NPASS Compound

Structure

CID3488 OpenBabel06191715322D 26 28 0 0 1 0 0 0 0 0999 V2000 3.0029 1.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 0.1691 0.0000 C 0 0 0 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 0.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 2 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 4.6665 1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 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 5.1665 1.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 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 1.7321 -2.0000 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 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 8 1 0 0 0 0 3 17 1 0 0 0 0 4 7 2 0 0 0 0 4 24 1 0 0 0 0 5 1 1 6 0 0 0 5 8 1 0 0 0 0 5 10 1 0 0 0 0 6 2 1 6 0 0 0 6 7 1 0 0 0 0 6 10 1 0 0 0 0 7 14 1 0 0 0 0 8 18 1 1 0 0 0 9 3 1 1 0 0 0 9 11 1 0 0 0 0 9 25 1 0 0 0 0 10 15 1 0 0 0 0 11 12 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 20 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 22 2 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 15 26 1 0 0 0 0 16 25 1 0 0 0 0 16 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.14
Volume:	342.252
LogP:	-0.388
LogD:	-0.4
LogS:	-0.893
# Rotatable Bonds:	4
TPSA:	166.14
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.316
Synthetic Accessibility Score:	4.729
Fsp3:	0.812
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.38
MDCK Permeability:	0.0001305758487433195
Pgp-inhibitor:	0.0
Pgp-substrate:	0.199
Human Intestinal Absorption (HIA):	0.885
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.237
Plasma Protein Binding (PPB):	19.468095779418945%
Volume Distribution (VD):	0.285
Pgp-substrate:	58.09699249267578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.062
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.102
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.027

ADMET: Excretion

Clearance (CL):	1.569
Half-life (T1/2):	0.904

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.252
Drug-inuced Liver Injury (DILI):	0.84
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.01
Skin Sensitization:	0.194
Carcinogencity:	0.94
Eye Corrosion:	0.004
Eye Irritation:	0.117
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC3488

Natural Product ID:	NPC3488
*Common Name:**	8-Epiloganic Acid
IUPAC Name:	(1S,4aS,6S,7S,7aS)-6-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
Synonyms:	8-Epiloganic Acid
Standard InCHIKey:	JNNGEAWILNVFFD-OZFVSFPVSA-N
Standard InCHI:	InChI=1S/C16H24O10/c1-5-8(18)2-6-7(14(22)23)4-24-15(10(5)6)26-16-13(21)12(20)11(19)9(3-17)25-16/h4-6,8-13,15-21H,2-3H2,1H3,(H,22,23)/t5-,6-,8+,9-,10-,11-,12+,13-,15+,16+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2[C@H](C)[C@H](C3)O)C(=O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079678
PubChem CID:	158144
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-glycosides

*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
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713409]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19555121]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19555121]
NPO23142	Lamium album	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19904996]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	fresh stems	n.a.	n.a.	PMID[20159656]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	Roots	n.a.	n.a.	PMID[22916954]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	aerial part	n.a.	n.a.	PMID[25442304]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25900014]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12531	Gmelina philippensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12531	Gmelina philippensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28192	Xenia puertogalerae	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23142	Lamium album	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9492	Maesopsis eminii	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4907	Torulopsis magnoliae	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1480	Dimocarpus fumatus	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6354	Trypetheliopsis boninensis	Species	Monoblastiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8031	Portulaca okinawensis	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7427	Fagara ailanthoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	-21.6	%	PMID[558442]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	Inhibition	=	5.3	%	PMID[558442]

☑ 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 NPC3488 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	215
0.1-0.2	1464
0.2-0.3	5417
0.3-0.4	10963
0.4-0.5	11265
0.5-0.6	7655
0.6-0.7	5227
0.7-0.8	439
0.8-0.85	22
0.85-0.9	12
0.9-0.95	10
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC287539
0.9684	High Similarity	NPC177013
0.9684	High Similarity	NPC474730
0.9684	High Similarity	NPC35185
0.9684	High Similarity	NPC4899
0.9588	High Similarity	NPC127235
0.9583	High Similarity	NPC37240
0.9388	High Similarity	NPC170432
0.9381	High Similarity	NPC475928
0.9362	High Similarity	NPC161293
0.9293	High Similarity	NPC148270
0.9293	High Similarity	NPC80338
0.9293	High Similarity	NPC197813
0.9082	High Similarity	NPC106668
0.9082	High Similarity	NPC304163
0.902	High Similarity	NPC193741
0.901	High Similarity	NPC110701
0.899	High Similarity	NPC27687
0.8947	High Similarity	NPC63897
0.8846	High Similarity	NPC475924
0.8846	High Similarity	NPC475851
0.8586	High Similarity	NPC37866
0.8542	High Similarity	NPC235051
0.8515	High Similarity	NPC80144
0.8469	Intermediate Similarity	NPC93869
0.8469	Intermediate Similarity	NPC6765
0.8416	Intermediate Similarity	NPC67296
0.8384	Intermediate Similarity	NPC474297
0.8367	Intermediate Similarity	NPC274588
0.83	Intermediate Similarity	NPC58267
0.83	Intermediate Similarity	NPC261372
0.83	Intermediate Similarity	NPC263674
0.8269	Intermediate Similarity	NPC41681
0.8247	Intermediate Similarity	NPC120021
0.8247	Intermediate Similarity	NPC270908
0.8247	Intermediate Similarity	NPC470573
0.8247	Intermediate Similarity	NPC216826
0.8247	Intermediate Similarity	NPC231710
0.8247	Intermediate Similarity	NPC65665
0.8235	Intermediate Similarity	NPC216911
0.8218	Intermediate Similarity	NPC49833
0.8218	Intermediate Similarity	NPC249171
0.8211	Intermediate Similarity	NPC470657
0.82	Intermediate Similarity	NPC284063
0.82	Intermediate Similarity	NPC241911
0.82	Intermediate Similarity	NPC170527
0.8144	Intermediate Similarity	NPC93190
0.8137	Intermediate Similarity	NPC476320
0.8137	Intermediate Similarity	NPC476211
0.8137	Intermediate Similarity	NPC22149
0.8137	Intermediate Similarity	NPC255677
0.8137	Intermediate Similarity	NPC306344
0.8125	Intermediate Similarity	NPC31349
0.8119	Intermediate Similarity	NPC86843
0.8119	Intermediate Similarity	NPC236580
0.8119	Intermediate Similarity	NPC304445
0.8119	Intermediate Similarity	NPC472290
0.8077	Intermediate Similarity	NPC329834
0.8077	Intermediate Similarity	NPC473148
0.8058	Intermediate Similarity	NPC27474
0.8058	Intermediate Similarity	NPC28304
0.8058	Intermediate Similarity	NPC476230
0.8058	Intermediate Similarity	NPC298255
0.7981	Intermediate Similarity	NPC195510
0.7981	Intermediate Similarity	NPC13171
0.798	Intermediate Similarity	NPC274274
0.798	Intermediate Similarity	NPC473150
0.798	Intermediate Similarity	NPC294643
0.7961	Intermediate Similarity	NPC473146
0.7959	Intermediate Similarity	NPC50464
0.7905	Intermediate Similarity	NPC284929
0.7905	Intermediate Similarity	NPC197541
0.7905	Intermediate Similarity	NPC118761
0.7905	Intermediate Similarity	NPC329704
0.7905	Intermediate Similarity	NPC267869
0.7905	Intermediate Similarity	NPC234304
0.7885	Intermediate Similarity	NPC476228
0.7879	Intermediate Similarity	NPC117596
0.7864	Intermediate Similarity	NPC472015
0.783	Intermediate Similarity	NPC86095
0.7812	Intermediate Similarity	NPC3464
0.7812	Intermediate Similarity	NPC151176
0.7812	Intermediate Similarity	NPC475963
0.781	Intermediate Similarity	NPC250545
0.781	Intermediate Similarity	NPC310804
0.781	Intermediate Similarity	NPC94919
0.781	Intermediate Similarity	NPC261117
0.781	Intermediate Similarity	NPC222062
0.78	Intermediate Similarity	NPC66504
0.78	Intermediate Similarity	NPC472124
0.78	Intermediate Similarity	NPC472125
0.78	Intermediate Similarity	NPC472126
0.7788	Intermediate Similarity	NPC13710
0.7745	Intermediate Similarity	NPC167893
0.7739	Intermediate Similarity	NPC470829
0.7739	Intermediate Similarity	NPC473228
0.7723	Intermediate Similarity	NPC61201
0.7714	Intermediate Similarity	NPC471401
0.7706	Intermediate Similarity	NPC118225
0.77	Intermediate Similarity	NPC246173
0.77	Intermediate Similarity	NPC307699
0.7685	Intermediate Similarity	NPC254538
0.7685	Intermediate Similarity	NPC474285
0.7636	Intermediate Similarity	NPC106760
0.7636	Intermediate Similarity	NPC114961
0.7636	Intermediate Similarity	NPC27551
0.7611	Intermediate Similarity	NPC88945
0.7603	Intermediate Similarity	NPC155529
0.7596	Intermediate Similarity	NPC471150
0.7593	Intermediate Similarity	NPC285927
0.7589	Intermediate Similarity	NPC132668
0.7586	Intermediate Similarity	NPC202051
0.7586	Intermediate Similarity	NPC42675
0.7573	Intermediate Similarity	NPC101051
0.7563	Intermediate Similarity	NPC152091
0.7547	Intermediate Similarity	NPC20673
0.7545	Intermediate Similarity	NPC208307
0.7544	Intermediate Similarity	NPC473304
0.7525	Intermediate Similarity	NPC303451
0.7525	Intermediate Similarity	NPC6414
0.7523	Intermediate Similarity	NPC287269
0.7521	Intermediate Similarity	NPC216866
0.7521	Intermediate Similarity	NPC213634
0.75	Intermediate Similarity	NPC243572
0.75	Intermediate Similarity	NPC281840
0.7478	Intermediate Similarity	NPC475309
0.7477	Intermediate Similarity	NPC255655
0.7477	Intermediate Similarity	NPC471599
0.7477	Intermediate Similarity	NPC98633
0.7476	Intermediate Similarity	NPC71589
0.7475	Intermediate Similarity	NPC149018
0.7475	Intermediate Similarity	NPC171484
0.7458	Intermediate Similarity	NPC1980
0.7458	Intermediate Similarity	NPC27363
0.7458	Intermediate Similarity	NPC238005
0.7458	Intermediate Similarity	NPC141196
0.7456	Intermediate Similarity	NPC229752
0.7456	Intermediate Similarity	NPC277583
0.7455	Intermediate Similarity	NPC230888
0.7455	Intermediate Similarity	NPC392
0.7455	Intermediate Similarity	NPC177524
0.7455	Intermediate Similarity	NPC224414
0.7455	Intermediate Similarity	NPC219900
0.7455	Intermediate Similarity	NPC88744
0.7453	Intermediate Similarity	NPC186861
0.7453	Intermediate Similarity	NPC244878
0.7453	Intermediate Similarity	NPC471381
0.7451	Intermediate Similarity	NPC472197
0.7449	Intermediate Similarity	NPC98276
0.7449	Intermediate Similarity	NPC259296
0.7449	Intermediate Similarity	NPC474780
0.7447	Intermediate Similarity	NPC70996
0.7434	Intermediate Similarity	NPC73455
0.7434	Intermediate Similarity	NPC200944
0.7434	Intermediate Similarity	NPC102619
0.7434	Intermediate Similarity	NPC73986
0.7431	Intermediate Similarity	NPC210178
0.7429	Intermediate Similarity	NPC476612
0.7429	Intermediate Similarity	NPC476613
0.7426	Intermediate Similarity	NPC22918
0.7419	Intermediate Similarity	NPC158350
0.7414	Intermediate Similarity	NPC319570
0.7411	Intermediate Similarity	NPC471251
0.7411	Intermediate Similarity	NPC122339
0.7411	Intermediate Similarity	NPC56025
0.7411	Intermediate Similarity	NPC213320
0.7411	Intermediate Similarity	NPC63244
0.7404	Intermediate Similarity	NPC472873
0.7395	Intermediate Similarity	NPC190846
0.7395	Intermediate Similarity	NPC277191
0.7395	Intermediate Similarity	NPC318135
0.7391	Intermediate Similarity	NPC78836
0.7387	Intermediate Similarity	NPC471250
0.7387	Intermediate Similarity	NPC51947
0.7387	Intermediate Similarity	NPC471400
0.7387	Intermediate Similarity	NPC91583
0.7387	Intermediate Similarity	NPC8431
0.7387	Intermediate Similarity	NPC473844
0.7387	Intermediate Similarity	NPC240125
0.7383	Intermediate Similarity	NPC476611
0.7383	Intermediate Similarity	NPC219038
0.7381	Intermediate Similarity	NPC470143
0.7381	Intermediate Similarity	NPC322503
0.7373	Intermediate Similarity	NPC28532
0.7368	Intermediate Similarity	NPC472274
0.7368	Intermediate Similarity	NPC471398
0.7368	Intermediate Similarity	NPC469821
0.736	Intermediate Similarity	NPC127656
0.736	Intermediate Similarity	NPC62172
0.736	Intermediate Similarity	NPC289700
0.7358	Intermediate Similarity	NPC151093
0.7345	Intermediate Similarity	NPC471245
0.7345	Intermediate Similarity	NPC473397
0.7345	Intermediate Similarity	NPC471244
0.7345	Intermediate Similarity	NPC473303
0.7345	Intermediate Similarity	NPC474927
0.7339	Intermediate Similarity	NPC223741
0.7333	Intermediate Similarity	NPC93368
0.7333	Intermediate Similarity	NPC306041
0.7333	Intermediate Similarity	NPC198714

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 NPC3488 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	2096
0.2-0.3	3936
0.3-0.4	1915
0.4-0.5	568
0.5-0.6	279
0.6-0.7	151
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7455	Intermediate Similarity	NPD6686	Approved
0.7364	Intermediate Similarity	NPD6412	Phase 2
0.7333	Intermediate Similarity	NPD7507	Approved
0.7281	Intermediate Similarity	NPD8133	Approved
0.7154	Intermediate Similarity	NPD7319	Approved
0.7143	Intermediate Similarity	NPD7503	Approved
0.7043	Intermediate Similarity	NPD6053	Discontinued
0.686	Remote Similarity	NPD8513	Phase 3
0.6857	Remote Similarity	NPD6698	Approved
0.6857	Remote Similarity	NPD46	Approved
0.681	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6009	Approved
0.6803	Remote Similarity	NPD6370	Approved
0.68	Remote Similarity	NPD7736	Approved
0.6796	Remote Similarity	NPD4249	Approved
0.6792	Remote Similarity	NPD7983	Approved
0.6777	Remote Similarity	NPD6319	Approved
0.6752	Remote Similarity	NPD6882	Approved
0.675	Remote Similarity	NPD7327	Approved
0.675	Remote Similarity	NPD7328	Approved
0.6733	Remote Similarity	NPD6435	Approved
0.6731	Remote Similarity	NPD4250	Approved
0.6731	Remote Similarity	NPD4251	Approved
0.6726	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD8516	Approved
0.6721	Remote Similarity	NPD8517	Approved
0.6721	Remote Similarity	NPD8515	Approved
0.672	Remote Similarity	NPD8293	Discontinued
0.6695	Remote Similarity	NPD4632	Approved
0.6694	Remote Similarity	NPD7492	Approved
0.6694	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.664	Remote Similarity	NPD6616	Approved
0.6639	Remote Similarity	NPD8377	Approved
0.6639	Remote Similarity	NPD8294	Approved
0.6639	Remote Similarity	NPD6054	Approved
0.661	Remote Similarity	NPD8297	Approved
0.6609	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7078	Approved
0.6585	Remote Similarity	NPD8033	Approved
0.6585	Remote Similarity	NPD6015	Approved
0.6585	Remote Similarity	NPD8296	Approved
0.6585	Remote Similarity	NPD6016	Approved
0.6585	Remote Similarity	NPD8335	Approved
0.6585	Remote Similarity	NPD8380	Approved
0.6585	Remote Similarity	NPD8378	Approved
0.6585	Remote Similarity	NPD8379	Approved
0.6581	Remote Similarity	NPD6371	Approved
0.6579	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5368	Approved
0.6532	Remote Similarity	NPD8080	Discontinued
0.6532	Remote Similarity	NPD5988	Approved
0.6505	Remote Similarity	NPD5362	Discontinued
0.6505	Remote Similarity	NPD7154	Phase 3
0.6504	Remote Similarity	NPD6059	Approved
0.6496	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.648	Remote Similarity	NPD8328	Phase 3
0.6475	Remote Similarity	NPD7641	Discontinued
0.6466	Remote Similarity	NPD5697	Approved
0.6452	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5779	Approved
0.6422	Remote Similarity	NPD5778	Approved
0.641	Remote Similarity	NPD6881	Approved
0.641	Remote Similarity	NPD6899	Approved
0.6396	Remote Similarity	NPD7839	Suspended
0.6393	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6650	Approved
0.6387	Remote Similarity	NPD6649	Approved
0.6379	Remote Similarity	NPD7128	Approved
0.6379	Remote Similarity	NPD5739	Approved
0.6379	Remote Similarity	NPD6402	Approved
0.6379	Remote Similarity	NPD6675	Approved
0.6373	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD6372	Approved
0.6356	Remote Similarity	NPD6013	Approved
0.6356	Remote Similarity	NPD6014	Approved
0.6356	Remote Similarity	NPD6012	Approved
0.6356	Remote Similarity	NPD6373	Approved
0.6349	Remote Similarity	NPD7830	Approved
0.6349	Remote Similarity	NPD7829	Approved
0.6325	Remote Similarity	NPD5701	Approved
0.6321	Remote Similarity	NPD5786	Approved
0.632	Remote Similarity	NPD5983	Phase 2
0.6303	Remote Similarity	NPD7102	Approved
0.6303	Remote Similarity	NPD6883	Approved
0.6303	Remote Similarity	NPD7290	Approved
0.6299	Remote Similarity	NPD8299	Approved
0.6299	Remote Similarity	NPD8342	Approved
0.6299	Remote Similarity	NPD8340	Approved
0.6299	Remote Similarity	NPD8341	Approved
0.6279	Remote Similarity	NPD8337	Approved
0.6279	Remote Similarity	NPD8336	Approved
0.6271	Remote Similarity	NPD7320	Approved
0.6271	Remote Similarity	NPD6011	Approved
0.6261	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD6869	Approved
0.625	Remote Similarity	NPD8130	Phase 1
0.625	Remote Similarity	NPD6847	Approved
0.625	Remote Similarity	NPD6617	Approved
0.6239	Remote Similarity	NPD7838	Discovery
0.6228	Remote Similarity	NPD7639	Approved
0.6228	Remote Similarity	NPD7640	Approved
0.6226	Remote Similarity	NPD5363	Approved
0.622	Remote Similarity	NPD7604	Phase 2
0.6214	Remote Similarity	NPD4822	Approved
0.6214	Remote Similarity	NPD4821	Approved
0.6214	Remote Similarity	NPD4819	Approved
0.6214	Remote Similarity	NPD4820	Approved
0.6202	Remote Similarity	NPD8074	Phase 3
0.6195	Remote Similarity	NPD6083	Phase 2
0.6195	Remote Similarity	NPD6084	Phase 2
0.619	Remote Similarity	NPD4788	Approved
0.6176	Remote Similarity	NPD4238	Approved
0.6176	Remote Similarity	NPD4271	Approved
0.6176	Remote Similarity	NPD4802	Phase 2
0.6176	Remote Similarity	NPD4268	Approved
0.6167	Remote Similarity	NPD4634	Approved
0.6161	Remote Similarity	NPD5695	Phase 3
0.6154	Remote Similarity	NPD5141	Approved
0.6147	Remote Similarity	NPD6101	Approved
0.6147	Remote Similarity	NPD1695	Approved
0.6147	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.614	Remote Similarity	NPD7638	Approved
0.6134	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7115	Discovery
0.6124	Remote Similarity	NPD8451	Approved
0.6124	Remote Similarity	NPD6336	Discontinued
0.6121	Remote Similarity	NPD8083	Approved
0.6121	Remote Similarity	NPD8084	Approved
0.6121	Remote Similarity	NPD8085	Approved
0.6121	Remote Similarity	NPD8138	Approved
0.6121	Remote Similarity	NPD8086	Approved
0.6121	Remote Similarity	NPD8082	Approved
0.6121	Remote Similarity	NPD8139	Approved
0.6102	Remote Similarity	NPD6008	Approved
0.6095	Remote Similarity	NPD4270	Approved
0.6095	Remote Similarity	NPD4269	Approved
0.6094	Remote Similarity	NPD6067	Discontinued
0.6094	Remote Similarity	NPD7642	Approved
0.6091	Remote Similarity	NPD5785	Approved
0.609	Remote Similarity	NPD8338	Approved
0.6087	Remote Similarity	NPD4696	Approved
0.6087	Remote Similarity	NPD5285	Approved
0.6087	Remote Similarity	NPD5286	Approved
0.6077	Remote Similarity	NPD8448	Approved
0.6075	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5282	Discontinued
0.6068	Remote Similarity	NPD8276	Approved
0.6068	Remote Similarity	NPD8275	Approved
0.6063	Remote Similarity	NPD8444	Approved
0.6053	Remote Similarity	NPD4755	Approved
0.6048	Remote Similarity	NPD6274	Approved
0.6038	Remote Similarity	NPD5331	Approved
0.6038	Remote Similarity	NPD5332	Approved
0.6036	Remote Similarity	NPD6411	Approved
0.6036	Remote Similarity	NPD8035	Phase 2
0.6036	Remote Similarity	NPD7637	Suspended
0.6036	Remote Similarity	NPD8034	Phase 2
0.6031	Remote Similarity	NPD6033	Approved
0.6029	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD8081	Approved
0.6	Remote Similarity	NPD5696	Approved
0.6	Remote Similarity	NPD4790	Discontinued
0.6	Remote Similarity	NPD5369	Approved
0.6	Remote Similarity	NPD4225	Approved
0.5984	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD4633	Approved
0.5983	Remote Similarity	NPD5224	Approved
0.5983	Remote Similarity	NPD5225	Approved
0.5983	Remote Similarity	NPD5226	Approved
0.5982	Remote Similarity	NPD8171	Discontinued
0.5982	Remote Similarity	NPD6399	Phase 3
0.5966	Remote Similarity	NPD8393	Approved
0.5963	Remote Similarity	NPD7524	Approved
0.595	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD4700	Approved
0.594	Remote Similarity	NPD5956	Approved
0.594	Remote Similarity	NPD8392	Approved
0.594	Remote Similarity	NPD8390	Approved
0.594	Remote Similarity	NPD8391	Approved
0.5938	Remote Similarity	NPD8268	Approved
0.5938	Remote Similarity	NPD8266	Approved
0.5938	Remote Similarity	NPD8269	Approved
0.5938	Remote Similarity	NPD8267	Approved
0.5932	Remote Similarity	NPD5174	Approved
0.5932	Remote Similarity	NPD5175	Approved
0.5926	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD8140	Approved
0.5917	Remote Similarity	NPD8307	Discontinued
0.5906	Remote Similarity	NPD7100	Approved
0.5906	Remote Similarity	NPD7101	Approved
0.5905	Remote Similarity	NPD4252	Approved
0.5897	Remote Similarity	NPD5223	Approved
0.5897	Remote Similarity	NPD5344	Discontinued
0.5896	Remote Similarity	NPD7260	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