NPASS Compound

Structure

CID189884 OpenBabel06191715572D 55 61 0 0 1 0 0 0 0 0999 V2000 2.5562 4.4274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7041 0.9839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0481 -2.3279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8521 -1.4758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8521 -0.4919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2122 3.8037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8521 1.4758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4082 2.9516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8521 -1.4758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4082 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5562 0.4919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4082 1.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7041 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5562 0.4919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6685 1.4758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8165 -0.9839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0642 -2.3279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5562 3.4435 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8521 1.4758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8165 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8165 0.9839 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7041 -0.9839 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8521 0.4919 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4082 -0.9839 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9644 0.4919 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8165 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9644 -0.4919 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1123 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1123 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7041 1.9677 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1123 -0.9839 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1123 0.9839 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4082 0.9839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7041 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5562 -1.4758 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8521 0.4919 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 1.7041 2.9516 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5562 1.4758 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.5206 0.9839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5562 -3.1799 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6685 0.4919 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9644 1.4758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6685 -0.4919 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9644 -1.4758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2603 0.4919 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2603 -0.4919 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4082 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7202 2.9516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9644 -1.4758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9644 1.4758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2603 -1.4758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2603 1.4758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 4 38 1 0 0 0 0 7 8 1 0 0 0 0 7 21 2 0 0 0 0 8 25 1 0 0 0 0 9 14 1 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 24 1 0 0 0 0 11 12 1 0 0 0 0 11 26 1 0 0 0 0 12 36 1 0 0 0 0 13 39 1 0 0 0 0 14 41 1 0 0 0 0 15 16 1 0 0 0 0 15 38 1 0 0 0 0 16 41 1 0 0 0 0 17 42 1 0 0 0 0 18 22 1 0 0 0 0 18 52 1 0 0 0 0 19 37 1 0 0 0 0 19 43 1 0 0 0 0 20 40 1 6 0 0 0 21 32 1 0 0 0 0 21 38 1 0 0 0 0 22 27 1 0 0 0 0 22 44 1 6 0 0 0 23 17 1 6 0 0 0 23 28 1 0 0 0 0 23 53 1 0 0 0 0 24 36 1 1 0 0 0 24 37 1 0 0 0 0 25 36 1 1 0 0 0 25 39 1 0 0 0 0 26 37 1 1 0 0 0 26 54 1 0 0 0 0 27 30 1 0 0 0 0 27 45 1 6 0 0 0 28 29 1 0 0 0 0 28 46 1 1 0 0 0 29 31 1 0 0 0 0 29 47 1 6 0 0 0 30 33 1 0 0 0 0 30 48 1 1 0 0 0 31 34 1 0 0 0 0 31 49 1 1 0 0 0 32 40 1 6 0 0 0 32 41 1 0 0 0 0 33 52 1 0 0 0 0 33 54 1 6 0 0 0 34 53 1 0 0 0 0 34 55 1 6 0 0 0 35 50 2 0 0 0 0 35 55 1 0 0 0 0 36 2 1 1 0 0 0 37 3 1 1 0 0 0 38 39 1 1 0 0 0 39 5 1 1 0 0 0 40 6 1 1 0 0 0 40 51 1 0 0 0 0 41 35 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	782.45
Volume:	775.587
LogP:	2.271
LogD:	2.205
LogS:	-3.732
# Rotatable Bonds:	7
TPSA:	236.06
# H-Bond Aceptor:	14
# H-Bond Donor:	9
# Rings:	7
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.104
Synthetic Accessibility Score:	5.97
Fsp3:	0.927
Lipinski Rule-of-5:	Rejected
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:	-5.735
MDCK Permeability:	3.140692933811806e-05
Pgp-inhibitor:	0.962
Pgp-substrate:	0.022
Human Intestinal Absorption (HIA):	0.905
20% Bioavailability (F20%):	0.113
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	79.89073944091797%
Volume Distribution (VD):	0.387
Pgp-substrate:	11.0431547164917%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.899
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.481
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.06
CYP3A4-inhibitor:	0.172
CYP3A4-substrate:	0.037

ADMET: Excretion

Clearance (CL):	0.975
Half-life (T1/2):	0.655

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.225
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.099
Rat Oral Acute Toxicity:	0.094
Maximum Recommended Daily Dose:	0.767
Skin Sensitization:	0.089
Carcinogencity:	0.019
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC189884

Natural Product ID:	NPC189884
*Common Name:**	Ilekudinoside D
IUPAC Name:	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,2R,4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-1-hydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms:	Ilekudinoside D
Standard InCHIKey:	OQQOYQUBUVPAAU-IHTHYQCPSA-N
Standard InCHI:	InChI=1S/C41H66O14/c1-20-9-14-41(35(50)55-34-31(49)29(47)28(46)23(17-42)53-34)16-15-38(4)21(32(41)40(20,6)51)7-8-25-36(2)12-11-26(54-33-30(48)27(45)22(44)18-52-33)37(3,19-43)24(36)10-13-39(25,38)5/h7,20,22-34,42-49,51H,8-19H2,1-6H3/t20-,22+,23-,24-,25-,26+,27+,28-,29+,30-,31-,32-,33+,34+,36+,37+,38-,39-,40-,41+/m1/s1
SMILES:	OC[C@H]1O[C@@H](OC(=O)[C@@]23CC[C@H]([C@@]([C@H]3C3=CC[C@H]4[C@@]([C@@]3(CC2)C)(C)CC[C@@H]2[C@]4(C)CC[C@@H]([C@@]2(C)CO)O[C@@H]2OC[C@@H]([C@@H]([C@H]2O)O)O)(C)O)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448619
PubChem CID:	21635824
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
NPO33035	ilex kudincha	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425145]
NPO33035	ilex kudincha	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479318]
NPO20508	Ilex kaushue	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20508	Ilex kaushue	Species	Aquifoliaceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1214	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase 1	Homo sapiens	Inhibition	=	18.9	%	PMID[522910]

☑ 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 NPC189884 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	268
0.1-0.2	1722
0.2-0.3	4919
0.3-0.4	10964
0.4-0.5	10753
0.5-0.6	6383
0.6-0.7	4437
0.7-0.8	1955
0.8-0.85	651
0.85-0.9	276
0.9-0.95	180
0.95-1	189

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC47063
1.0	High Similarity	NPC138334
1.0	High Similarity	NPC204458
0.9904	High Similarity	NPC256798
0.9904	High Similarity	NPC128925
0.9904	High Similarity	NPC37739
0.9904	High Similarity	NPC46388
0.9811	High Similarity	NPC160415
0.9811	High Similarity	NPC58448
0.981	High Similarity	NPC269315
0.981	High Similarity	NPC271138
0.9808	High Similarity	NPC235841
0.9808	High Similarity	NPC30397
0.9808	High Similarity	NPC211798
0.9808	High Similarity	NPC191763
0.9808	High Similarity	NPC473481
0.9808	High Similarity	NPC297208
0.9808	High Similarity	NPC108748
0.972	High Similarity	NPC68175
0.9714	High Similarity	NPC116794
0.9712	High Similarity	NPC474589
0.9712	High Similarity	NPC164194
0.9712	High Similarity	NPC90856
0.9712	High Similarity	NPC270667
0.9712	High Similarity	NPC279554
0.9712	High Similarity	NPC29069
0.9712	High Similarity	NPC127056
0.9712	High Similarity	NPC174679
0.9712	High Similarity	NPC475296
0.9712	High Similarity	NPC59804
0.9712	High Similarity	NPC136877
0.9712	High Similarity	NPC56713
0.9712	High Similarity	NPC274507
0.963	High Similarity	NPC36831
0.9626	High Similarity	NPC161674
0.9626	High Similarity	NPC471384
0.9623	High Similarity	NPC124296
0.9623	High Similarity	NPC258885
0.9619	High Similarity	NPC179434
0.9619	High Similarity	NPC164419
0.9615	High Similarity	NPC237503
0.9615	High Similarity	NPC167383
0.9615	High Similarity	NPC306746
0.9615	High Similarity	NPC204407
0.9615	High Similarity	NPC57362
0.9537	High Similarity	NPC148417
0.9537	High Similarity	NPC136768
0.9537	High Similarity	NPC110633
0.9533	High Similarity	NPC475633
0.9528	High Similarity	NPC139044
0.9528	High Similarity	NPC473383
0.9528	High Similarity	NPC324875
0.9528	High Similarity	NPC139894
0.9528	High Similarity	NPC475516
0.9528	High Similarity	NPC104400
0.9528	High Similarity	NPC1046
0.9528	High Similarity	NPC276093
0.9528	High Similarity	NPC292677
0.9528	High Similarity	NPC257468
0.9528	High Similarity	NPC469946
0.9528	High Similarity	NPC475504
0.9528	High Similarity	NPC101744
0.9528	High Similarity	NPC473373
0.9528	High Similarity	NPC471383
0.9528	High Similarity	NPC102439
0.9528	High Similarity	NPC109079
0.9528	High Similarity	NPC10320
0.9528	High Similarity	NPC79718
0.9528	High Similarity	NPC80843
0.9528	High Similarity	NPC104071
0.9524	High Similarity	NPC7870
0.9524	High Similarity	NPC476881
0.9524	High Similarity	NPC476880
0.9524	High Similarity	NPC269095
0.9524	High Similarity	NPC476883
0.9524	High Similarity	NPC476886
0.9524	High Similarity	NPC78046
0.9524	High Similarity	NPC75747
0.9524	High Similarity	NPC110139
0.9524	High Similarity	NPC476885
0.9524	High Similarity	NPC108709
0.9524	High Similarity	NPC476887
0.9524	High Similarity	NPC476884
0.9524	High Similarity	NPC68419
0.9524	High Similarity	NPC476882
0.9524	High Similarity	NPC102914
0.9524	High Similarity	NPC199457
0.9519	High Similarity	NPC177246
0.9519	High Similarity	NPC476123
0.9519	High Similarity	NPC284807
0.9519	High Similarity	NPC28198
0.9455	High Similarity	NPC268184
0.9444	High Similarity	NPC291903
0.9444	High Similarity	NPC37134
0.9439	High Similarity	NPC114304
0.9439	High Similarity	NPC133818
0.9439	High Similarity	NPC323341
0.9439	High Similarity	NPC192600
0.9439	High Similarity	NPC134835
0.9439	High Similarity	NPC96641
0.9439	High Similarity	NPC475208
0.9439	High Similarity	NPC475287
0.9439	High Similarity	NPC46665
0.9439	High Similarity	NPC150400
0.9439	High Similarity	NPC475467
0.9439	High Similarity	NPC219180
0.9439	High Similarity	NPC251263
0.9439	High Similarity	NPC238935
0.9439	High Similarity	NPC163183
0.9439	High Similarity	NPC114287
0.9439	High Similarity	NPC151543
0.9439	High Similarity	NPC473826
0.9439	High Similarity	NPC174720
0.9439	High Similarity	NPC241909
0.9439	High Similarity	NPC73318
0.9439	High Similarity	NPC295823
0.9439	High Similarity	NPC309714
0.9439	High Similarity	NPC166422
0.9439	High Similarity	NPC473343
0.9439	High Similarity	NPC155410
0.9434	High Similarity	NPC31839
0.9429	High Similarity	NPC137917
0.9429	High Similarity	NPC127853
0.9423	High Similarity	NPC283849
0.9423	High Similarity	NPC473538
0.9369	High Similarity	NPC75417
0.9358	High Similarity	NPC473824
0.9358	High Similarity	NPC475119
0.9358	High Similarity	NPC300419
0.9352	High Similarity	NPC161717
0.9352	High Similarity	NPC236638
0.9352	High Similarity	NPC76972
0.9352	High Similarity	NPC79643
0.9352	High Similarity	NPC4328
0.9352	High Similarity	NPC475140
0.9352	High Similarity	NPC204414
0.9352	High Similarity	NPC250247
0.9352	High Similarity	NPC164389
0.9352	High Similarity	NPC41061
0.9352	High Similarity	NPC305981
0.9352	High Similarity	NPC469782
0.9352	High Similarity	NPC293330
0.9352	High Similarity	NPC123199
0.9352	High Similarity	NPC57484
0.9352	High Similarity	NPC476068
0.9352	High Similarity	NPC43550
0.9352	High Similarity	NPC473714
0.9352	High Similarity	NPC60557
0.9352	High Similarity	NPC67857
0.9352	High Similarity	NPC475486
0.9352	High Similarity	NPC71065
0.9352	High Similarity	NPC261506
0.9352	High Similarity	NPC65105
0.9352	High Similarity	NPC475160
0.9352	High Similarity	NPC70809
0.9352	High Similarity	NPC471385
0.9352	High Similarity	NPC298034
0.9352	High Similarity	NPC309907
0.9352	High Similarity	NPC294453
0.9352	High Similarity	NPC202828
0.9352	High Similarity	NPC54636
0.9352	High Similarity	NPC119592
0.9352	High Similarity	NPC100639
0.9352	High Similarity	NPC224381
0.9352	High Similarity	NPC227551
0.9352	High Similarity	NPC471550
0.9346	High Similarity	NPC161434
0.9346	High Similarity	NPC471967
0.9346	High Similarity	NPC195132
0.9346	High Similarity	NPC48249
0.934	High Similarity	NPC475501
0.934	High Similarity	NPC220984
0.934	High Similarity	NPC242611
0.9333	High Similarity	NPC285576
0.9327	High Similarity	NPC475611
0.9279	High Similarity	NPC473645
0.9273	High Similarity	NPC109588
0.9273	High Similarity	NPC232237
0.9273	High Similarity	NPC105800
0.9273	High Similarity	NPC475899
0.9266	High Similarity	NPC51465
0.9266	High Similarity	NPC476992
0.9266	High Similarity	NPC26626
0.9266	High Similarity	NPC75287
0.9266	High Similarity	NPC288205
0.9266	High Similarity	NPC305267
0.9252	High Similarity	NPC190837
0.9231	High Similarity	NPC173583
0.9189	High Similarity	NPC309780
0.9189	High Similarity	NPC208381
0.9189	High Similarity	NPC157868
0.9189	High Similarity	NPC469945
0.9189	High Similarity	NPC6377
0.9189	High Similarity	NPC475171
0.9189	High Similarity	NPC114441
0.9189	High Similarity	NPC35405
0.9189	High Similarity	NPC473884
0.9189	High Similarity	NPC51564
0.9189	High Similarity	NPC471577
0.9189	High Similarity	NPC135849

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 NPC189884 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	2017
0.2-0.3	3810
0.3-0.4	1985
0.4-0.5	624
0.5-0.6	300
0.6-0.7	133
0.7-0.8	22
0.8-0.85	9
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9009	High Similarity	NPD8295	Clinical (unspecified phase)
0.8889	High Similarity	NPD8132	Clinical (unspecified phase)
0.887	High Similarity	NPD8328	Phase 3
0.8407	Intermediate Similarity	NPD8133	Approved
0.8067	Intermediate Similarity	NPD8033	Approved
0.8036	Intermediate Similarity	NPD6412	Phase 2
0.7983	Intermediate Similarity	NPD8294	Approved
0.7983	Intermediate Similarity	NPD8377	Approved
0.7965	Intermediate Similarity	NPD6686	Approved
0.7963	Intermediate Similarity	NPD7902	Approved
0.7951	Intermediate Similarity	NPD7507	Approved
0.7917	Intermediate Similarity	NPD8379	Approved
0.7917	Intermediate Similarity	NPD8513	Phase 3
0.7917	Intermediate Similarity	NPD8296	Approved
0.7917	Intermediate Similarity	NPD8516	Approved
0.7917	Intermediate Similarity	NPD8515	Approved
0.7917	Intermediate Similarity	NPD8378	Approved
0.7917	Intermediate Similarity	NPD8335	Approved
0.7917	Intermediate Similarity	NPD8380	Approved
0.7917	Intermediate Similarity	NPD8517	Approved
0.785	Intermediate Similarity	NPD7748	Approved
0.776	Intermediate Similarity	NPD7319	Approved
0.7685	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD7900	Approved
0.768	Intermediate Similarity	NPD7736	Approved
0.7667	Intermediate Similarity	NPD7327	Approved
0.7667	Intermediate Similarity	NPD7328	Approved
0.7664	Intermediate Similarity	NPD7515	Phase 2
0.7603	Intermediate Similarity	NPD7516	Approved
0.748	Intermediate Similarity	NPD7503	Approved
0.746	Intermediate Similarity	NPD8293	Discontinued
0.7458	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD8035	Phase 2
0.7339	Intermediate Similarity	NPD8034	Phase 2
0.728	Intermediate Similarity	NPD6370	Approved
0.7273	Intermediate Similarity	NPD6399	Phase 3
0.725	Intermediate Similarity	NPD8297	Approved
0.725	Intermediate Similarity	NPD6882	Approved
0.7241	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7492	Approved
0.7154	Intermediate Similarity	NPD7115	Discovery
0.7154	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD6373	Approved
0.7143	Intermediate Similarity	NPD6372	Approved
0.7143	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6319	Approved
0.712	Intermediate Similarity	NPD6059	Approved
0.712	Intermediate Similarity	NPD6054	Approved
0.7109	Intermediate Similarity	NPD6616	Approved
0.7105	Intermediate Similarity	NPD7638	Approved
0.7083	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD8074	Phase 3
0.7054	Intermediate Similarity	NPD7078	Approved
0.7049	Intermediate Similarity	NPD4632	Approved
0.7043	Intermediate Similarity	NPD7639	Approved
0.7043	Intermediate Similarity	NPD7640	Approved
0.7034	Intermediate Similarity	NPD6402	Approved
0.7034	Intermediate Similarity	NPD7128	Approved
0.7034	Intermediate Similarity	NPD5739	Approved
0.7034	Intermediate Similarity	NPD6675	Approved
0.7025	Intermediate Similarity	NPD6650	Approved
0.7025	Intermediate Similarity	NPD6649	Approved
0.7019	Intermediate Similarity	NPD7645	Phase 2
0.6953	Remote Similarity	NPD6067	Discontinued
0.6944	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6016	Approved
0.6929	Remote Similarity	NPD6015	Approved
0.6917	Remote Similarity	NPD6899	Approved
0.6917	Remote Similarity	NPD7320	Approved
0.6917	Remote Similarity	NPD6881	Approved
0.6891	Remote Similarity	NPD6008	Approved
0.6885	Remote Similarity	NPD8130	Phase 1
0.6875	Remote Similarity	NPD5988	Approved
0.6875	Remote Similarity	NPD6411	Approved
0.6833	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5697	Approved
0.6833	Remote Similarity	NPD5701	Approved
0.6814	Remote Similarity	NPD8171	Discontinued
0.681	Remote Similarity	NPD4225	Approved
0.681	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6883	Approved
0.6803	Remote Similarity	NPD7102	Approved
0.6803	Remote Similarity	NPD7290	Approved
0.6786	Remote Similarity	NPD46	Approved
0.6786	Remote Similarity	NPD6698	Approved
0.6759	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD3669	Approved
0.6748	Remote Similarity	NPD6869	Approved
0.6748	Remote Similarity	NPD6847	Approved
0.6748	Remote Similarity	NPD6617	Approved
0.6727	Remote Similarity	NPD3618	Phase 1
0.6724	Remote Similarity	NPD6084	Phase 2
0.6724	Remote Similarity	NPD6083	Phase 2
0.6721	Remote Similarity	NPD6014	Approved
0.6721	Remote Similarity	NPD6013	Approved
0.6721	Remote Similarity	NPD6012	Approved
0.6697	Remote Similarity	NPD4786	Approved
0.6696	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6101	Approved
0.6692	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD6921	Approved
0.6639	Remote Similarity	NPD6011	Approved
0.6617	Remote Similarity	NPD6033	Approved
0.6613	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6336	Discontinued
0.6581	Remote Similarity	NPD4755	Approved
0.6579	Remote Similarity	NPD7983	Approved
0.6574	Remote Similarity	NPD1779	Approved
0.6574	Remote Similarity	NPD1780	Approved
0.6549	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5328	Approved
0.6544	Remote Similarity	NPD8449	Approved
0.6532	Remote Similarity	NPD4634	Approved
0.6525	Remote Similarity	NPD5696	Approved
0.6522	Remote Similarity	NPD5778	Approved
0.6522	Remote Similarity	NPD5779	Approved
0.6522	Remote Similarity	NPD4202	Approved
0.6515	Remote Similarity	NPD8341	Approved
0.6515	Remote Similarity	NPD8299	Approved
0.6515	Remote Similarity	NPD8340	Approved
0.6515	Remote Similarity	NPD8342	Approved
0.65	Remote Similarity	NPD7632	Discontinued
0.6496	Remote Similarity	NPD8450	Suspended
0.6484	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7525	Registered
0.6471	Remote Similarity	NPD4700	Approved
0.6471	Remote Similarity	NPD5285	Approved
0.6471	Remote Similarity	NPD5286	Approved
0.6471	Remote Similarity	NPD4696	Approved
0.6466	Remote Similarity	NPD8451	Approved
0.6435	Remote Similarity	NPD6079	Approved
0.6429	Remote Similarity	NPD6684	Approved
0.6429	Remote Similarity	NPD6409	Approved
0.6429	Remote Similarity	NPD7521	Approved
0.6429	Remote Similarity	NPD7146	Approved
0.6429	Remote Similarity	NPD5330	Approved
0.6429	Remote Similarity	NPD7334	Approved
0.6418	Remote Similarity	NPD8448	Approved
0.6417	Remote Similarity	NPD5344	Discontinued
0.6414	Remote Similarity	NPD7625	Phase 1
0.641	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5695	Phase 3
0.6406	Remote Similarity	NPD6940	Discontinued
0.6406	Remote Similarity	NPD6274	Approved
0.6397	Remote Similarity	NPD8391	Approved
0.6397	Remote Similarity	NPD8390	Approved
0.6397	Remote Similarity	NPD8392	Approved
0.6385	Remote Similarity	NPD7100	Approved
0.6385	Remote Similarity	NPD7101	Approved
0.6364	Remote Similarity	NPD5224	Approved
0.6364	Remote Similarity	NPD4633	Approved
0.6364	Remote Similarity	NPD5211	Phase 2
0.6364	Remote Similarity	NPD5225	Approved
0.6364	Remote Similarity	NPD5226	Approved
0.6356	Remote Similarity	NPD4697	Phase 3
0.6341	Remote Similarity	NPD4767	Approved
0.6341	Remote Similarity	NPD4768	Approved
0.6316	Remote Similarity	NPD5737	Approved
0.6316	Remote Similarity	NPD6903	Approved
0.6316	Remote Similarity	NPD6672	Approved
0.6311	Remote Similarity	NPD5174	Approved
0.6311	Remote Similarity	NPD5175	Approved
0.6308	Remote Similarity	NPD7641	Discontinued
0.6308	Remote Similarity	NPD6335	Approved
0.6299	Remote Similarity	NPD6053	Discontinued
0.6296	Remote Similarity	NPD6697	Approved
0.6296	Remote Similarity	NPD6114	Approved
0.6296	Remote Similarity	NPD6115	Approved
0.6296	Remote Similarity	NPD6118	Approved
0.629	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD6909	Approved
0.6288	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD6908	Approved
0.6281	Remote Similarity	NPD5223	Approved
0.627	Remote Similarity	NPD6371	Approved
0.6261	Remote Similarity	NPD4753	Phase 2
0.626	Remote Similarity	NPD5141	Approved
0.625	Remote Similarity	NPD3668	Phase 3
0.625	Remote Similarity	NPD3665	Phase 1
0.625	Remote Similarity	NPD8336	Approved
0.625	Remote Similarity	NPD3666	Approved
0.625	Remote Similarity	NPD8337	Approved
0.625	Remote Similarity	NPD3133	Approved
0.6241	Remote Similarity	NPD8080	Discontinued
0.624	Remote Similarity	NPD4730	Approved
0.624	Remote Similarity	NPD4729	Approved
0.6231	Remote Similarity	NPD6317	Approved
0.6228	Remote Similarity	NPD7524	Approved
0.6218	Remote Similarity	NPD5221	Approved
0.6218	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD5222	Approved
0.6218	Remote Similarity	NPD7839	Suspended
0.6207	Remote Similarity	NPD7838	Discovery
0.6204	Remote Similarity	NPD6116	Phase 1
0.6194	Remote Similarity	NPD7829	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