NPASS Compound

Structure

CID41681 OpenBabel06191715372D 33 36 0 0 1 0 0 0 0 0999 V2000 4.0828 5.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8987 0.9414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0825 1.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2659 1.8846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8168 -1.4138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2660 3.7701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4491 -0.4720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0825 2.3558 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2659 0.9419 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0826 3.2985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2656 -0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4496 2.3559 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8165 -0.4711 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4496 1.4134 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6328 0.0004 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6326 0.9431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8160 1.4143 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8991 3.7698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0819 -0.4724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6331 0.9423 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0002 0.9427 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6333 -1.8850 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4493 -0.4707 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4489 1.4147 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8158 2.3570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7155 3.2984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0817 -1.4151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8992 4.7126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8984 -0.0013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4497 3.2986 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6328 -0.0004 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 0.8168 1.4138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 29 1 0 0 0 0 4 8 1 0 0 0 0 5 22 1 0 0 0 0 6 10 2 0 0 0 0 6 30 1 0 0 0 0 7 11 2 0 0 0 0 7 31 1 0 0 0 0 8 3 1 6 0 0 0 8 10 1 0 0 0 0 9 3 1 6 0 0 0 9 11 1 0 0 0 0 9 14 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 4 1 1 0 0 0 12 14 1 0 0 0 0 12 30 1 0 0 0 0 13 5 1 6 0 0 0 13 15 1 0 0 0 0 13 32 1 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 24 1 0 0 0 0 17 21 1 0 0 0 0 17 25 1 0 0 0 0 18 26 2 0 0 0 0 18 28 1 0 0 0 0 19 27 2 0 0 0 0 19 29 1 0 0 0 0 20 31 1 0 0 0 0 20 33 1 0 0 0 0 21 32 1 0 0 0 0 21 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.16
Volume:	432.483
LogP:	0.318
LogD:	0.889
LogS:	-1.379
# Rotatable Bonds:	7
TPSA:	170.44
# H-Bond Aceptor:	12
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.335
Synthetic Accessibility Score:	5.705
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.858
MDCK Permeability:	0.00012579654867295176
Pgp-inhibitor:	0.001
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.943
20% Bioavailability (F20%):	0.052
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.228
Plasma Protein Binding (PPB):	33.023841857910156%
Volume Distribution (VD):	0.734
Pgp-substrate:	36.52475357055664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.25
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.311
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.11
CYP3A4-substrate:	0.186

ADMET: Excretion

Clearance (CL):	2.061
Half-life (T1/2):	0.895

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.644
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.404
Rat Oral Acute Toxicity:	0.108
Maximum Recommended Daily Dose:	0.902
Skin Sensitization:	0.219
Carcinogencity:	0.965
Eye Corrosion:	0.003
Eye Irritation:	0.043
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC41681

Natural Product ID:	NPC41681
*Common Name:**	IKHUTBGZCJCCQG-SAAHHQEESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IKHUTBGZCJCCQG-SAAHHQEESA-N
Standard InCHI:	InChI=1S/C21H28O12/c1-28-18(26)10-6-30-12-4-8(10)3-9-11(19(27)29-2)7-31-20(14(9)12)33-21-17(25)16(24)15(23)13(5-22)32-21/h6-9,12-17,20-25H,3-5H2,1-2H3/t8-,9-,12-,13-,14+,15-,16+,17-,20+,21+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2[C@@H]2OC=C([C@@H](C2)C3)C(=O)OC)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3092672
PubChem CID:	76331806
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11141124]
NPO3699	Acacia aulacocarpa	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11735581]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844965]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17602526]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
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]
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]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7569	Guatteria boliviana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8418	Anemone flaccida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19948	Neolentinus lepideus	Species	Gloeophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4823	Psiadia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	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]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6237	Cryptocarya aschersoniana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4823	Psiadia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19948	Neolentinus lepideus	Species	Gloeophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8418	Anemone flaccida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5155	Peritassa compta	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5196	Eupatorium argentinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7569	Guatteria boliviana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3699	Acacia aulacocarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO471	Ardisia neriifolia	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6729	Juniperus brevifolia	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3597	Rheedia acuminata	Species	Clusiaceae	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
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	<	30.0	%	PMID[549426]

☑ 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 NPC41681 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	254
0.1-0.2	1735
0.2-0.3	4839
0.3-0.4	8110
0.4-0.5	12727
0.5-0.6	8659
0.6-0.7	4924
0.7-0.8	1406
0.8-0.85	34
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8544	High Similarity	NPC474730
0.8544	High Similarity	NPC177013
0.8544	High Similarity	NPC4899
0.8544	High Similarity	NPC35185
0.8469	Intermediate Similarity	NPC120021
0.8469	Intermediate Similarity	NPC470573
0.8469	Intermediate Similarity	NPC65665
0.8469	Intermediate Similarity	NPC216826
0.8469	Intermediate Similarity	NPC231710
0.8469	Intermediate Similarity	NPC270908
0.8462	Intermediate Similarity	NPC37240
0.8365	Intermediate Similarity	NPC106668
0.8302	Intermediate Similarity	NPC170432
0.8286	Intermediate Similarity	NPC27687
0.8286	Intermediate Similarity	NPC475928
0.8269	Intermediate Similarity	NPC3488
0.8269	Intermediate Similarity	NPC287539
0.8224	Intermediate Similarity	NPC80338
0.8224	Intermediate Similarity	NPC148270
0.8224	Intermediate Similarity	NPC197813
0.8165	Intermediate Similarity	NPC83005
0.8058	Intermediate Similarity	NPC161293
0.8053	Intermediate Similarity	NPC474483
0.802	Intermediate Similarity	NPC472125
0.802	Intermediate Similarity	NPC472126
0.802	Intermediate Similarity	NPC472124
0.8	Intermediate Similarity	NPC193741
0.7982	Intermediate Similarity	NPC219900
0.7982	Intermediate Similarity	NPC392
0.7982	Intermediate Similarity	NPC177524
0.7965	Intermediate Similarity	NPC88945
0.7963	Intermediate Similarity	NPC127235
0.7946	Intermediate Similarity	NPC75167
0.7946	Intermediate Similarity	NPC311592
0.7946	Intermediate Similarity	NPC132668
0.7934	Intermediate Similarity	NPC155529
0.7931	Intermediate Similarity	NPC476204
0.7931	Intermediate Similarity	NPC170084
0.7921	Intermediate Similarity	NPC307699
0.7921	Intermediate Similarity	NPC117596
0.7913	Intermediate Similarity	NPC122971
0.7895	Intermediate Similarity	NPC473968
0.7895	Intermediate Similarity	NPC473304
0.7885	Intermediate Similarity	NPC148872
0.7876	Intermediate Similarity	NPC472274
0.7876	Intermediate Similarity	NPC181145
0.7864	Intermediate Similarity	NPC63897
0.7857	Intermediate Similarity	NPC475924
0.7857	Intermediate Similarity	NPC475851
0.785	Intermediate Similarity	NPC94919
0.7845	Intermediate Similarity	NPC48692
0.7845	Intermediate Similarity	NPC476127
0.7845	Intermediate Similarity	NPC476150
0.7845	Intermediate Similarity	NPC470312
0.7838	Intermediate Similarity	NPC85391
0.7838	Intermediate Similarity	NPC137104
0.7838	Intermediate Similarity	NPC474786
0.7838	Intermediate Similarity	NPC320383
0.7833	Intermediate Similarity	NPC245094
0.7818	Intermediate Similarity	NPC473410
0.7818	Intermediate Similarity	NPC469984
0.7818	Intermediate Similarity	NPC63841
0.7818	Intermediate Similarity	NPC471094
0.7818	Intermediate Similarity	NPC232133
0.7818	Intermediate Similarity	NPC272576
0.7818	Intermediate Similarity	NPC110701
0.7818	Intermediate Similarity	NPC88744
0.7807	Intermediate Similarity	NPC229752
0.7807	Intermediate Similarity	NPC471816
0.7797	Intermediate Similarity	NPC27363
0.7788	Intermediate Similarity	NPC73986
0.7778	Intermediate Similarity	NPC202051
0.7768	Intermediate Similarity	NPC63244
0.7768	Intermediate Similarity	NPC471251
0.7768	Intermediate Similarity	NPC213320
0.7768	Intermediate Similarity	NPC122339
0.7767	Intermediate Similarity	NPC61201
0.7759	Intermediate Similarity	NPC476529
0.7759	Intermediate Similarity	NPC127530
0.7759	Intermediate Similarity	NPC475775
0.7748	Intermediate Similarity	NPC57362
0.7748	Intermediate Similarity	NPC274827
0.7748	Intermediate Similarity	NPC167383
0.7748	Intermediate Similarity	NPC204407
0.7748	Intermediate Similarity	NPC473844
0.7748	Intermediate Similarity	NPC306746
0.7748	Intermediate Similarity	NPC131903
0.7748	Intermediate Similarity	NPC240125
0.7748	Intermediate Similarity	NPC471250
0.7748	Intermediate Similarity	NPC469983
0.7748	Intermediate Similarity	NPC91583
0.7748	Intermediate Similarity	NPC51947
0.7748	Intermediate Similarity	NPC8431
0.7748	Intermediate Similarity	NPC237503
0.7748	Intermediate Similarity	NPC137917
0.7742	Intermediate Similarity	NPC158350
0.7739	Intermediate Similarity	NPC78836
0.7739	Intermediate Similarity	NPC309433
0.7739	Intermediate Similarity	NPC473405
0.7727	Intermediate Similarity	NPC471474
0.7727	Intermediate Similarity	NPC293512
0.7727	Intermediate Similarity	NPC186054
0.7719	Intermediate Similarity	NPC475633
0.7699	Intermediate Similarity	NPC471967
0.7699	Intermediate Similarity	NPC471245
0.7699	Intermediate Similarity	NPC474927
0.7699	Intermediate Similarity	NPC471244
0.7699	Intermediate Similarity	NPC473303
0.7699	Intermediate Similarity	NPC174836
0.7699	Intermediate Similarity	NPC473397
0.7692	Intermediate Similarity	NPC109607
0.7692	Intermediate Similarity	NPC107338
0.7692	Intermediate Similarity	NPC281840
0.7685	Intermediate Similarity	NPC13171
0.7685	Intermediate Similarity	NPC80144
0.7685	Intermediate Similarity	NPC195510
0.7685	Intermediate Similarity	NPC121423
0.768	Intermediate Similarity	NPC289700
0.768	Intermediate Similarity	NPC127656
0.768	Intermediate Similarity	NPC62172
0.7679	Intermediate Similarity	NPC75747
0.7679	Intermediate Similarity	NPC270667
0.7679	Intermediate Similarity	NPC78046
0.7679	Intermediate Similarity	NPC476885
0.7679	Intermediate Similarity	NPC68419
0.7679	Intermediate Similarity	NPC474589
0.7679	Intermediate Similarity	NPC476884
0.7679	Intermediate Similarity	NPC471476
0.7679	Intermediate Similarity	NPC475296
0.7679	Intermediate Similarity	NPC279554
0.7679	Intermediate Similarity	NPC164194
0.7679	Intermediate Similarity	NPC136877
0.7679	Intermediate Similarity	NPC56713
0.7679	Intermediate Similarity	NPC473324
0.7679	Intermediate Similarity	NPC471093
0.7679	Intermediate Similarity	NPC90856
0.7679	Intermediate Similarity	NPC29069
0.7679	Intermediate Similarity	NPC476883
0.7679	Intermediate Similarity	NPC274507
0.7679	Intermediate Similarity	NPC174679
0.7679	Intermediate Similarity	NPC124053
0.7679	Intermediate Similarity	NPC476886
0.7679	Intermediate Similarity	NPC476881
0.7679	Intermediate Similarity	NPC129340
0.7679	Intermediate Similarity	NPC199457
0.7679	Intermediate Similarity	NPC127056
0.7679	Intermediate Similarity	NPC476882
0.7679	Intermediate Similarity	NPC102914
0.7679	Intermediate Similarity	NPC476880
0.7679	Intermediate Similarity	NPC220984
0.7679	Intermediate Similarity	NPC476887
0.7679	Intermediate Similarity	NPC269095
0.7679	Intermediate Similarity	NPC110139
0.7679	Intermediate Similarity	NPC108709
0.7679	Intermediate Similarity	NPC7870
0.7679	Intermediate Similarity	NPC59804
0.7672	Intermediate Similarity	NPC471249
0.7672	Intermediate Similarity	NPC471548
0.7672	Intermediate Similarity	NPC176005
0.7667	Intermediate Similarity	NPC250556
0.7667	Intermediate Similarity	NPC469750
0.7658	Intermediate Similarity	NPC177246
0.7658	Intermediate Similarity	NPC284807
0.7658	Intermediate Similarity	NPC37628
0.7658	Intermediate Similarity	NPC476123
0.7658	Intermediate Similarity	NPC195708
0.7658	Intermediate Similarity	NPC230888
0.7658	Intermediate Similarity	NPC28198
0.7642	Intermediate Similarity	NPC474395
0.7636	Intermediate Similarity	NPC164600
0.7636	Intermediate Similarity	NPC130511
0.7636	Intermediate Similarity	NPC103172
0.7636	Intermediate Similarity	NPC307660
0.7636	Intermediate Similarity	NPC56656
0.7632	Intermediate Similarity	NPC293038
0.7632	Intermediate Similarity	NPC473159
0.7632	Intermediate Similarity	NPC471252
0.7632	Intermediate Similarity	NPC94141
0.7632	Intermediate Similarity	NPC62696
0.7632	Intermediate Similarity	NPC157441
0.7627	Intermediate Similarity	NPC275675
0.7623	Intermediate Similarity	NPC477196
0.7619	Intermediate Similarity	NPC101051
0.7615	Intermediate Similarity	NPC139347
0.7615	Intermediate Similarity	NPC61442
0.7611	Intermediate Similarity	NPC240734
0.7611	Intermediate Similarity	NPC211798
0.7611	Intermediate Similarity	NPC473481
0.7611	Intermediate Similarity	NPC274833
0.7611	Intermediate Similarity	NPC108748
0.7611	Intermediate Similarity	NPC164419
0.7611	Intermediate Similarity	NPC263827
0.7611	Intermediate Similarity	NPC297208
0.7611	Intermediate Similarity	NPC11035
0.7611	Intermediate Similarity	NPC91838
0.7611	Intermediate Similarity	NPC204392
0.7611	Intermediate Similarity	NPC179434
0.7611	Intermediate Similarity	NPC31839
0.7611	Intermediate Similarity	NPC30397
0.7611	Intermediate Similarity	NPC270586

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 NPC41681 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	256
0.1-0.2	2101
0.2-0.3	3724
0.3-0.4	1947
0.4-0.5	708
0.5-0.6	278
0.6-0.7	127
0.7-0.8	9
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
0.7982	Intermediate Similarity	NPD6686	Approved
0.7788	Intermediate Similarity	NPD8133	Approved
0.7667	Intermediate Similarity	NPD7507	Approved
0.748	Intermediate Similarity	NPD7319	Approved
0.7479	Intermediate Similarity	NPD7503	Approved
0.7434	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD8328	Phase 3
0.7333	Intermediate Similarity	NPD8513	Phase 3
0.7288	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6412	Phase 2
0.7193	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD8517	Approved
0.719	Intermediate Similarity	NPD8516	Approved
0.719	Intermediate Similarity	NPD8515	Approved
0.7083	Intermediate Similarity	NPD7328	Approved
0.7083	Intermediate Similarity	NPD7327	Approved
0.7025	Intermediate Similarity	NPD7516	Approved
0.6967	Remote Similarity	NPD8377	Approved
0.6967	Remote Similarity	NPD8294	Approved
0.6949	Remote Similarity	NPD6053	Discontinued
0.6916	Remote Similarity	NPD6698	Approved
0.6916	Remote Similarity	NPD46	Approved
0.6911	Remote Similarity	NPD8378	Approved
0.6911	Remote Similarity	NPD8380	Approved
0.6911	Remote Similarity	NPD8033	Approved
0.6911	Remote Similarity	NPD8379	Approved
0.6911	Remote Similarity	NPD8335	Approved
0.6911	Remote Similarity	NPD8296	Approved
0.6864	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7736	Approved
0.6838	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD3669	Approved
0.6721	Remote Similarity	NPD6009	Approved
0.672	Remote Similarity	NPD6370	Approved
0.6699	Remote Similarity	NPD1779	Approved
0.6699	Remote Similarity	NPD1780	Approved
0.6694	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6641	Remote Similarity	NPD8293	Discontinued
0.664	Remote Similarity	NPD6921	Approved
0.6639	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7638	Approved
0.6614	Remote Similarity	NPD7492	Approved
0.6612	Remote Similarity	NPD4632	Approved
0.6585	Remote Similarity	NPD7115	Discovery
0.6579	Remote Similarity	NPD7640	Approved
0.6579	Remote Similarity	NPD7639	Approved
0.6562	Remote Similarity	NPD6616	Approved
0.656	Remote Similarity	NPD6054	Approved
0.6529	Remote Similarity	NPD8297	Approved
0.6512	Remote Similarity	NPD8074	Phase 3
0.6512	Remote Similarity	NPD7078	Approved
0.6508	Remote Similarity	NPD6015	Approved
0.6508	Remote Similarity	NPD6016	Approved
0.6491	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4225	Approved
0.6457	Remote Similarity	NPD5988	Approved
0.6429	Remote Similarity	NPD6059	Approved
0.6406	Remote Similarity	NPD7830	Approved
0.6406	Remote Similarity	NPD7829	Approved
0.6396	Remote Similarity	NPD8034	Phase 2
0.6396	Remote Similarity	NPD8035	Phase 2
0.6396	Remote Similarity	NPD7983	Approved
0.6387	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5697	Approved
0.6379	Remote Similarity	NPD5344	Discontinued
0.6364	Remote Similarity	NPD6101	Approved
0.6364	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5779	Approved
0.6339	Remote Similarity	NPD5778	Approved
0.6333	Remote Similarity	NPD6899	Approved
0.6333	Remote Similarity	NPD6881	Approved
0.632	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6649	Approved
0.6311	Remote Similarity	NPD6650	Approved
0.6306	Remote Similarity	NPD7838	Discovery
0.6303	Remote Similarity	NPD5739	Approved
0.6303	Remote Similarity	NPD6402	Approved
0.6303	Remote Similarity	NPD6675	Approved
0.6303	Remote Similarity	NPD7128	Approved
0.6296	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD7748	Approved
0.6281	Remote Similarity	NPD6372	Approved
0.6281	Remote Similarity	NPD6013	Approved
0.6281	Remote Similarity	NPD6373	Approved
0.6281	Remote Similarity	NPD6012	Approved
0.6281	Remote Similarity	NPD6014	Approved
0.627	Remote Similarity	NPD7641	Discontinued
0.6261	Remote Similarity	NPD7902	Approved
0.625	Remote Similarity	NPD7515	Phase 2
0.625	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD5701	Approved
0.625	Remote Similarity	NPD5983	Phase 2
0.623	Remote Similarity	NPD7102	Approved
0.623	Remote Similarity	NPD6883	Approved
0.623	Remote Similarity	NPD7290	Approved
0.6202	Remote Similarity	NPD8080	Discontinued
0.6198	Remote Similarity	NPD7320	Approved
0.6198	Remote Similarity	NPD6011	Approved
0.6194	Remote Similarity	NPD7260	Phase 2
0.6186	Remote Similarity	NPD7632	Discontinued
0.6183	Remote Similarity	NPD8451	Approved
0.6182	Remote Similarity	NPD3573	Approved
0.6179	Remote Similarity	NPD6869	Approved
0.6179	Remote Similarity	NPD6847	Approved
0.6179	Remote Similarity	NPD8130	Phase 1
0.6179	Remote Similarity	NPD6617	Approved
0.6176	Remote Similarity	NPD1811	Approved
0.6176	Remote Similarity	NPD1810	Approved
0.6154	Remote Similarity	NPD7604	Phase 2
0.6154	Remote Similarity	NPD7642	Approved
0.6154	Remote Similarity	NPD6067	Discontinued
0.6136	Remote Similarity	NPD8448	Approved
0.6124	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD8444	Approved
0.6119	Remote Similarity	NPD8390	Approved
0.6119	Remote Similarity	NPD8392	Approved
0.6119	Remote Similarity	NPD8391	Approved
0.6116	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD4634	Approved
0.6087	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6336	Discontinued
0.605	Remote Similarity	NPD5211	Phase 2
0.6034	Remote Similarity	NPD7839	Suspended
0.6033	Remote Similarity	NPD6008	Approved
0.6029	Remote Similarity	NPD6845	Suspended
0.6019	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD6648	Approved
0.6017	Remote Similarity	NPD5285	Approved
0.6017	Remote Similarity	NPD4696	Approved
0.6017	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD8266	Approved
0.6	Remote Similarity	NPD8267	Approved
0.6	Remote Similarity	NPD8268	Approved
0.6	Remote Similarity	NPD7900	Approved
0.6	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8269	Approved
0.5985	Remote Similarity	NPD8341	Approved
0.5985	Remote Similarity	NPD8299	Approved
0.5985	Remote Similarity	NPD8340	Approved
0.5985	Remote Similarity	NPD8342	Approved
0.5984	Remote Similarity	NPD6940	Discontinued
0.5984	Remote Similarity	NPD6274	Approved
0.5983	Remote Similarity	NPD4755	Approved
0.597	Remote Similarity	NPD8336	Approved
0.597	Remote Similarity	NPD6033	Approved
0.597	Remote Similarity	NPD8337	Approved
0.5968	Remote Similarity	NPD6371	Approved
0.5965	Remote Similarity	NPD6079	Approved
0.595	Remote Similarity	NPD5141	Approved
0.5948	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD5328	Approved
0.592	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD5226	Approved
0.5917	Remote Similarity	NPD8085	Approved
0.5917	Remote Similarity	NPD8084	Approved
0.5917	Remote Similarity	NPD8138	Approved
0.5917	Remote Similarity	NPD8083	Approved
0.5917	Remote Similarity	NPD4633	Approved
0.5917	Remote Similarity	NPD5224	Approved
0.5917	Remote Similarity	NPD8082	Approved
0.5917	Remote Similarity	NPD5225	Approved
0.5917	Remote Similarity	NPD8086	Approved
0.5917	Remote Similarity	NPD8139	Approved
0.5913	Remote Similarity	NPD8171	Discontinued
0.5913	Remote Similarity	NPD6399	Phase 3
0.5899	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD5222	Approved
0.5897	Remote Similarity	NPD5221	Approved
0.5897	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD2686	Approved
0.5882	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4700	Approved
0.5882	Remote Similarity	NPD2687	Approved
0.5882	Remote Similarity	NPD2254	Approved
0.5868	Remote Similarity	NPD5175	Approved
0.5868	Remote Similarity	NPD8276	Approved
0.5868	Remote Similarity	NPD5174	Approved
0.5868	Remote Similarity	NPD8275	Approved
0.5856	Remote Similarity	NPD1694	Approved
0.5847	Remote Similarity	NPD5173	Approved
0.5847	Remote Similarity	NPD6084	Phase 2
0.5847	Remote Similarity	NPD6083	Phase 2
0.5846	Remote Similarity	NPD7100	Approved
0.5846	Remote Similarity	NPD7101	Approved
0.5833	Remote Similarity	NPD5223	Approved
0.5827	Remote Similarity	NPD8415	Approved
0.582	Remote Similarity	NPD8081	Approved
0.5818	Remote Similarity	NPD4788	Approved
0.5814	Remote Similarity	NPD6317	Approved
0.5812	Remote Similarity	NPD5695	Phase 3
0.5806	Remote Similarity	NPD4730	Approved
0.5806	Remote Similarity	NPD4729	Approved
0.5804	Remote Similarity	NPD3618	Phase 1
0.5797	Remote Similarity	NPD8338	Approved
0.5794	Remote Similarity	NPD6114	Approved
0.5794	Remote Similarity	NPD6697	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