NPASS Compound

Structure

NPC77435 OpenBabel07101719132D 33 35 0 0 1 0 0 0 0 0999 V2000 2.3566 -3.3406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5622 -1.9612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5622 -2.9612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 1.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8301 -1.9612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6962 -0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5933 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6962 -1.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -1.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8301 0.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1810 -1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5823 -0.7045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1756 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9945 0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0981 -1.9612 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.8301 1.0388 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.7743 -2.6361 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.5768 -0.6000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -6.4282 -3.4612 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 3.0388 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4013 1.0181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 3.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7634 -2.4271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 0.0388 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 31 1 0 0 0 0 2 5 1 0 0 0 0 2 6 1 0 0 0 0 3 4 1 0 0 0 0 3 11 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 32 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 11 1 0 0 0 0 8 13 2 0 0 0 0 9 14 2 0 0 0 0 10 15 1 0 0 0 0 10 21 1 0 0 0 0 12 17 2 0 0 0 0 12 22 1 0 0 0 0 13 17 1 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 14 24 1 0 0 0 0 15 20 1 0 0 0 0 15 28 2 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 16 25 1 0 0 0 0 17 32 1 0 0 0 0 18 31 1 0 0 0 0 19 21 1 6 0 0 0 19 29 1 0 0 0 0 20 27 1 0 0 0 0 20 30 2 0 0 0 0 21 9 1 6 0 0 0 21 33 1 0 0 0 0 28 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	712.84
Volume:	481.723
LogP:	3.605
LogD:	2.289
LogS:	-3.817
# Rotatable Bonds:	10
TPSA:	115.4
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.333
Synthetic Accessibility Score:	4.509
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.204
MDCK Permeability:	1.7829030184657313e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.475
20% Bioavailability (F20%):	0.753
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.986
Plasma Protein Binding (PPB):	97.53436279296875%
Volume Distribution (VD):	1.177
Pgp-substrate:	4.791567325592041%

ADMET: Metabolism

CYP1A2-inhibitor:	0.91
CYP1A2-substrate:	0.264
CYP2C19-inhibitor:	0.927
CYP2C19-substrate:	0.655
CYP2C9-inhibitor:	0.799
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.938
CYP2D6-substrate:	0.608
CYP3A4-inhibitor:	0.947
CYP3A4-substrate:	0.228

ADMET: Excretion

Clearance (CL):	1.077
Half-life (T1/2):	0.172

ADMET: Toxicity

hERG Blockers:	0.605
Human Hepatotoxicity (H-HT):	0.794
Drug-inuced Liver Injury (DILI):	0.13
AMES Toxicity:	0.71
Rat Oral Acute Toxicity:	0.977
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.557
Carcinogencity:	0.814
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC77435

Natural Product ID:	NPC77435
*Common Name:**	Araplysillin 1
IUPAC Name:	(5R,6S)-N-[3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl]-7,9-dibromo-6-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carboxamide
Synonyms:	Araplysillin 1
Standard InCHIKey:	DJOILUOUAWXGIG-CTNGQTDRSA-N
Standard InCHI:	InChI=1S/C21H23Br4N3O5/c1-31-18-14(24)9-21(19(29)16(18)25)10-15(28-33-21)20(30)27-5-2-6-32-17-12(22)7-11(3-4-26)8-13(17)23/h7-9,19,29H,2-6,10,26H2,1H3,(H,27,30)/t19-,21+/m1/s1
SMILES:	COC1=C([C@H]([C@]2(C=C1Br)CC(=NO2)C(=O)NCCCOc1c(cc(CCN)cc1Br)Br)O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518416
PubChem CID:	180014
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000186] Phenethylamines

*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
NPO33394	druinella sp.	Species	n.a.	n.a.	n.a.	Fujian, China	n.a.	PMID[12502317]
NPO40724	Pseudoceratina cf. verrucosa	Strain	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28085276]

☑ 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
Others	15

Activity Type	# Activity
Cell Line	6
Individual Protein	1
NON-MOLECULAR	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	ID50	=	18.57	ug ml-1	PMID[483246]
NPT111	Cell Line	K562	Homo sapiens	ID50	=	27.93	ug ml-1	PMID[483246]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	16.0	%	PMID[483247]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	17.0	%	PMID[483247]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	71.0	%	PMID[483247]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	36.0	%	PMID[483247]
NPT27	Others	Unspecified		Activity	=	38.0	%	PMID[483247]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	14.0	%	PMID[483247]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	8.0	%	PMID[483247]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	22.0	%	PMID[483247]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	11.0	%	PMID[483247]
NPT27	Others	Unspecified		Activity	=	7.0	%	PMID[483247]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	Inhibition	=	27.0	%	PMID[483247]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	32.0	%	PMID[483247]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	30.0	%	PMID[483247]

☑ 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 NPC77435 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	233
0.1-0.2	1830
0.2-0.3	9712
0.3-0.4	8601
0.4-0.5	15990
0.5-0.6	5907
0.6-0.7	364
0.7-0.8	35
0.8-0.85	3
0.85-0.9	8
0.9-0.95	10
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC259071
0.9649	High Similarity	NPC227953
0.9593	High Similarity	NPC202866
0.9471	High Similarity	NPC174607
0.9415	High Similarity	NPC147847
0.9075	High Similarity	NPC8093
0.9075	High Similarity	NPC121571
0.8876	High Similarity	NPC474678
0.8876	High Similarity	NPC477255
0.8876	High Similarity	NPC471338
0.8827	High Similarity	NPC475843
0.8636	High Similarity	NPC477254
0.8587	High Similarity	NPC471337
0.8486	Intermediate Similarity	NPC123140
0.8272	Intermediate Similarity	NPC471336
0.8272	Intermediate Similarity	NPC470746
0.8177	Intermediate Similarity	NPC471339
0.798	Intermediate Similarity	NPC471335
0.7965	Intermediate Similarity	NPC156311
0.7791	Intermediate Similarity	NPC469711
0.7674	Intermediate Similarity	NPC76412
0.7665	Intermediate Similarity	NPC128877
0.7633	Intermediate Similarity	NPC308571
0.763	Intermediate Similarity	NPC258222
0.7586	Intermediate Similarity	NPC47672
0.7557	Intermediate Similarity	NPC233926
0.7529	Intermediate Similarity	NPC109968
0.7487	Intermediate Similarity	NPC248822
0.7485	Intermediate Similarity	NPC78530
0.7384	Intermediate Similarity	NPC135349
0.7356	Intermediate Similarity	NPC71629
0.7294	Intermediate Similarity	NPC474673
0.7292	Intermediate Similarity	NPC246591
0.7283	Intermediate Similarity	NPC470472
0.7278	Intermediate Similarity	NPC470471
0.7273	Intermediate Similarity	NPC473450
0.7257	Intermediate Similarity	NPC296085
0.7193	Intermediate Similarity	NPC470470
0.7168	Intermediate Similarity	NPC474128
0.7107	Intermediate Similarity	NPC80514
0.7091	Intermediate Similarity	NPC272463
0.7062	Intermediate Similarity	NPC96275
0.7048	Intermediate Similarity	NPC110131
0.7005	Intermediate Similarity	NPC102245
0.7	Intermediate Similarity	NPC143450
0.6919	Remote Similarity	NPC64066
0.6888	Remote Similarity	NPC473892
0.6888	Remote Similarity	NPC471591
0.6888	Remote Similarity	NPC475658
0.6853	Remote Similarity	NPC473409
0.6853	Remote Similarity	NPC82741
0.6853	Remote Similarity	NPC141405
0.6823	Remote Similarity	NPC226001
0.6818	Remote Similarity	NPC283207
0.6802	Remote Similarity	NPC247018
0.6802	Remote Similarity	NPC307123
0.6802	Remote Similarity	NPC97870
0.68	Remote Similarity	NPC65714
0.6788	Remote Similarity	NPC207819
0.6788	Remote Similarity	NPC473462
0.6788	Remote Similarity	NPC298981
0.6788	Remote Similarity	NPC126128
0.6788	Remote Similarity	NPC110454
0.6751	Remote Similarity	NPC49172
0.6736	Remote Similarity	NPC469979
0.6734	Remote Similarity	NPC230539
0.6718	Remote Similarity	NPC475396
0.6717	Remote Similarity	NPC80337
0.67	Remote Similarity	NPC471592
0.6686	Remote Similarity	NPC474087
0.6684	Remote Similarity	NPC74618
0.6684	Remote Similarity	NPC225130
0.6684	Remote Similarity	NPC301941
0.6684	Remote Similarity	NPC214188
0.6683	Remote Similarity	NPC469721
0.6667	Remote Similarity	NPC254700
0.6648	Remote Similarity	NPC20755
0.6647	Remote Similarity	NPC475735
0.6647	Remote Similarity	NPC473724
0.6618	Remote Similarity	NPC469731
0.6616	Remote Similarity	NPC138083
0.661	Remote Similarity	NPC213471
0.659	Remote Similarity	NPC474091
0.6582	Remote Similarity	NPC290534
0.6571	Remote Similarity	NPC169766
0.6571	Remote Similarity	NPC132308
0.657	Remote Similarity	NPC477220
0.6557	Remote Similarity	NPC324081
0.6555	Remote Similarity	NPC81845
0.655	Remote Similarity	NPC144823
0.6514	Remote Similarity	NPC474753
0.6505	Remote Similarity	NPC235033
0.6505	Remote Similarity	NPC73132
0.6505	Remote Similarity	NPC476268
0.6505	Remote Similarity	NPC471235
0.65	Remote Similarity	NPC204546
0.65	Remote Similarity	NPC276120
0.6497	Remote Similarity	NPC235633
0.6492	Remote Similarity	NPC469479
0.6491	Remote Similarity	NPC158672
0.6491	Remote Similarity	NPC1702
0.648	Remote Similarity	NPC40321
0.6461	Remote Similarity	NPC470248
0.6461	Remote Similarity	NPC470249
0.6453	Remote Similarity	NPC320242
0.645	Remote Similarity	NPC66855
0.645	Remote Similarity	NPC299806
0.645	Remote Similarity	NPC315542
0.6443	Remote Similarity	NPC89831
0.6441	Remote Similarity	NPC303993
0.6425	Remote Similarity	NPC280022
0.6425	Remote Similarity	NPC197045
0.642	Remote Similarity	NPC470392
0.6414	Remote Similarity	NPC32064
0.6406	Remote Similarity	NPC67658
0.6404	Remote Similarity	NPC196708
0.6402	Remote Similarity	NPC295795
0.6402	Remote Similarity	NPC319320
0.6402	Remote Similarity	NPC287757
0.64	Remote Similarity	NPC135173
0.6392	Remote Similarity	NPC196091
0.6392	Remote Similarity	NPC475123
0.6392	Remote Similarity	NPC475204
0.6392	Remote Similarity	NPC471568
0.6392	Remote Similarity	NPC473693
0.6392	Remote Similarity	NPC46009
0.6389	Remote Similarity	NPC470886
0.6378	Remote Similarity	NPC164608
0.6378	Remote Similarity	NPC471165
0.6374	Remote Similarity	NPC116562
0.6374	Remote Similarity	NPC313173
0.6364	Remote Similarity	NPC242728
0.6364	Remote Similarity	NPC11449
0.6355	Remote Similarity	NPC124626
0.6354	Remote Similarity	NPC470709
0.6349	Remote Similarity	NPC56635
0.6345	Remote Similarity	NPC50016
0.634	Remote Similarity	NPC186617
0.634	Remote Similarity	NPC469505
0.6333	Remote Similarity	NPC473262
0.6333	Remote Similarity	NPC300912
0.6333	Remote Similarity	NPC202166
0.6333	Remote Similarity	NPC473261
0.633	Remote Similarity	NPC256689
0.633	Remote Similarity	NPC470710
0.633	Remote Similarity	NPC123011
0.6327	Remote Similarity	NPC273755
0.6325	Remote Similarity	NPC115803
0.6324	Remote Similarity	NPC132771
0.6324	Remote Similarity	NPC64140
0.6324	Remote Similarity	NPC174122
0.6321	Remote Similarity	NPC14339
0.6305	Remote Similarity	NPC94862
0.6301	Remote Similarity	NPC260270
0.6296	Remote Similarity	NPC92235
0.6293	Remote Similarity	NPC473378
0.6293	Remote Similarity	NPC473407
0.6289	Remote Similarity	NPC473502
0.6287	Remote Similarity	NPC206061
0.6286	Remote Similarity	NPC477551
0.6281	Remote Similarity	NPC119652
0.6281	Remote Similarity	NPC97526
0.6281	Remote Similarity	NPC475615
0.6278	Remote Similarity	NPC309667
0.6278	Remote Similarity	NPC106606
0.6275	Remote Similarity	NPC470951
0.6275	Remote Similarity	NPC234069
0.627	Remote Similarity	NPC313414
0.627	Remote Similarity	NPC9373
0.6269	Remote Similarity	NPC158900
0.6269	Remote Similarity	NPC63931
0.6269	Remote Similarity	NPC472923
0.6268	Remote Similarity	NPC477550
0.6268	Remote Similarity	NPC477552
0.6264	Remote Similarity	NPC136112
0.6264	Remote Similarity	NPC141739
0.6262	Remote Similarity	NPC79130
0.6256	Remote Similarity	NPC156055
0.625	Remote Similarity	NPC283079
0.625	Remote Similarity	NPC308709
0.625	Remote Similarity	NPC197125
0.6244	Remote Similarity	NPC240130
0.6244	Remote Similarity	NPC61332
0.6244	Remote Similarity	NPC306804
0.6243	Remote Similarity	NPC145149
0.6233	Remote Similarity	NPC243633
0.6233	Remote Similarity	NPC175150
0.6229	Remote Similarity	NPC218323
0.6225	Remote Similarity	NPC4910
0.6224	Remote Similarity	NPC40234
0.6223	Remote Similarity	NPC56685
0.622	Remote Similarity	NPC144314
0.6219	Remote Similarity	NPC473404
0.6218	Remote Similarity	NPC67080
0.6216	Remote Similarity	NPC119569
0.6215	Remote Similarity	NPC99280
0.6212	Remote Similarity	NPC26108
0.6212	Remote Similarity	NPC473354
0.6209	Remote Similarity	NPC470250
0.6207	Remote Similarity	NPC235194

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 NPC77435 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	591
0.2-0.3	1362
0.3-0.4	2424
0.4-0.5	3108
0.5-0.6	1384
0.6-0.7	130
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6979	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD1423	Approved
0.6761	Remote Similarity	NPD2240	Approved
0.6761	Remote Similarity	NPD2239	Approved
0.675	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7485	Phase 3
0.6684	Remote Similarity	NPD7484	Phase 3
0.6667	Remote Similarity	NPD7131	Phase 3
0.6573	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD1725	Approved
0.6567	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7608	Discontinued
0.6557	Remote Similarity	NPD3536	Discontinued
0.6556	Remote Similarity	NPD2458	Approved
0.6556	Remote Similarity	NPD2460	Phase 3
0.6556	Remote Similarity	NPD4162	Approved
0.6556	Remote Similarity	NPD2459	Approved
0.655	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD8031	Discontinued
0.6524	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD3052	Approved
0.6497	Remote Similarity	NPD3054	Approved
0.6494	Remote Similarity	NPD9718	Approved
0.6467	Remote Similarity	NPD2874	Phase 2
0.6467	Remote Similarity	NPD3985	Discontinued
0.6457	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD1819	Approved
0.6453	Remote Similarity	NPD1817	Approved
0.6453	Remote Similarity	NPD1818	Approved
0.6453	Remote Similarity	NPD1820	Approved
0.6453	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.642	Remote Similarity	NPD2245	Discovery
0.641	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5163	Phase 2
0.64	Remote Similarity	NPD3166	Approved
0.64	Remote Similarity	NPD3167	Approved
0.64	Remote Similarity	NPD3180	Approved
0.64	Remote Similarity	NPD3179	Approved
0.64	Remote Similarity	NPD3164	Approved
0.64	Remote Similarity	NPD3165	Approved
0.6398	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.639	Remote Similarity	NPD4466	Phase 1
0.6382	Remote Similarity	NPD1298	Discontinued
0.6378	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3687	Approved
0.6364	Remote Similarity	NPD3686	Approved
0.6354	Remote Similarity	NPD1307	Phase 2
0.6354	Remote Similarity	NPD1309	Phase 2
0.6349	Remote Similarity	NPD6677	Suspended
0.6349	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD6087	Phase 1
0.6321	Remote Similarity	NPD6315	Phase 2
0.6319	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5355	Approved
0.6316	Remote Similarity	NPD5356	Approved
0.6294	Remote Similarity	NPD5605	Phase 2
0.629	Remote Similarity	NPD6419	Discontinued
0.6289	Remote Similarity	NPD2904	Discontinued
0.6284	Remote Similarity	NPD3060	Approved
0.6283	Remote Similarity	NPD5773	Approved
0.6283	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5772	Approved
0.6281	Remote Similarity	NPD5557	Phase 1
0.6269	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD1794	Approved
0.6257	Remote Similarity	NPD7526	Approved
0.6257	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD52	Approved
0.6257	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD3153	Approved
0.6256	Remote Similarity	NPD3154	Approved
0.6243	Remote Similarity	NPD2649	Approved
0.6243	Remote Similarity	NPD2651	Approved
0.6243	Remote Similarity	NPD824	Approved
0.6238	Remote Similarity	NPD7811	Phase 3
0.6238	Remote Similarity	NPD7810	Phase 3
0.6237	Remote Similarity	NPD6862	Phase 2
0.6236	Remote Similarity	NPD3162	Approved
0.6236	Remote Similarity	NPD3163	Approved
0.6231	Remote Similarity	NPD6042	Phase 2
0.6231	Remote Similarity	NPD42	Phase 2
0.623	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7153	Discontinued
0.6223	Remote Similarity	NPD1670	Discontinued
0.6219	Remote Similarity	NPD7038	Approved
0.6219	Remote Similarity	NPD7039	Approved
0.6212	Remote Similarity	NPD3366	Approved
0.6211	Remote Similarity	NPD2592	Discontinued
0.6209	Remote Similarity	NPD2161	Phase 2
0.6207	Remote Similarity	NPD6853	Approved
0.6207	Remote Similarity	NPD6851	Approved
0.6203	Remote Similarity	NPD3157	Approved
0.6203	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD4662	Approved
0.6203	Remote Similarity	NPD3158	Phase 1
0.6203	Remote Similarity	NPD4661	Approved
0.6202	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD7972	Discontinued
0.619	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD5295	Discontinued
0.6181	Remote Similarity	NPD6620	Discovery
0.6181	Remote Similarity	NPD3909	Discontinued
0.6178	Remote Similarity	NPD6072	Discontinued
0.6175	Remote Similarity	NPD3656	Approved
0.617	Remote Similarity	NPD2183	Approved
0.617	Remote Similarity	NPD7613	Discontinued
0.617	Remote Similarity	NPD2184	Approved
0.6169	Remote Similarity	NPD6297	Approved
0.6166	Remote Similarity	NPD7318	Phase 3
0.6166	Remote Similarity	NPD5967	Approved
0.6158	Remote Similarity	NPD2614	Approved
0.6154	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD2428	Approved
0.6149	Remote Similarity	NPD2429	Approved
0.6138	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD2653	Approved
0.6129	Remote Similarity	NPD2677	Approved
0.6126	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD3136	Phase 2
0.6122	Remote Similarity	NPD4666	Phase 3
0.6117	Remote Similarity	NPD7020	Approved
0.6117	Remote Similarity	NPD7019	Approved
0.6117	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD2977	Approved
0.6114	Remote Similarity	NPD2978	Approved
0.6111	Remote Similarity	NPD3140	Approved
0.6111	Remote Similarity	NPD5137	Approved
0.6111	Remote Similarity	NPD3142	Approved
0.6111	Remote Similarity	NPD2216	Approved
0.6111	Remote Similarity	NPD2215	Approved
0.6108	Remote Similarity	NPD5061	Approved
0.6108	Remote Similarity	NPD5062	Approved
0.6105	Remote Similarity	NPD2556	Approved
0.6105	Remote Similarity	NPD2554	Approved
0.6102	Remote Similarity	NPD2250	Discontinued
0.6092	Remote Similarity	NPD2231	Phase 2
0.6092	Remote Similarity	NPD2235	Phase 2
0.6089	Remote Similarity	NPD3823	Discontinued
0.6085	Remote Similarity	NPD2186	Approved
0.6082	Remote Similarity	NPD2296	Approved
0.6075	Remote Similarity	NPD6863	Phase 2
0.6075	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD4971	Clinical (unspecified phase)
0.6073	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5709	Phase 3
0.6068	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD2154	Approved
0.6066	Remote Similarity	NPD2156	Approved
0.6066	Remote Similarity	NPD2155	Approved
0.6062	Remote Similarity	NPD7577	Discontinued
0.6062	Remote Similarity	NPD7317	Phase 3
0.6056	Remote Similarity	NPD5745	Approved
0.6056	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD839	Approved
0.6056	Remote Similarity	NPD840	Approved
0.6051	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD3692	Discontinued
0.6043	Remote Similarity	NPD5160	Discontinued
0.6042	Remote Similarity	NPD6876	Approved
0.6042	Remote Similarity	NPD6875	Approved
0.6039	Remote Similarity	NPD3490	Discontinued
0.6033	Remote Similarity	NPD3156	Discontinued
0.603	Remote Similarity	NPD2388	Discontinued
0.603	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.602	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD821	Approved
0.6011	Remote Similarity	NPD6667	Approved
0.6011	Remote Similarity	NPD743	Approved
0.6011	Remote Similarity	NPD6666	Approved
0.6011	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.601	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.601	Remote Similarity	NPD7110	Phase 1
0.601	Remote Similarity	NPD3511	Discontinued
0.6	Remote Similarity	NPD6390	Discontinued
0.6	Remote Similarity	NPD7316	Discontinued
0.599	Remote Similarity	NPD5095	Phase 3
0.599	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.599	Remote Similarity	NPD3933	Discontinued
0.599	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.599	Remote Similarity	NPD5096	Phase 3
0.5983	Remote Similarity	NPD8059	Phase 3
0.5983	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD6519	Phase 2
0.598	Remote Similarity	NPD4010	Discontinued
0.5979	Remote Similarity	NPD1774	Approved
0.5973	Remote Similarity	NPD3336	Discovery
0.5972	Remote Similarity	NPD7256	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