NPASS Compound

Structure

NPC7124 OpenBabel07101719252D 36 39 0 0 1 0 0 0 0 0999 V2000 -6.7688 -4.2017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 -2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0997 -4.9449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1216 -4.7370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 -1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 -2.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 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 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8126 -3.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 -1.2601 -1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 1 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 2.5981 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5254 -2.6270 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 2 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 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1945 -1.8838 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8344 -3.5780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 6 30 1 0 0 0 0 8 9 1 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 19 1 0 0 0 0 11 25 1 0 0 0 0 12 15 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 36 1 0 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 18 22 1 0 0 0 0 18 31 1 0 0 0 0 19 2 1 6 0 0 0 19 20 1 0 0 0 0 20 31 1 1 0 0 0 21 27 1 0 0 0 0 21 32 1 1 0 0 0 22 26 1 0 0 0 0 22 33 2 0 0 0 0 23 28 1 0 0 0 0 23 29 1 1 0 0 0 24 28 1 0 0 0 0 24 34 1 1 0 0 0 25 35 2 0 0 0 0 25 36 1 0 0 0 0 26 27 2 0 0 0 0 26 29 1 0 0 0 0 27 30 1 0 0 0 0 29 5 1 1 0 0 0 30 31 1 6 0 0 0 31 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.37
Volume:	546.548
LogP:	5.484
LogD:	5.342
LogS:	-5.098
# Rotatable Bonds:	8
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.334
Synthetic Accessibility Score:	4.723
Fsp3:	0.903
Lipinski Rule-of-5:	Rejected
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:	-5.089
MDCK Permeability:	2.4648656108183786e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.941
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.721
Plasma Protein Binding (PPB):	92.10321807861328%
Volume Distribution (VD):	0.595
Pgp-substrate:	3.1726901531219482%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.192
CYP2C19-inhibitor:	0.151
CYP2C19-substrate:	0.926
CYP2C9-inhibitor:	0.406
CYP2C9-substrate:	0.107
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.113
CYP3A4-inhibitor:	0.858
CYP3A4-substrate:	0.668

ADMET: Excretion

Clearance (CL):	14.601
Half-life (T1/2):	0.24

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.305
Drug-inuced Liver Injury (DILI):	0.202
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.888
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.129
Carcinogencity:	0.022
Eye Corrosion:	0.056
Eye Irritation:	0.021
Respiratory Toxicity:	0.895

Download Data

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

Natural Product: NPC7124

Natural Product ID:	NPC7124
*Common Name:**	N-Butyl Lucidenate N
IUPAC Name:	butyl (4R)-4-[(3S,5R,7S,10S,13R,14R,17R)-3,7-dihydroxy-4,4,10,13,14-pentamethyl-11-oxo-1,2,3,5,6,7,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]pentanoate
Synonyms:	N-Butyl Lucidenate N
Standard InCHIKey:	CYIDHGULAFNHLR-CGMRBEOHSA-N
Standard InCHI:	InChI=1S/C31H50O5/c1-8-9-16-36-25(35)11-10-19(2)20-12-15-30(6)27-21(32)17-23-28(3,4)24(34)13-14-29(23,5)26(27)22(33)18-31(20,30)7/h19-21,23-24,32,34H,8-18H2,1-7H3/t19-,20-,21+,23+,24+,29+,30+,31-/m1/s1
SMILES:	CCCCOC(=O)CC[C@H]([C@H]1CC[C@@]2([C@]1(C)CC(=O)C1=C2[C@@H](O)C[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1915765
PubChem CID:	57390352
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytochem.2005.10.025]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[11520245]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12045343]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695801]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791484]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	spore	n.a.	PMID[18827358]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	Nagano, Japan	2008-MAY	PMID[20039640]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384295]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[20702092]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[21924611]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22014750]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[22044278]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[22047696]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222905]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[9635497]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	11580.0	nM	PMID[481339]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	IC50	>	200000.0	nM	PMID[481339]

☑ 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 NPC7124 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	190
0.1-0.2	1262
0.2-0.3	4550
0.3-0.4	10449
0.4-0.5	11240
0.5-0.6	6253
0.6-0.7	6119
0.7-0.8	2277
0.8-0.85	247
0.85-0.9	95
0.9-0.95	13
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9674	High Similarity	NPC307954
0.9468	High Similarity	NPC281702
0.9462	High Similarity	NPC299971
0.9462	High Similarity	NPC144660
0.9457	High Similarity	NPC320306
0.9457	High Similarity	NPC122294
0.9355	High Similarity	NPC16021
0.9341	High Similarity	NPC184870
0.9255	High Similarity	NPC327431
0.9121	High Similarity	NPC233116
0.9082	High Similarity	NPC473037
0.9072	High Similarity	NPC28656
0.9062	High Similarity	NPC234892
0.9062	High Similarity	NPC293753
0.9043	High Similarity	NPC121339
0.9032	High Similarity	NPC297199
0.9011	High Similarity	NPC477149
0.9011	High Similarity	NPC477147
0.8969	High Similarity	NPC55872
0.8969	High Similarity	NPC251017
0.8936	High Similarity	NPC328371
0.8936	High Similarity	NPC3772
0.8901	High Similarity	NPC214387
0.89	High Similarity	NPC77947
0.89	High Similarity	NPC286174
0.8842	High Similarity	NPC18319
0.8842	High Similarity	NPC106557
0.883	High Similarity	NPC173875
0.883	High Similarity	NPC174948
0.883	High Similarity	NPC470016
0.883	High Similarity	NPC317586
0.883	High Similarity	NPC469995
0.883	High Similarity	NPC318282
0.883	High Similarity	NPC37646
0.8817	High Similarity	NPC470254
0.8812	High Similarity	NPC129689
0.8812	High Similarity	NPC272898
0.8812	High Similarity	NPC473036
0.8804	High Similarity	NPC469400
0.8788	High Similarity	NPC51452
0.8788	High Similarity	NPC323834
0.8763	High Similarity	NPC472924
0.8737	High Similarity	NPC472941
0.8737	High Similarity	NPC456
0.8737	High Similarity	NPC40765
0.8737	High Similarity	NPC243525
0.8725	High Similarity	NPC115303
0.8723	High Similarity	NPC166906
0.8723	High Similarity	NPC471720
0.8723	High Similarity	NPC469406
0.871	High Similarity	NPC63748
0.871	High Similarity	NPC107690
0.87	High Similarity	NPC472925
0.8696	High Similarity	NPC474889
0.8673	High Similarity	NPC308726
0.8673	High Similarity	NPC119601
0.8673	High Similarity	NPC56498
0.866	High Similarity	NPC205899
0.866	High Similarity	NPC476274
0.8646	High Similarity	NPC108078
0.8646	High Similarity	NPC253826
0.8632	High Similarity	NPC255809
0.8632	High Similarity	NPC271195
0.8617	High Similarity	NPC69454
0.8602	High Similarity	NPC111585
0.8602	High Similarity	NPC175628
0.8602	High Similarity	NPC20388
0.8602	High Similarity	NPC148414
0.8587	High Similarity	NPC242864
0.8571	High Similarity	NPC476240
0.8571	High Similarity	NPC163372
0.8571	High Similarity	NPC224720
0.8571	High Similarity	NPC72133
0.8571	High Similarity	NPC302537
0.8571	High Similarity	NPC55309
0.8571	High Similarity	NPC28252
0.8571	High Similarity	NPC476223
0.8558	High Similarity	NPC472926
0.8557	High Similarity	NPC478056
0.8557	High Similarity	NPC10364
0.8542	High Similarity	NPC305483
0.8542	High Similarity	NPC328162
0.8542	High Similarity	NPC249954
0.8542	High Similarity	NPC96859
0.8542	High Similarity	NPC95565
0.8526	High Similarity	NPC474922
0.8511	High Similarity	NPC473998
0.8511	High Similarity	NPC26888
0.8511	High Similarity	NPC73457
0.8511	High Similarity	NPC297265
0.8495	Intermediate Similarity	NPC473999
0.8495	Intermediate Similarity	NPC309603
0.8485	Intermediate Similarity	NPC22388
0.8485	Intermediate Similarity	NPC136289
0.8478	Intermediate Similarity	NPC159046
0.8478	Intermediate Similarity	NPC233836
0.8478	Intermediate Similarity	NPC187376
0.8469	Intermediate Similarity	NPC287833
0.8469	Intermediate Similarity	NPC266955
0.8469	Intermediate Similarity	NPC154072
0.8469	Intermediate Similarity	NPC88198
0.8469	Intermediate Similarity	NPC51370
0.8469	Intermediate Similarity	NPC251680
0.8454	Intermediate Similarity	NPC141401
0.8438	Intermediate Similarity	NPC200702
0.8438	Intermediate Similarity	NPC48330
0.8438	Intermediate Similarity	NPC279974
0.8438	Intermediate Similarity	NPC69548
0.8438	Intermediate Similarity	NPC184848
0.8438	Intermediate Similarity	NPC259286
0.8438	Intermediate Similarity	NPC473648
0.8421	Intermediate Similarity	NPC38232
0.8421	Intermediate Similarity	NPC214697
0.8421	Intermediate Similarity	NPC472930
0.8404	Intermediate Similarity	NPC48010
0.8404	Intermediate Similarity	NPC471896
0.8404	Intermediate Similarity	NPC289213
0.8404	Intermediate Similarity	NPC136801
0.84	Intermediate Similarity	NPC471208
0.84	Intermediate Similarity	NPC478057
0.84	Intermediate Similarity	NPC33973
0.84	Intermediate Similarity	NPC95899
0.84	Intermediate Similarity	NPC236390
0.84	Intermediate Similarity	NPC70967
0.8387	Intermediate Similarity	NPC131470
0.8387	Intermediate Similarity	NPC471722
0.8387	Intermediate Similarity	NPC143767
0.8384	Intermediate Similarity	NPC81530
0.8384	Intermediate Similarity	NPC115899
0.8384	Intermediate Similarity	NPC99411
0.8381	Intermediate Similarity	NPC962
0.8381	Intermediate Similarity	NPC250109
0.837	Intermediate Similarity	NPC322159
0.8367	Intermediate Similarity	NPC103051
0.8367	Intermediate Similarity	NPC197386
0.8367	Intermediate Similarity	NPC114274
0.8367	Intermediate Similarity	NPC166745
0.8367	Intermediate Similarity	NPC235464
0.8367	Intermediate Similarity	NPC48647
0.8367	Intermediate Similarity	NPC471717
0.8365	Intermediate Similarity	NPC472928
0.8351	Intermediate Similarity	NPC173272
0.8351	Intermediate Similarity	NPC120708
0.8351	Intermediate Similarity	NPC250757
0.8351	Intermediate Similarity	NPC301534
0.8333	Intermediate Similarity	NPC8993
0.8333	Intermediate Similarity	NPC196485
0.8333	Intermediate Similarity	NPC245972
0.8333	Intermediate Similarity	NPC279410
0.8333	Intermediate Similarity	NPC119562
0.8333	Intermediate Similarity	NPC111015
0.8318	Intermediate Similarity	NPC472927
0.8317	Intermediate Similarity	NPC2436
0.8317	Intermediate Similarity	NPC135854
0.8317	Intermediate Similarity	NPC216245
0.8317	Intermediate Similarity	NPC470251
0.8317	Intermediate Similarity	NPC96268
0.8316	Intermediate Similarity	NPC475806
0.8316	Intermediate Similarity	NPC23434
0.8316	Intermediate Similarity	NPC212948
0.83	Intermediate Similarity	NPC204450
0.83	Intermediate Similarity	NPC195290
0.83	Intermediate Similarity	NPC165250
0.8298	Intermediate Similarity	NPC475921
0.8298	Intermediate Similarity	NPC472240
0.8298	Intermediate Similarity	NPC275740
0.8298	Intermediate Similarity	NPC77168
0.8298	Intermediate Similarity	NPC84271
0.8298	Intermediate Similarity	NPC102414
0.8298	Intermediate Similarity	NPC474704
0.8298	Intermediate Similarity	NPC262858
0.8298	Intermediate Similarity	NPC86319
0.8283	Intermediate Similarity	NPC157787
0.8283	Intermediate Similarity	NPC201406
0.8283	Intermediate Similarity	NPC470074
0.8283	Intermediate Similarity	NPC471041
0.8283	Intermediate Similarity	NPC316964
0.828	Intermediate Similarity	NPC474684
0.828	Intermediate Similarity	NPC138756
0.828	Intermediate Similarity	NPC142361
0.8269	Intermediate Similarity	NPC197428
0.8265	Intermediate Similarity	NPC132753
0.8265	Intermediate Similarity	NPC43747
0.8265	Intermediate Similarity	NPC121402
0.8265	Intermediate Similarity	NPC475894
0.8265	Intermediate Similarity	NPC224356
0.8265	Intermediate Similarity	NPC151681
0.8265	Intermediate Similarity	NPC175351
0.8261	Intermediate Similarity	NPC474083
0.8261	Intermediate Similarity	NPC197823
0.8252	Intermediate Similarity	NPC472218
0.8252	Intermediate Similarity	NPC472219
0.8252	Intermediate Similarity	NPC472217
0.8252	Intermediate Similarity	NPC295244
0.8247	Intermediate Similarity	NPC476174
0.8229	Intermediate Similarity	NPC470224
0.8229	Intermediate Similarity	NPC141497
0.8229	Intermediate Similarity	NPC107674
0.8229	Intermediate Similarity	NPC206810
0.8229	Intermediate Similarity	NPC25750

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 NPC7124 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	1661
0.2-0.3	3883
0.3-0.4	2297
0.4-0.5	654
0.5-0.6	172
0.6-0.7	191
0.7-0.8	124
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8469	Intermediate Similarity	NPD7640	Approved
0.8469	Intermediate Similarity	NPD7639	Approved
0.8367	Intermediate Similarity	NPD7638	Approved
0.83	Intermediate Similarity	NPD7632	Discontinued
0.8105	Intermediate Similarity	NPD5328	Approved
0.8058	Intermediate Similarity	NPD6675	Approved
0.8058	Intermediate Similarity	NPD6402	Approved
0.8058	Intermediate Similarity	NPD5739	Approved
0.8058	Intermediate Similarity	NPD7128	Approved
0.8041	Intermediate Similarity	NPD6399	Phase 3
0.7979	Intermediate Similarity	NPD3618	Phase 1
0.7959	Intermediate Similarity	NPD7748	Approved
0.7938	Intermediate Similarity	NPD7515	Phase 2
0.7938	Intermediate Similarity	NPD6079	Approved
0.7905	Intermediate Similarity	NPD6899	Approved
0.7905	Intermediate Similarity	NPD6881	Approved
0.7905	Intermediate Similarity	NPD7320	Approved
0.79	Intermediate Similarity	NPD6083	Phase 2
0.79	Intermediate Similarity	NPD6084	Phase 2
0.7879	Intermediate Similarity	NPD5695	Phase 3
0.783	Intermediate Similarity	NPD6373	Approved
0.783	Intermediate Similarity	NPD6372	Approved
0.7818	Intermediate Similarity	NPD7115	Discovery
0.7812	Intermediate Similarity	NPD6672	Approved
0.7812	Intermediate Similarity	NPD5737	Approved
0.781	Intermediate Similarity	NPD5701	Approved
0.781	Intermediate Similarity	NPD5697	Approved
0.7789	Intermediate Similarity	NPD6409	Approved
0.7789	Intermediate Similarity	NPD6684	Approved
0.7789	Intermediate Similarity	NPD7334	Approved
0.7789	Intermediate Similarity	NPD7521	Approved
0.7789	Intermediate Similarity	NPD5330	Approved
0.7789	Intermediate Similarity	NPD7146	Approved
0.7766	Intermediate Similarity	NPD4786	Approved
0.7757	Intermediate Similarity	NPD7290	Approved
0.7757	Intermediate Similarity	NPD6883	Approved
0.7757	Intermediate Similarity	NPD7102	Approved
0.7736	Intermediate Similarity	NPD6011	Approved
0.7723	Intermediate Similarity	NPD7902	Approved
0.7692	Intermediate Similarity	NPD6115	Approved
0.7692	Intermediate Similarity	NPD6118	Approved
0.7692	Intermediate Similarity	NPD6114	Approved
0.7692	Intermediate Similarity	NPD6697	Approved
0.7685	Intermediate Similarity	NPD8130	Phase 1
0.7685	Intermediate Similarity	NPD6869	Approved
0.7685	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD6649	Approved
0.7685	Intermediate Similarity	NPD6847	Approved
0.7685	Intermediate Similarity	NPD6617	Approved
0.7685	Intermediate Similarity	NPD6650	Approved
0.7684	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD4202	Approved
0.7664	Intermediate Similarity	NPD6013	Approved
0.7664	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD6012	Approved
0.7664	Intermediate Similarity	NPD6014	Approved
0.7629	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD6903	Approved
0.7624	Intermediate Similarity	NPD5221	Approved
0.7624	Intermediate Similarity	NPD4697	Phase 3
0.7624	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD5222	Approved
0.7615	Intermediate Similarity	NPD6882	Approved
0.7615	Intermediate Similarity	NPD8297	Approved
0.7604	Intermediate Similarity	NPD5279	Phase 3
0.7596	Intermediate Similarity	NPD5211	Phase 2
0.7579	Intermediate Similarity	NPD3666	Approved
0.7579	Intermediate Similarity	NPD3133	Approved
0.7579	Intermediate Similarity	NPD3665	Phase 1
0.7576	Intermediate Similarity	NPD8034	Phase 2
0.7576	Intermediate Similarity	NPD8035	Phase 2
0.7553	Intermediate Similarity	NPD3667	Approved
0.7549	Intermediate Similarity	NPD5173	Approved
0.7549	Intermediate Similarity	NPD4755	Approved
0.7547	Intermediate Similarity	NPD6008	Approved
0.7545	Intermediate Similarity	NPD4632	Approved
0.7525	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD5696	Approved
0.7473	Intermediate Similarity	NPD6117	Approved
0.7453	Intermediate Similarity	NPD5141	Approved
0.7431	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7900	Approved
0.7426	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD6868	Approved
0.7404	Intermediate Similarity	NPD5286	Approved
0.7404	Intermediate Similarity	NPD4700	Approved
0.7404	Intermediate Similarity	NPD4696	Approved
0.7404	Intermediate Similarity	NPD5285	Approved
0.74	Intermediate Similarity	NPD6050	Approved
0.74	Intermediate Similarity	NPD5281	Approved
0.74	Intermediate Similarity	NPD5284	Approved
0.7391	Intermediate Similarity	NPD6116	Phase 1
0.7374	Intermediate Similarity	NPD6673	Approved
0.7374	Intermediate Similarity	NPD4753	Phase 2
0.7374	Intermediate Similarity	NPD6904	Approved
0.7374	Intermediate Similarity	NPD6080	Approved
0.7345	Intermediate Similarity	NPD6009	Approved
0.7339	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5223	Approved
0.7327	Intermediate Similarity	NPD5779	Approved
0.7327	Intermediate Similarity	NPD5778	Approved
0.732	Intermediate Similarity	NPD1694	Approved
0.7315	Intermediate Similarity	NPD6412	Phase 2
0.7312	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3617	Approved
0.7304	Intermediate Similarity	NPD6319	Approved
0.73	Intermediate Similarity	NPD5692	Phase 3
0.7281	Intermediate Similarity	NPD6335	Approved
0.7265	Intermediate Similarity	NPD7604	Phase 2
0.7264	Intermediate Similarity	NPD5224	Approved
0.7264	Intermediate Similarity	NPD5226	Approved
0.7264	Intermediate Similarity	NPD4633	Approved
0.7264	Intermediate Similarity	NPD5225	Approved
0.7257	Intermediate Similarity	NPD6274	Approved
0.7253	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5983	Phase 2
0.7228	Intermediate Similarity	NPD5693	Phase 1
0.7228	Intermediate Similarity	NPD5694	Approved
0.7228	Intermediate Similarity	NPD7637	Suspended
0.7217	Intermediate Similarity	NPD7100	Approved
0.7217	Intermediate Similarity	NPD7101	Approved
0.7203	Intermediate Similarity	NPD7492	Approved
0.7196	Intermediate Similarity	NPD5175	Approved
0.7196	Intermediate Similarity	NPD5174	Approved
0.7196	Intermediate Similarity	NPD4754	Approved
0.7193	Intermediate Similarity	NPD6317	Approved
0.7188	Intermediate Similarity	NPD4223	Phase 3
0.7188	Intermediate Similarity	NPD4221	Approved
0.7156	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD6059	Approved
0.7155	Intermediate Similarity	NPD6054	Approved
0.7143	Intermediate Similarity	NPD6616	Approved
0.7143	Intermediate Similarity	NPD4225	Approved
0.7143	Intermediate Similarity	NPD6336	Discontinued
0.7143	Intermediate Similarity	NPD6053	Discontinued
0.7143	Intermediate Similarity	NPD5329	Approved
0.7143	Intermediate Similarity	NPD7507	Approved
0.713	Intermediate Similarity	NPD6313	Approved
0.713	Intermediate Similarity	NPD6314	Approved
0.7129	Intermediate Similarity	NPD5207	Approved
0.7117	Intermediate Similarity	NPD4634	Approved
0.71	Intermediate Similarity	NPD5208	Approved
0.7094	Intermediate Similarity	NPD6909	Approved
0.7094	Intermediate Similarity	NPD6908	Approved
0.7091	Intermediate Similarity	NPD6686	Approved
0.7087	Intermediate Similarity	NPD6001	Approved
0.7083	Intermediate Similarity	NPD4139	Approved
0.7083	Intermediate Similarity	NPD7078	Approved
0.7083	Intermediate Similarity	NPD4692	Approved
0.7083	Intermediate Similarity	NPD8293	Discontinued
0.7075	Intermediate Similarity	NPD6404	Discontinued
0.7071	Intermediate Similarity	NPD5690	Phase 2
0.7071	Intermediate Similarity	NPD6098	Approved
0.7071	Intermediate Similarity	NPD5280	Approved
0.7071	Intermediate Similarity	NPD4694	Approved
0.7064	Intermediate Similarity	NPD4767	Approved
0.7064	Intermediate Similarity	NPD4768	Approved
0.7059	Intermediate Similarity	NPD6411	Approved
0.7041	Intermediate Similarity	NPD3668	Phase 3
0.7041	Intermediate Similarity	NPD4197	Approved
0.7034	Intermediate Similarity	NPD6370	Approved
0.7033	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7736	Approved
0.7019	Intermediate Similarity	NPD5210	Approved
0.7019	Intermediate Similarity	NPD5654	Approved
0.7019	Intermediate Similarity	NPD4629	Approved
0.701	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3573	Approved
0.6989	Remote Similarity	NPD3703	Phase 2
0.6979	Remote Similarity	NPD7525	Registered
0.6967	Remote Similarity	NPD7319	Approved
0.6961	Remote Similarity	NPD5785	Approved
0.6949	Remote Similarity	NPD6015	Approved
0.6949	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6016	Approved
0.6939	Remote Similarity	NPD5362	Discontinued
0.6939	Remote Similarity	NPD4788	Approved
0.6937	Remote Similarity	NPD4729	Approved
0.6937	Remote Similarity	NPD4730	Approved
0.6937	Remote Similarity	NPD5128	Approved
0.6937	Remote Similarity	NPD5168	Approved
0.69	Remote Similarity	NPD4689	Approved
0.69	Remote Similarity	NPD4519	Discontinued
0.69	Remote Similarity	NPD4693	Phase 3
0.69	Remote Similarity	NPD4688	Approved
0.69	Remote Similarity	NPD4138	Approved
0.69	Remote Similarity	NPD4623	Approved
0.69	Remote Similarity	NPD4690	Approved
0.69	Remote Similarity	NPD5205	Approved
0.6891	Remote Similarity	NPD5988	Approved
0.6887	Remote Similarity	NPD5959	Approved
0.6863	Remote Similarity	NPD6101	Approved
0.6863	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6051	Approved
0.6838	Remote Similarity	NPD7328	Approved
0.6838	Remote Similarity	NPD7327	Approved
0.6833	Remote Similarity	NPD6067	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