NPASS Compound

Structure

CID64081 OpenBabel06191715402D 34 38 0 0 1 0 0 0 0 0999 V2000 4.1451 1.4080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1452 2.3927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8703 2.6375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5769 1.7345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7932 2.3934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8231 -1.4946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8530 -0.4925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1331 -0.2031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6451 -0.9498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4693 0.4753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4687 3.3256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3073 2.0022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6459 2.8508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8225 -1.4247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6462 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8326 1.1800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 1.9006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6457 -0.0003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8226 1.4254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4693 1.4257 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8231 1.4257 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2918 2.8504 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2360 1.8048 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8226 0.4749 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2921 1.9004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9416 2.4401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6462 1.9009 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8231 0.4752 0.0000 C 0 0 1 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 -2.4679 0.4744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6661 1.9124 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1353 3.3375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7442 3.3688 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3353 0.8606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 22 1 0 0 0 0 12 16 1 0 0 0 0 12 23 1 0 0 0 0 13 27 1 0 0 0 0 14 29 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 19 1 0 0 0 0 17 21 1 0 0 0 0 18 9 1 6 0 0 0 18 24 1 0 0 0 0 18 30 1 0 0 0 0 19 24 1 0 0 0 0 19 31 1 6 0 0 0 20 25 1 0 0 0 0 20 27 1 6 0 0 0 21 27 1 6 0 0 0 21 28 1 0 0 0 0 22 25 1 0 0 0 0 22 32 1 6 0 0 0 23 26 1 6 0 0 0 23 34 1 0 0 0 0 24 29 1 1 0 0 0 26 33 1 0 0 0 0 27 5 1 6 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 30 8 1 6 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.39
Volume:	519.815
LogP:	5.066
LogD:	4.745
LogS:	-4.429
# Rotatable Bonds:	2
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.477
Synthetic Accessibility Score:	4.959
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.816
MDCK Permeability:	3.5337856388650835e-05
Pgp-inhibitor:	0.969
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.392

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.07
Plasma Protein Binding (PPB):	91.29235076904297%
Volume Distribution (VD):	0.993
Pgp-substrate:	4.808503150939941%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.197
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.108
CYP2C9-substrate:	0.115
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.485
CYP3A4-inhibitor:	0.187
CYP3A4-substrate:	0.29

ADMET: Excretion

Clearance (CL):	3.727
Half-life (T1/2):	0.196

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.262
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.321
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.853
Carcinogencity:	0.011
Eye Corrosion:	0.783
Eye Irritation:	0.128
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC64081

Natural Product ID:	NPC64081
*Common Name:**	(20S,24S)-Epoxydammarane-3,12,25-Triol
IUPAC Name:	(3S,5R,8R,9R,10R,12R,13R,14R,17S)-17-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol
Synonyms:
Standard InCHIKey:	DOAJFZJEGHSYOI-BVGXOPESSA-N
Standard InCHI:	InChI=1S/C30H52O4/c1-25(2)20-10-15-28(6)21(27(20,5)13-11-22(25)32)17-19(31)24-18(9-14-29(24,28)7)30(8)16-12-23(34-30)26(3,4)33/h18-24,31-33H,9-17H2,1-8H3/t18-,19+,20-,21+,22-,23-,24-,27-,28+,29+,30-/m0/s1
SMILES:	CC1(C)[C@@H]2CC[C@]3(C)[C@H](C[C@H]([C@@H]4[C@H](CC[C@@]34C)[C@]3(C)CC[C@@H](C(C)(C)O)O3)O)[C@@]2(C)CC[C@@H]1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL466363
PubChem CID:	12314836
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO22221	Ibicella lutea	Species	Martyniaceae	Eukaryota	n.a.	El Volcan, Dpto. La Capital, Province of San Luis, Argentina	2001-MAR	PMID[14695802]
NPO23888	Chrysothamnus viscidiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22221	Ibicella lutea	Species	Martyniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15834	Bonellia viridis	Species	Bonelliidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22484	Aplidium cyaneum	Species	Polyclinidae	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	4
MIC	6
Others	15

Activity Type	# Activity
Cell Line	3
Individual Protein	1
NON-MOLECULAR	1
Organism	10
Others	9
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5.0	ug.mL-1	PMID[487897]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	154.26	ug.mL-1	PMID[487898]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	47.64	ug.mL-1	PMID[487898]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5.0	ug.mL-1	PMID[487897]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	MIC	>	128.0	ug.mL-1	PMID[487898]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	128.0	ug.mL-1	PMID[487898]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[487898]
NPT2	Others	Unspecified		Selectivity Index	=	6.0	n.a.	PMID[487898]
NPT2	Others	Unspecified		Selectivity Index	=	19.3	n.a.	PMID[487898]
NPT2709	Organism	Bacillus subtilis subsp. subtilis str. 168	Bacillus subtilis subsp. subtilis str. 168	FICI	=	1.25	n.a.	PMID[487898]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	FICI	=	1.5	n.a.	PMID[487898]
NPT2709	Organism	Bacillus subtilis subsp. subtilis str. 168	Bacillus subtilis subsp. subtilis str. 168	FICI	=	1.03	n.a.	PMID[487898]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	FICI	=	0.14	n.a.	PMID[487898]
NPT2709	Organism	Bacillus subtilis subsp. subtilis str. 168	Bacillus subtilis subsp. subtilis str. 168	MIC	=	8.0	ug.mL-1	PMID[487898]
NPT1101	Organism	Staphylococcus aureus subsp. aureus RN4220	Staphylococcus aureus subsp. aureus RN4220	MIC	=	8.0	ug.mL-1	PMID[487898]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8.0	ug.mL-1	PMID[487898]
NPT626	Tissue	Liver microsome	Homo sapiens	Retention_time	=	19.2	min	PMID[487899]
NPT35	Others	n.a.		Retention_time	=	19.2	min	PMID[487899]
NPT2	Others	Unspecified		Survival	=	111.0	%	PMID[487900]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Survival	=	104.0	%	PMID[487900]
NPT2	Others	Unspecified		Activity	=	81.0	%	PMID[487902]
NPT2	Others	Unspecified		Activity	=	72.0	%	PMID[487902]
NPT2	Others	Unspecified		Activity	=	74.0	%	PMID[487902]

☑ 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 NPC64081 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	417
0.1-0.2	4007
0.2-0.3	13978
0.3-0.4	10731
0.4-0.5	5381
0.5-0.6	4650
0.6-0.7	2614
0.7-0.8	744
0.8-0.85	109
0.85-0.9	46
0.9-0.95	11
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474574
0.9726	High Similarity	NPC81074
0.9726	High Similarity	NPC477282
0.9722	High Similarity	NPC133596
0.9722	High Similarity	NPC11907
0.9718	High Similarity	NPC270306
0.9718	High Similarity	NPC91387
0.9718	High Similarity	NPC231680
0.9342	High Similarity	NPC475388
0.9221	High Similarity	NPC111582
0.9221	High Similarity	NPC470070
0.9221	High Similarity	NPC477285
0.9091	High Similarity	NPC286719
0.9091	High Similarity	NPC477286
0.9028	High Similarity	NPC470071
0.9028	High Similarity	NPC187471
0.9028	High Similarity	NPC1340
0.9028	High Similarity	NPC131506
0.9028	High Similarity	NPC157777
0.9028	High Similarity	NPC252182
0.9014	High Similarity	NPC66407
0.8961	High Similarity	NPC190940
0.8919	High Similarity	NPC196136
0.8919	High Similarity	NPC317242
0.8919	High Similarity	NPC243027
0.8919	High Similarity	NPC158208
0.8904	High Similarity	NPC153719
0.8904	High Similarity	NPC470610
0.8875	High Similarity	NPC155531
0.8875	High Similarity	NPC215968
0.8861	High Similarity	NPC320824
0.8846	High Similarity	NPC470611
0.8831	High Similarity	NPC16449
0.88	High Similarity	NPC163597
0.8784	High Similarity	NPC48795
0.8784	High Similarity	NPC192501
0.8784	High Similarity	NPC10476
0.8784	High Similarity	NPC228994
0.8767	High Similarity	NPC127094
0.8767	High Similarity	NPC100586
0.8767	High Similarity	NPC157422
0.8767	High Similarity	NPC109457
0.8765	High Similarity	NPC210658
0.8765	High Similarity	NPC161928
0.875	High Similarity	NPC107919
0.8684	High Similarity	NPC477227
0.8684	High Similarity	NPC105208
0.8684	High Similarity	NPC185915
0.8684	High Similarity	NPC128951
0.8684	High Similarity	NPC192046
0.8684	High Similarity	NPC302578
0.8667	High Similarity	NPC472950
0.8667	High Similarity	NPC472952
0.8659	High Similarity	NPC128475
0.8649	High Similarity	NPC473238
0.8649	High Similarity	NPC472341
0.8642	High Similarity	NPC80700
0.8642	High Similarity	NPC477283
0.863	High Similarity	NPC192192
0.863	High Similarity	NPC251201
0.863	High Similarity	NPC232925
0.863	High Similarity	NPC63588
0.863	High Similarity	NPC282454
0.8608	High Similarity	NPC202688
0.8608	High Similarity	NPC154043
0.8608	High Similarity	NPC60018
0.8571	High Similarity	NPC67657
0.8571	High Similarity	NPC18857
0.8571	High Similarity	NPC147993
0.8554	High Similarity	NPC82955
0.8553	High Similarity	NPC470145
0.8533	High Similarity	NPC304499
0.8519	High Similarity	NPC273290
0.8519	High Similarity	NPC232044
0.8519	High Similarity	NPC290612
0.8514	High Similarity	NPC8004
0.8514	High Similarity	NPC127283
0.8493	Intermediate Similarity	NPC254037
0.8493	Intermediate Similarity	NPC470833
0.8493	Intermediate Similarity	NPC470830
0.8493	Intermediate Similarity	NPC241085
0.8493	Intermediate Similarity	NPC477820
0.8493	Intermediate Similarity	NPC129829
0.8493	Intermediate Similarity	NPC299948
0.8462	Intermediate Similarity	NPC477287
0.8462	Intermediate Similarity	NPC287452
0.8442	Intermediate Similarity	NPC476233
0.8434	Intermediate Similarity	NPC473436
0.8434	Intermediate Similarity	NPC56777
0.8434	Intermediate Similarity	NPC201607
0.8415	Intermediate Similarity	NPC103782
0.8415	Intermediate Similarity	NPC114378
0.8395	Intermediate Similarity	NPC227260
0.8378	Intermediate Similarity	NPC231945
0.8375	Intermediate Similarity	NPC296734
0.8356	Intermediate Similarity	NPC472741
0.8353	Intermediate Similarity	NPC229801
0.8353	Intermediate Similarity	NPC210759
0.8353	Intermediate Similarity	NPC473066
0.8353	Intermediate Similarity	NPC307167
0.8333	Intermediate Similarity	NPC471769
0.8333	Intermediate Similarity	NPC20822
0.8333	Intermediate Similarity	NPC228059
0.8333	Intermediate Similarity	NPC471045
0.8313	Intermediate Similarity	NPC140446
0.8313	Intermediate Similarity	NPC43912
0.8312	Intermediate Similarity	NPC477602
0.8312	Intermediate Similarity	NPC477601
0.8312	Intermediate Similarity	NPC473916
0.8293	Intermediate Similarity	NPC266651
0.8289	Intermediate Similarity	NPC470151
0.8272	Intermediate Similarity	NPC268578
0.8272	Intermediate Similarity	NPC217559
0.8272	Intermediate Similarity	NPC292458
0.8267	Intermediate Similarity	NPC473279
0.8267	Intermediate Similarity	NPC195530
0.8256	Intermediate Similarity	NPC311246
0.8256	Intermediate Similarity	NPC182740
0.8256	Intermediate Similarity	NPC256104
0.8256	Intermediate Similarity	NPC211845
0.8256	Intermediate Similarity	NPC122083
0.8256	Intermediate Similarity	NPC167644
0.825	Intermediate Similarity	NPC73515
0.8235	Intermediate Similarity	NPC473542
0.8228	Intermediate Similarity	NPC476176
0.8228	Intermediate Similarity	NPC245029
0.8228	Intermediate Similarity	NPC31302
0.8228	Intermediate Similarity	NPC220379
0.8228	Intermediate Similarity	NPC269333
0.8219	Intermediate Similarity	NPC48079
0.8219	Intermediate Similarity	NPC63190
0.8205	Intermediate Similarity	NPC212453
0.8205	Intermediate Similarity	NPC171658
0.8194	Intermediate Similarity	NPC472946
0.8193	Intermediate Similarity	NPC471240
0.8169	Intermediate Similarity	NPC114891
0.8161	Intermediate Similarity	NPC45959
0.8161	Intermediate Similarity	NPC113500
0.8161	Intermediate Similarity	NPC3538
0.8161	Intermediate Similarity	NPC30687
0.8161	Intermediate Similarity	NPC175
0.8161	Intermediate Similarity	NPC477224
0.8161	Intermediate Similarity	NPC252253
0.8161	Intermediate Similarity	NPC305418
0.8148	Intermediate Similarity	NPC477284
0.814	Intermediate Similarity	NPC5632
0.814	Intermediate Similarity	NPC59006
0.814	Intermediate Similarity	NPC149966
0.8125	Intermediate Similarity	NPC472943
0.8125	Intermediate Similarity	NPC7479
0.8125	Intermediate Similarity	NPC257296
0.8125	Intermediate Similarity	NPC472951
0.8125	Intermediate Similarity	NPC248944
0.8118	Intermediate Similarity	NPC131466
0.8095	Intermediate Similarity	NPC202937
0.8082	Intermediate Similarity	NPC44122
0.8082	Intermediate Similarity	NPC142712
0.8068	Intermediate Similarity	NPC473065
0.8068	Intermediate Similarity	NPC473067
0.8068	Intermediate Similarity	NPC473064
0.8052	Intermediate Similarity	NPC475458
0.8052	Intermediate Similarity	NPC477508
0.8052	Intermediate Similarity	NPC472945
0.8052	Intermediate Similarity	NPC472944
0.8049	Intermediate Similarity	NPC85095
0.8049	Intermediate Similarity	NPC216420
0.8049	Intermediate Similarity	NPC478054
0.8049	Intermediate Similarity	NPC211135
0.8046	Intermediate Similarity	NPC88962
0.8046	Intermediate Similarity	NPC144790
0.8046	Intermediate Similarity	NPC149400
0.8028	Intermediate Similarity	NPC148174
0.8028	Intermediate Similarity	NPC218585
0.8028	Intermediate Similarity	NPC71460
0.8026	Intermediate Similarity	NPC478103
0.8023	Intermediate Similarity	NPC279329
0.8	Intermediate Similarity	NPC99264
0.8	Intermediate Similarity	NPC281004
0.7978	Intermediate Similarity	NPC116683
0.7978	Intermediate Similarity	NPC476510
0.7978	Intermediate Similarity	NPC304011
0.7978	Intermediate Similarity	NPC156377
0.7978	Intermediate Similarity	NPC238796
0.7978	Intermediate Similarity	NPC142264
0.7978	Intermediate Similarity	NPC237071
0.7978	Intermediate Similarity	NPC203434
0.7978	Intermediate Similarity	NPC139271
0.7976	Intermediate Similarity	NPC474448
0.7973	Intermediate Similarity	NPC475884
0.7973	Intermediate Similarity	NPC473230
0.7955	Intermediate Similarity	NPC475436
0.7955	Intermediate Similarity	NPC312678
0.7955	Intermediate Similarity	NPC473851
0.7955	Intermediate Similarity	NPC253268
0.7955	Intermediate Similarity	NPC473774
0.7955	Intermediate Similarity	NPC174024
0.7955	Intermediate Similarity	NPC179859
0.7955	Intermediate Similarity	NPC291547
0.7955	Intermediate Similarity	NPC131693
0.7955	Intermediate Similarity	NPC24960

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 NPC64081 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	409
0.1-0.2	4132
0.2-0.3	3230
0.3-0.4	775
0.4-0.5	282
0.5-0.6	234
0.6-0.7	69
0.7-0.8	17
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD4267	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6928	Phase 2
0.7841	Intermediate Similarity	NPD8171	Discontinued
0.7662	Intermediate Similarity	NPD4787	Phase 1
0.7654	Intermediate Similarity	NPD6118	Approved
0.7654	Intermediate Similarity	NPD6114	Approved
0.7654	Intermediate Similarity	NPD6115	Approved
0.7654	Intermediate Similarity	NPD6697	Approved
0.7531	Intermediate Similarity	NPD6116	Phase 1
0.747	Intermediate Similarity	NPD7525	Registered
0.7407	Intermediate Similarity	NPD6117	Approved
0.7342	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD371	Approved
0.7284	Intermediate Similarity	NPD3703	Phase 2
0.716	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD5360	Phase 3
0.6915	Remote Similarity	NPD7991	Discontinued
0.679	Remote Similarity	NPD4245	Approved
0.679	Remote Similarity	NPD4244	Approved
0.679	Remote Similarity	NPD4789	Approved
0.6747	Remote Similarity	NPD1811	Approved
0.6747	Remote Similarity	NPD1810	Approved
0.6703	Remote Similarity	NPD7524	Approved
0.6667	Remote Similarity	NPD3698	Phase 2
0.6667	Remote Similarity	NPD6700	Approved
0.6667	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6703	Approved
0.6596	Remote Similarity	NPD8035	Phase 2
0.6596	Remote Similarity	NPD6702	Approved
0.6596	Remote Similarity	NPD8034	Phase 2
0.6582	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD4758	Discontinued
0.6484	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3702	Approved
0.6471	Remote Similarity	NPD7339	Approved
0.6471	Remote Similarity	NPD6942	Approved
0.6444	Remote Similarity	NPD6695	Phase 3
0.6437	Remote Similarity	NPD3671	Phase 1
0.6437	Remote Similarity	NPD5364	Discontinued
0.6422	Remote Similarity	NPD7327	Approved
0.6422	Remote Similarity	NPD7328	Approved
0.6413	Remote Similarity	NPD8308	Discontinued
0.6395	Remote Similarity	NPD6933	Approved
0.6386	Remote Similarity	NPD2686	Approved
0.6386	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD2687	Approved
0.6386	Remote Similarity	NPD2254	Approved
0.6364	Remote Similarity	NPD7516	Approved
0.6364	Remote Similarity	NPD7645	Phase 2
0.6364	Remote Similarity	NPD7638	Approved
0.6341	Remote Similarity	NPD6705	Phase 1
0.631	Remote Similarity	NPD5777	Approved
0.631	Remote Similarity	NPD6081	Approved
0.6306	Remote Similarity	NPD8294	Approved
0.6306	Remote Similarity	NPD8377	Approved
0.63	Remote Similarity	NPD7640	Approved
0.63	Remote Similarity	NPD7639	Approved
0.6292	Remote Similarity	NPD4748	Discontinued
0.625	Remote Similarity	NPD8033	Approved
0.625	Remote Similarity	NPD8296	Approved
0.625	Remote Similarity	NPD8380	Approved
0.625	Remote Similarity	NPD8378	Approved
0.625	Remote Similarity	NPD8379	Approved
0.625	Remote Similarity	NPD8335	Approved
0.6238	Remote Similarity	NPD1700	Approved
0.6207	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD8133	Approved
0.6176	Remote Similarity	NPD7632	Discontinued
0.617	Remote Similarity	NPD7750	Discontinued
0.617	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD6926	Approved
0.6163	Remote Similarity	NPD6924	Approved
0.6161	Remote Similarity	NPD6054	Approved
0.6161	Remote Similarity	NPD6059	Approved
0.6139	Remote Similarity	NPD8418	Phase 2
0.6111	Remote Similarity	NPD6931	Approved
0.6111	Remote Similarity	NPD6930	Phase 2
0.6098	Remote Similarity	NPD4224	Phase 2
0.6091	Remote Similarity	NPD6940	Discontinued
0.6087	Remote Similarity	NPD4788	Approved
0.6087	Remote Similarity	NPD3669	Approved
0.6087	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD4159	Approved
0.6056	Remote Similarity	NPD384	Approved
0.6056	Remote Similarity	NPD385	Approved
0.6055	Remote Similarity	NPD4632	Approved
0.6053	Remote Similarity	NPD6370	Approved
0.6042	Remote Similarity	NPD5328	Approved
0.6038	Remote Similarity	NPD7320	Approved
0.6038	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD8174	Phase 2
0.6034	Remote Similarity	NPD7507	Approved
0.6022	Remote Similarity	NPD4786	Approved
0.602	Remote Similarity	NPD6399	Phase 3
0.602	Remote Similarity	NPD4202	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD6929	Approved
0.5981	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6016	Approved
0.5965	Remote Similarity	NPD6015	Approved
0.5963	Remote Similarity	NPD8297	Approved
0.5955	Remote Similarity	NPD6932	Approved
0.5948	Remote Similarity	NPD7492	Approved
0.5943	Remote Similarity	NPD6412	Phase 2
0.5941	Remote Similarity	NPD7920	Phase 3
0.5941	Remote Similarity	NPD4755	Approved
0.5941	Remote Similarity	NPD7919	Phase 3
0.5934	Remote Similarity	NPD7509	Discontinued
0.5932	Remote Similarity	NPD7736	Approved
0.593	Remote Similarity	NPD4243	Approved
0.5926	Remote Similarity	NPD4634	Approved
0.5918	Remote Similarity	NPD6079	Approved
0.5918	Remote Similarity	NPD7087	Discontinued
0.5915	Remote Similarity	NPD386	Approved
0.5915	Remote Similarity	NPD388	Approved
0.5913	Remote Similarity	NPD5988	Approved
0.5897	Remote Similarity	NPD6616	Approved
0.5895	Remote Similarity	NPD3618	Phase 1
0.5888	Remote Similarity	NPD6881	Approved
0.5888	Remote Similarity	NPD6899	Approved
0.5882	Remote Similarity	NPD7319	Approved
0.5882	Remote Similarity	NPD8088	Phase 1
0.5877	Remote Similarity	NPD6319	Approved
0.5849	Remote Similarity	NPD6920	Discontinued
0.5849	Remote Similarity	NPD6008	Approved
0.5847	Remote Similarity	NPD8293	Discontinued
0.5847	Remote Similarity	NPD7078	Approved
0.5833	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6372	Approved
0.5833	Remote Similarity	NPD6373	Approved
0.5826	Remote Similarity	NPD7503	Approved
0.5825	Remote Similarity	NPD5286	Approved
0.5825	Remote Similarity	NPD4696	Approved
0.5825	Remote Similarity	NPD5285	Approved
0.5825	Remote Similarity	NPD4700	Approved
0.5824	Remote Similarity	NPD6683	Phase 2
0.5806	Remote Similarity	NPD3667	Approved
0.5798	Remote Similarity	NPD6033	Approved
0.5795	Remote Similarity	NPD4785	Approved
0.5795	Remote Similarity	NPD4784	Approved
0.5794	Remote Similarity	NPD5697	Approved
0.5794	Remote Similarity	NPD5701	Approved
0.5789	Remote Similarity	NPD6893	Approved
0.578	Remote Similarity	NPD6883	Approved
0.578	Remote Similarity	NPD7102	Approved
0.578	Remote Similarity	NPD7290	Approved
0.5778	Remote Similarity	NPD5776	Phase 2
0.5778	Remote Similarity	NPD6925	Approved
0.5769	Remote Similarity	NPD5223	Approved
0.5761	Remote Similarity	NPD7514	Phase 3
0.5752	Remote Similarity	NPD7115	Discovery
0.5752	Remote Similarity	NPD6009	Approved
0.5747	Remote Similarity	NPD7150	Approved
0.5747	Remote Similarity	NPD7152	Approved
0.5747	Remote Similarity	NPD7151	Approved
0.5741	Remote Similarity	NPD6011	Approved
0.5728	Remote Similarity	NPD4225	Approved
0.5727	Remote Similarity	NPD6649	Approved
0.5727	Remote Similarity	NPD6617	Approved
0.5727	Remote Similarity	NPD8130	Phase 1
0.5727	Remote Similarity	NPD6869	Approved
0.5727	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6847	Approved
0.5727	Remote Similarity	NPD6650	Approved
0.5726	Remote Similarity	NPD6067	Discontinued
0.5726	Remote Similarity	NPD7604	Phase 2
0.5714	Remote Similarity	NPD4633	Approved
0.5714	Remote Similarity	NPD5225	Approved
0.5714	Remote Similarity	NPD5224	Approved
0.5714	Remote Similarity	NPD5226	Approved
0.5714	Remote Similarity	NPD5211	Phase 2
0.5714	Remote Similarity	NPD7145	Approved
0.5698	Remote Similarity	NPD6923	Approved
0.5698	Remote Similarity	NPD6922	Approved
0.569	Remote Similarity	NPD5983	Phase 2
0.5688	Remote Similarity	NPD6014	Approved
0.5688	Remote Similarity	NPD6013	Approved
0.5688	Remote Similarity	NPD6012	Approved
0.5686	Remote Similarity	NPD5221	Approved
0.5686	Remote Similarity	NPD5222	Approved
0.5686	Remote Similarity	NPD4697	Phase 3
0.5686	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD6882	Approved
0.566	Remote Similarity	NPD5175	Approved
0.566	Remote Similarity	NPD4754	Approved
0.566	Remote Similarity	NPD5174	Approved
0.5644	Remote Similarity	NPD7748	Approved
0.5636	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD7144	Approved
0.5632	Remote Similarity	NPD7143	Approved
0.5631	Remote Similarity	NPD6083	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