NPASS Compound

Structure

NPC473828 OpenBabel07101718192D 45 48 0 0 1 0 0 0 0 0999 V2000 -1.5451 4.7553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1924 4.2200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2653 1.3669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6984 -3.1805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9248 -5.6907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8268 -5.0567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8268 -5.0567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4607 -1.6907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1409 -3.4997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 -0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3383 -1.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9052 3.0611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 2.8532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5947 -4.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1928 -2.6907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7287 -3.6907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3268 -2.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3868 -1.2125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2142 4.0121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0074 -2.2294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0588 -5.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3923 -1.1080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 -1.1590 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6180 1.9021 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.4607 -3.6907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5947 -2.1907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1928 -3.6907 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9855 -2.0215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9563 -0.4158 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6473 0.5352 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3268 -4.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4607 -2.6907 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7287 -2.6907 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.1928 -5.6907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8923 -0.2420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5962 -2.1100 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9344 -0.6237 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3164 1.2784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0588 -4.1907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 1.6942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 35 1 0 0 0 0 7 35 1 0 0 0 0 10 11 1 0 0 0 0 10 12 2 0 0 0 0 11 22 2 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 21 2 0 0 0 0 14 27 1 0 0 0 0 15 17 1 0 0 0 0 15 28 1 0 0 0 0 16 18 1 0 0 0 0 16 30 1 0 0 0 0 17 37 1 0 0 0 0 18 36 1 0 0 0 0 19 25 1 0 0 0 0 19 29 1 0 0 0 0 20 26 1 0 0 0 0 20 43 1 0 0 0 0 22 27 1 0 0 0 0 23 31 2 0 0 0 0 24 38 2 0 0 0 0 24 44 1 0 0 0 0 25 31 1 0 0 0 0 25 39 2 0 0 0 0 26 32 1 0 0 0 0 26 40 1 1 0 0 0 27 45 1 0 0 0 0 28 35 1 0 0 0 0 28 36 1 1 0 0 0 29 36 1 6 0 0 0 29 37 1 0 0 0 0 30 35 1 0 0 0 0 30 44 1 6 0 0 0 31 37 1 0 0 0 0 32 33 1 0 0 0 0 32 41 1 1 0 0 0 33 34 1 0 0 0 0 33 42 1 1 0 0 0 34 43 1 0 0 0 0 34 45 1 1 0 0 0 36 8 1 1 0 0 0 37 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	628.4
Volume:	668.785
LogP:	4.87
LogD:	4.349
LogS:	-5.124
# Rotatable Bonds:	9
TPSA:	122.52
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.134
Synthetic Accessibility Score:	5.43
Fsp3:	0.73
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.964
MDCK Permeability:	1.828710810514167e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.955
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.073

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	93.9469985961914%
Volume Distribution (VD):	2.349
Pgp-substrate:	4.514919281005859%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.771
CYP2C9-inhibitor:	0.16
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.37
CYP3A4-substrate:	0.439

ADMET: Excretion

Clearance (CL):	1.044
Half-life (T1/2):	0.069

ADMET: Toxicity

hERG Blockers:	0.553
Human Hepatotoxicity (H-HT):	0.629
Drug-inuced Liver Injury (DILI):	0.202
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.371
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.774
Carcinogencity:	0.07
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC473828

Natural Product ID:	NPC473828
*Common Name:**	13Z-Stelliferin Riboside
IUPAC Name:	[(3Z,3aS,5aR,7R,9aR,9bS)-3-[(3E,5E)-6,10-dimethyl-7-[(2S,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyundeca-3,5,9-trien-2-ylidene]-3a,6,6,9a-tetramethyl-2-oxo-1,4,5,5a,7,8,9,9b-octahydrocyclopenta[a]naphthalen-7-yl] acetate
Synonyms:	13Z-Stelliferin Riboside
Standard InCHIKey:	DIFMBIWQHJHMSC-DMRCYMPXSA-N
Standard InCHI:	InChI=1S/C37H56O8/c1-21(2)13-14-27(45-34-33(42)32(41)26(40)20-43-34)22(3)11-10-12-23(4)31-25(39)19-29-36(8)18-16-30(44-24(5)38)35(6,7)28(36)15-17-37(29,31)9/h10-13,26-30,32-34,40-42H,14-20H2,1-9H3/b12-10+,22-11+,31-23+/t26-,27?,28-,29-,30+,32-,33-,34-,36-,37-/m0/s1
SMILES:	CC(=O)O[C@@H]1CC[C@]2([C@H](C1(C)C)CC[C@]1([C@H]2CC(=O)/C/1=C(C=CC=C(C(O[C@@H]1OC[C@@H]([C@@H]([C@@H]1O)O)O)CC=C(C)C)/C)/C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452921
PubChem CID:	10974202
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
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858759]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499318]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562838]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17524651]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20627740]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20718449]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	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
ED50	3
Others	6

Activity Type	# Activity
Cell Line	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	Inhibition	=	100.0	%	PMID[476399]
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	56.0	%	PMID[476399]
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	0.0	%	PMID[476399]
NPT681	Cell Line	PC-12	Rattus norvegicus	Inhibition	=	38.0	%	PMID[476399]
NPT681	Cell Line	PC-12	Rattus norvegicus	Inhibition	=	0.0	%	PMID[476399]
NPT1864	Cell Line	L5178Y	Mus musculus	ED50	=	0.22	nmol	PMID[476399]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	=	22.76	nmol	PMID[476399]
NPT681	Cell Line	PC-12	Rattus norvegicus	ED50	=	21.54	nmol	PMID[476399]

☑ 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 NPC473828 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	228
0.1-0.2	1147
0.2-0.3	3575
0.3-0.4	6583
0.4-0.5	12369
0.5-0.6	8300
0.6-0.7	6199
0.7-0.8	3688
0.8-0.85	543
0.85-0.9	61
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473617
0.9722	High Similarity	NPC475163
0.8957	High Similarity	NPC470312
0.8889	High Similarity	NPC41129
0.8833	High Similarity	NPC476966
0.8833	High Similarity	NPC471407
0.875	High Similarity	NPC245094
0.875	High Similarity	NPC292196
0.8739	High Similarity	NPC475065
0.8718	High Similarity	NPC202051
0.8707	High Similarity	NPC477071
0.8704	High Similarity	NPC155332
0.8704	High Similarity	NPC114540
0.8704	High Similarity	NPC32577
0.8696	High Similarity	NPC474483
0.8689	High Similarity	NPC471855
0.8689	High Similarity	NPC231240
0.8684	High Similarity	NPC220293
0.8661	High Similarity	NPC119550
0.8661	High Similarity	NPC83005
0.8655	High Similarity	NPC318135
0.8649	High Similarity	NPC473482
0.8649	High Similarity	NPC219900
0.8649	High Similarity	NPC392
0.8649	High Similarity	NPC318363
0.8649	High Similarity	NPC475418
0.8649	High Similarity	NPC177524
0.8632	High Similarity	NPC48692
0.8632	High Similarity	NPC476150
0.8632	High Similarity	NPC476127
0.8621	High Similarity	NPC45475
0.8621	High Similarity	NPC239293
0.8621	High Similarity	NPC291564
0.8618	High Similarity	NPC316915
0.8609	High Similarity	NPC207637
0.8607	High Similarity	NPC173347
0.8596	High Similarity	NPC75167
0.8596	High Similarity	NPC260665
0.8596	High Similarity	NPC311592
0.8595	High Similarity	NPC311534
0.8584	High Similarity	NPC285410
0.8584	High Similarity	NPC250481
0.8584	High Similarity	NPC263827
0.8571	High Similarity	NPC40728
0.8571	High Similarity	NPC265655
0.8571	High Similarity	NPC316974
0.8571	High Similarity	NPC27363
0.8559	High Similarity	NPC170084
0.8559	High Similarity	NPC184512
0.8559	High Similarity	NPC129434
0.8559	High Similarity	NPC329048
0.8559	High Similarity	NPC330011
0.8559	High Similarity	NPC476204
0.8547	High Similarity	NPC232258
0.8522	High Similarity	NPC472274
0.8522	High Similarity	NPC74727
0.8522	High Similarity	NPC181145
0.8522	High Similarity	NPC473882
0.8512	High Similarity	NPC240070
0.8512	High Similarity	NPC42399
0.8512	High Similarity	NPC329784
0.8509	High Similarity	NPC317460
0.8509	High Similarity	NPC328074
0.8509	High Similarity	NPC471967
0.8509	High Similarity	NPC470025
0.8509	High Similarity	NPC321272
0.8509	High Similarity	NPC477253
0.8496	Intermediate Similarity	NPC316708
0.8496	Intermediate Similarity	NPC129340
0.8496	Intermediate Similarity	NPC52241
0.8496	Intermediate Similarity	NPC154856
0.8496	Intermediate Similarity	NPC475317
0.8482	Intermediate Similarity	NPC217921
0.8482	Intermediate Similarity	NPC295389
0.8482	Intermediate Similarity	NPC311223
0.8482	Intermediate Similarity	NPC135015
0.8482	Intermediate Similarity	NPC128795
0.8482	Intermediate Similarity	NPC48548
0.8482	Intermediate Similarity	NPC195708
0.848	Intermediate Similarity	NPC158350
0.8468	Intermediate Similarity	NPC218158
0.8468	Intermediate Similarity	NPC252296
0.8468	Intermediate Similarity	NPC82251
0.8462	Intermediate Similarity	NPC234522
0.844	Intermediate Similarity	NPC115899
0.8435	Intermediate Similarity	NPC264153
0.8435	Intermediate Similarity	NPC470027
0.8435	Intermediate Similarity	NPC251309
0.843	Intermediate Similarity	NPC469750
0.843	Intermediate Similarity	NPC250556
0.8421	Intermediate Similarity	NPC470026
0.8421	Intermediate Similarity	NPC190837
0.8421	Intermediate Similarity	NPC17791
0.8407	Intermediate Similarity	NPC118225
0.8407	Intermediate Similarity	NPC284828
0.8407	Intermediate Similarity	NPC472216
0.8407	Intermediate Similarity	NPC246205
0.8407	Intermediate Similarity	NPC173905
0.8407	Intermediate Similarity	NPC5475
0.8393	Intermediate Similarity	NPC125423
0.8393	Intermediate Similarity	NPC473284
0.8393	Intermediate Similarity	NPC293512
0.8393	Intermediate Similarity	NPC109376
0.8393	Intermediate Similarity	NPC88013
0.839	Intermediate Similarity	NPC44899
0.839	Intermediate Similarity	NPC29639
0.839	Intermediate Similarity	NPC304260
0.839	Intermediate Similarity	NPC122971
0.839	Intermediate Similarity	NPC5883
0.839	Intermediate Similarity	NPC475775
0.839	Intermediate Similarity	NPC476529
0.8387	Intermediate Similarity	NPC155529
0.8378	Intermediate Similarity	NPC473207
0.8378	Intermediate Similarity	NPC81567
0.8378	Intermediate Similarity	NPC201880
0.8378	Intermediate Similarity	NPC470321
0.8378	Intermediate Similarity	NPC264867
0.8376	Intermediate Similarity	NPC473968
0.8376	Intermediate Similarity	NPC477252
0.8376	Intermediate Similarity	NPC473405
0.8376	Intermediate Similarity	NPC203862
0.8376	Intermediate Similarity	NPC93883
0.8374	Intermediate Similarity	NPC329986
0.8374	Intermediate Similarity	NPC125077
0.8374	Intermediate Similarity	NPC188234
0.8374	Intermediate Similarity	NPC140092
0.8374	Intermediate Similarity	NPC276838
0.8374	Intermediate Similarity	NPC232785
0.8374	Intermediate Similarity	NPC473593
0.8364	Intermediate Similarity	NPC470571
0.8364	Intermediate Similarity	NPC121423
0.8361	Intermediate Similarity	NPC298841
0.8361	Intermediate Similarity	NPC146456
0.8361	Intermediate Similarity	NPC179412
0.8361	Intermediate Similarity	NPC117702
0.8361	Intermediate Similarity	NPC469757
0.8361	Intermediate Similarity	NPC471356
0.8361	Intermediate Similarity	NPC471357
0.8349	Intermediate Similarity	NPC266955
0.8348	Intermediate Similarity	NPC233003
0.8348	Intermediate Similarity	NPC195132
0.8348	Intermediate Similarity	NPC130427
0.8348	Intermediate Similarity	NPC212968
0.8348	Intermediate Similarity	NPC65590
0.8348	Intermediate Similarity	NPC174836
0.8348	Intermediate Similarity	NPC64106
0.8348	Intermediate Similarity	NPC210420
0.8348	Intermediate Similarity	NPC125923
0.8348	Intermediate Similarity	NPC161434
0.8348	Intermediate Similarity	NPC474265
0.8347	Intermediate Similarity	NPC3381
0.8333	Intermediate Similarity	NPC101450
0.8333	Intermediate Similarity	NPC177047
0.8333	Intermediate Similarity	NPC28532
0.8333	Intermediate Similarity	NPC274507
0.8333	Intermediate Similarity	NPC110937
0.8333	Intermediate Similarity	NPC471082
0.8319	Intermediate Similarity	NPC476123
0.8319	Intermediate Similarity	NPC135369
0.8319	Intermediate Similarity	NPC284807
0.8319	Intermediate Similarity	NPC109607
0.8319	Intermediate Similarity	NPC471406
0.8319	Intermediate Similarity	NPC107338
0.8319	Intermediate Similarity	NPC28198
0.8319	Intermediate Similarity	NPC88701
0.8319	Intermediate Similarity	NPC224660
0.8319	Intermediate Similarity	NPC470024
0.8319	Intermediate Similarity	NPC177246
0.8305	Intermediate Similarity	NPC471548
0.8304	Intermediate Similarity	NPC266570
0.8304	Intermediate Similarity	NPC172867
0.8304	Intermediate Similarity	NPC162033
0.8293	Intermediate Similarity	NPC473620
0.8293	Intermediate Similarity	NPC220838
0.8293	Intermediate Similarity	NPC45606
0.8291	Intermediate Similarity	NPC193382
0.8291	Intermediate Similarity	NPC99620
0.8291	Intermediate Similarity	NPC244127
0.8291	Intermediate Similarity	NPC471816
0.8291	Intermediate Similarity	NPC5311
0.8291	Intermediate Similarity	NPC473126
0.8291	Intermediate Similarity	NPC310341
0.8291	Intermediate Similarity	NPC199428
0.8288	Intermediate Similarity	NPC127933
0.8288	Intermediate Similarity	NPC7644
0.8288	Intermediate Similarity	NPC134270
0.8288	Intermediate Similarity	NPC7613
0.8288	Intermediate Similarity	NPC475889
0.8281	Intermediate Similarity	NPC75616
0.8279	Intermediate Similarity	NPC47113
0.8279	Intermediate Similarity	NPC297950
0.8279	Intermediate Similarity	NPC174367
0.8276	Intermediate Similarity	NPC62696
0.8276	Intermediate Similarity	NPC474410
0.8276	Intermediate Similarity	NPC200944
0.8276	Intermediate Similarity	NPC293038
0.8276	Intermediate Similarity	NPC473159
0.8276	Intermediate Similarity	NPC293658
0.8276	Intermediate Similarity	NPC73455
0.8273	Intermediate Similarity	NPC198992

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 NPC473828 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	1238
0.2-0.3	3407
0.3-0.4	2690
0.4-0.5	974
0.5-0.6	337
0.6-0.7	216
0.7-0.8	73
0.8-0.85	12
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8649	High Similarity	NPD6686	Approved
0.843	Intermediate Similarity	NPD7507	Approved
0.825	Intermediate Similarity	NPD7503	Approved
0.825	Intermediate Similarity	NPD8033	Approved
0.823	Intermediate Similarity	NPD6412	Phase 2
0.8226	Intermediate Similarity	NPD7319	Approved
0.8167	Intermediate Similarity	NPD8294	Approved
0.8167	Intermediate Similarity	NPD8377	Approved
0.8151	Intermediate Similarity	NPD7328	Approved
0.8151	Intermediate Similarity	NPD7327	Approved
0.8099	Intermediate Similarity	NPD8296	Approved
0.8099	Intermediate Similarity	NPD8380	Approved
0.8099	Intermediate Similarity	NPD8335	Approved
0.8099	Intermediate Similarity	NPD8378	Approved
0.8099	Intermediate Similarity	NPD8379	Approved
0.8083	Intermediate Similarity	NPD7516	Approved
0.7966	Intermediate Similarity	NPD8133	Approved
0.7931	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7928	Intermediate Similarity	NPD7638	Approved
0.7917	Intermediate Similarity	NPD7115	Discovery
0.7857	Intermediate Similarity	NPD7640	Approved
0.7857	Intermediate Similarity	NPD7639	Approved
0.7823	Intermediate Similarity	NPD8328	Phase 3
0.7805	Intermediate Similarity	NPD8515	Approved
0.7805	Intermediate Similarity	NPD8516	Approved
0.7805	Intermediate Similarity	NPD8517	Approved
0.7805	Intermediate Similarity	NPD8513	Phase 3
0.7731	Intermediate Similarity	NPD6882	Approved
0.7731	Intermediate Similarity	NPD8297	Approved
0.7717	Intermediate Similarity	NPD7736	Approved
0.7638	Intermediate Similarity	NPD8293	Discontinued
0.76	Intermediate Similarity	NPD6370	Approved
0.748	Intermediate Similarity	NPD6009	Approved
0.748	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD7492	Approved
0.7479	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD4225	Approved
0.744	Intermediate Similarity	NPD6319	Approved
0.744	Intermediate Similarity	NPD6054	Approved
0.7422	Intermediate Similarity	NPD6616	Approved
0.7395	Intermediate Similarity	NPD6899	Approved
0.7395	Intermediate Similarity	NPD6881	Approved
0.7377	Intermediate Similarity	NPD4632	Approved
0.7373	Intermediate Similarity	NPD7128	Approved
0.7373	Intermediate Similarity	NPD5739	Approved
0.7373	Intermediate Similarity	NPD6675	Approved
0.7373	Intermediate Similarity	NPD6402	Approved
0.7364	Intermediate Similarity	NPD7078	Approved
0.7355	Intermediate Similarity	NPD8130	Phase 1
0.7355	Intermediate Similarity	NPD6650	Approved
0.7355	Intermediate Similarity	NPD6649	Approved
0.7333	Intermediate Similarity	NPD6373	Approved
0.7333	Intermediate Similarity	NPD6372	Approved
0.7321	Intermediate Similarity	NPD6399	Phase 3
0.7311	Intermediate Similarity	NPD5697	Approved
0.7304	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6059	Approved
0.7297	Intermediate Similarity	NPD6698	Approved
0.7297	Intermediate Similarity	NPD46	Approved
0.7273	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7290	Approved
0.7273	Intermediate Similarity	NPD7102	Approved
0.7273	Intermediate Similarity	NPD6883	Approved
0.7266	Intermediate Similarity	NPD6067	Discontinued
0.7265	Intermediate Similarity	NPD7632	Discontinued
0.7257	Intermediate Similarity	NPD7748	Approved
0.725	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7320	Approved
0.7244	Intermediate Similarity	NPD6016	Approved
0.7244	Intermediate Similarity	NPD6015	Approved
0.7231	Intermediate Similarity	NPD8074	Phase 3
0.7217	Intermediate Similarity	NPD7902	Approved
0.7213	Intermediate Similarity	NPD6617	Approved
0.7213	Intermediate Similarity	NPD6869	Approved
0.7213	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD6847	Approved
0.719	Intermediate Similarity	NPD6013	Approved
0.719	Intermediate Similarity	NPD6014	Approved
0.719	Intermediate Similarity	NPD6012	Approved
0.7188	Intermediate Similarity	NPD5988	Approved
0.7167	Intermediate Similarity	NPD5701	Approved
0.7143	Intermediate Similarity	NPD7838	Discovery
0.7143	Intermediate Similarity	NPD7260	Phase 2
0.7107	Intermediate Similarity	NPD6011	Approved
0.7091	Intermediate Similarity	NPD3618	Phase 1
0.708	Intermediate Similarity	NPD6079	Approved
0.708	Intermediate Similarity	NPD7515	Phase 2
0.7069	Intermediate Similarity	NPD6083	Phase 2
0.7069	Intermediate Similarity	NPD6084	Phase 2
0.7054	Intermediate Similarity	NPD5328	Approved
0.7025	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7604	Phase 2
0.6977	Remote Similarity	NPD5983	Phase 2
0.6975	Remote Similarity	NPD5211	Phase 2
0.6957	Remote Similarity	NPD7900	Approved
0.6957	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD4696	Approved
0.6949	Remote Similarity	NPD5285	Approved
0.6949	Remote Similarity	NPD5286	Approved
0.6942	Remote Similarity	NPD6008	Approved
0.6937	Remote Similarity	NPD7521	Approved
0.6937	Remote Similarity	NPD7334	Approved
0.6937	Remote Similarity	NPD6684	Approved
0.6937	Remote Similarity	NPD6409	Approved
0.6937	Remote Similarity	NPD7146	Approved
0.6937	Remote Similarity	NPD5330	Approved
0.6935	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6411	Approved
0.693	Remote Similarity	NPD8034	Phase 2
0.693	Remote Similarity	NPD8035	Phase 2
0.693	Remote Similarity	NPD7637	Suspended
0.693	Remote Similarity	NPD7983	Approved
0.6923	Remote Similarity	NPD4755	Approved
0.6909	Remote Similarity	NPD4786	Approved
0.6894	Remote Similarity	NPD6336	Discontinued
0.6891	Remote Similarity	NPD5344	Discontinued
0.6881	Remote Similarity	NPD3667	Approved
0.688	Remote Similarity	NPD6053	Discontinued
0.687	Remote Similarity	NPD7830	Approved
0.687	Remote Similarity	NPD7829	Approved
0.687	Remote Similarity	NPD4202	Approved
0.686	Remote Similarity	NPD5141	Approved
0.686	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4634	Approved
0.6838	Remote Similarity	NPD5222	Approved
0.6838	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5221	Approved
0.6833	Remote Similarity	NPD5226	Approved
0.6833	Remote Similarity	NPD4633	Approved
0.6833	Remote Similarity	NPD5224	Approved
0.6833	Remote Similarity	NPD5225	Approved
0.6822	Remote Similarity	NPD7100	Approved
0.6822	Remote Similarity	NPD7101	Approved
0.6814	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6903	Approved
0.6814	Remote Similarity	NPD5737	Approved
0.6814	Remote Similarity	NPD6672	Approved
0.6807	Remote Similarity	NPD6648	Approved
0.6807	Remote Similarity	NPD4700	Approved
0.6791	Remote Similarity	NPD6033	Approved
0.6783	Remote Similarity	NPD5284	Approved
0.6783	Remote Similarity	NPD5281	Approved
0.678	Remote Similarity	NPD5173	Approved
0.6777	Remote Similarity	NPD5174	Approved
0.6777	Remote Similarity	NPD5175	Approved
0.6757	Remote Similarity	NPD3666	Approved
0.6757	Remote Similarity	NPD3133	Approved
0.6757	Remote Similarity	NPD3665	Phase 1
0.6754	Remote Similarity	NPD6101	Approved
0.6754	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5695	Phase 3
0.675	Remote Similarity	NPD5223	Approved
0.6748	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6335	Approved
0.6727	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5778	Approved
0.6724	Remote Similarity	NPD5779	Approved
0.6723	Remote Similarity	NPD5696	Approved
0.672	Remote Similarity	NPD6371	Approved
0.6719	Remote Similarity	NPD6868	Approved
0.6719	Remote Similarity	NPD6274	Approved
0.6718	Remote Similarity	NPD6921	Approved
0.6718	Remote Similarity	NPD8444	Approved
0.6715	Remote Similarity	NPD6845	Suspended
0.6696	Remote Similarity	NPD5785	Approved
0.6696	Remote Similarity	NPD1694	Approved
0.6696	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD4697	Phase 3
0.6694	Remote Similarity	NPD4730	Approved
0.6694	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD7799	Discontinued
0.6667	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD4768	Approved
0.6667	Remote Similarity	NPD4767	Approved
0.6642	Remote Similarity	NPD8451	Approved
0.6638	Remote Similarity	NPD5693	Phase 1
0.6637	Remote Similarity	NPD5279	Phase 3
0.6615	Remote Similarity	NPD7641	Discontinued
0.6615	Remote Similarity	NPD6313	Approved
0.6615	Remote Similarity	NPD6314	Approved
0.661	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD4753	Phase 2
0.6607	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD8448	Approved
0.6591	Remote Similarity	NPD6909	Approved
0.6591	Remote Similarity	NPD6908	Approved
0.6587	Remote Similarity	NPD5247	Approved
0.6587	Remote Similarity	NPD5250	Approved
0.6587	Remote Similarity	NPD5251	Approved
0.6587	Remote Similarity	NPD5249	Phase 3
0.6587	Remote Similarity	NPD5248	Approved
0.6579	Remote Similarity	NPD3573	Approved
0.6579	Remote Similarity	NPD7524	Approved
0.6575	Remote Similarity	NPD7625	Phase 1
0.6569	Remote Similarity	NPD8392	Approved
0.6569	Remote Similarity	NPD8390	Approved
0.6569	Remote Similarity	NPD8391	Approved
0.6555	Remote Similarity	NPD7839	Suspended
0.6525	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD4754	Approved

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