NPASS Compound

Structure

CID133011 OpenBabel06191715492D 22 25 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 -5.1952 -0.9834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0098 2.0171 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 -2.5831 0.5168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7072 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 -1.7023 2.0254 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7121 0.0083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4590 0.0168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4639 -0.9918 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 -4.3223 0.5208 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5415 2.5357 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3320 -1.4874 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 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 17 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 13 18 1 0 0 0 0 14 21 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 22 1 0 0 0 0 18 19 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	299.15
Volume:	309.844
LogP:	2.172
LogD:	2.157
LogS:	-2.412
# Rotatable Bonds:	2
TPSA:	41.93
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.91
Synthetic Accessibility Score:	4.543
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:	-4.786
MDCK Permeability:	2.4463539375574328e-05
Pgp-inhibitor:	0.39
Pgp-substrate:	0.941
Human Intestinal Absorption (HIA):	0.051
20% Bioavailability (F20%):	0.883
30% Bioavailability (F30%):	0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.998
Plasma Protein Binding (PPB):	64.25745391845703%
Volume Distribution (VD):	2.805
Pgp-substrate:	19.944700241088867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.426
CYP2C19-inhibitor:	0.073
CYP2C19-substrate:	0.898
CYP2C9-inhibitor:	0.315
CYP2C9-substrate:	0.674
CYP2D6-inhibitor:	0.109
CYP2D6-substrate:	0.542
CYP3A4-inhibitor:	0.705
CYP3A4-substrate:	0.934

ADMET: Excretion

Clearance (CL):	17.144
Half-life (T1/2):	0.714

ADMET: Toxicity

hERG Blockers:	0.366
Human Hepatotoxicity (H-HT):	0.827
Drug-inuced Liver Injury (DILI):	0.231
AMES Toxicity:	0.788
Rat Oral Acute Toxicity:	0.113
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.914
Carcinogencity:	0.892
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.888

Download Data

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

Natural Product: NPC133011

Natural Product ID:	NPC133011
*Common Name:**	Erysovine
IUPAC Name:	(2R,13bS)-2,11-dimethoxy-2,6,8,9-tetrahydro-1H-indolo[7a,1-a]isoquinolin-12-ol
Synonyms:	Erysovine
Standard InCHIKey:	IHPMURIXWRKEKD-KSSFIOAISA-N
Standard InCHI:	InChI=1S/C18H21NO3/c1-21-14-4-3-13-6-8-19-7-5-12-9-17(22-2)16(20)10-15(12)18(13,19)11-14/h3-4,6,9-10,14,20H,5,7-8,11H2,1-2H3/t14-,18-/m0/s1
SMILES:	CO[C@H]1C=CC2=CCN3CCc4cc(c(cc4[C@]23C1)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517778
PubChem CID:	5317203
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
NPO14905	Erythrina variegata	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[10869220]
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]
NPO13279	Berberis zycium	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7457	Erythrina berteroana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14905	Erythrina variegata	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]
NPO17657	Erythrina arborescens	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]
NPO17657	Erythrina arborescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16399	Erythrina folkersii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14905	Erythrina variegata	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]
NPO7457	Erythrina berteroana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28361	Erythrina salviiflora	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]
NPO14905	Erythrina variegata	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]
NPO30554	Erythrina folkersll	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29998	Erythrina salvllflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17657	Erythrina arborescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8301	Erythrina suberosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14905	Erythrina variegata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7457	Erythrina berteroana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17657	Erythrina arborescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3174	Sulfolobus shibatae	Species	Sulfolobaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO16399	Erythrina folkersii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24842	Bulla gouldiana	Species	Bullidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28361	Erythrina salviiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	24.0	ug.mL-1	PMID[554321]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	14.2	ug.mL-1	PMID[554321]

☑ 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 NPC133011 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	255
0.1-0.2	1412
0.2-0.3	6460
0.3-0.4	11580
0.4-0.5	6545
0.5-0.6	11703
0.6-0.7	3761
0.7-0.8	708
0.8-0.85	178
0.85-0.9	70
0.9-0.95	21
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC82285
0.9722	High Similarity	NPC274026
0.951	High Similarity	NPC130926
0.9463	High Similarity	NPC475326
0.9396	High Similarity	NPC147091
0.9272	High Similarity	NPC59028
0.9272	High Similarity	NPC92191
0.9247	High Similarity	NPC191376
0.9247	High Similarity	NPC179825
0.9247	High Similarity	NPC321505
0.9184	High Similarity	NPC147390
0.9184	High Similarity	NPC246587
0.9184	High Similarity	NPC135538
0.9184	High Similarity	NPC476571
0.9184	High Similarity	NPC428
0.9184	High Similarity	NPC24233
0.9122	High Similarity	NPC477565
0.9122	High Similarity	NPC103379
0.911	High Similarity	NPC185838
0.9085	High Similarity	NPC205167
0.9085	High Similarity	NPC249274
0.9067	High Similarity	NPC148898
0.8986	High Similarity	NPC476151
0.8951	High Similarity	NPC301050
0.8951	High Similarity	NPC131204
0.8947	High Similarity	NPC278799
0.8947	High Similarity	NPC249797
0.8947	High Similarity	NPC189266
0.8947	High Similarity	NPC110416
0.8947	High Similarity	NPC193949
0.8947	High Similarity	NPC5238
0.8947	High Similarity	NPC207757
0.8947	High Similarity	NPC204828
0.8947	High Similarity	NPC172765
0.8947	High Similarity	NPC127674
0.8947	High Similarity	NPC276588
0.8947	High Similarity	NPC2413
0.8947	High Similarity	NPC184026
0.8947	High Similarity	NPC469817
0.8947	High Similarity	NPC295691
0.8947	High Similarity	NPC39701
0.8947	High Similarity	NPC54379
0.8933	High Similarity	NPC151895
0.8933	High Similarity	NPC97221
0.8933	High Similarity	NPC220858
0.8933	High Similarity	NPC192768
0.8933	High Similarity	NPC88249
0.8874	High Similarity	NPC277669
0.8874	High Similarity	NPC76213
0.8767	High Similarity	NPC314682
0.8758	High Similarity	NPC477564
0.8758	High Similarity	NPC2295
0.8742	High Similarity	NPC207824
0.8742	High Similarity	NPC60538
0.8718	High Similarity	NPC215829
0.8718	High Similarity	NPC97072
0.8707	High Similarity	NPC213206
0.8707	High Similarity	NPC474915
0.8707	High Similarity	NPC328750
0.8707	High Similarity	NPC188163
0.8693	High Similarity	NPC37272
0.8671	High Similarity	NPC238530
0.8671	High Similarity	NPC232514
0.8671	High Similarity	NPC276944
0.8658	High Similarity	NPC294249
0.8654	High Similarity	NPC111485
0.8642	High Similarity	NPC49353
0.8599	High Similarity	NPC166014
0.8599	High Similarity	NPC27410
0.8581	High Similarity	NPC78733
0.8562	High Similarity	NPC210140
0.8562	High Similarity	NPC100566
0.8553	High Similarity	NPC231198
0.8531	High Similarity	NPC160193
0.8519	High Similarity	NPC476331
0.8509	High Similarity	NPC470324
0.85	High Similarity	NPC13916
0.85	High Similarity	NPC124657
0.85	High Similarity	NPC264850
0.8487	Intermediate Similarity	NPC476144
0.8487	Intermediate Similarity	NPC210437
0.8487	Intermediate Similarity	NPC106295
0.8487	Intermediate Similarity	NPC51957
0.8487	Intermediate Similarity	NPC16107
0.8481	Intermediate Similarity	NPC18402
0.8467	Intermediate Similarity	NPC476567
0.8467	Intermediate Similarity	NPC128019
0.8467	Intermediate Similarity	NPC136860
0.8447	Intermediate Similarity	NPC190332
0.8447	Intermediate Similarity	NPC181653
0.8438	Intermediate Similarity	NPC134858
0.8438	Intermediate Similarity	NPC24465
0.8431	Intermediate Similarity	NPC7467
0.8431	Intermediate Similarity	NPC475959
0.8428	Intermediate Similarity	NPC60186
0.8415	Intermediate Similarity	NPC187678
0.8408	Intermediate Similarity	NPC186063
0.8405	Intermediate Similarity	NPC477640
0.8405	Intermediate Similarity	NPC470739
0.8405	Intermediate Similarity	NPC225597
0.8395	Intermediate Similarity	NPC158148
0.8395	Intermediate Similarity	NPC83198
0.8395	Intermediate Similarity	NPC475686
0.8395	Intermediate Similarity	NPC82533
0.8395	Intermediate Similarity	NPC204908
0.8395	Intermediate Similarity	NPC266176
0.8395	Intermediate Similarity	NPC58766
0.8395	Intermediate Similarity	NPC290759
0.8385	Intermediate Similarity	NPC256012
0.8385	Intermediate Similarity	NPC42549
0.8385	Intermediate Similarity	NPC250846
0.8385	Intermediate Similarity	NPC268503
0.8385	Intermediate Similarity	NPC240841
0.8385	Intermediate Similarity	NPC317272
0.8375	Intermediate Similarity	NPC233650
0.8375	Intermediate Similarity	NPC320104
0.8375	Intermediate Similarity	NPC324144
0.8344	Intermediate Similarity	NPC474475
0.8333	Intermediate Similarity	NPC306555
0.8333	Intermediate Similarity	NPC26601
0.8333	Intermediate Similarity	NPC145832
0.8333	Intermediate Similarity	NPC474931
0.8333	Intermediate Similarity	NPC81218
0.8333	Intermediate Similarity	NPC158376
0.8333	Intermediate Similarity	NPC12053
0.8333	Intermediate Similarity	NPC117188
0.8333	Intermediate Similarity	NPC205421
0.8323	Intermediate Similarity	NPC284183
0.8323	Intermediate Similarity	NPC477563
0.8323	Intermediate Similarity	NPC4138
0.8323	Intermediate Similarity	NPC212794
0.8323	Intermediate Similarity	NPC121275
0.8323	Intermediate Similarity	NPC13504
0.8323	Intermediate Similarity	NPC78222
0.8323	Intermediate Similarity	NPC136508
0.8323	Intermediate Similarity	NPC306843
0.8323	Intermediate Similarity	NPC253043
0.8323	Intermediate Similarity	NPC196447
0.8323	Intermediate Similarity	NPC96603
0.8272	Intermediate Similarity	NPC81247
0.8272	Intermediate Similarity	NPC476002
0.8272	Intermediate Similarity	NPC476573
0.8272	Intermediate Similarity	NPC35627
0.8269	Intermediate Similarity	NPC476579
0.8263	Intermediate Similarity	NPC32154
0.8261	Intermediate Similarity	NPC1229
0.8255	Intermediate Similarity	NPC253429
0.8253	Intermediate Similarity	NPC237044
0.8242	Intermediate Similarity	NPC152680
0.8242	Intermediate Similarity	NPC232386
0.8242	Intermediate Similarity	NPC2314
0.8242	Intermediate Similarity	NPC190783
0.8239	Intermediate Similarity	NPC148014
0.8239	Intermediate Similarity	NPC78359
0.8239	Intermediate Similarity	NPC65490
0.8239	Intermediate Similarity	NPC40389
0.8239	Intermediate Similarity	NPC315707
0.8228	Intermediate Similarity	NPC41178
0.8228	Intermediate Similarity	NPC138487
0.8228	Intermediate Similarity	NPC216459
0.8221	Intermediate Similarity	NPC298979
0.8221	Intermediate Similarity	NPC150879
0.8217	Intermediate Similarity	NPC223124
0.8204	Intermediate Similarity	NPC474325
0.8193	Intermediate Similarity	NPC304675
0.8188	Intermediate Similarity	NPC7018
0.8176	Intermediate Similarity	NPC146288
0.8176	Intermediate Similarity	NPC37205
0.8176	Intermediate Similarity	NPC160931
0.8171	Intermediate Similarity	NPC66573
0.8171	Intermediate Similarity	NPC164429
0.8155	Intermediate Similarity	NPC474745
0.8153	Intermediate Similarity	NPC81733
0.8153	Intermediate Similarity	NPC326316
0.8148	Intermediate Similarity	NPC59567
0.8144	Intermediate Similarity	NPC474470
0.8144	Intermediate Similarity	NPC241704
0.8141	Intermediate Similarity	NPC219162
0.8138	Intermediate Similarity	NPC172403
0.8137	Intermediate Similarity	NPC226428
0.8137	Intermediate Similarity	NPC4304
0.8133	Intermediate Similarity	NPC193528
0.8121	Intermediate Similarity	NPC168753
0.8121	Intermediate Similarity	NPC109925
0.8121	Intermediate Similarity	NPC118274
0.8121	Intermediate Similarity	NPC311991
0.8108	Intermediate Similarity	NPC160692
0.8101	Intermediate Similarity	NPC210148
0.8101	Intermediate Similarity	NPC233029
0.8098	Intermediate Similarity	NPC255607
0.8098	Intermediate Similarity	NPC3375
0.8095	Intermediate Similarity	NPC114364
0.8095	Intermediate Similarity	NPC320223
0.8095	Intermediate Similarity	NPC21885
0.8089	Intermediate Similarity	NPC223125
0.8084	Intermediate Similarity	NPC128560
0.8084	Intermediate Similarity	NPC229166
0.8084	Intermediate Similarity	NPC199465
0.8079	Intermediate Similarity	NPC211468
0.8079	Intermediate Similarity	NPC170170

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 NPC133011 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	722
0.2-0.3	987
0.3-0.4	2013
0.4-0.5	2680
0.5-0.6	1721
0.6-0.7	678
0.7-0.8	160
0.8-0.85	17
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8707	High Similarity	NPD4664	Clinical (unspecified phase)
0.8636	High Similarity	NPD4772	Phase 2
0.8636	High Similarity	NPD4773	Phase 2
0.8509	High Similarity	NPD2898	Approved
0.8487	Intermediate Similarity	NPD4584	Approved
0.8289	Intermediate Similarity	NPD5241	Discontinued
0.8282	Intermediate Similarity	NPD27	Approved
0.8282	Intermediate Similarity	NPD2489	Approved
0.8272	Intermediate Similarity	NPD6071	Discontinued
0.8272	Intermediate Similarity	NPD4010	Discontinued
0.8247	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD2563	Approved
0.8239	Intermediate Similarity	NPD2560	Approved
0.8153	Intermediate Similarity	NPD4017	Approved
0.8141	Intermediate Similarity	NPD3639	Approved
0.8141	Intermediate Similarity	NPD3640	Phase 3
0.8141	Intermediate Similarity	NPD3641	Approved
0.8137	Intermediate Similarity	NPD7833	Phase 2
0.8137	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7831	Phase 2
0.811	Intermediate Similarity	NPD2969	Approved
0.811	Intermediate Similarity	NPD2970	Approved
0.8063	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD2674	Phase 3
0.8037	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD6030	Approved
0.8025	Intermediate Similarity	NPD6031	Approved
0.7953	Intermediate Similarity	NPD8053	Approved
0.7953	Intermediate Similarity	NPD8054	Approved
0.7939	Intermediate Similarity	NPD3051	Approved
0.7888	Intermediate Similarity	NPD7298	Approved
0.7879	Intermediate Similarity	NPD6107	Approved
0.7852	Intermediate Similarity	NPD5718	Phase 2
0.7852	Intermediate Similarity	NPD3145	Approved
0.7852	Intermediate Similarity	NPD3144	Approved
0.7834	Intermediate Similarity	NPD2421	Approved
0.7834	Intermediate Similarity	NPD2420	Approved
0.7806	Intermediate Similarity	NPD5177	Phase 3
0.7791	Intermediate Similarity	NPD7312	Approved
0.7791	Intermediate Similarity	NPD7310	Approved
0.7791	Intermediate Similarity	NPD7311	Approved
0.7791	Intermediate Similarity	NPD7313	Approved
0.7778	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3845	Phase 1
0.7746	Intermediate Similarity	NPD7309	Approved
0.7727	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2161	Phase 2
0.7718	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7906	Approved
0.7692	Intermediate Similarity	NPD3060	Approved
0.7688	Intermediate Similarity	NPD4577	Approved
0.7688	Intermediate Similarity	NPD4578	Approved
0.7662	Intermediate Similarity	NPD1753	Discontinued
0.7658	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2978	Approved
0.7622	Intermediate Similarity	NPD2977	Approved
0.7619	Intermediate Similarity	NPD4166	Phase 2
0.761	Intermediate Similarity	NPD3124	Discontinued
0.7602	Intermediate Similarity	NPD5313	Approved
0.7602	Intermediate Similarity	NPD5312	Approved
0.7602	Intermediate Similarity	NPD8156	Discontinued
0.758	Intermediate Similarity	NPD4237	Approved
0.758	Intermediate Similarity	NPD4236	Phase 3
0.758	Intermediate Similarity	NPD4162	Approved
0.7557	Intermediate Similarity	NPD4663	Approved
0.7544	Intermediate Similarity	NPD8099	Discontinued
0.7544	Intermediate Similarity	NPD8252	Approved
0.7544	Intermediate Similarity	NPD8251	Approved
0.753	Intermediate Similarity	NPD6788	Approved
0.7529	Intermediate Similarity	NPD4481	Phase 3
0.7528	Intermediate Similarity	NPD2488	Approved
0.7528	Intermediate Similarity	NPD2490	Approved
0.7516	Intermediate Similarity	NPD2238	Phase 2
0.7515	Intermediate Similarity	NPD5773	Approved
0.7515	Intermediate Similarity	NPD5772	Approved
0.7514	Intermediate Similarity	NPD6297	Approved
0.7486	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD824	Approved
0.7485	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6895	Approved
0.7484	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6896	Approved
0.747	Intermediate Similarity	NPD5977	Approved
0.747	Intermediate Similarity	NPD5978	Approved
0.7466	Intermediate Similarity	NPD2668	Approved
0.7466	Intermediate Similarity	NPD2667	Approved
0.7456	Intermediate Similarity	NPD7802	Discontinued
0.7453	Intermediate Similarity	NPD1424	Approved
0.7443	Intermediate Similarity	NPD6851	Approved
0.7443	Intermediate Similarity	NPD6853	Approved
0.7432	Intermediate Similarity	NPD2233	Approved
0.7432	Intermediate Similarity	NPD2232	Approved
0.7432	Intermediate Similarity	NPD2230	Approved
0.7425	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6331	Phase 2
0.7419	Intermediate Similarity	NPD823	Approved
0.7419	Intermediate Similarity	NPD817	Approved
0.7378	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD3692	Discontinued
0.7342	Intermediate Similarity	NPD3656	Approved
0.7342	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4474	Approved
0.7338	Intermediate Similarity	NPD4475	Approved
0.7312	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6090	Discontinued
0.7296	Intermediate Similarity	NPD7153	Discontinued
0.729	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD3109	Approved
0.729	Intermediate Similarity	NPD3110	Approved
0.729	Intermediate Similarity	NPD3620	Phase 2
0.7285	Intermediate Similarity	NPD3055	Approved
0.7285	Intermediate Similarity	NPD3053	Approved
0.7273	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6687	Approved
0.7267	Intermediate Similarity	NPD6688	Approved
0.7248	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD4123	Phase 3
0.7238	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1375	Discontinued
0.7226	Intermediate Similarity	NPD1136	Approved
0.7226	Intermediate Similarity	NPD1130	Approved
0.7226	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1132	Approved
0.7219	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4210	Discontinued
0.7203	Intermediate Similarity	NPD228	Approved
0.72	Intermediate Similarity	NPD4873	Discontinued
0.7191	Intermediate Similarity	NPD7280	Phase 3
0.7191	Intermediate Similarity	NPD7281	Phase 3
0.719	Intermediate Similarity	NPD3635	Approved
0.719	Intermediate Similarity	NPD3636	Approved
0.719	Intermediate Similarity	NPD3637	Approved
0.7188	Intermediate Similarity	NPD7037	Approved
0.7186	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7110	Phase 1
0.7176	Intermediate Similarity	NPD5604	Discontinued
0.7174	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4103	Phase 2
0.7171	Intermediate Similarity	NPD4098	Discontinued
0.7169	Intermediate Similarity	NPD4005	Discontinued
0.7169	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD3450	Approved
0.7166	Intermediate Similarity	NPD2493	Approved
0.7166	Intermediate Similarity	NPD2494	Approved
0.7166	Intermediate Similarity	NPD3452	Approved
0.7162	Intermediate Similarity	NPD4093	Discontinued
0.7161	Intermediate Similarity	NPD598	Approved
0.7161	Intermediate Similarity	NPD601	Approved
0.7161	Intermediate Similarity	NPD597	Approved
0.716	Intermediate Similarity	NPD5160	Discontinued
0.716	Intermediate Similarity	NPD2677	Approved
0.716	Intermediate Similarity	NPD5967	Approved
0.7152	Intermediate Similarity	NPD2122	Discontinued
0.7143	Intermediate Similarity	NPD4040	Phase 1
0.7135	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6584	Phase 3
0.7117	Intermediate Similarity	NPD7124	Phase 2
0.7115	Intermediate Similarity	NPD3530	Approved
0.7115	Intermediate Similarity	NPD3532	Approved
0.7115	Intermediate Similarity	NPD3531	Approved
0.7114	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5311	Approved
0.7105	Intermediate Similarity	NPD5310	Approved
0.7099	Intermediate Similarity	NPD6748	Discontinued
0.7095	Intermediate Similarity	NPD2968	Approved
0.7095	Intermediate Similarity	NPD2971	Approved
0.7093	Intermediate Similarity	NPD2904	Discontinued
0.7091	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7526	Approved
0.7091	Intermediate Similarity	NPD52	Approved
0.7089	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2492	Phase 1
0.7081	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5582	Discontinued
0.7076	Intermediate Similarity	NPD4055	Discovery
0.707	Intermediate Similarity	NPD3059	Approved
0.707	Intermediate Similarity	NPD3061	Approved
0.707	Intermediate Similarity	NPD3062	Approved
0.7063	Intermediate Similarity	NPD3156	Discontinued
0.7062	Intermediate Similarity	NPD7479	Phase 2
0.7053	Intermediate Similarity	NPD4583	Approved
0.7053	Intermediate Similarity	NPD4582	Approved
0.7051	Intermediate Similarity	NPD1039	Discontinued
0.7048	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5720	Discontinued
0.7039	Intermediate Similarity	NPD4659	Approved
0.7039	Intermediate Similarity	NPD1669	Approved
0.7037	Intermediate Similarity	NPD3448	Approved
0.7037	Intermediate Similarity	NPD2491	Approved
0.7033	Intermediate Similarity	NPD7291	Discontinued
0.7032	Intermediate Similarity	NPD3594	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