NPASS Compound

Structure

CID130926 OpenBabel06191715492D 23 26 0 0 1 0 0 0 0 0999 V2000 -3.4031 2.0642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1953 -0.9834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1904 0.0252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0098 2.0172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8325 2.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8518 -1.4998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0322 1.0040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0049 -1.0086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0273 -0.0050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5929 -1.5003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5832 0.5168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7073 1.0173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7170 -1.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0049 1.0090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7024 2.0255 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7122 0.0083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4640 -0.9918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4591 0.0168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8421 0.4998 0.0000 C 0 0 2 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 -2.5416 2.5358 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3321 -1.4874 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3223 0.5208 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 8 1 0 0 0 0 6 13 1 0 0 0 0 7 9 1 0 0 0 0 7 14 2 0 0 0 0 8 20 1 0 0 0 0 9 20 1 0 0 0 0 10 13 2 0 0 0 0 10 17 1 0 0 0 0 11 16 2 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 13 16 1 0 0 0 0 14 19 1 0 0 0 0 15 21 1 1 0 0 0 16 19 1 0 0 0 0 17 18 2 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 20 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	313.17
Volume:	327.139
LogP:	2.478
LogD:	2.339
LogS:	-3.126
# Rotatable Bonds:	3
TPSA:	30.93
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.858
Synthetic Accessibility Score:	4.379
Fsp3:	0.474
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:	-4.781
MDCK Permeability:	2.912940544774756e-05
Pgp-inhibitor:	0.863
Pgp-substrate:	0.885
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.863
30% Bioavailability (F30%):	0.317

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.997
Plasma Protein Binding (PPB):	64.36698150634766%
Volume Distribution (VD):	1.645
Pgp-substrate:	21.907306671142578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.501
CYP2C19-inhibitor:	0.102
CYP2C19-substrate:	0.942
CYP2C9-inhibitor:	0.213
CYP2C9-substrate:	0.488
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.672
CYP3A4-inhibitor:	0.612
CYP3A4-substrate:	0.942

ADMET: Excretion

Clearance (CL):	13.149
Half-life (T1/2):	0.713

ADMET: Toxicity

hERG Blockers:	0.379
Human Hepatotoxicity (H-HT):	0.881
Drug-inuced Liver Injury (DILI):	0.308
AMES Toxicity:	0.783
Rat Oral Acute Toxicity:	0.187
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.862
Carcinogencity:	0.86
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC130926

Natural Product ID:	NPC130926
*Common Name:**	Erysotrine
IUPAC Name:	(2R,13bS)-2,11,12-trimethoxy-2,6,8,9-tetrahydro-1H-indolo[7a,1-a]isoquinoline
Synonyms:	Erysotrine
Standard InCHIKey:	WXVSPYOOFCCEII-KXBFYZLASA-N
Standard InCHI:	InChI=1S/C19H23NO3/c1-21-15-5-4-14-7-9-20-8-6-13-10-17(22-2)18(23-3)11-16(13)19(14,20)12-15/h4-5,7,10-11,15H,6,8-9,12H2,1-3H3/t15-,19-/m0/s1
SMILES:	CO[C@H]1C=CC2=CCN3CCc4cc(c(cc4[C@]23C1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL442947
PubChem CID:	442219
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]
NPO8301	Erythrina suberosa	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[5348524]
NPO27356	Erythrina glauca	Species	Fabaceae	Eukaryota	n.a.	bark	n.a.	PMID[9170286]
NPO13279	Berberis zycium	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27356	Erythrina glauca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8301	Erythrina suberosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13279	Berberis zycium	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27356	Erythrina glauca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8301	Erythrina suberosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8301	Erythrina suberosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13279	Berberis zycium	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27356	Erythrina glauca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4371	Rissoella verruculosa	Species	Rissoellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20031	Erythrina velutina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6005	Osmundaria fimbriata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8301	Erythrina suberosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27356	Erythrina glauca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5332	Smallanthus fruticosus	Species	Asteraceae	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
Ki	2
Others	1

Activity Type	# Activity
Cell Line	3
Protein Complex	2

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[484695]
NPT15	Cell Line	Jurkat	Homo sapiens	Inhibition	=	45.0	%	PMID[484695]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	7.2	ug.mL-1	PMID[484695]
NPT409	Protein Complex	Neuronal acetylcholine receptor; alpha4/beta2	Homo sapiens	Ki	=	600.0	nM	PMID[484696]
NPT409	Protein Complex	Neuronal acetylcholine receptor; alpha4/beta2	Homo sapiens	Ki	=	600.0	nM	PMID[484697]

☑ 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 NPC130926 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	286
0.1-0.2	1585
0.2-0.3	8162
0.3-0.4	9802
0.4-0.5	8592
0.5-0.6	10813
0.6-0.7	2607
0.7-0.8	607
0.8-0.85	178
0.85-0.9	51
0.9-0.95	11
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9645	High Similarity	NPC274026
0.951	High Similarity	NPC148898
0.951	High Similarity	NPC82285
0.951	High Similarity	NPC133011
0.9209	High Similarity	NPC314682
0.9189	High Similarity	NPC92191
0.9189	High Similarity	NPC59028
0.9143	High Similarity	NPC328750
0.9143	High Similarity	NPC474915
0.9143	High Similarity	NPC188163
0.9143	High Similarity	NPC213206
0.8993	High Similarity	NPC475326
0.8986	High Similarity	NPC78733
0.8971	High Similarity	NPC160193
0.8947	High Similarity	NPC231198
0.8926	High Similarity	NPC147091
0.8897	High Similarity	NPC16107
0.8897	High Similarity	NPC476144
0.8897	High Similarity	NPC210437
0.8897	High Similarity	NPC106295
0.8897	High Similarity	NPC51957
0.8889	High Similarity	NPC185838
0.8881	High Similarity	NPC136860
0.8881	High Similarity	NPC128019
0.8881	High Similarity	NPC476567
0.8836	High Similarity	NPC7467
0.8836	High Similarity	NPC475959
0.8767	High Similarity	NPC191376
0.8767	High Similarity	NPC476151
0.8767	High Similarity	NPC179825
0.8767	High Similarity	NPC321505
0.8707	High Similarity	NPC135538
0.8707	High Similarity	NPC147390
0.8707	High Similarity	NPC476571
0.8707	High Similarity	NPC246587
0.8707	High Similarity	NPC428
0.8707	High Similarity	NPC24233
0.8662	High Similarity	NPC253429
0.8658	High Similarity	NPC476579
0.8649	High Similarity	NPC103379
0.8649	High Similarity	NPC477565
0.8627	High Similarity	NPC249274
0.8627	High Similarity	NPC205167
0.8627	High Similarity	NPC97072
0.8627	High Similarity	NPC215829
0.8609	High Similarity	NPC216459
0.8609	High Similarity	NPC41178
0.8609	High Similarity	NPC138487
0.8592	High Similarity	NPC7018
0.8553	High Similarity	NPC146288
0.8553	High Similarity	NPC49353
0.8551	High Similarity	NPC172403
0.8533	High Similarity	NPC81733
0.8533	High Similarity	NPC326316
0.8523	High Similarity	NPC60538
0.8523	High Similarity	NPC219162
0.8523	High Similarity	NPC207824
0.8511	High Similarity	NPC160692
0.8487	Intermediate Similarity	NPC54379
0.8487	Intermediate Similarity	NPC184026
0.8487	Intermediate Similarity	NPC193949
0.8487	Intermediate Similarity	NPC172765
0.8487	Intermediate Similarity	NPC207757
0.8487	Intermediate Similarity	NPC295691
0.8487	Intermediate Similarity	NPC110416
0.8487	Intermediate Similarity	NPC39701
0.8487	Intermediate Similarity	NPC189266
0.8487	Intermediate Similarity	NPC276588
0.8487	Intermediate Similarity	NPC278799
0.8487	Intermediate Similarity	NPC249797
0.8487	Intermediate Similarity	NPC5238
0.8487	Intermediate Similarity	NPC127674
0.8487	Intermediate Similarity	NPC469817
0.8487	Intermediate Similarity	NPC204828
0.8487	Intermediate Similarity	NPC2413
0.8477	Intermediate Similarity	NPC210148
0.8477	Intermediate Similarity	NPC233029
0.8467	Intermediate Similarity	NPC151895
0.8467	Intermediate Similarity	NPC192768
0.8467	Intermediate Similarity	NPC223125
0.8467	Intermediate Similarity	NPC88249
0.8467	Intermediate Similarity	NPC97221
0.8467	Intermediate Similarity	NPC220858
0.8462	Intermediate Similarity	NPC301050
0.8462	Intermediate Similarity	NPC131204
0.8442	Intermediate Similarity	NPC118804
0.8431	Intermediate Similarity	NPC234392
0.8431	Intermediate Similarity	NPC31311
0.8431	Intermediate Similarity	NPC180756
0.8431	Intermediate Similarity	NPC323443
0.8418	Intermediate Similarity	NPC290759
0.8418	Intermediate Similarity	NPC266176
0.8418	Intermediate Similarity	NPC158148
0.8418	Intermediate Similarity	NPC82533
0.8411	Intermediate Similarity	NPC277669
0.8411	Intermediate Similarity	NPC476568
0.8411	Intermediate Similarity	NPC76213
0.84	Intermediate Similarity	NPC92541
0.8397	Intermediate Similarity	NPC320104
0.8389	Intermediate Similarity	NPC90844
0.8389	Intermediate Similarity	NPC95075
0.8389	Intermediate Similarity	NPC253883
0.8366	Intermediate Similarity	NPC93593
0.8365	Intermediate Similarity	NPC75958
0.8355	Intermediate Similarity	NPC223124
0.8355	Intermediate Similarity	NPC470924
0.8354	Intermediate Similarity	NPC57812
0.8354	Intermediate Similarity	NPC474324
0.8354	Intermediate Similarity	NPC100566
0.8344	Intermediate Similarity	NPC247972
0.8333	Intermediate Similarity	NPC130941
0.8323	Intermediate Similarity	NPC477080
0.8323	Intermediate Similarity	NPC106786
0.8313	Intermediate Similarity	NPC477640
0.8313	Intermediate Similarity	NPC470739
0.8313	Intermediate Similarity	NPC225597
0.8312	Intermediate Similarity	NPC247639
0.8312	Intermediate Similarity	NPC25084
0.8302	Intermediate Similarity	NPC58766
0.8302	Intermediate Similarity	NPC475686
0.8302	Intermediate Similarity	NPC475845
0.8301	Intermediate Similarity	NPC2295
0.8301	Intermediate Similarity	NPC477564
0.828	Intermediate Similarity	NPC233650
0.828	Intermediate Similarity	NPC59567
0.8269	Intermediate Similarity	NPC477559
0.8269	Intermediate Similarity	NPC160298
0.8269	Intermediate Similarity	NPC306902
0.8269	Intermediate Similarity	NPC232924
0.8269	Intermediate Similarity	NPC266753
0.8267	Intermediate Similarity	NPC144863
0.8264	Intermediate Similarity	NPC11147
0.8258	Intermediate Similarity	NPC476572
0.825	Intermediate Similarity	NPC474708
0.825	Intermediate Similarity	NPC474475
0.8247	Intermediate Similarity	NPC99659
0.8247	Intermediate Similarity	NPC80129
0.8247	Intermediate Similarity	NPC325871
0.8247	Intermediate Similarity	NPC187022
0.8239	Intermediate Similarity	NPC190332
0.8239	Intermediate Similarity	NPC181653
0.8235	Intermediate Similarity	NPC476580
0.8235	Intermediate Similarity	NPC37272
0.8228	Intermediate Similarity	NPC238530
0.8228	Intermediate Similarity	NPC276944
0.8228	Intermediate Similarity	NPC134858
0.8228	Intermediate Similarity	NPC232514
0.821	Intermediate Similarity	NPC187678
0.8205	Intermediate Similarity	NPC111485
0.8194	Intermediate Similarity	NPC170503
0.8194	Intermediate Similarity	NPC203784
0.8194	Intermediate Similarity	NPC126519
0.8188	Intermediate Similarity	NPC294249
0.8182	Intermediate Similarity	NPC118419
0.8176	Intermediate Similarity	NPC476002
0.816	Intermediate Similarity	NPC474470
0.8153	Intermediate Similarity	NPC27410
0.8153	Intermediate Similarity	NPC166014
0.8148	Intermediate Similarity	NPC2314
0.8141	Intermediate Similarity	NPC78359
0.8141	Intermediate Similarity	NPC40389
0.8141	Intermediate Similarity	NPC148014
0.8141	Intermediate Similarity	NPC315707
0.8141	Intermediate Similarity	NPC65490
0.8129	Intermediate Similarity	NPC244112
0.8125	Intermediate Similarity	NPC210140
0.8125	Intermediate Similarity	NPC150879
0.8117	Intermediate Similarity	NPC26601
0.8113	Intermediate Similarity	NPC39103
0.8113	Intermediate Similarity	NPC2770
0.8113	Intermediate Similarity	NPC225774
0.8108	Intermediate Similarity	NPC470925
0.8098	Intermediate Similarity	NPC304675
0.8092	Intermediate Similarity	NPC37144
0.8092	Intermediate Similarity	NPC59907
0.8089	Intermediate Similarity	NPC216816
0.8086	Intermediate Similarity	NPC476331
0.8086	Intermediate Similarity	NPC65403
0.8077	Intermediate Similarity	NPC57512
0.8075	Intermediate Similarity	NPC470324
0.8063	Intermediate Similarity	NPC219341
0.8063	Intermediate Similarity	NPC476432
0.8063	Intermediate Similarity	NPC264850
0.8063	Intermediate Similarity	NPC24264
0.8063	Intermediate Similarity	NPC124657
0.8063	Intermediate Similarity	NPC13916
0.8061	Intermediate Similarity	NPC244554
0.8052	Intermediate Similarity	NPC8337
0.8052	Intermediate Similarity	NPC85747
0.805	Intermediate Similarity	NPC476569
0.805	Intermediate Similarity	NPC475393
0.8049	Intermediate Similarity	NPC237044
0.8038	Intermediate Similarity	NPC18402
0.8038	Intermediate Similarity	NPC4304
0.8025	Intermediate Similarity	NPC311991
0.8025	Intermediate Similarity	NPC129603
0.8013	Intermediate Similarity	NPC76079
0.8012	Intermediate Similarity	NPC247389
0.8012	Intermediate Similarity	NPC298979
0.8	Intermediate Similarity	NPC294790

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 NPC130926 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	765
0.2-0.3	972
0.3-0.4	2003
0.4-0.5	2712
0.5-0.6	1669
0.6-0.7	676
0.7-0.8	149
0.8-0.85	15
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9143	High Similarity	NPD4664	Clinical (unspecified phase)
0.8897	High Similarity	NPD4584	Approved
0.8667	High Similarity	NPD4773	Phase 2
0.8667	High Similarity	NPD4772	Phase 2
0.8533	High Similarity	NPD4017	Approved
0.8523	High Similarity	NPD3641	Approved
0.8523	High Similarity	NPD3640	Phase 3
0.8523	High Similarity	NPD3639	Approved
0.8429	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD6030	Approved
0.84	Intermediate Similarity	NPD6031	Approved
0.8247	Intermediate Similarity	NPD7298	Approved
0.8239	Intermediate Similarity	NPD5718	Phase 2
0.8228	Intermediate Similarity	NPD6107	Approved
0.8188	Intermediate Similarity	NPD5241	Discontinued
0.8176	Intermediate Similarity	NPD6071	Discontinued
0.8151	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD2563	Approved
0.8141	Intermediate Similarity	NPD2560	Approved
0.8099	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD2898	Approved
0.805	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD3124	Discontinued
0.795	Intermediate Similarity	NPD4166	Phase 2
0.7927	Intermediate Similarity	NPD8156	Discontinued
0.7927	Intermediate Similarity	NPD5312	Approved
0.7927	Intermediate Similarity	NPD5313	Approved
0.7925	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD7831	Phase 2
0.7925	Intermediate Similarity	NPD7833	Phase 2
0.7901	Intermediate Similarity	NPD2969	Approved
0.7901	Intermediate Similarity	NPD2970	Approved
0.7866	Intermediate Similarity	NPD8251	Approved
0.7866	Intermediate Similarity	NPD8252	Approved
0.7866	Intermediate Similarity	NPD8099	Discontinued
0.7862	Intermediate Similarity	NPD6788	Approved
0.7853	Intermediate Similarity	NPD27	Approved
0.7853	Intermediate Similarity	NPD4481	Phase 3
0.7853	Intermediate Similarity	NPD2489	Approved
0.784	Intermediate Similarity	NPD3051	Approved
0.784	Intermediate Similarity	NPD4010	Discontinued
0.7838	Intermediate Similarity	NPD6896	Approved
0.7838	Intermediate Similarity	NPD6895	Approved
0.7829	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD5978	Approved
0.7799	Intermediate Similarity	NPD5977	Approved
0.7792	Intermediate Similarity	NPD1424	Approved
0.7792	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7802	Discontinued
0.7733	Intermediate Similarity	NPD2161	Phase 2
0.7707	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5177	Phase 3
0.7687	Intermediate Similarity	NPD4475	Approved
0.7687	Intermediate Similarity	NPD4474	Approved
0.7647	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD3110	Approved
0.7635	Intermediate Similarity	NPD3109	Approved
0.759	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD4236	Phase 3
0.7582	Intermediate Similarity	NPD4237	Approved
0.7582	Intermediate Similarity	NPD4162	Approved
0.7576	Intermediate Similarity	NPD6688	Approved
0.7576	Intermediate Similarity	NPD6687	Approved
0.7569	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD2674	Phase 3
0.7568	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD8053	Approved
0.7544	Intermediate Similarity	NPD8054	Approved
0.7532	Intermediate Similarity	NPD4210	Discontinued
0.7517	Intermediate Similarity	NPD4098	Discontinued
0.7515	Intermediate Similarity	NPD6297	Approved
0.75	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7110	Phase 1
0.7468	Intermediate Similarity	NPD3060	Approved
0.7465	Intermediate Similarity	NPD2668	Approved
0.7465	Intermediate Similarity	NPD2667	Approved
0.745	Intermediate Similarity	NPD3530	Approved
0.745	Intermediate Similarity	NPD3532	Approved
0.745	Intermediate Similarity	NPD3531	Approved
0.7442	Intermediate Similarity	NPD6851	Approved
0.7442	Intermediate Similarity	NPD6853	Approved
0.7438	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7124	Phase 2
0.7434	Intermediate Similarity	NPD1753	Discontinued
0.7419	Intermediate Similarity	NPD6748	Discontinued
0.7419	Intermediate Similarity	NPD6331	Phase 2
0.7417	Intermediate Similarity	NPD2492	Phase 1
0.7407	Intermediate Similarity	NPD5773	Approved
0.7407	Intermediate Similarity	NPD5772	Approved
0.7403	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2238	Phase 2
0.7389	Intermediate Similarity	NPD2420	Approved
0.7389	Intermediate Similarity	NPD2421	Approved
0.7384	Intermediate Similarity	NPD7313	Approved
0.7384	Intermediate Similarity	NPD7312	Approved
0.7384	Intermediate Similarity	NPD7310	Approved
0.7384	Intermediate Similarity	NPD7311	Approved
0.7384	Intermediate Similarity	NPD2968	Approved
0.7384	Intermediate Similarity	NPD2971	Approved
0.7383	Intermediate Similarity	NPD3144	Approved
0.7383	Intermediate Similarity	NPD3145	Approved
0.7358	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7905	Discontinued
0.7346	Intermediate Similarity	NPD5720	Discontinued
0.7342	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7309	Approved
0.7338	Intermediate Similarity	NPD1375	Discontinued
0.7338	Intermediate Similarity	NPD3656	Approved
0.7325	Intermediate Similarity	NPD3845	Phase 1
0.7317	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7291	Discontinued
0.7314	Intermediate Similarity	NPD7906	Approved
0.731	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2233	Approved
0.731	Intermediate Similarity	NPD2232	Approved
0.731	Intermediate Similarity	NPD2230	Approved
0.7308	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7153	Discontinued
0.7283	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4577	Approved
0.7283	Intermediate Similarity	NPD4578	Approved
0.7278	Intermediate Similarity	NPD4420	Approved
0.7273	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1336	Approved
0.7261	Intermediate Similarity	NPD3692	Discontinued
0.726	Intermediate Similarity	NPD1421	Approved
0.726	Intermediate Similarity	NPD1420	Approved
0.7256	Intermediate Similarity	NPD5967	Approved
0.7255	Intermediate Similarity	NPD6111	Discontinued
0.7251	Intermediate Similarity	NPD3920	Phase 2
0.725	Intermediate Similarity	NPD5976	Discontinued
0.7239	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6875	Approved
0.7222	Intermediate Similarity	NPD6876	Approved
0.7215	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2120	Phase 2
0.7214	Intermediate Similarity	NPD5283	Phase 1
0.7213	Intermediate Similarity	NPD5006	Approved
0.7213	Intermediate Similarity	NPD5005	Approved
0.7197	Intermediate Similarity	NPD5754	Discontinued
0.7195	Intermediate Similarity	NPD2978	Approved
0.7195	Intermediate Similarity	NPD2977	Approved
0.719	Intermediate Similarity	NPD2653	Approved
0.719	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD5677	Discontinued
0.7184	Intermediate Similarity	NPD7281	Phase 3
0.7184	Intermediate Similarity	NPD7280	Phase 3
0.717	Intermediate Similarity	NPD7598	Phase 2
0.7169	Intermediate Similarity	NPD4055	Discovery
0.7167	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD3156	Discontinued
0.716	Intermediate Similarity	NPD6357	Discontinued
0.716	Intermediate Similarity	NPD4005	Discontinued
0.7159	Intermediate Similarity	NPD4663	Approved
0.7153	Intermediate Similarity	NPD2595	Approved
0.7153	Intermediate Similarity	NPD2594	Approved
0.7152	Intermediate Similarity	NPD1039	Discontinued
0.7152	Intermediate Similarity	NPD5160	Discontinued
0.7143	Intermediate Similarity	NPD1669	Approved
0.7143	Intermediate Similarity	NPD4727	Phase 1
0.7143	Intermediate Similarity	NPD6618	Phase 2
0.7135	Intermediate Similarity	NPD4498	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2488	Approved
0.7135	Intermediate Similarity	NPD2490	Approved
0.7126	Intermediate Similarity	NPD7400	Phase 3
0.7126	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4123	Phase 3
0.7102	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3693	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3924	Approved
0.7095	Intermediate Similarity	NPD3923	Approved
0.7095	Intermediate Similarity	NPD3922	Approved
0.7095	Intermediate Similarity	NPD3921	Approved
0.7086	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD52	Approved
0.7081	Intermediate Similarity	NPD6090	Discontinued
0.7081	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7526	Approved
0.707	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5604	Discontinued
0.7055	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD824	Approved
0.7049	Intermediate Similarity	NPD8095	Phase 1
0.7044	Intermediate Similarity	NPD2677	Approved
0.7039	Intermediate Similarity	NPD5109	Approved
0.7039	Intermediate Similarity	NPD5111	Phase 2
0.7039	Intermediate Similarity	NPD5110	Phase 2
0.7037	Intermediate Similarity	NPD2122	Discontinued
0.7034	Intermediate Similarity	NPD3444	Approved
0.7034	Intermediate Similarity	NPD3443	Approved
0.7034	Intermediate Similarity	NPD6382	Discontinued
0.7034	Intermediate Similarity	NPD3445	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