NPASS Compound

Structure

CID78733 OpenBabel06191715412D 21 25 0 0 1 0 0 0 0 0999 V2000 -1.4774 3.4244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 2.5974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7497 2.1645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1160 1.2987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4329 0.7498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2494 -0.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7498 1.2987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2494 1.2987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7498 -0.4329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3315 0.4330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4996 0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7499 2.1644 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4996 0.8659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9992 0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9992 0.8659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.8658 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7498 1.2987 0.0000 C 0 0 1 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 -1.4773 2.5844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8226 -0.2675 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8226 1.1334 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 3 2 0 0 0 0 2 12 1 0 0 0 0 4 5 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 11 2 0 0 0 0 6 14 1 0 0 0 0 7 12 1 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 10 20 1 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 12 19 1 1 0 0 0 13 17 1 0 0 0 0 14 15 2 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 17 1 6 0 0 0 16 18 1 0 0 0 0 17 3 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	285.14
Volume:	286.628
LogP:	2.051
LogD:	1.622
LogS:	-2.649
# Rotatable Bonds:	1
TPSA:	30.93
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.74
Synthetic Accessibility Score:	4.872
Fsp3:	0.529
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:	-4.679
MDCK Permeability:	2.674292409210466e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.933
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.565
30% Bioavailability (F30%):	0.626

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.996
Plasma Protein Binding (PPB):	63.03092956542969%
Volume Distribution (VD):	3.0
Pgp-substrate:	26.73576545715332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.638
CYP1A2-substrate:	0.684
CYP2C19-inhibitor:	0.377
CYP2C19-substrate:	0.851
CYP2C9-inhibitor:	0.067
CYP2C9-substrate:	0.262
CYP2D6-inhibitor:	0.968
CYP2D6-substrate:	0.795
CYP3A4-inhibitor:	0.91
CYP3A4-substrate:	0.757

ADMET: Excretion

Clearance (CL):	14.17
Half-life (T1/2):	0.433

ADMET: Toxicity

hERG Blockers:	0.363
Human Hepatotoxicity (H-HT):	0.542
Drug-inuced Liver Injury (DILI):	0.247
AMES Toxicity:	0.134
Rat Oral Acute Toxicity:	0.613
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.076
Carcinogencity:	0.672
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.856

Download Data

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

Natural Product: NPC78733

Natural Product ID:	NPC78733
*Common Name:**	Buphanisine
IUPAC Name:	n.a.
Synonyms:	(-)-Buphanisine; Buphanisine
Standard InCHIKey:	HATSAIPBKRRCME-JCURWCKSSA-N
Standard InCHI:	InChI=1S/C17H19NO3/c1-19-12-2-3-17-4-5-18(16(17)7-12)9-11-6-14-15(8-13(11)17)21-10-20-14/h2-3,6,8,12,16H,4-5,7,9-10H2,1H3/t12-,16+,17+/m0/s1
SMILES:	CO[C@H]1C=C[C@@]23[C@@H](C1)N(CC2)Cc1c3cc2OCOc2c1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512945
PubChem CID:	12302149
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004123] Crinine- and Haemanthamine-type amaryllidaceae alkaloids

*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
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562843]
NPO22317	Crinum amabile	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8229016]
NPO22317	Crinum amabile	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22317	Crinum amabile	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22317	Crinum amabile	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23091	Halocarpus bidwillii	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21398	Jasminum laurifolium f. nitidum	Species	Oleaceae	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
ED50	14
IC50	9
MIC	2

Activity Type	# Activity
Cell Line	10
NON-MOLECULAR	8
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[476521]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[476521]
NPT168	Cell Line	P388	Mus musculus	ED50	>	5.0	ug ml-1	PMID[476521]
NPT762	Cell Line	A-431	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[476521]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[476521]
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[476521]
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[476521]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[476522]
NPT916	Cell Line	SK-MEL	Homo sapiens	IC50	>	10000.0	nM	PMID[476522]
NPT169	Cell Line	B16-F10	Mus musculus	IC50	>	10000.0	nM	PMID[476522]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	20.0	ug ml-1	PMID[476521]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	19.8	ug ml-1	PMID[476521]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	=	3500.0	ug ml-1	PMID[476521]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	=	5340.0	ug ml-1	PMID[476521]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	97000.0	nM	PMID[476522]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[476522]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	1024.0	ug.mL-1	PMID[476523]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1024.0	ug.mL-1	PMID[476523]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	16.5	ug.mL-1	PMID[476524]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	100.0	ug.mL-1	PMID[476524]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	55.55	ug.mL-1	PMID[476524]

☑ 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 NPC78733 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	288
0.1-0.2	1403
0.2-0.3	5588
0.3-0.4	12175
0.4-0.5	9742
0.5-0.6	10468
0.6-0.7	2202
0.7-0.8	585
0.8-0.85	150
0.85-0.9	66
0.9-0.95	27
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.96	High Similarity	NPC97072
0.96	High Similarity	NPC215829
0.9459	High Similarity	NPC148898
0.9355	High Similarity	NPC266176
0.9355	High Similarity	NPC82533
0.9355	High Similarity	NPC290759
0.9355	High Similarity	NPC158148
0.9295	High Similarity	NPC75958
0.9286	High Similarity	NPC247972
0.9236	High Similarity	NPC470739
0.9236	High Similarity	NPC477640
0.9236	High Similarity	NPC225597
0.9231	High Similarity	NPC58766
0.9231	High Similarity	NPC475686
0.9189	High Similarity	NPC475959
0.9172	High Similarity	NPC474475
0.9097	High Similarity	NPC320104
0.9073	High Similarity	NPC233029
0.9073	High Similarity	NPC210148
0.9067	High Similarity	NPC223125
0.9062	High Similarity	NPC474470
0.9045	High Similarity	NPC57812
0.9045	High Similarity	NPC474324
0.9045	High Similarity	NPC100566
0.902	High Similarity	NPC31311
0.902	High Similarity	NPC234392
0.902	High Similarity	NPC147091
0.8994	High Similarity	NPC65403
0.8987	High Similarity	NPC475845
0.8986	High Similarity	NPC130926
0.8954	High Similarity	NPC138487
0.8954	High Similarity	NPC216459
0.8954	High Similarity	NPC41178
0.8951	High Similarity	NPC244554
0.8947	High Similarity	NPC223124
0.8931	High Similarity	NPC311991
0.8931	High Similarity	NPC474708
0.8924	High Similarity	NPC181653
0.8924	High Similarity	NPC190332
0.8917	High Similarity	NPC231198
0.8903	High Similarity	NPC477080
0.8896	High Similarity	NPC146288
0.8854	High Similarity	NPC218614
0.8841	High Similarity	NPC102760
0.8828	High Similarity	NPC7018
0.8776	High Similarity	NPC314682
0.8765	High Similarity	NPC304675
0.8716	High Similarity	NPC328750
0.8716	High Similarity	NPC474915
0.8716	High Similarity	NPC188163
0.8716	High Similarity	NPC213206
0.8712	High Similarity	NPC237044
0.871	High Similarity	NPC76079
0.8693	High Similarity	NPC274026
0.8688	High Similarity	NPC252960
0.8659	High Similarity	NPC474325
0.8659	High Similarity	NPC15919
0.8625	High Similarity	NPC476002
0.8608	High Similarity	NPC266753
0.8608	High Similarity	NPC306902
0.8608	High Similarity	NPC160298
0.8608	High Similarity	NPC232924
0.8608	High Similarity	NPC477559
0.8606	High Similarity	NPC474745
0.859	High Similarity	NPC93593
0.8581	High Similarity	NPC82285
0.8581	High Similarity	NPC133011
0.8562	High Similarity	NPC276944
0.8562	High Similarity	NPC238530
0.8562	High Similarity	NPC232514
0.8545	High Similarity	NPC148693
0.8545	High Similarity	NPC294790
0.8545	High Similarity	NPC118633
0.8544	High Similarity	NPC106786
0.8544	High Similarity	NPC111485
0.85	High Similarity	NPC59567
0.8497	Intermediate Similarity	NPC16107
0.8497	Intermediate Similarity	NPC476144
0.8497	Intermediate Similarity	NPC51957
0.8497	Intermediate Similarity	NPC210437
0.8497	Intermediate Similarity	NPC106295
0.8491	Intermediate Similarity	NPC249274
0.8491	Intermediate Similarity	NPC205167
0.8487	Intermediate Similarity	NPC185838
0.8477	Intermediate Similarity	NPC128019
0.8477	Intermediate Similarity	NPC136860
0.8477	Intermediate Similarity	NPC476567
0.8476	Intermediate Similarity	NPC2314
0.8457	Intermediate Similarity	NPC210918
0.8452	Intermediate Similarity	NPC475981
0.8452	Intermediate Similarity	NPC474746
0.8447	Intermediate Similarity	NPC225774
0.8442	Intermediate Similarity	NPC7467
0.8424	Intermediate Similarity	NPC187678
0.8418	Intermediate Similarity	NPC323443
0.8418	Intermediate Similarity	NPC180756
0.8414	Intermediate Similarity	NPC160193
0.8402	Intermediate Similarity	NPC9867
0.8395	Intermediate Similarity	NPC24264
0.8395	Intermediate Similarity	NPC476432
0.8395	Intermediate Similarity	NPC219341
0.8387	Intermediate Similarity	NPC219162
0.8377	Intermediate Similarity	NPC321505
0.8377	Intermediate Similarity	NPC476151
0.8377	Intermediate Similarity	NPC191376
0.8377	Intermediate Similarity	NPC179825
0.8375	Intermediate Similarity	NPC4304
0.8353	Intermediate Similarity	NPC230098
0.8344	Intermediate Similarity	NPC247389
0.8344	Intermediate Similarity	NPC298979
0.8333	Intermediate Similarity	NPC180306
0.8333	Intermediate Similarity	NPC302527
0.8333	Intermediate Similarity	NPC16805
0.8333	Intermediate Similarity	NPC167546
0.8323	Intermediate Similarity	NPC24233
0.8323	Intermediate Similarity	NPC246587
0.8323	Intermediate Similarity	NPC59907
0.8323	Intermediate Similarity	NPC428
0.8323	Intermediate Similarity	NPC135538
0.8323	Intermediate Similarity	NPC37144
0.8323	Intermediate Similarity	NPC147390
0.8323	Intermediate Similarity	NPC476571
0.8313	Intermediate Similarity	NPC118804
0.8313	Intermediate Similarity	NPC59028
0.8313	Intermediate Similarity	NPC49353
0.8313	Intermediate Similarity	NPC92191
0.8293	Intermediate Similarity	NPC241055
0.8282	Intermediate Similarity	NPC86144
0.8282	Intermediate Similarity	NPC304659
0.8269	Intermediate Similarity	NPC103379
0.8269	Intermediate Similarity	NPC477565
0.8267	Intermediate Similarity	NPC253429
0.8261	Intermediate Similarity	NPC165797
0.8258	Intermediate Similarity	NPC253883
0.8258	Intermediate Similarity	NPC95075
0.8258	Intermediate Similarity	NPC90844
0.8221	Intermediate Similarity	NPC168409
0.821	Intermediate Similarity	NPC24954
0.8208	Intermediate Similarity	NPC63152
0.8205	Intermediate Similarity	NPC130941
0.82	Intermediate Similarity	NPC416184
0.8176	Intermediate Similarity	NPC275132
0.8166	Intermediate Similarity	NPC126284
0.8165	Intermediate Similarity	NPC476579
0.8165	Intermediate Similarity	NPC81733
0.8165	Intermediate Similarity	NPC326316
0.816	Intermediate Similarity	NPC189470
0.816	Intermediate Similarity	NPC233650
0.8155	Intermediate Similarity	NPC283999
0.8153	Intermediate Similarity	NPC60538
0.8153	Intermediate Similarity	NPC207824
0.8137	Intermediate Similarity	NPC475326
0.8133	Intermediate Similarity	NPC11147
0.8125	Intermediate Similarity	NPC193949
0.8125	Intermediate Similarity	NPC184026
0.8125	Intermediate Similarity	NPC189266
0.8125	Intermediate Similarity	NPC5238
0.8125	Intermediate Similarity	NPC276588
0.8125	Intermediate Similarity	NPC204828
0.8125	Intermediate Similarity	NPC110416
0.8125	Intermediate Similarity	NPC2413
0.8125	Intermediate Similarity	NPC295691
0.8125	Intermediate Similarity	NPC39701
0.8125	Intermediate Similarity	NPC54379
0.8125	Intermediate Similarity	NPC207757
0.8125	Intermediate Similarity	NPC172765
0.8125	Intermediate Similarity	NPC278799
0.8125	Intermediate Similarity	NPC249797
0.8125	Intermediate Similarity	NPC127674
0.8125	Intermediate Similarity	NPC469817
0.811	Intermediate Similarity	NPC134858
0.8101	Intermediate Similarity	NPC88249
0.8101	Intermediate Similarity	NPC220858
0.8101	Intermediate Similarity	NPC151895
0.8101	Intermediate Similarity	NPC97221
0.8101	Intermediate Similarity	NPC192768
0.8084	Intermediate Similarity	NPC149090
0.8084	Intermediate Similarity	NPC19520
0.807	Intermediate Similarity	NPC248642
0.8061	Intermediate Similarity	NPC124657
0.8059	Intermediate Similarity	NPC267408
0.8059	Intermediate Similarity	NPC27887
0.8054	Intermediate Similarity	NPC118419
0.805	Intermediate Similarity	NPC476568
0.805	Intermediate Similarity	NPC76213
0.805	Intermediate Similarity	NPC277669
0.8038	Intermediate Similarity	NPC92541
0.8027	Intermediate Similarity	NPC172403
0.8025	Intermediate Similarity	NPC315707
0.8025	Intermediate Similarity	NPC78359
0.8025	Intermediate Similarity	NPC148014
0.8025	Intermediate Similarity	NPC40389
0.8025	Intermediate Similarity	NPC65490
0.8024	Intermediate Similarity	NPC6152
0.8023	Intermediate Similarity	NPC156576
0.8013	Intermediate Similarity	NPC145304
0.8012	Intermediate Similarity	NPC210140
0.8012	Intermediate Similarity	NPC150879
0.8012	Intermediate Similarity	NPC244112
0.8	Intermediate Similarity	NPC160692

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 NPC78733 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	698
0.2-0.3	883
0.3-0.4	2257
0.4-0.5	2753
0.5-0.6	1695
0.6-0.7	549
0.7-0.8	117
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
0.8716	High Similarity	NPD4664	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD4584	Approved
0.8421	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD4773	Phase 2
0.8291	Intermediate Similarity	NPD4772	Phase 2
0.8247	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD4017	Approved
0.8153	Intermediate Similarity	NPD3641	Approved
0.8153	Intermediate Similarity	NPD3639	Approved
0.8153	Intermediate Similarity	NPD3640	Phase 3
0.8061	Intermediate Similarity	NPD6071	Discontinued
0.8041	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD2563	Approved
0.8025	Intermediate Similarity	NPD2560	Approved
0.8	Intermediate Similarity	NPD6107	Approved
0.7964	Intermediate Similarity	NPD2898	Approved
0.7964	Intermediate Similarity	NPD4481	Phase 3
0.7933	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD6031	Approved
0.7925	Intermediate Similarity	NPD6030	Approved
0.7904	Intermediate Similarity	NPD2969	Approved
0.7904	Intermediate Similarity	NPD2970	Approved
0.7901	Intermediate Similarity	NPD7298	Approved
0.7857	Intermediate Similarity	NPD27	Approved
0.7857	Intermediate Similarity	NPD2489	Approved
0.7844	Intermediate Similarity	NPD4166	Phase 2
0.7844	Intermediate Similarity	NPD3051	Approved
0.7834	Intermediate Similarity	NPD5241	Discontinued
0.7803	Intermediate Similarity	NPD7281	Phase 3
0.7803	Intermediate Similarity	NPD7280	Phase 3
0.7778	Intermediate Similarity	NPD4420	Approved
0.7748	Intermediate Similarity	NPD5718	Phase 2
0.7725	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD5313	Approved
0.7719	Intermediate Similarity	NPD5312	Approved
0.7711	Intermediate Similarity	NPD7831	Phase 2
0.7711	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7833	Phase 2
0.7705	Intermediate Similarity	NPD5005	Approved
0.7705	Intermediate Similarity	NPD5006	Approved
0.7677	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2492	Phase 1
0.7636	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD3124	Discontinued
0.7616	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD8156	Discontinued
0.7613	Intermediate Similarity	NPD6896	Approved
0.7613	Intermediate Similarity	NPD6895	Approved
0.7593	Intermediate Similarity	NPD4727	Phase 1
0.7558	Intermediate Similarity	NPD8099	Discontinued
0.7558	Intermediate Similarity	NPD8252	Approved
0.7558	Intermediate Similarity	NPD8251	Approved
0.7546	Intermediate Similarity	NPD4210	Discontinued
0.7545	Intermediate Similarity	NPD6788	Approved
0.7532	Intermediate Similarity	NPD3110	Approved
0.7532	Intermediate Similarity	NPD3109	Approved
0.753	Intermediate Similarity	NPD2977	Approved
0.753	Intermediate Similarity	NPD2978	Approved
0.7529	Intermediate Similarity	NPD4010	Discontinued
0.7484	Intermediate Similarity	NPD4237	Approved
0.7484	Intermediate Similarity	NPD4236	Phase 3
0.7473	Intermediate Similarity	NPD5582	Discontinued
0.7469	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7313	Approved
0.7401	Intermediate Similarity	NPD7312	Approved
0.7401	Intermediate Similarity	NPD7310	Approved
0.7401	Intermediate Similarity	NPD7311	Approved
0.7401	Intermediate Similarity	NPD2968	Approved
0.7401	Intermediate Similarity	NPD2971	Approved
0.7384	Intermediate Similarity	NPD6688	Approved
0.7384	Intermediate Similarity	NPD6687	Approved
0.7381	Intermediate Similarity	NPD5978	Approved
0.7381	Intermediate Similarity	NPD5977	Approved
0.7368	Intermediate Similarity	NPD7802	Discontinued
0.7362	Intermediate Similarity	NPD1424	Approved
0.736	Intermediate Similarity	NPD7309	Approved
0.7355	Intermediate Similarity	NPD4474	Approved
0.7355	Intermediate Similarity	NPD4475	Approved
0.7333	Intermediate Similarity	NPD7906	Approved
0.733	Intermediate Similarity	NPD6297	Approved
0.7321	Intermediate Similarity	NPD5772	Approved
0.7321	Intermediate Similarity	NPD5773	Approved
0.7312	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7296	Approved
0.7303	Intermediate Similarity	NPD4577	Approved
0.7303	Intermediate Similarity	NPD4578	Approved
0.7299	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5604	Discontinued
0.7289	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5177	Phase 3
0.7263	Intermediate Similarity	NPD8054	Approved
0.7263	Intermediate Similarity	NPD6851	Approved
0.7263	Intermediate Similarity	NPD8053	Approved
0.7263	Intermediate Similarity	NPD6853	Approved
0.7262	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7124	Phase 2
0.7222	Intermediate Similarity	NPD5754	Discontinued
0.7222	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7149	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2161	Phase 2
0.7182	Intermediate Similarity	NPD4663	Approved
0.7175	Intermediate Similarity	NPD3885	Approved
0.716	Intermediate Similarity	NPD5720	Discontinued
0.716	Intermediate Similarity	NPD4162	Approved
0.7158	Intermediate Similarity	NPD2488	Approved
0.7158	Intermediate Similarity	NPD2490	Approved
0.7152	Intermediate Similarity	NPD3705	Approved
0.7151	Intermediate Similarity	NPD7400	Phase 3
0.7143	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3349	Phase 2
0.7143	Intermediate Similarity	NPD7905	Discontinued
0.7135	Intermediate Similarity	NPD4859	Phase 1
0.7134	Intermediate Similarity	NPD2674	Phase 3
0.7125	Intermediate Similarity	NPD1753	Discontinued
0.7124	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5600	Discontinued
0.7117	Intermediate Similarity	NPD6748	Discontinued
0.7108	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7110	Phase 1
0.7101	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2421	Approved
0.7091	Intermediate Similarity	NPD2420	Approved
0.7078	Intermediate Similarity	NPD4098	Discontinued
0.7069	Intermediate Similarity	NPD3984	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD3983	Phase 3
0.7067	Intermediate Similarity	NPD1357	Approved
0.7066	Intermediate Similarity	NPD5976	Discontinued
0.7063	Intermediate Similarity	NPD6111	Discontinued
0.7059	Intermediate Similarity	NPD3384	Approved
0.7059	Intermediate Similarity	NPD1421	Approved
0.7059	Intermediate Similarity	NPD3383	Approved
0.7059	Intermediate Similarity	NPD3382	Approved
0.7059	Intermediate Similarity	NPD1420	Approved
0.7055	Intermediate Similarity	NPD3060	Approved
0.7052	Intermediate Similarity	NPD4796	Discontinued
0.7049	Intermediate Similarity	NPD7291	Discontinued
0.7048	Intermediate Similarity	NPD7019	Approved
0.7048	Intermediate Similarity	NPD7020	Approved
0.7041	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3656	Approved
0.7037	Intermediate Similarity	NPD1375	Discontinued
0.7035	Intermediate Similarity	NPD1742	Approved
0.7035	Intermediate Similarity	NPD1743	Approved
0.7035	Intermediate Similarity	NPD19	Approved
0.7033	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7247	Discontinued
0.703	Intermediate Similarity	NPD2120	Phase 2
0.703	Intermediate Similarity	NPD3845	Phase 1
0.7025	Intermediate Similarity	NPD3531	Approved
0.7025	Intermediate Similarity	NPD3532	Approved
0.7025	Intermediate Similarity	NPD3530	Approved
0.702	Intermediate Similarity	NPD2668	Approved
0.702	Intermediate Similarity	NPD2667	Approved
0.7019	Intermediate Similarity	NPD4108	Discontinued
0.7017	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6331	Phase 2
0.7012	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2238	Phase 2
0.6978	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3692	Discontinued
0.6968	Remote Similarity	NPD2973	Approved
0.6968	Remote Similarity	NPD2975	Approved
0.6968	Remote Similarity	NPD2974	Approved
0.6964	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD3145	Approved
0.6962	Remote Similarity	NPD3144	Approved
0.6947	Remote Similarity	NPD4107	Approved
0.6928	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5677	Discontinued
0.6905	Remote Similarity	NPD52	Approved
0.6905	Remote Similarity	NPD7526	Approved
0.6905	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD3815	Phase 1
0.6904	Remote Similarity	NPD3816	Phase 1
0.6897	Remote Similarity	NPD4055	Discovery
0.6894	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD2653	Approved
0.689	Remote Similarity	NPD7153	Discontinued
0.6889	Remote Similarity	NPD3920	Phase 2
0.6886	Remote Similarity	NPD7598	Phase 2
0.6883	Remote Similarity	NPD2232	Approved
0.6883	Remote Similarity	NPD2233	Approved
0.6883	Remote Similarity	NPD2230	Approved
0.6882	Remote Similarity	NPD4005	Discontinued
0.6879	Remote Similarity	NPD3636	Approved
0.6879	Remote Similarity	NPD3635	Approved
0.6879	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3637	Approved
0.6878	Remote Similarity	NPD5564	Approved
0.6872	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5160	Discontinued

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