NPASS Compound

Structure

NPC162748 OpenBabel07101719252D 43 52 0 0 1 0 0 0 0 0999 V2000 -1.2590 2.8933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3204 -0.6358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2813 2.6835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3551 -0.3747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4478 3.8790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0411 2.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4869 0.8884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3770 1.0626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4423 3.9835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6288 2.1564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5005 -0.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7963 -1.1279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4440 2.1005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7723 3.3896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9740 1.7468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8511 0.5194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6462 2.2576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5775 -0.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2801 1.8124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9999 0.0150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4884 3.0042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6579 -0.7531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2325 0.0918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0301 3.1745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0246 3.0700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5005 0.0918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6234 2.2610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3665 0.5918 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0921 -0.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8186 1.3788 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0921 0.0918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7963 0.4984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2325 2.0918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0986 1.5918 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5129 0.8584 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0259 1.7319 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0986 0.5918 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4878 0.6359 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6272 1.2938 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.6336 2.2042 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 4.3665 1.5918 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2261 -1.2213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 15 1 0 0 0 0 7 20 1 0 0 0 0 8 16 1 0 0 0 0 8 19 1 0 0 0 0 9 24 2 0 0 0 0 10 27 2 0 0 0 0 11 12 2 0 0 0 0 11 26 1 0 0 0 0 12 29 1 0 0 0 0 13 17 1 0 0 0 0 13 30 1 0 0 0 0 14 21 1 0 0 0 0 14 25 1 0 0 0 0 15 36 1 0 0 0 0 16 37 1 0 0 0 0 17 36 1 0 0 0 0 18 22 1 0 0 0 0 19 40 1 0 0 0 0 20 41 1 0 0 0 0 21 40 1 0 0 0 0 22 41 1 0 0 0 0 23 28 1 0 0 0 0 23 37 1 0 0 0 0 24 25 1 0 0 0 0 24 27 1 0 0 0 0 25 33 2 0 0 0 0 26 32 2 0 0 0 0 27 42 1 0 0 0 0 28 26 1 1 0 0 0 28 42 1 0 0 0 0 29 31 2 0 0 0 0 29 43 1 0 0 0 0 30 38 1 1 0 0 0 30 39 1 0 0 0 0 31 32 1 0 0 0 0 31 38 1 0 0 0 0 32 39 1 0 0 0 0 33 34 1 0 0 0 0 33 42 1 0 0 0 0 34 37 1 6 0 0 0 34 40 1 0 0 0 0 35 36 1 6 0 0 0 35 38 1 0 0 0 0 35 41 1 0 0 0 0 36 3 1 1 0 0 0 37 4 1 1 0 0 0 38 18 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.38
Volume:	614.561
LogP:	6.933
LogD:	5.084
LogS:	-5.184
# Rotatable Bonds:	3
TPSA:	43.67
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	10
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.339
Synthetic Accessibility Score:	5.573
Fsp3:	0.632
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.586
MDCK Permeability:	8.119730409816839e-06
Pgp-inhibitor:	0.734
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.983
Plasma Protein Binding (PPB):	95.3313980102539%
Volume Distribution (VD):	1.7
Pgp-substrate:	1.5313630104064941%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.845
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.931
CYP2C9-inhibitor:	0.093
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.947
CYP2D6-substrate:	0.908
CYP3A4-inhibitor:	0.933
CYP3A4-substrate:	0.91

ADMET: Excretion

Clearance (CL):	6.02
Half-life (T1/2):	0.099

ADMET: Toxicity

hERG Blockers:	0.823
Human Hepatotoxicity (H-HT):	0.973
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.139
Rat Oral Acute Toxicity:	0.132
Maximum Recommended Daily Dose:	0.998
Skin Sensitization:	0.364
Carcinogencity:	0.036
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.351

Download Data

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

Natural Product: NPC162748

Natural Product ID:	NPC162748
*Common Name:**	Bisleuconothine A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HHCOPHVLECRPRE-UQYJQATHSA-N
Standard InCHI:	InChI=1S/C38H48N4O/c1-3-36-15-7-20-41-22-18-38(35(36)41)30(13-17-36)39-32-26(11-12-29(43)31(32)38)28-23-37(4-2)16-8-19-40-21-14-25-24-9-5-6-10-27(24)42(28)33(25)34(37)40/h5-6,9-12,28,30,34-35,39,43H,3-4,7-8,13-23H2,1-2H3/t28-,30+,34-,35+,36+,37+,38-/m0/s1
SMILES:	CC[C@@]12CCCN3CC[C@@]4([C@@H](CC1)Nc1c(ccc(c41)O)[C@@H]1C[C@@]4(CC)CCCN5CCc6c7ccccc7n1c6[C@@H]45)[C@@H]23
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077259
PubChem CID:	46881778
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002671] Eburnan-type 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
NPO10199	Leuconotis griffithii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20153644]
NPO10199	Leuconotis griffithii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[23647487]
NPO10199	Leuconotis griffithii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[30362746]
NPO10199	Leuconotis griffithii	n.a.	n.a.	n.a.	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	5
Others	3

Activity Type	# Activity
Cell Line	8

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[447953]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	5700.0	nM	PMID[447953]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	9200.0	nM	PMID[447953]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	7000.0	nM	PMID[447953]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	72.0	%	PMID[447953]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	75.1	%	PMID[447953]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	79.5	%	PMID[447953]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	8000.0	nM	PMID[447954]

☑ 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 NPC162748 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	626
0.1-0.2	3169
0.2-0.3	12725
0.3-0.4	15247
0.4-0.5	5863
0.5-0.6	3107
0.6-0.7	1607
0.7-0.8	339
0.8-0.85	12
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9303	High Similarity	NPC183407
0.8688	High Similarity	NPC469734
0.863	High Similarity	NPC477861
0.8465	Intermediate Similarity	NPC2497
0.8387	Intermediate Similarity	NPC253580
0.8341	Intermediate Similarity	NPC470126
0.8104	Intermediate Similarity	NPC476116
0.8066	Intermediate Similarity	NPC475422
0.8057	Intermediate Similarity	NPC87755
0.796	Intermediate Similarity	NPC94943
0.7926	Intermediate Similarity	NPC476041
0.7926	Intermediate Similarity	NPC304926
0.791	Intermediate Similarity	NPC190007
0.7895	Intermediate Similarity	NPC249040
0.7861	Intermediate Similarity	NPC212535
0.785	Intermediate Similarity	NPC469589
0.7788	Intermediate Similarity	NPC469592
0.7788	Intermediate Similarity	NPC471080
0.7768	Intermediate Similarity	NPC473185
0.7768	Intermediate Similarity	NPC6215
0.7759	Intermediate Similarity	NPC81939
0.7742	Intermediate Similarity	NPC294620
0.7734	Intermediate Similarity	NPC472294
0.7731	Intermediate Similarity	NPC126066
0.7725	Intermediate Similarity	NPC475666
0.7703	Intermediate Similarity	NPC477532
0.7668	Intermediate Similarity	NPC280272
0.7667	Intermediate Similarity	NPC153042
0.7658	Intermediate Similarity	NPC477533
0.7647	Intermediate Similarity	NPC469594
0.7639	Intermediate Similarity	NPC475910
0.7639	Intermediate Similarity	NPC470931
0.7636	Intermediate Similarity	NPC330009
0.7624	Intermediate Similarity	NPC72980
0.76	Intermediate Similarity	NPC474409
0.7588	Intermediate Similarity	NPC476451
0.7583	Intermediate Similarity	NPC70956
0.7583	Intermediate Similarity	NPC243834
0.7581	Intermediate Similarity	NPC475070
0.7566	Intermediate Similarity	NPC214980
0.7565	Intermediate Similarity	NPC325976
0.7559	Intermediate Similarity	NPC329747
0.7554	Intermediate Similarity	NPC81175
0.7542	Intermediate Similarity	NPC471891
0.7536	Intermediate Similarity	NPC46580
0.7534	Intermediate Similarity	NPC193267
0.7534	Intermediate Similarity	NPC213530
0.7511	Intermediate Similarity	NPC475253
0.75	Intermediate Similarity	NPC473183
0.7488	Intermediate Similarity	NPC291535
0.7488	Intermediate Similarity	NPC475112
0.7488	Intermediate Similarity	NPC475085
0.7468	Intermediate Similarity	NPC41679
0.7467	Intermediate Similarity	NPC326363
0.7467	Intermediate Similarity	NPC209174
0.7455	Intermediate Similarity	NPC473179
0.7451	Intermediate Similarity	NPC232340
0.7435	Intermediate Similarity	NPC477531
0.7432	Intermediate Similarity	NPC470549
0.7424	Intermediate Similarity	NPC314954
0.7424	Intermediate Similarity	NPC252251
0.7416	Intermediate Similarity	NPC246700
0.7414	Intermediate Similarity	NPC473184
0.7399	Intermediate Similarity	NPC170114
0.7395	Intermediate Similarity	NPC11017
0.7393	Intermediate Similarity	NPC324149
0.7393	Intermediate Similarity	NPC99666
0.7386	Intermediate Similarity	NPC329982
0.7381	Intermediate Similarity	NPC469497
0.7381	Intermediate Similarity	NPC106833
0.7371	Intermediate Similarity	NPC242209
0.7366	Intermediate Similarity	NPC88363
0.7352	Intermediate Similarity	NPC473362
0.7352	Intermediate Similarity	NPC193777
0.7352	Intermediate Similarity	NPC166492
0.7333	Intermediate Similarity	NPC128751
0.733	Intermediate Similarity	NPC11464
0.733	Intermediate Similarity	NPC167860
0.733	Intermediate Similarity	NPC123976
0.7321	Intermediate Similarity	NPC469928
0.7318	Intermediate Similarity	NPC477111
0.7308	Intermediate Similarity	NPC295228
0.7306	Intermediate Similarity	NPC472111
0.7306	Intermediate Similarity	NPC477113
0.73	Intermediate Similarity	NPC473312
0.7294	Intermediate Similarity	NPC200836
0.7294	Intermediate Similarity	NPC53144
0.7293	Intermediate Similarity	NPC98371
0.7293	Intermediate Similarity	NPC313884
0.729	Intermediate Similarity	NPC472193
0.729	Intermediate Similarity	NPC70259
0.7289	Intermediate Similarity	NPC305984
0.7282	Intermediate Similarity	NPC133261
0.7281	Intermediate Similarity	NPC267423
0.7273	Intermediate Similarity	NPC195788
0.7273	Intermediate Similarity	NPC237901
0.7269	Intermediate Similarity	NPC132642
0.7265	Intermediate Similarity	NPC48353
0.726	Intermediate Similarity	NPC285558
0.726	Intermediate Similarity	NPC472110
0.726	Intermediate Similarity	NPC472109
0.7257	Intermediate Similarity	NPC264285
0.7256	Intermediate Similarity	NPC77555
0.7255	Intermediate Similarity	NPC471294
0.7255	Intermediate Similarity	NPC472123
0.7255	Intermediate Similarity	NPC259545
0.725	Intermediate Similarity	NPC17437
0.7244	Intermediate Similarity	NPC477110
0.7243	Intermediate Similarity	NPC205934
0.7243	Intermediate Similarity	NPC43787
0.7238	Intermediate Similarity	NPC171171
0.7235	Intermediate Similarity	NPC329793
0.7233	Intermediate Similarity	NPC96890
0.7232	Intermediate Similarity	NPC475602
0.7232	Intermediate Similarity	NPC478074
0.7229	Intermediate Similarity	NPC476492
0.7227	Intermediate Similarity	NPC477067
0.7227	Intermediate Similarity	NPC476106
0.7227	Intermediate Similarity	NPC478081
0.7227	Intermediate Similarity	NPC478082
0.7222	Intermediate Similarity	NPC265576
0.7222	Intermediate Similarity	NPC72211
0.7215	Intermediate Similarity	NPC223427
0.7213	Intermediate Similarity	NPC478080
0.7203	Intermediate Similarity	NPC28945
0.7202	Intermediate Similarity	NPC476044
0.72	Intermediate Similarity	NPC255229
0.72	Intermediate Similarity	NPC81229
0.7198	Intermediate Similarity	NPC477607
0.7198	Intermediate Similarity	NPC477608
0.7196	Intermediate Similarity	NPC473178
0.7196	Intermediate Similarity	NPC106937
0.7188	Intermediate Similarity	NPC94157
0.7185	Intermediate Similarity	NPC477066
0.7181	Intermediate Similarity	NPC473041
0.7176	Intermediate Similarity	NPC232130
0.7175	Intermediate Similarity	NPC5145
0.7174	Intermediate Similarity	NPC211416
0.7163	Intermediate Similarity	NPC472105
0.7163	Intermediate Similarity	NPC187827
0.7163	Intermediate Similarity	NPC131017
0.7162	Intermediate Similarity	NPC471506
0.716	Intermediate Similarity	NPC260909
0.7156	Intermediate Similarity	NPC473757
0.7155	Intermediate Similarity	NPC473540
0.7149	Intermediate Similarity	NPC474145
0.7149	Intermediate Similarity	NPC475841
0.7143	Intermediate Similarity	NPC306376
0.7143	Intermediate Similarity	NPC23294
0.7143	Intermediate Similarity	NPC204717
0.7136	Intermediate Similarity	NPC162484
0.7131	Intermediate Similarity	NPC153400
0.7126	Intermediate Similarity	NPC471303
0.7124	Intermediate Similarity	NPC250835
0.7123	Intermediate Similarity	NPC232727
0.7112	Intermediate Similarity	NPC24370
0.7112	Intermediate Similarity	NPC319232
0.7112	Intermediate Similarity	NPC202503
0.7112	Intermediate Similarity	NPC227908
0.7111	Intermediate Similarity	NPC264176
0.7109	Intermediate Similarity	NPC314002
0.7108	Intermediate Similarity	NPC317430
0.7105	Intermediate Similarity	NPC303658
0.7105	Intermediate Similarity	NPC477714
0.7104	Intermediate Similarity	NPC470500
0.7101	Intermediate Similarity	NPC470784
0.7098	Intermediate Similarity	NPC303951
0.7098	Intermediate Similarity	NPC85273
0.7095	Intermediate Similarity	NPC19679
0.7095	Intermediate Similarity	NPC220765
0.7093	Intermediate Similarity	NPC152768
0.7093	Intermediate Similarity	NPC472027
0.7093	Intermediate Similarity	NPC148183
0.7093	Intermediate Similarity	NPC251936
0.7089	Intermediate Similarity	NPC473187
0.7087	Intermediate Similarity	NPC310118
0.7083	Intermediate Similarity	NPC195314
0.708	Intermediate Similarity	NPC477610
0.7078	Intermediate Similarity	NPC471564
0.7076	Intermediate Similarity	NPC473105
0.7076	Intermediate Similarity	NPC473182
0.7073	Intermediate Similarity	NPC474897
0.7067	Intermediate Similarity	NPC326575
0.7065	Intermediate Similarity	NPC474880
0.7065	Intermediate Similarity	NPC221786
0.7062	Intermediate Similarity	NPC84478
0.7061	Intermediate Similarity	NPC477715
0.7059	Intermediate Similarity	NPC476098
0.7059	Intermediate Similarity	NPC184680
0.7056	Intermediate Similarity	NPC220851
0.7056	Intermediate Similarity	NPC16352
0.7054	Intermediate Similarity	NPC201697
0.7048	Intermediate Similarity	NPC237740
0.7046	Intermediate Similarity	NPC277351
0.7044	Intermediate Similarity	NPC159319
0.7043	Intermediate Similarity	NPC472099
0.7035	Intermediate Similarity	NPC202605
0.7035	Intermediate Similarity	NPC112206
0.7034	Intermediate Similarity	NPC132329
0.7031	Intermediate Similarity	NPC473310

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 NPC162748 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	593
0.2-0.3	865
0.3-0.4	1618
0.4-0.5	2766
0.5-0.6	2195
0.6-0.7	740
0.7-0.8	72
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
0.7871	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD2916	Discontinued
0.7685	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7948	Phase 1
0.7557	Intermediate Similarity	NPD7112	Discontinued
0.7512	Intermediate Similarity	NPD8395	Approved
0.7512	Intermediate Similarity	NPD8396	Approved
0.7465	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD8364	Approved
0.7449	Intermediate Similarity	NPD8363	Approved
0.7442	Intermediate Similarity	NPD4511	Phase 1
0.7434	Intermediate Similarity	NPD7221	Approved
0.7434	Intermediate Similarity	NPD7219	Approved
0.739	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD7222	Phase 2
0.7333	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD5658	Approved
0.7313	Intermediate Similarity	NPD7726	Phase 1
0.7306	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8465	Approved
0.7273	Intermediate Similarity	NPD8467	Approved
0.7273	Intermediate Similarity	NPD8466	Approved
0.7273	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD8358	Approved
0.7246	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1325	Approved
0.7241	Intermediate Similarity	NPD1326	Approved
0.7229	Intermediate Similarity	NPD6978	Phase 2
0.7229	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD5530	Phase 1
0.7225	Intermediate Similarity	NPD7194	Discontinued
0.7222	Intermediate Similarity	NPD7558	Phase 2
0.7215	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD8016	Phase 3
0.7196	Intermediate Similarity	NPD802	Phase 2
0.719	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD3814	Phase 1
0.7169	Intermediate Similarity	NPD6975	Discontinued
0.716	Intermediate Similarity	NPD8425	Approved
0.716	Intermediate Similarity	NPD8459	Approved
0.716	Intermediate Similarity	NPD8426	Approved
0.716	Intermediate Similarity	NPD8460	Approved
0.7157	Intermediate Similarity	NPD2882	Phase 1
0.715	Intermediate Similarity	NPD6159	Phase 2
0.7149	Intermediate Similarity	NPD3003	Approved
0.7143	Intermediate Similarity	NPD5936	Approved
0.7143	Intermediate Similarity	NPD5939	Approved
0.7137	Intermediate Similarity	NPD8428	Approved
0.7137	Intermediate Similarity	NPD8427	Approved
0.7137	Intermediate Similarity	NPD8429	Approved
0.7136	Intermediate Similarity	NPD4886	Phase 2
0.7136	Intermediate Similarity	NPD5065	Approved
0.7129	Intermediate Similarity	NPD7867	Phase 1
0.7117	Intermediate Similarity	NPD7452	Approved
0.7117	Intermediate Similarity	NPD7453	Approved
0.7111	Intermediate Similarity	NPD3330	Phase 1
0.7089	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6158	Phase 2
0.707	Intermediate Similarity	NPD3404	Approved
0.7032	Intermediate Similarity	NPD2176	Approved
0.7032	Intermediate Similarity	NPD2177	Approved
0.7032	Intermediate Similarity	NPD2175	Phase 3
0.7027	Intermediate Similarity	NPD4795	Phase 2
0.7019	Intermediate Similarity	NPD2381	Approved
0.7019	Intermediate Similarity	NPD2380	Approved
0.7019	Intermediate Similarity	NPD2382	Approved
0.7009	Intermediate Similarity	NPD7665	Phase 2
0.7009	Intermediate Similarity	NPD7666	Phase 3
0.6996	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6220	Phase 3
0.6983	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5902	Approved
0.6974	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5903	Approved
0.6972	Remote Similarity	NPD3127	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6492	Phase 2
0.6966	Remote Similarity	NPD7603	Discontinued
0.6964	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD2383	Phase 1
0.6958	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7181	Phase 3
0.6938	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3928	Approved
0.6937	Remote Similarity	NPD3931	Approved
0.692	Remote Similarity	NPD8403	Phase 1
0.6912	Remote Similarity	NPD1684	Approved
0.6912	Remote Similarity	NPD1685	Approved
0.6908	Remote Similarity	NPD8244	Phase 2
0.6895	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6969	Phase 2
0.6878	Remote Similarity	NPD7824	Approved
0.6878	Remote Similarity	NPD6968	Phase 2
0.6878	Remote Similarity	NPD1768	Approved
0.6872	Remote Similarity	NPD8386	Phase 2
0.687	Remote Similarity	NPD5612	Discontinued
0.687	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD8489	Phase 1
0.6862	Remote Similarity	NPD7950	Approved
0.6862	Remote Similarity	NPD7789	Approved
0.6862	Remote Similarity	NPD7953	Approved
0.6862	Remote Similarity	NPD7951	Approved
0.6862	Remote Similarity	NPD7791	Approved
0.6862	Remote Similarity	NPD7952	Approved
0.6862	Remote Similarity	NPD7790	Approved
0.6851	Remote Similarity	NPD4403	Phase 3
0.6851	Remote Similarity	NPD4401	Phase 2
0.685	Remote Similarity	NPD8284	Discontinued
0.6847	Remote Similarity	NPD1740	Approved
0.6847	Remote Similarity	NPD1739	Approved
0.6845	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4502	Phase 2
0.6825	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5930	Phase 3
0.6822	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7675	Phase 3
0.6822	Remote Similarity	NPD7674	Phase 3
0.682	Remote Similarity	NPD4885	Approved
0.6814	Remote Similarity	NPD6290	Phase 2
0.6813	Remote Similarity	NPD8091	Phase 3
0.6812	Remote Similarity	NPD3816	Phase 1
0.6812	Remote Similarity	NPD8093	Discontinued
0.6812	Remote Similarity	NPD3815	Phase 1
0.681	Remote Similarity	NPD6985	Discontinued
0.6808	Remote Similarity	NPD4203	Approved
0.6808	Remote Similarity	NPD4204	Approved
0.6806	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD8431	Approved
0.6802	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5138	Approved
0.6796	Remote Similarity	NPD5140	Approved
0.6793	Remote Similarity	NPD7730	Approved
0.6793	Remote Similarity	NPD7731	Approved
0.6793	Remote Similarity	NPD6327	Phase 1
0.6792	Remote Similarity	NPD6494	Phase 2
0.6791	Remote Similarity	NPD2762	Phase 2
0.6789	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5913	Phase 3
0.6786	Remote Similarity	NPD7955	Approved
0.6786	Remote Similarity	NPD7956	Approved
0.6784	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7672	Approved
0.6784	Remote Similarity	NPD7671	Approved
0.6781	Remote Similarity	NPD6455	Phase 3
0.678	Remote Similarity	NPD7271	Approved
0.678	Remote Similarity	NPD6246	Approved
0.6776	Remote Similarity	NPD7067	Approved
0.6776	Remote Similarity	NPD7068	Approved
0.6774	Remote Similarity	NPD3986	Discontinued
0.6773	Remote Similarity	NPD4998	Phase 3
0.6773	Remote Similarity	NPD4418	Discontinued
0.6773	Remote Similarity	NPD4999	Phase 3
0.6773	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD7423	Phase 2
0.6752	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7797	Approved
0.675	Remote Similarity	NPD7796	Approved
0.674	Remote Similarity	NPD1392	Approved
0.6727	Remote Similarity	NPD1038	Approved
0.6726	Remote Similarity	NPD4036	Approved
0.6726	Remote Similarity	NPD31	Approved
0.6726	Remote Similarity	NPD32	Approved
0.6726	Remote Similarity	NPD4122	Approved
0.6726	Remote Similarity	NPD4039	Approved
0.6726	Remote Similarity	NPD4038	Approved
0.6726	Remote Similarity	NPD4035	Approved
0.6726	Remote Similarity	NPD4033	Approved
0.6726	Remote Similarity	NPD4034	Approved
0.6726	Remote Similarity	NPD5426	Phase 3
0.6726	Remote Similarity	NPD4037	Approved
0.6723	Remote Similarity	NPD6326	Phase 2
0.6721	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6227	Discontinued
0.6711	Remote Similarity	NPD6376	Discontinued
0.671	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.671	Remote Similarity	NPD8094	Discontinued
0.6709	Remote Similarity	NPD3763	Approved
0.6709	Remote Similarity	NPD3402	Phase 1
0.67	Remote Similarity	NPD1683	Approved
0.6697	Remote Similarity	NPD3017	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4600	Approved
0.6696	Remote Similarity	NPD484	Approved
0.6696	Remote Similarity	NPD4601	Approved
0.6695	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6595	Phase 3
0.6682	Remote Similarity	NPD6452	Discontinued
0.6682	Remote Similarity	NPD6569	Phase 2

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