NPASS Compound

Structure

NPC44542 OpenBabel07101719242D 22 21 0 0 1 0 0 0 0 0999 V2000 1.7321 -0.0000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 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 -9.5263 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 3.0000 0.0000 C 0 0 0 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 2.0000 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 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.2583 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 18 1 0 0 0 0 3 15 1 0 0 0 0 4 5 1 0 0 0 0 4 6 3 0 0 0 0 5 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 3 0 0 0 0 9 11 2 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 2 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 19 15 1 1 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.17
Volume:	342.459
LogP:	3.287
LogD:	2.634
LogS:	-4.002
# Rotatable Bonds:	9
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.425
Synthetic Accessibility Score:	4.088
Fsp3:	0.421
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-3.987
MDCK Permeability:	9.849807975115255e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.064
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	100.22542572021484%
Volume Distribution (VD):	1.128
Pgp-substrate:	2.935798406600952%

ADMET: Metabolism

CYP1A2-inhibitor:	0.879
CYP1A2-substrate:	0.14
CYP2C19-inhibitor:	0.953
CYP2C19-substrate:	0.462
CYP2C9-inhibitor:	0.929
CYP2C9-substrate:	0.978
CYP2D6-inhibitor:	0.913
CYP2D6-substrate:	0.794
CYP3A4-inhibitor:	0.932
CYP3A4-substrate:	0.218

ADMET: Excretion

Clearance (CL):	4.484
Half-life (T1/2):	0.567

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.992
Drug-inuced Liver Injury (DILI):	0.988
AMES Toxicity:	0.913
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.965
Carcinogencity:	0.66
Eye Corrosion:	0.957
Eye Irritation:	0.991
Respiratory Toxicity:	0.632

Download Data

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

Natural Product: NPC44542

Natural Product ID:	NPC44542
*Common Name:**	Acetylbupleurotoxin
IUPAC Name:	[(4R,7E,9E,15Z)-17-hydroxyheptadeca-7,9,15-trien-11,13-diyn-4-yl] acetate
Synonyms:	Acetylbupleurotoxin
Standard InCHIKey:	SFZVRHWQKJMBGD-VSXZLIJLSA-N
Standard InCHI:	InChI=1S/C19H24O3/c1-3-15-19(22-18(2)21)16-13-11-9-7-5-4-6-8-10-12-14-17-20/h5,7,9,11-12,14,19-20H,3,13,15-17H2,1-2H3/b7-5+,11-9+,14-12-/t19-/m1/s1
SMILES:	CCC[C@@H](OC(=O)C)CC/C=C/C=C/C#CC#C/C=CCO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1086772
PubChem CID:	44613555
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002951] Long-chain fatty alcohols

*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
NPO16425	Bupleurum longiradiatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19994846]
NPO16425	Bupleurum longiradiatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16425	Bupleurum longiradiatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16425	Bupleurum longiradiatum	Species	Apiaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	11000.0	nM	PMID[516386]

☑ 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 NPC44542 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	140
0.1-0.2	2903
0.2-0.3	16518
0.3-0.4	14885
0.4-0.5	5794
0.5-0.6	1760
0.6-0.7	497
0.7-0.8	170
0.8-0.85	20
0.85-0.9	7
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC222852
0.9273	High Similarity	NPC472445
0.8929	High Similarity	NPC265551
0.8929	High Similarity	NPC212730
0.8644	High Similarity	NPC271282
0.8644	High Similarity	NPC325929
0.8644	High Similarity	NPC66460
0.8519	High Similarity	NPC71053
0.8519	High Similarity	NPC59408
0.85	High Similarity	NPC29697
0.8475	Intermediate Similarity	NPC471278
0.8364	Intermediate Similarity	NPC106531
0.8246	Intermediate Similarity	NPC470963
0.8246	Intermediate Similarity	NPC474913
0.8246	Intermediate Similarity	NPC152668
0.8246	Intermediate Similarity	NPC146551
0.8246	Intermediate Similarity	NPC474513
0.8214	Intermediate Similarity	NPC61177
0.8167	Intermediate Similarity	NPC327112
0.8136	Intermediate Similarity	NPC469373
0.8103	Intermediate Similarity	NPC470964
0.8103	Intermediate Similarity	NPC311648
0.8103	Intermediate Similarity	NPC472808
0.8103	Intermediate Similarity	NPC324224
0.807	Intermediate Similarity	NPC110732
0.807	Intermediate Similarity	NPC269615
0.8036	Intermediate Similarity	NPC142092
0.8	Intermediate Similarity	NPC291437
0.8	Intermediate Similarity	NPC328784
0.7966	Intermediate Similarity	NPC48968
0.7966	Intermediate Similarity	NPC594
0.7966	Intermediate Similarity	NPC193975
0.7857	Intermediate Similarity	NPC151782
0.7818	Intermediate Similarity	NPC302310
0.7818	Intermediate Similarity	NPC153538
0.7818	Intermediate Similarity	NPC248884
0.7818	Intermediate Similarity	NPC85079
0.7818	Intermediate Similarity	NPC31194
0.7812	Intermediate Similarity	NPC146811
0.7778	Intermediate Similarity	NPC35141
0.7778	Intermediate Similarity	NPC180575
0.7778	Intermediate Similarity	NPC124183
0.7778	Intermediate Similarity	NPC470320
0.7742	Intermediate Similarity	NPC113293
0.7742	Intermediate Similarity	NPC475984
0.7742	Intermediate Similarity	NPC26810
0.7705	Intermediate Similarity	NPC322186
0.7705	Intermediate Similarity	NPC318306
0.7705	Intermediate Similarity	NPC322002
0.7705	Intermediate Similarity	NPC474267
0.7679	Intermediate Similarity	NPC72699
0.7667	Intermediate Similarity	NPC471279
0.7667	Intermediate Similarity	NPC471277
0.7656	Intermediate Similarity	NPC136164
0.7656	Intermediate Similarity	NPC255863
0.7656	Intermediate Similarity	NPC245947
0.7619	Intermediate Similarity	NPC470965
0.7612	Intermediate Similarity	NPC476037
0.7586	Intermediate Similarity	NPC284224
0.7581	Intermediate Similarity	NPC299730
0.7581	Intermediate Similarity	NPC328311
0.7544	Intermediate Similarity	NPC93639
0.75	Intermediate Similarity	NPC471276
0.75	Intermediate Similarity	NPC125122
0.75	Intermediate Similarity	NPC476658
0.75	Intermediate Similarity	NPC226592
0.75	Intermediate Similarity	NPC471275
0.75	Intermediate Similarity	NPC471280
0.746	Intermediate Similarity	NPC55376
0.746	Intermediate Similarity	NPC477829
0.7458	Intermediate Similarity	NPC49059
0.7458	Intermediate Similarity	NPC256209
0.7458	Intermediate Similarity	NPC48058
0.7455	Intermediate Similarity	NPC55063
0.7455	Intermediate Similarity	NPC19834
0.7419	Intermediate Similarity	NPC329249
0.7407	Intermediate Similarity	NPC101616
0.7391	Intermediate Similarity	NPC329890
0.7385	Intermediate Similarity	NPC476655
0.7385	Intermediate Similarity	NPC323045
0.7385	Intermediate Similarity	NPC476654
0.7385	Intermediate Similarity	NPC317881
0.7385	Intermediate Similarity	NPC476657
0.7368	Intermediate Similarity	NPC249670
0.7368	Intermediate Similarity	NPC477727
0.7368	Intermediate Similarity	NPC474642
0.7368	Intermediate Similarity	NPC473913
0.7368	Intermediate Similarity	NPC471281
0.7368	Intermediate Similarity	NPC199286
0.7358	Intermediate Similarity	NPC206906
0.7353	Intermediate Similarity	NPC476012
0.7353	Intermediate Similarity	NPC329904
0.7353	Intermediate Similarity	NPC473361
0.7344	Intermediate Similarity	NPC473737
0.7333	Intermediate Similarity	NPC471239
0.7313	Intermediate Similarity	NPC474823
0.7302	Intermediate Similarity	NPC477424
0.7288	Intermediate Similarity	NPC34577
0.7286	Intermediate Similarity	NPC470686
0.7273	Intermediate Similarity	NPC269074
0.7273	Intermediate Similarity	NPC276825
0.7273	Intermediate Similarity	NPC476656
0.7273	Intermediate Similarity	NPC476659
0.7246	Intermediate Similarity	NPC316185
0.7246	Intermediate Similarity	NPC293114
0.7241	Intermediate Similarity	NPC329608
0.7241	Intermediate Similarity	NPC170776
0.7241	Intermediate Similarity	NPC55383
0.7241	Intermediate Similarity	NPC256656
0.7241	Intermediate Similarity	NPC224148
0.7241	Intermediate Similarity	NPC165447
0.7241	Intermediate Similarity	NPC197272
0.7241	Intermediate Similarity	NPC471959
0.7241	Intermediate Similarity	NPC475477
0.7241	Intermediate Similarity	NPC477723
0.7241	Intermediate Similarity	NPC89824
0.7241	Intermediate Similarity	NPC294278
0.7241	Intermediate Similarity	NPC76198
0.7241	Intermediate Similarity	NPC9273
0.7213	Intermediate Similarity	NPC327388
0.7206	Intermediate Similarity	NPC236208
0.7206	Intermediate Similarity	NPC470436
0.7206	Intermediate Similarity	NPC143396
0.7206	Intermediate Similarity	NPC475004
0.7193	Intermediate Similarity	NPC207815
0.7183	Intermediate Similarity	NPC260396
0.7167	Intermediate Similarity	NPC473532
0.7167	Intermediate Similarity	NPC137538
0.7164	Intermediate Similarity	NPC25298
0.7164	Intermediate Similarity	NPC478097
0.7164	Intermediate Similarity	NPC49863
0.7164	Intermediate Similarity	NPC225272
0.7143	Intermediate Similarity	NPC284006
0.7143	Intermediate Similarity	NPC329914
0.7143	Intermediate Similarity	NPC97570
0.7121	Intermediate Similarity	NPC478098
0.7121	Intermediate Similarity	NPC326268
0.7121	Intermediate Similarity	NPC478099
0.7121	Intermediate Similarity	NPC96414
0.7121	Intermediate Similarity	NPC19769
0.7121	Intermediate Similarity	NPC323477
0.7121	Intermediate Similarity	NPC318420
0.7097	Intermediate Similarity	NPC211752
0.7097	Intermediate Similarity	NPC323597
0.7097	Intermediate Similarity	NPC129150
0.7097	Intermediate Similarity	NPC323498
0.7083	Intermediate Similarity	NPC188860
0.7077	Intermediate Similarity	NPC179087
0.7077	Intermediate Similarity	NPC210303
0.7077	Intermediate Similarity	NPC44343
0.7059	Intermediate Similarity	NPC63873
0.7049	Intermediate Similarity	NPC477725
0.7049	Intermediate Similarity	NPC473725
0.7049	Intermediate Similarity	NPC473910
0.7049	Intermediate Similarity	NPC473721
0.7049	Intermediate Similarity	NPC475353
0.7049	Intermediate Similarity	NPC52264
0.7049	Intermediate Similarity	NPC473735
0.7049	Intermediate Similarity	NPC473896
0.7049	Intermediate Similarity	NPC317899
0.7049	Intermediate Similarity	NPC477726
0.7042	Intermediate Similarity	NPC315843
0.7037	Intermediate Similarity	NPC304151
0.7031	Intermediate Similarity	NPC81896
0.7031	Intermediate Similarity	NPC321919
0.7015	Intermediate Similarity	NPC201356
0.7015	Intermediate Similarity	NPC37382
0.7015	Intermediate Similarity	NPC328653
0.7	Intermediate Similarity	NPC217188
0.6986	Remote Similarity	NPC233071
0.6984	Remote Similarity	NPC223679
0.6957	Remote Similarity	NPC473772
0.6957	Remote Similarity	NPC130618
0.6957	Remote Similarity	NPC151481
0.6949	Remote Similarity	NPC129263
0.6949	Remote Similarity	NPC474495
0.6949	Remote Similarity	NPC473672
0.6935	Remote Similarity	NPC161838
0.6935	Remote Similarity	NPC470967
0.6935	Remote Similarity	NPC470969
0.6935	Remote Similarity	NPC477661
0.6935	Remote Similarity	NPC471960
0.6935	Remote Similarity	NPC473847
0.6935	Remote Similarity	NPC470966
0.6935	Remote Similarity	NPC470968
0.6935	Remote Similarity	NPC475384
0.6923	Remote Similarity	NPC320305
0.6923	Remote Similarity	NPC328776
0.6923	Remote Similarity	NPC201939
0.6912	Remote Similarity	NPC99619
0.6912	Remote Similarity	NPC122627
0.6912	Remote Similarity	NPC473752
0.6912	Remote Similarity	NPC478100
0.6912	Remote Similarity	NPC26500
0.6901	Remote Similarity	NPC325627
0.6901	Remote Similarity	NPC470435
0.6885	Remote Similarity	NPC300121
0.6875	Remote Similarity	NPC22897
0.6875	Remote Similarity	NPC159650
0.6875	Remote Similarity	NPC478095

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 NPC44542 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	110
0.1-0.2	3060
0.2-0.3	4243
0.3-0.4	1472
0.4-0.5	175
0.5-0.6	63
0.6-0.7	24
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8167	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4220	Pre-registration
0.7164	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6096	Approved
0.6786	Remote Similarity	NPD6097	Approved
0.6724	Remote Similarity	NPD5343	Approved
0.6719	Remote Similarity	NPD6109	Phase 1
0.6667	Remote Similarity	NPD6927	Phase 3
0.6667	Remote Similarity	NPD39	Approved
0.6471	Remote Similarity	NPD3197	Phase 1
0.6471	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD4194	Approved
0.6418	Remote Similarity	NPD4191	Approved
0.6418	Remote Similarity	NPD4192	Approved
0.6418	Remote Similarity	NPD4193	Approved
0.6379	Remote Similarity	NPD4265	Approved
0.6379	Remote Similarity	NPD4222	Approved
0.6377	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD3173	Approved
0.6316	Remote Similarity	NPD5326	Phase 3
0.6282	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD585	Clinical (unspecified phase)
0.619	Remote Similarity	NPD3172	Approved
0.6154	Remote Similarity	NPD4219	Approved
0.6102	Remote Similarity	NPD3174	Discontinued
0.6094	Remote Similarity	NPD3194	Approved
0.6094	Remote Similarity	NPD3196	Approved
0.6094	Remote Similarity	NPD4266	Approved
0.6094	Remote Similarity	NPD3195	Phase 2
0.6087	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD5332	Approved
0.6049	Remote Similarity	NPD7154	Phase 3
0.6049	Remote Similarity	NPD5331	Approved
0.6026	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD4271	Approved
0.6026	Remote Similarity	NPD4268	Approved
0.5904	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD4756	Discovery
0.5875	Remote Similarity	NPD4819	Approved
0.5875	Remote Similarity	NPD4821	Approved
0.5875	Remote Similarity	NPD4252	Approved
0.5875	Remote Similarity	NPD4822	Approved
0.5875	Remote Similarity	NPD4820	Approved
0.5873	Remote Similarity	NPD28	Approved
0.5873	Remote Similarity	NPD29	Approved
0.5862	Remote Similarity	NPD7637	Suspended
0.5862	Remote Similarity	NPD7983	Approved
0.5854	Remote Similarity	NPD5362	Discontinued
0.5844	Remote Similarity	NPD8039	Approved
0.5833	Remote Similarity	NPD4249	Approved
0.5795	Remote Similarity	NPD5779	Approved
0.5795	Remote Similarity	NPD5778	Approved
0.5789	Remote Similarity	NPD4732	Discontinued
0.5783	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD4251	Approved
0.5765	Remote Similarity	NPD4250	Approved
0.5747	Remote Similarity	NPD7838	Discovery
0.5732	Remote Similarity	NPD4270	Approved
0.5732	Remote Similarity	NPD4269	Approved
0.5732	Remote Similarity	NPD5209	Approved
0.5714	Remote Similarity	NPD368	Approved
0.5647	Remote Similarity	NPD5786	Approved
0.5641	Remote Similarity	NPD8264	Approved
0.561	Remote Similarity	NPD4790	Discontinued
0.5604	Remote Similarity	NPD7839	Suspended

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