NPASS Compound

Structure

CID216245 OpenBabel06191716002D 41 44 0 0 1 0 0 0 0 0999 V2000 -0.8495 9.2107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8244 2.4425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1979 4.1011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3878 -2.9681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2651 -2.4614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5405 0.5252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3608 8.3648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 7.5187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3594 3.2889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8481 4.1348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2334 -0.4877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3869 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3604 6.6729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6929 0.9768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6943 -1.9552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 2.4428 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5003 3.1712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8473 1.4659 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8473 -1.4665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5411 -1.4661 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2336 -1.4656 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6926 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3599 4.9809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8470 -0.4887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6938 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6935 0.9777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8465 1.4664 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3875 -1.9547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5408 -0.4882 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0003 0.9773 0.0000 C 0 0 2 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 2.4569 2.9682 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0205 -1.9679 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1018 -1.9663 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4010 -0.7094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6170 4.9812 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5613 1.4791 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8485 5.8267 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8462 2.4443 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 3 19 1 0 0 0 0 4 30 1 0 0 0 0 5 30 1 0 0 0 0 7 32 1 0 0 0 0 9 10 1 0 0 0 0 10 15 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 23 1 0 0 0 0 14 31 1 0 0 0 0 15 40 1 0 0 0 0 16 20 1 0 0 0 0 16 24 1 0 0 0 0 17 21 1 0 0 0 0 17 22 1 0 0 0 0 18 2 1 6 0 0 0 18 20 1 0 0 0 0 19 34 2 0 0 0 0 19 41 1 0 0 0 0 20 32 1 6 0 0 0 21 26 1 0 0 0 0 21 35 2 0 0 0 0 22 30 1 0 0 0 0 22 31 1 6 0 0 0 23 30 1 0 0 0 0 23 36 1 6 0 0 0 24 33 1 0 0 0 0 24 37 2 0 0 0 0 25 38 2 0 0 0 0 25 40 1 0 0 0 0 26 27 2 0 0 0 0 26 33 1 0 0 0 0 27 28 1 0 0 0 0 27 31 1 0 0 0 0 28 29 1 0 0 0 0 28 39 2 0 0 0 0 29 32 1 6 0 0 0 29 41 1 0 0 0 0 31 6 1 6 0 0 0 32 33 1 6 0 0 0 33 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	572.33
Volume:	599.601
LogP:	4.339
LogD:	3.875
LogS:	-4.964
# Rotatable Bonds:	10
TPSA:	124.04
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.321
Synthetic Accessibility Score:	5.047
Fsp3:	0.788
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:	-4.945
MDCK Permeability:	2.3641154257347807e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.965
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.657
Plasma Protein Binding (PPB):	84.88097381591797%
Volume Distribution (VD):	0.397
Pgp-substrate:	13.42109489440918%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.194
CYP2C19-inhibitor:	0.486
CYP2C19-substrate:	0.816
CYP2C9-inhibitor:	0.796
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.037
CYP3A4-inhibitor:	0.876
CYP3A4-substrate:	0.749

ADMET: Excretion

Clearance (CL):	6.943
Half-life (T1/2):	0.421

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.256
Drug-inuced Liver Injury (DILI):	0.479
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.184
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.467
Carcinogencity:	0.056
Eye Corrosion:	0.004
Eye Irritation:	0.017
Respiratory Toxicity:	0.813

Download Data

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

Natural Product: NPC216245

Natural Product ID:	NPC216245
*Common Name:**	Butyl Lucidenate E2
IUPAC Name:	butyl (4R)-4-[(3S,5R,10S,12S,13R,14R,17R)-12-acetyloxy-3-hydroxy-4,4,10,13,14-pentamethyl-7,11,15-trioxo-1,2,3,5,6,12,16,17-octahydrocyclopenta[a]phenanthren-17-yl]pentanoate
Synonyms:	Butyl Lucidenate E2
Standard InCHIKey:	GEKHMMSACYDGPN-MMOMKNLBSA-N
Standard InCHI:	InChI=1S/C33H48O8/c1-9-10-15-40-25(38)12-11-18(2)20-16-24(37)33(8)26-21(35)17-22-30(4,5)23(36)13-14-31(22,6)27(26)28(39)29(32(20,33)7)41-19(3)34/h18,20,22-23,29,36H,9-17H2,1-8H3/t18-,20-,22+,23+,29-,31+,32+,33+/m1/s1
SMILES:	CCCCOC(=O)CC[C@H]([C@H]1CC(=O)[C@@]2([C@]1(C)[C@H](OC(=O)C)C(=O)C1=C2C(=O)C[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2337650
PubChem CID:	71561377
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]
NPO16609	Ganoderma sinense	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16609	Ganoderma sinense	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	6400.0	nM	PMID[540474]

☑ 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 NPC216245 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	229
0.1-0.2	1596
0.2-0.3	5904
0.3-0.4	12258
0.4-0.5	9287
0.5-0.6	7043
0.6-0.7	5099
0.7-0.8	1111
0.8-0.85	113
0.85-0.9	37
0.9-0.95	11
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC135854
1.0	High Similarity	NPC2436
1.0	High Similarity	NPC470251
0.9896	High Similarity	NPC70967
0.9896	High Similarity	NPC33973
0.9792	High Similarity	NPC53222
0.9688	High Similarity	NPC124211
0.9583	High Similarity	NPC88198
0.9583	High Similarity	NPC157787
0.9479	High Similarity	NPC112753
0.9479	High Similarity	NPC275439
0.9412	High Similarity	NPC115303
0.9375	High Similarity	NPC216904
0.9314	High Similarity	NPC129689
0.9216	High Similarity	NPC286174
0.9216	High Similarity	NPC77947
0.9167	High Similarity	NPC255809
0.9109	High Similarity	NPC51452
0.9048	High Similarity	NPC472929
0.898	High Similarity	NPC43747
0.8932	High Similarity	NPC295244
0.8911	High Similarity	NPC251017
0.8878	High Similarity	NPC95565
0.8878	High Similarity	NPC125622
0.8878	High Similarity	NPC96859
0.8878	High Similarity	NPC305483
0.8878	High Similarity	NPC328162
0.8812	High Similarity	NPC281702
0.8796	High Similarity	NPC472927
0.8788	High Similarity	NPC121339
0.8788	High Similarity	NPC106557
0.8776	High Similarity	NPC470016
0.8776	High Similarity	NPC317586
0.8776	High Similarity	NPC241156
0.8762	High Similarity	NPC272898
0.8762	High Similarity	NPC473036
0.8687	High Similarity	NPC243525
0.8687	High Similarity	NPC3772
0.8687	High Similarity	NPC40765
0.8673	High Similarity	NPC166906
0.8654	High Similarity	NPC473037
0.8636	High Similarity	NPC472933
0.8627	High Similarity	NPC56498
0.8624	High Similarity	NPC472934
0.8614	High Similarity	NPC299971
0.8614	High Similarity	NPC307954
0.8614	High Similarity	NPC144660
0.86	High Similarity	NPC23680
0.8586	High Similarity	NPC37646
0.8586	High Similarity	NPC477437
0.8586	High Similarity	NPC477438
0.8571	High Similarity	NPC25750
0.8519	High Similarity	NPC472926
0.8515	High Similarity	NPC16021
0.8505	High Similarity	NPC472928
0.8485	Intermediate Similarity	NPC477439
0.8485	Intermediate Similarity	NPC184870
0.8462	Intermediate Similarity	NPC28656
0.8447	Intermediate Similarity	NPC308726
0.8447	Intermediate Similarity	NPC119601
0.8431	Intermediate Similarity	NPC51370
0.8431	Intermediate Similarity	NPC205899
0.8431	Intermediate Similarity	NPC316964
0.8426	Intermediate Similarity	NPC264634
0.8426	Intermediate Similarity	NPC147180
0.8416	Intermediate Similarity	NPC122294
0.84	Intermediate Similarity	NPC473648
0.8384	Intermediate Similarity	NPC477436
0.8384	Intermediate Similarity	NPC470254
0.8384	Intermediate Similarity	NPC477435
0.8381	Intermediate Similarity	NPC475494
0.8367	Intermediate Similarity	NPC20388
0.8365	Intermediate Similarity	NPC55872
0.8364	Intermediate Similarity	NPC270958
0.835	Intermediate Similarity	NPC473514
0.835	Intermediate Similarity	NPC163372
0.835	Intermediate Similarity	NPC302537
0.8349	Intermediate Similarity	NPC202889
0.8333	Intermediate Similarity	NPC10364
0.8333	Intermediate Similarity	NPC43775
0.8317	Intermediate Similarity	NPC7124
0.8317	Intermediate Similarity	NPC328371
0.8283	Intermediate Similarity	NPC107690
0.8283	Intermediate Similarity	NPC297265
0.8283	Intermediate Similarity	NPC26888
0.8269	Intermediate Similarity	NPC473788
0.8269	Intermediate Similarity	NPC475558
0.8269	Intermediate Similarity	NPC234892
0.8265	Intermediate Similarity	NPC474889
0.8257	Intermediate Similarity	NPC71348
0.8252	Intermediate Similarity	NPC327431
0.8252	Intermediate Similarity	NPC287833
0.8241	Intermediate Similarity	NPC470496
0.8235	Intermediate Similarity	NPC226986
0.8235	Intermediate Similarity	NPC18319
0.8229	Intermediate Similarity	NPC473038
0.8218	Intermediate Similarity	NPC173875
0.8218	Intermediate Similarity	NPC297199
0.8218	Intermediate Similarity	NPC184848
0.8218	Intermediate Similarity	NPC318282
0.8218	Intermediate Similarity	NPC69548
0.8218	Intermediate Similarity	NPC174948
0.8218	Intermediate Similarity	NPC469995
0.8214	Intermediate Similarity	NPC118638
0.8208	Intermediate Similarity	NPC181357
0.819	Intermediate Similarity	NPC236390
0.819	Intermediate Similarity	NPC275583
0.8182	Intermediate Similarity	NPC148414
0.8182	Intermediate Similarity	NPC175628
0.8182	Intermediate Similarity	NPC111585
0.8165	Intermediate Similarity	NPC34315
0.8163	Intermediate Similarity	NPC242864
0.8163	Intermediate Similarity	NPC143767
0.8163	Intermediate Similarity	NPC131470
0.8148	Intermediate Similarity	NPC304495
0.8137	Intermediate Similarity	NPC120708
0.8137	Intermediate Similarity	NPC192428
0.8131	Intermediate Similarity	NPC220974
0.8131	Intermediate Similarity	NPC44063
0.8131	Intermediate Similarity	NPC475294
0.8131	Intermediate Similarity	NPC472925
0.8125	Intermediate Similarity	NPC471854
0.8125	Intermediate Similarity	NPC209882
0.8119	Intermediate Similarity	NPC159410
0.8113	Intermediate Similarity	NPC96268
0.81	Intermediate Similarity	NPC168027
0.81	Intermediate Similarity	NPC185936
0.8095	Intermediate Similarity	NPC136289
0.8095	Intermediate Similarity	NPC293753
0.8095	Intermediate Similarity	NPC195290
0.8095	Intermediate Similarity	NPC80781
0.8095	Intermediate Similarity	NPC204450
0.8091	Intermediate Similarity	NPC475524
0.8091	Intermediate Similarity	NPC100267
0.8091	Intermediate Similarity	NPC170487
0.8091	Intermediate Similarity	NPC285956
0.8091	Intermediate Similarity	NPC221144
0.8091	Intermediate Similarity	NPC280782
0.8081	Intermediate Similarity	NPC86319
0.8081	Intermediate Similarity	NPC473039
0.8081	Intermediate Similarity	NPC275740
0.8077	Intermediate Similarity	NPC472972
0.8077	Intermediate Similarity	NPC476274
0.8073	Intermediate Similarity	NPC197428
0.8058	Intermediate Similarity	NPC320306
0.8056	Intermediate Similarity	NPC94529
0.8053	Intermediate Similarity	NPC257457
0.8053	Intermediate Similarity	NPC311554
0.8039	Intermediate Similarity	NPC48330
0.8039	Intermediate Similarity	NPC200702
0.8039	Intermediate Similarity	NPC469599
0.8037	Intermediate Similarity	NPC181265
0.8037	Intermediate Similarity	NPC196528
0.8021	Intermediate Similarity	NPC469561
0.8021	Intermediate Similarity	NPC271784
0.802	Intermediate Similarity	NPC107674
0.802	Intermediate Similarity	NPC170220
0.802	Intermediate Similarity	NPC141497
0.8019	Intermediate Similarity	NPC159442
0.8019	Intermediate Similarity	NPC264048
0.8018	Intermediate Similarity	NPC52634
0.8	Intermediate Similarity	NPC183283
0.8	Intermediate Similarity	NPC471896
0.8	Intermediate Similarity	NPC81530
0.8	Intermediate Similarity	NPC231589
0.8	Intermediate Similarity	NPC224720
0.8	Intermediate Similarity	NPC476223
0.8	Intermediate Similarity	NPC476240
0.8	Intermediate Similarity	NPC469327
0.8	Intermediate Similarity	NPC214797
0.8	Intermediate Similarity	NPC118860
0.7982	Intermediate Similarity	NPC258543
0.7982	Intermediate Similarity	NPC241927
0.7982	Intermediate Similarity	NPC2766
0.7981	Intermediate Similarity	NPC114274
0.7981	Intermediate Similarity	NPC477813
0.798	Intermediate Similarity	NPC471722
0.7961	Intermediate Similarity	NPC42042
0.7961	Intermediate Similarity	NPC472941
0.7961	Intermediate Similarity	NPC456
0.7961	Intermediate Similarity	NPC173272
0.7959	Intermediate Similarity	NPC55309
0.7959	Intermediate Similarity	NPC72133
0.7959	Intermediate Similarity	NPC28252
0.7944	Intermediate Similarity	NPC137657
0.7944	Intermediate Similarity	NPC235889
0.7941	Intermediate Similarity	NPC245972
0.7941	Intermediate Similarity	NPC471720
0.7941	Intermediate Similarity	NPC196485
0.7925	Intermediate Similarity	NPC296879
0.7925	Intermediate Similarity	NPC471119
0.7925	Intermediate Similarity	NPC163249
0.7921	Intermediate Similarity	NPC63748
0.7921	Intermediate Similarity	NPC86266
0.7921	Intermediate Similarity	NPC23434
0.7921	Intermediate Similarity	NPC248913
0.7921	Intermediate Similarity	NPC110657
0.7921	Intermediate Similarity	NPC212301
0.7913	Intermediate Similarity	NPC109973
0.7909	Intermediate Similarity	NPC210005

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 NPC216245 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	2047
0.2-0.3	3971
0.3-0.4	1950
0.4-0.5	542
0.5-0.6	192
0.6-0.7	138
0.7-0.8	96
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD6372	Approved
0.8667	High Similarity	NPD6373	Approved
0.8505	High Similarity	NPD6649	Approved
0.8505	High Similarity	NPD6650	Approved
0.8381	Intermediate Similarity	NPD6675	Approved
0.8381	Intermediate Similarity	NPD7128	Approved
0.8381	Intermediate Similarity	NPD5739	Approved
0.8381	Intermediate Similarity	NPD6402	Approved
0.8257	Intermediate Similarity	NPD8297	Approved
0.8224	Intermediate Similarity	NPD6899	Approved
0.8224	Intermediate Similarity	NPD6881	Approved
0.8224	Intermediate Similarity	NPD7320	Approved
0.8165	Intermediate Similarity	NPD8130	Phase 1
0.8137	Intermediate Similarity	NPD4697	Phase 3
0.8131	Intermediate Similarity	NPD5701	Approved
0.8131	Intermediate Similarity	NPD5697	Approved
0.8091	Intermediate Similarity	NPD6882	Approved
0.8073	Intermediate Similarity	NPD7290	Approved
0.8073	Intermediate Similarity	NPD7102	Approved
0.8073	Intermediate Similarity	NPD6883	Approved
0.8056	Intermediate Similarity	NPD6011	Approved
0.802	Intermediate Similarity	NPD6399	Phase 3
0.8	Intermediate Similarity	NPD6869	Approved
0.8	Intermediate Similarity	NPD6617	Approved
0.8	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6847	Approved
0.7982	Intermediate Similarity	NPD6013	Approved
0.7982	Intermediate Similarity	NPD6014	Approved
0.7982	Intermediate Similarity	NPD6012	Approved
0.7981	Intermediate Similarity	NPD5696	Approved
0.79	Intermediate Similarity	NPD5328	Approved
0.7885	Intermediate Similarity	NPD6084	Phase 2
0.7885	Intermediate Similarity	NPD6083	Phase 2
0.7864	Intermediate Similarity	NPD5695	Phase 3
0.78	Intermediate Similarity	NPD6672	Approved
0.78	Intermediate Similarity	NPD5737	Approved
0.7788	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD5222	Approved
0.7788	Intermediate Similarity	NPD5221	Approved
0.7745	Intermediate Similarity	NPD6079	Approved
0.7719	Intermediate Similarity	NPD6868	Approved
0.7714	Intermediate Similarity	NPD4755	Approved
0.7714	Intermediate Similarity	NPD5173	Approved
0.7714	Intermediate Similarity	NPD7902	Approved
0.76	Intermediate Similarity	NPD3618	Phase 1
0.7596	Intermediate Similarity	NPD7748	Approved
0.7586	Intermediate Similarity	NPD6335	Approved
0.7573	Intermediate Similarity	NPD8034	Phase 2
0.7573	Intermediate Similarity	NPD8035	Phase 2
0.757	Intermediate Similarity	NPD5286	Approved
0.757	Intermediate Similarity	NPD4696	Approved
0.757	Intermediate Similarity	NPD4700	Approved
0.757	Intermediate Similarity	NPD5285	Approved
0.7565	Intermediate Similarity	NPD6274	Approved
0.7521	Intermediate Similarity	NPD7101	Approved
0.7521	Intermediate Similarity	NPD7100	Approved
0.75	Intermediate Similarity	NPD5223	Approved
0.75	Intermediate Similarity	NPD6317	Approved
0.7458	Intermediate Similarity	NPD6319	Approved
0.7436	Intermediate Similarity	NPD6314	Approved
0.7436	Intermediate Similarity	NPD6313	Approved
0.7431	Intermediate Similarity	NPD5224	Approved
0.7431	Intermediate Similarity	NPD5226	Approved
0.7431	Intermediate Similarity	NPD5211	Phase 2
0.7431	Intermediate Similarity	NPD4633	Approved
0.7431	Intermediate Similarity	NPD5225	Approved
0.7429	Intermediate Similarity	NPD7900	Approved
0.7429	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD5279	Phase 3
0.7404	Intermediate Similarity	NPD7515	Phase 2
0.7404	Intermediate Similarity	NPD6050	Approved
0.74	Intermediate Similarity	NPD4786	Approved
0.7395	Intermediate Similarity	NPD6909	Approved
0.7395	Intermediate Similarity	NPD6908	Approved
0.7391	Intermediate Similarity	NPD4632	Approved
0.7387	Intermediate Similarity	NPD4767	Approved
0.7387	Intermediate Similarity	NPD6008	Approved
0.7387	Intermediate Similarity	NPD4768	Approved
0.7379	Intermediate Similarity	NPD6673	Approved
0.7379	Intermediate Similarity	NPD6904	Approved
0.7379	Intermediate Similarity	NPD6080	Approved
0.7364	Intermediate Similarity	NPD5175	Approved
0.7364	Intermediate Similarity	NPD4754	Approved
0.7364	Intermediate Similarity	NPD5174	Approved
0.7358	Intermediate Similarity	NPD4629	Approved
0.7358	Intermediate Similarity	NPD5210	Approved
0.735	Intermediate Similarity	NPD6009	Approved
0.7308	Intermediate Similarity	NPD5692	Phase 3
0.7297	Intermediate Similarity	NPD5141	Approved
0.7273	Intermediate Similarity	NPD7604	Phase 2
0.7257	Intermediate Similarity	NPD4730	Approved
0.7257	Intermediate Similarity	NPD4729	Approved
0.7255	Intermediate Similarity	NPD7334	Approved
0.7255	Intermediate Similarity	NPD6409	Approved
0.7255	Intermediate Similarity	NPD5330	Approved
0.7255	Intermediate Similarity	NPD6684	Approved
0.7255	Intermediate Similarity	NPD7146	Approved
0.7255	Intermediate Similarity	NPD7521	Approved
0.725	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5983	Phase 2
0.7238	Intermediate Similarity	NPD5694	Approved
0.7236	Intermediate Similarity	NPD8293	Discontinued
0.7213	Intermediate Similarity	NPD7492	Approved
0.7212	Intermediate Similarity	NPD4753	Phase 2
0.7203	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD7115	Discovery
0.72	Intermediate Similarity	NPD3667	Approved
0.7196	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD7736	Approved
0.717	Intermediate Similarity	NPD4202	Approved
0.7167	Intermediate Similarity	NPD6054	Approved
0.7167	Intermediate Similarity	NPD6059	Approved
0.7157	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7638	Approved
0.7154	Intermediate Similarity	NPD6336	Discontinued
0.7154	Intermediate Similarity	NPD6616	Approved
0.7143	Intermediate Similarity	NPD3617	Approved
0.7131	Intermediate Similarity	NPD8328	Phase 3
0.713	Intermediate Similarity	NPD5249	Phase 3
0.713	Intermediate Similarity	NPD5251	Approved
0.713	Intermediate Similarity	NPD5250	Approved
0.713	Intermediate Similarity	NPD5247	Approved
0.713	Intermediate Similarity	NPD5248	Approved
0.7115	Intermediate Similarity	NPD6903	Approved
0.7115	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5128	Approved
0.7105	Intermediate Similarity	NPD5168	Approved
0.7097	Intermediate Similarity	NPD7078	Approved
0.7091	Intermediate Similarity	NPD7640	Approved
0.7091	Intermediate Similarity	NPD7639	Approved
0.7087	Intermediate Similarity	NPD6098	Approved
0.7075	Intermediate Similarity	NPD5693	Phase 1
0.7075	Intermediate Similarity	NPD6411	Approved
0.7075	Intermediate Similarity	NPD5281	Approved
0.7075	Intermediate Similarity	NPD5284	Approved
0.7059	Intermediate Similarity	NPD3666	Approved
0.7059	Intermediate Similarity	NPD3133	Approved
0.7059	Intermediate Similarity	NPD3665	Phase 1
0.7049	Intermediate Similarity	NPD6370	Approved
0.7048	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5654	Approved
0.699	Remote Similarity	NPD5329	Approved
0.6983	Remote Similarity	NPD5169	Approved
0.6983	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4634	Approved
0.6983	Remote Similarity	NPD5135	Approved
0.6967	Remote Similarity	NPD6016	Approved
0.6967	Remote Similarity	NPD6015	Approved
0.6964	Remote Similarity	NPD7632	Discontinued
0.6939	Remote Similarity	NPD6117	Approved
0.6923	Remote Similarity	NPD4694	Approved
0.6923	Remote Similarity	NPD5690	Phase 2
0.6923	Remote Similarity	NPD5127	Approved
0.6923	Remote Similarity	NPD5215	Approved
0.6923	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5217	Approved
0.6923	Remote Similarity	NPD5280	Approved
0.6923	Remote Similarity	NPD5216	Approved
0.6911	Remote Similarity	NPD5988	Approved
0.6909	Remote Similarity	NPD5959	Approved
0.6893	Remote Similarity	NPD4197	Approved
0.6887	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6101	Approved
0.6875	Remote Similarity	NPD7260	Phase 2
0.687	Remote Similarity	NPD6614	Approved
0.6869	Remote Similarity	NPD6116	Phase 1
0.6857	Remote Similarity	NPD3573	Approved
0.6838	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6845	Suspended
0.6822	Remote Similarity	NPD5207	Approved
0.68	Remote Similarity	NPD6114	Approved
0.68	Remote Similarity	NPD6115	Approved
0.68	Remote Similarity	NPD6118	Approved
0.68	Remote Similarity	NPD6697	Approved
0.6789	Remote Similarity	NPD6001	Approved
0.6772	Remote Similarity	NPD6033	Approved
0.675	Remote Similarity	NPD5167	Approved
0.6735	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD3668	Phase 3
0.6699	Remote Similarity	NPD4223	Phase 3
0.6699	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD7614	Phase 1
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD7732	Phase 3
0.6636	Remote Similarity	NPD5208	Approved
0.6614	Remote Similarity	NPD7507	Approved
0.661	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD4139	Approved
0.6602	Remote Similarity	NPD4692	Approved
0.6583	Remote Similarity	NPD6053	Discontinued
0.6581	Remote Similarity	NPD6412	Phase 2
0.6581	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD4225	Approved
0.6545	Remote Similarity	NPD5133	Approved
0.6545	Remote Similarity	NPD5779	Approved
0.6545	Remote Similarity	NPD5778	Approved
0.6531	Remote Similarity	NPD4809	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