	Approved
0.6804	Remote Similarity	NPD2972	Approved
0.6792	Remote Similarity	NPD3637	Approved
0.6792	Remote Similarity	NPD3635	Approved
0.6792	Remote Similarity	NPD3636	Approved
0.6791	Remote Similarity	NPD3398	Discontinued
0.679	Remote Similarity	NPD3062	Approved
0.679	Remote Similarity	NPD3061	Approved
0.679	Remote Similarity	NPD3059	Approved
0.6786	Remote Similarity	NPD5160	Discontinued
0.6784	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD2122	Discontinued
0.6779	Remote Similarity	NPD228	Approved
0.6772	Remote Similarity	NPD4103	Phase 2
0.6772	Remote Similarity	NPD7296	Approved
0.6772	Remote Similarity	NPD4098	Discontinued
0.6772	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4420	Approved
0.677	Remote Similarity	NPD598	Approved
0.677	Remote Similarity	NPD601	Approved
0.677	Remote Similarity	NPD597	Approved
0.6769	Remote Similarity	NPD4002	Approved
0.6769	Remote Similarity	NPD4004	Approved
0.6763	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4678	Approved
0.6763	Remote Similarity	NPD4675	Approved
0.6757	Remote Similarity	NPD2968	Approved
0.6757	Remote Similarity	NPD2971	Approved
0.6753	Remote Similarity	NPD4093	Discontinued
0.6744	Remote Similarity	NPD3686	Approved
0.6744	Remote Similarity	NPD3687	Approved
0.6742	Remote Similarity	NPD2904	Discontinued
0.673	Remote Similarity	NPD6584	Phase 3
0.6728	Remote Similarity	NPD3530	Approved
0.6728	Remote Similarity	NPD3531	Approved
0.6728	Remote Similarity	NPD3532	Approved
0.6726	Remote Similarity	NPD6748	Discontinued
0.6725	Remote Similarity	NPD3647	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