NPASS Compound

Structure

NPC93343 OpenBabel07101718192D 40 44 0 0 1 0 0 0 0 0999 V2000 2.1800 -2.1485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4037 2.4481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5539 1.7913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7419 -1.8102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8507 0.5257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0306 -1.3900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2500 1.9253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3840 2.4253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2500 0.9253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5180 1.9253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3840 0.4253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0539 -1.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4060 1.0488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4311 0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9199 -0.5747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8678 -1.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 -1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4060 -1.1982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6117 0.7911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5539 1.7913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3143 -1.1575 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3046 2.0143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5180 0.9253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1878 -0.5747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4311 -0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1878 0.4253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9972 -0.0747 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5531 0.4537 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9199 0.4253 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5232 -0.5458 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6519 0.4253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0539 0.9253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5633 -0.8262 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2396 -0.7783 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.7859 0.9253 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5539 1.7913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1309 2.5776 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6519 -0.5747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3793 1.0171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 22 1 0 0 0 0 4 33 1 0 0 0 0 6 35 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 23 2 0 0 0 0 11 23 1 0 0 0 0 12 15 1 0 0 0 0 12 24 1 0 0 0 0 13 14 1 0 0 0 0 13 26 1 0 0 0 0 14 27 1 0 0 0 0 15 29 1 0 0 0 0 16 17 1 0 0 0 0 16 25 2 0 0 0 0 17 33 1 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 19 28 1 0 0 0 0 19 34 1 0 0 0 0 20 32 1 0 0 0 0 20 37 2 0 0 0 0 21 1 1 1 0 0 0 21 30 1 0 0 0 0 21 35 1 0 0 0 0 22 38 2 0 0 0 0 22 40 1 0 0 0 0 23 31 1 0 0 0 0 24 26 1 0 0 0 0 25 27 1 0 0 0 0 26 32 1 6 0 0 0 27 34 1 1 0 0 0 28 30 1 0 0 0 0 28 40 1 1 0 0 0 29 32 1 6 0 0 0 29 36 1 0 0 0 0 30 33 1 6 0 0 0 31 36 2 3 0 0 0 31 39 1 0 0 0 0 32 3 1 6 0 0 0 33 34 1 6 0 0 0 34 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	546.35
Volume:	589.9
LogP:	4.749
LogD:	3.752
LogS:	-5.827
# Rotatable Bonds:	8
TPSA:	84.5
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.356
Synthetic Accessibility Score:	5.141
Fsp3:	0.618
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.195
MDCK Permeability:	2.2946796889300458e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.737
Human Intestinal Absorption (HIA):	0.419
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.918
Plasma Protein Binding (PPB):	62.58403015136719%
Volume Distribution (VD):	1.32
Pgp-substrate:	29.060396194458008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.088
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.351
CYP2C9-inhibitor:	0.235
CYP2C9-substrate:	0.052
CYP2D6-inhibitor:	0.879
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.918
CYP3A4-substrate:	0.596

ADMET: Excretion

Clearance (CL):	2.543
Half-life (T1/2):	0.535

ADMET: Toxicity

hERG Blockers:	0.78
Human Hepatotoxicity (H-HT):	0.815
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.938
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.94
Carcinogencity:	0.121
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC93343

Natural Product ID:	NPC93343
*Common Name:**	SDNUQXYEIKHCSC-YCRBMUDLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SDNUQXYEIKHCSC-YCRBMUDLSA-N
Standard InCHI:	InChI=1S/C34H46N2O4/c1-21(35-6)30-28(40-22(2)38)19-34(5)27-14-13-26-24(18-25(27)16-17-33(30,34)4)12-15-29(32(26,3)20-37)36-31(39)23-10-8-7-9-11-23/h7-11,16,18,20-21,26-30,35H,12-15,17,19H2,1-6H3,(H,36,39)/t21-,26+,27+,28+,29-,30-,32-,33+,34-/m0/s1
SMILES:	C[C@@H]([C@H]1[C@@H](C[C@@]2(C)[C@@H]3CC[C@@H]4C(=CC3=CC[C@]12C)CC[C@@H]([C@@]4(C)C=O)N=C(c1ccccc1)O)OC(=O)C)NC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501652
PubChem CID:	10768953
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002724] Steroidal alkaloids [CHEMONTID:0002726] Buxus 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
NPO6372	Buxus longifolia	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20954721]
NPO6372	Buxus longifolia	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358638]
NPO6372	Buxus longifolia	Species	Buxaceae	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
MIC	3
Others	6

Activity Type	# Activity
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1242	Organism	Salmonella typhi	Salmonella enterica subsp. enterica serovar Typhi	IZ	=	6.0	nm	PMID[509826]
NPT2909	Organism	Shigella flexneri	Shigella flexneri	IZ	=	6.0	nm	PMID[509826]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	8.0	nm	PMID[509826]
NPT1242	Organism	Salmonella typhi	Salmonella enterica subsp. enterica serovar Typhi	IZ	=	8.0	nm	PMID[509826]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	9.0	nm	PMID[509826]
NPT1242	Organism	Salmonella typhi	Salmonella enterica subsp. enterica serovar Typhi	MIC	=	100.0	ug	PMID[509826]
NPT1242	Organism	Salmonella typhi	Salmonella enterica subsp. enterica serovar Typhi	MIC	=	200.0	ug	PMID[509826]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	50.0	ug	PMID[509826]

☑ 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 NPC93343 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	151
0.1-0.2	785
0.2-0.3	1885
0.3-0.4	6627
0.4-0.5	23903
0.5-0.6	8391
0.6-0.7	927
0.7-0.8	25
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8851	High Similarity	NPC475578
0.8355	Intermediate Similarity	NPC328824
0.8247	Intermediate Similarity	NPC476757
0.8137	Intermediate Similarity	NPC476750
0.811	Intermediate Similarity	NPC476749
0.7987	Intermediate Similarity	NPC473922
0.7771	Intermediate Similarity	NPC44649
0.7702	Intermediate Similarity	NPC275839
0.7669	Intermediate Similarity	NPC217801
0.7632	Intermediate Similarity	NPC3202
0.7613	Intermediate Similarity	NPC153007
0.7576	Intermediate Similarity	NPC235460
0.7514	Intermediate Similarity	NPC203005
0.7468	Intermediate Similarity	NPC132847
0.7362	Intermediate Similarity	NPC470274
0.7315	Intermediate Similarity	NPC109151
0.7261	Intermediate Similarity	NPC478140
0.7181	Intermediate Similarity	NPC190663
0.7171	Intermediate Similarity	NPC4974
0.7115	Intermediate Similarity	NPC246913
0.7086	Intermediate Similarity	NPC160493
0.7081	Intermediate Similarity	NPC57976
0.7078	Intermediate Similarity	NPC210950
0.7078	Intermediate Similarity	NPC199738
0.707	Intermediate Similarity	NPC313663
0.703	Intermediate Similarity	NPC94602
0.6993	Remote Similarity	NPC473938
0.6943	Remote Similarity	NPC183722
0.6933	Remote Similarity	NPC475128
0.6928	Remote Similarity	NPC35996
0.6923	Remote Similarity	NPC116057
0.6923	Remote Similarity	NPC472413
0.6919	Remote Similarity	NPC73644
0.6918	Remote Similarity	NPC90693
0.6918	Remote Similarity	NPC64897
0.6914	Remote Similarity	NPC239770
0.6897	Remote Similarity	NPC71205
0.6842	Remote Similarity	NPC80150
0.6839	Remote Similarity	NPC293164
0.6839	Remote Similarity	NPC472414
0.6839	Remote Similarity	NPC471394
0.6839	Remote Similarity	NPC47667
0.6832	Remote Similarity	NPC208725
0.6821	Remote Similarity	NPC310467
0.6818	Remote Similarity	NPC472415
0.6815	Remote Similarity	NPC40488
0.6807	Remote Similarity	NPC260194
0.6782	Remote Similarity	NPC67080
0.677	Remote Similarity	NPC203486
0.6766	Remote Similarity	NPC473541
0.6761	Remote Similarity	NPC278887
0.6755	Remote Similarity	NPC169328
0.6748	Remote Similarity	NPC243893
0.6748	Remote Similarity	NPC262324
0.6747	Remote Similarity	NPC262216
0.6728	Remote Similarity	NPC471864
0.672	Remote Similarity	NPC476256
0.672	Remote Similarity	NPC476206
0.672	Remote Similarity	NPC259791
0.672	Remote Similarity	NPC476205
0.672	Remote Similarity	NPC476212
0.672	Remote Similarity	NPC476207
0.672	Remote Similarity	NPC476257
0.672	Remote Similarity	NPC476129
0.6711	Remote Similarity	NPC314992
0.6709	Remote Similarity	NPC71271
0.6688	Remote Similarity	NPC65310
0.6687	Remote Similarity	NPC42423
0.6687	Remote Similarity	NPC326966
0.6687	Remote Similarity	NPC72915
0.6684	Remote Similarity	NPC476218
0.6684	Remote Similarity	NPC108804
0.6667	Remote Similarity	NPC161069
0.6667	Remote Similarity	NPC325651
0.6667	Remote Similarity	NPC476751
0.6667	Remote Similarity	NPC79921
0.6667	Remote Similarity	NPC91953
0.6649	Remote Similarity	NPC40539
0.6646	Remote Similarity	NPC244866
0.6645	Remote Similarity	NPC84281
0.6645	Remote Similarity	NPC169485
0.6645	Remote Similarity	NPC291027
0.6645	Remote Similarity	NPC45794
0.6645	Remote Similarity	NPC213126
0.6645	Remote Similarity	NPC317474
0.6644	Remote Similarity	NPC474584
0.6631	Remote Similarity	NPC327699
0.6627	Remote Similarity	NPC132771
0.6623	Remote Similarity	NPC9274
0.6623	Remote Similarity	NPC470585
0.6623	Remote Similarity	NPC197470
0.6614	Remote Similarity	NPC163578
0.6614	Remote Similarity	NPC108276
0.6606	Remote Similarity	NPC197921
0.6604	Remote Similarity	NPC296712
0.6582	Remote Similarity	NPC477937
0.6579	Remote Similarity	NPC242764
0.6579	Remote Similarity	NPC2265
0.6579	Remote Similarity	NPC105141
0.6579	Remote Similarity	NPC166521
0.6579	Remote Similarity	NPC212891
0.6579	Remote Similarity	NPC184195
0.6579	Remote Similarity	NPC172769
0.6579	Remote Similarity	NPC205
0.6579	Remote Similarity	NPC124690
0.6579	Remote Similarity	NPC281470
0.6576	Remote Similarity	NPC475962
0.6575	Remote Similarity	NPC274089
0.6575	Remote Similarity	NPC191215
0.6566	Remote Similarity	NPC261709
0.6566	Remote Similarity	NPC234548
0.6566	Remote Similarity	NPC111586
0.6566	Remote Similarity	NPC248287
0.6566	Remote Similarity	NPC108852
0.6564	Remote Similarity	NPC113325
0.6564	Remote Similarity	NPC279045
0.6562	Remote Similarity	NPC478147
0.6562	Remote Similarity	NPC198390
0.6561	Remote Similarity	NPC285394
0.6561	Remote Similarity	NPC140118
0.6561	Remote Similarity	NPC12881
0.6556	Remote Similarity	NPC89831
0.6554	Remote Similarity	NPC63931
0.6552	Remote Similarity	NPC207675
0.6552	Remote Similarity	NPC212699
0.6548	Remote Similarity	NPC314114
0.6529	Remote Similarity	NPC2672
0.6527	Remote Similarity	NPC471862
0.6527	Remote Similarity	NPC471516
0.6516	Remote Similarity	NPC478015
0.6516	Remote Similarity	NPC476183
0.6516	Remote Similarity	NPC478014
0.6516	Remote Similarity	NPC478016
0.6512	Remote Similarity	NPC473341
0.6512	Remote Similarity	NPC472761
0.651	Remote Similarity	NPC95126
0.651	Remote Similarity	NPC475002
0.651	Remote Similarity	NPC319579
0.6509	Remote Similarity	NPC138775
0.6509	Remote Similarity	NPC311658
0.6506	Remote Similarity	NPC269398
0.6506	Remote Similarity	NPC150712
0.6506	Remote Similarity	NPC263493
0.6503	Remote Similarity	NPC228511
0.6494	Remote Similarity	NPC237420
0.6491	Remote Similarity	NPC475168
0.6491	Remote Similarity	NPC7817
0.6489	Remote Similarity	NPC94862
0.6488	Remote Similarity	NPC209509
0.6485	Remote Similarity	NPC472804
0.6481	Remote Similarity	NPC470278
0.6481	Remote Similarity	NPC246079
0.6478	Remote Similarity	NPC470649
0.6478	Remote Similarity	NPC478107
0.6478	Remote Similarity	NPC470816
0.6478	Remote Similarity	NPC275576
0.6477	Remote Similarity	NPC114806
0.6477	Remote Similarity	NPC475544
0.6474	Remote Similarity	NPC476281
0.6474	Remote Similarity	NPC473300
0.6474	Remote Similarity	NPC453583
0.6474	Remote Similarity	NPC476184
0.6474	Remote Similarity	NPC475336
0.6467	Remote Similarity	NPC469360
0.6467	Remote Similarity	NPC329011
0.6467	Remote Similarity	NPC471188
0.6463	Remote Similarity	NPC48929
0.6463	Remote Similarity	NPC329913
0.6463	Remote Similarity	NPC314835
0.6463	Remote Similarity	NPC126516
0.646	Remote Similarity	NPC69496
0.6458	Remote Similarity	NPC21483
0.6458	Remote Similarity	NPC198205
0.6456	Remote Similarity	NPC476260
0.6456	Remote Similarity	NPC476241
0.645	Remote Similarity	NPC49565
0.6448	Remote Similarity	NPC88378
0.6448	Remote Similarity	NPC211713
0.6447	Remote Similarity	NPC221275
0.6443	Remote Similarity	NPC112752
0.6443	Remote Similarity	NPC311054
0.644	Remote Similarity	NPC67246
0.644	Remote Similarity	NPC33372
0.6438	Remote Similarity	NPC473220
0.6438	Remote Similarity	NPC169913
0.6438	Remote Similarity	NPC470753
0.6433	Remote Similarity	NPC369
0.6433	Remote Similarity	NPC293831
0.6429	Remote Similarity	NPC35037
0.6425	Remote Similarity	NPC215892
0.6425	Remote Similarity	NPC242662
0.6425	Remote Similarity	NPC471771
0.6425	Remote Similarity	NPC304074
0.6425	Remote Similarity	NPC191193
0.6425	Remote Similarity	NPC321072
0.6425	Remote Similarity	NPC290755
0.6425	Remote Similarity	NPC471396
0.6424	Remote Similarity	NPC194970
0.6424	Remote Similarity	NPC127741
0.6424	Remote Similarity	NPC206414

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 NPC93343 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	112
0.1-0.2	390
0.2-0.3	745
0.3-0.4	1548
0.4-0.5	3768
0.5-0.6	2217
0.6-0.7	353
0.7-0.8	17
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
0.7283	Intermediate Similarity	NPD7997	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7715	Approved
0.707	Intermediate Similarity	NPD7714	Approved
0.7012	Intermediate Similarity	NPD8131	Suspended
0.7	Intermediate Similarity	NPD6852	Discontinued
0.6937	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5618	Discontinued
0.6821	Remote Similarity	NPD4479	Discontinued
0.6818	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7084	Phase 3
0.6802	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD4766	Approved
0.6776	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2607	Approved
0.675	Remote Similarity	NPD6663	Approved
0.6747	Remote Similarity	NPD6676	Phase 2
0.6747	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4031	Approved
0.6733	Remote Similarity	NPD4032	Approved
0.6726	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD6620	Discovery
0.6711	Remote Similarity	NPD2218	Phase 2
0.6711	Remote Similarity	NPD1373	Approved
0.6711	Remote Similarity	NPD1371	Approved
0.6711	Remote Similarity	NPD2217	Approved
0.6711	Remote Similarity	NPD1370	Approved
0.6711	Remote Similarity	NPD1374	Approved
0.6711	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD5736	Approved
0.6708	Remote Similarity	NPD6310	Approved
0.6708	Remote Similarity	NPD6623	Phase 3
0.6708	Remote Similarity	NPD6311	Approved
0.6708	Remote Similarity	NPD6309	Approved
0.6707	Remote Similarity	NPD7740	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7495	Discontinued
0.6705	Remote Similarity	NPD6315	Phase 2
0.6689	Remote Similarity	NPD3123	Discovery
0.6688	Remote Similarity	NPD2625	Approved
0.6688	Remote Similarity	NPD2628	Approved
0.6688	Remote Similarity	NPD2160	Approved
0.6688	Remote Similarity	NPD2627	Approved
0.6688	Remote Similarity	NPD2626	Approved
0.6688	Remote Similarity	NPD2159	Approved
0.6687	Remote Similarity	NPD3638	Discontinued
0.6667	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5981	Approved
0.6647	Remote Similarity	NPD7253	Phase 3
0.6647	Remote Similarity	NPD6677	Suspended
0.6645	Remote Similarity	NPD2610	Approved
0.6645	Remote Similarity	NPD4216	Approved
0.6645	Remote Similarity	NPD4217	Approved
0.6645	Remote Similarity	NPD4218	Approved
0.6645	Remote Similarity	NPD4215	Approved
0.6645	Remote Similarity	NPD3131	Approved
0.6645	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD2611	Approved
0.6645	Remote Similarity	NPD2612	Approved
0.6645	Remote Similarity	NPD2609	Approved
0.6645	Remote Similarity	NPD2608	Approved
0.6645	Remote Similarity	NPD3132	Approved
0.6644	Remote Similarity	NPD6858	Approved
0.6644	Remote Similarity	NPD7094	Approved
0.6627	Remote Similarity	NPD6681	Discovery
0.6625	Remote Similarity	NPD3136	Phase 2
0.6624	Remote Similarity	NPD2198	Approved
0.6624	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD2199	Approved
0.6623	Remote Similarity	NPD1348	Approved
0.6622	Remote Similarity	NPD3643	Approved
0.6622	Remote Similarity	NPD3644	Approved
0.6622	Remote Similarity	NPD3642	Approved
0.6609	Remote Similarity	NPD8019	Approved
0.6605	Remote Similarity	NPD6346	Approved
0.6604	Remote Similarity	NPD3662	Phase 3
0.6604	Remote Similarity	NPD3664	Approved
0.6604	Remote Similarity	NPD3663	Approved
0.6604	Remote Similarity	NPD5204	Approved
0.6604	Remote Similarity	NPD3661	Approved
0.659	Remote Similarity	NPD7463	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD8147	Approved
0.6585	Remote Similarity	NPD8148	Approved
0.6584	Remote Similarity	NPD4619	Approved
0.6584	Remote Similarity	NPD4621	Approved
0.6564	Remote Similarity	NPD8643	Discontinued
0.6564	Remote Similarity	NPD6086	Phase 2
0.6562	Remote Similarity	NPD4617	Approved
0.6562	Remote Similarity	NPD4620	Approved
0.6562	Remote Similarity	NPD5201	Approved
0.6562	Remote Similarity	NPD5203	Approved
0.6561	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD5159	Phase 2
0.6561	Remote Similarity	NPD5157	Phase 1
0.6558	Remote Similarity	NPD1710	Approved
0.655	Remote Similarity	NPD7613	Discontinued
0.6543	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4807	Approved
0.6538	Remote Similarity	NPD4806	Approved
0.6534	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6073	Approved
0.6522	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4738	Phase 2
0.6516	Remote Similarity	NPD5305	Approved
0.6516	Remote Similarity	NPD5306	Approved
0.6512	Remote Similarity	NPD7523	Phase 3
0.6503	Remote Similarity	NPD5119	Approved
0.6503	Remote Similarity	NPD5121	Approved
0.6503	Remote Similarity	NPD8416	Discontinued
0.6503	Remote Similarity	NPD5120	Approved
0.6497	Remote Similarity	NPD6624	Discontinued
0.6481	Remote Similarity	NPD8011	Discontinued
0.6474	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5162	Approved
0.6471	Remote Similarity	NPD7236	Approved
0.6471	Remote Similarity	NPD7554	Discontinued
0.6467	Remote Similarity	NPD7978	Discontinued
0.6463	Remote Similarity	NPD5705	Approved
0.6463	Remote Similarity	NPD5706	Approved
0.6463	Remote Similarity	NPD5704	Approved
0.646	Remote Similarity	NPD2613	Approved
0.6447	Remote Similarity	NPD2629	Approved
0.6437	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.642	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5667	Approved
0.6413	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7725	Approved
0.6409	Remote Similarity	NPD7315	Approved
0.6407	Remote Similarity	NPD4173	Approved
0.6407	Remote Similarity	NPD4172	Approved
0.6402	Remote Similarity	NPD3373	Approved
0.6395	Remote Similarity	NPD3645	Discontinued
0.6392	Remote Similarity	NPD8485	Approved
0.6387	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD6295	Approved
0.6386	Remote Similarity	NPD6294	Approved
0.6384	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD7239	Suspended
0.6379	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD4135	Approved
0.6369	Remote Similarity	NPD4136	Approved
0.6369	Remote Similarity	NPD4106	Approved
0.6369	Remote Similarity	NPD4152	Approved
0.6364	Remote Similarity	NPD4574	Approved
0.6364	Remote Similarity	NPD4576	Approved
0.6353	Remote Similarity	NPD2575	Approved
0.6352	Remote Similarity	NPD4677	Discontinued
0.6352	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD6864	Phase 2
0.6347	Remote Similarity	NPD6865	Phase 2
0.6347	Remote Similarity	NPD7305	Phase 1
0.6346	Remote Similarity	NPD4102	Approved
0.6346	Remote Similarity	NPD4105	Approved
0.6341	Remote Similarity	NPD7713	Phase 3
0.6341	Remote Similarity	NPD2574	Discontinued
0.6341	Remote Similarity	NPD3615	Approved
0.6341	Remote Similarity	NPD4745	Approved
0.6341	Remote Similarity	NPD2571	Approved
0.6341	Remote Similarity	NPD3088	Approved
0.6341	Remote Similarity	NPD3614	Approved
0.6341	Remote Similarity	NPD7086	Phase 2
0.6341	Remote Similarity	NPD4746	Phase 3
0.6341	Remote Similarity	NPD2566	Approved
0.6341	Remote Similarity	NPD3090	Approved
0.6341	Remote Similarity	NPD3087	Approved
0.6341	Remote Similarity	NPD3616	Approved
0.6341	Remote Similarity	NPD3089	Approved
0.6341	Remote Similarity	NPD2570	Approved
0.6341	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD2573	Approved
0.6333	Remote Similarity	NPD5236	Approved
0.6333	Remote Similarity	NPD5237	Approved
0.6333	Remote Similarity	NPD5235	Approved
0.6333	Remote Similarity	NPD5239	Approved
0.6333	Remote Similarity	NPD5240	Approved
0.6331	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD6287	Discontinued
0.6325	Remote Similarity	NPD5725	Approved
0.6323	Remote Similarity	NPD1758	Phase 1
0.6323	Remote Similarity	NPD7522	Discontinued
0.6322	Remote Similarity	NPD7606	Phase 3
0.6322	Remote Similarity	NPD4727	Phase 1
0.6312	Remote Similarity	NPD3125	Approved
0.631	Remote Similarity	NPD7450	Phase 2
0.6309	Remote Similarity	NPD6406	Approved
0.6303	Remote Similarity	NPD5323	Approved
0.6303	Remote Similarity	NPD4153	Approved
0.6301	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD7508	Discontinued
0.6296	Remote Similarity	NPD8407	Phase 2
0.6296	Remote Similarity	NPD4177	Approved
0.6296	Remote Similarity	NPD4175	Approved
0.6296	Remote Similarity	NPD6556	Clinical (unspecified phase)

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