NPASS Compound

Structure

CID179434 OpenBabel06191715552D 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 0.8521 3.4435 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 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 -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 -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 -5.1123 -3.9355 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 1.7041 2.9516 0.0000 C 0 0 1 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 2 0 0 0 0 0 0 0 0 0 -4.2603 -4.4274 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 1.7041 1.9677 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4082 -3.9355 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 -3.4082 -2.9516 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 -3.4082 -0.9839 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2603 -2.4597 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 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 -4.2603 0.4919 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2603 -5.4113 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5562 -4.4274 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 -2.5562 -2.4597 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 -5.1123 -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 -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 5 39 1 0 0 0 0 7 8 1 0 0 0 0 7 21 2 0 0 0 0 8 26 1 0 0 0 0 9 12 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 25 1 0 0 0 0 11 40 1 0 0 0 0 12 41 1 0 0 0 0 13 14 1 0 0 0 0 13 39 1 0 0 0 0 14 41 1 0 0 0 0 15 22 1 0 0 0 0 15 37 1 0 0 0 0 16 42 1 0 0 0 0 17 23 1 0 0 0 0 17 52 1 0 0 0 0 18 38 1 0 0 0 0 18 43 1 0 0 0 0 19 1 1 6 0 0 0 19 20 1 0 0 0 0 20 2 1 1 0 0 0 20 27 1 0 0 0 0 21 27 1 0 0 0 0 21 39 1 0 0 0 0 22 33 1 0 0 0 0 22 44 1 6 0 0 0 23 28 1 0 0 0 0 23 45 1 1 0 0 0 24 16 1 6 0 0 0 24 29 1 0 0 0 0 24 53 1 0 0 0 0 25 37 1 1 0 0 0 25 38 1 0 0 0 0 26 37 1 1 0 0 0 26 40 1 0 0 0 0 27 41 1 6 0 0 0 28 31 1 0 0 0 0 28 46 1 1 0 0 0 29 30 1 0 0 0 0 29 47 1 1 0 0 0 30 32 1 0 0 0 0 30 48 1 6 0 0 0 31 34 1 0 0 0 0 31 49 1 6 0 0 0 32 35 1 0 0 0 0 32 50 1 1 0 0 0 33 38 1 1 0 0 0 33 54 1 0 0 0 0 34 52 1 0 0 0 0 34 54 1 1 0 0 0 35 53 1 0 0 0 0 35 55 1 6 0 0 0 36 51 2 0 0 0 0 36 55 1 0 0 0 0 37 3 1 1 0 0 0 38 4 1 1 0 0 0 39 40 1 1 0 0 0 40 6 1 1 0 0 0 41 36 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	782.45
Volume:	775.587
LogP:	2.279
LogD:	2.401
LogS:	-3.606
# 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:	0.103
Synthetic Accessibility Score:	5.992
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:	-5.997
MDCK Permeability:	3.95338938687928e-05
Pgp-inhibitor:	0.664
Pgp-substrate:	0.041
Human Intestinal Absorption (HIA):	0.884
20% Bioavailability (F20%):	0.146
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	86.80750274658203%
Volume Distribution (VD):	0.4
Pgp-substrate:	8.244731903076172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.889
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.606
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.052
CYP3A4-inhibitor:	0.197
CYP3A4-substrate:	0.053

ADMET: Excretion

Clearance (CL):	0.907
Half-life (T1/2):	0.645

ADMET: Toxicity

hERG Blockers:	0.113
Human Hepatotoxicity (H-HT):	0.245
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.083
Rat Oral Acute Toxicity:	0.098
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.028
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.874

Download Data

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

Natural Product: NPC179434

Natural Product ID:	NPC179434
*Common Name:**	Ilekudinoside C
IUPAC Name:	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,2R,4aS,6aR,6aS,6bR,8aR,9R,10R,11R,12aR,14bS)-11-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-tetradecahydro-1H-picene-4a-carboxylate
Synonyms:	Ilekudinoside C
Standard InCHIKey:	JEUZHXDEBVXESF-SMFLOBOHSA-N
Standard InCHI:	InChI=1S/C41H66O14/c1-19-9-12-41(36(51)55-35-32(50)30(48)29(47)24(16-42)53-35)14-13-39(5)21(27(41)20(19)2)7-8-26-37(3)15-22(44)33(54-34-31(49)28(46)23(45)17-52-34)38(4,18-43)25(37)10-11-40(26,39)6/h7,19-20,22-35,42-50H,8-18H2,1-6H3/t19-,20+,22-,23+,24-,25-,26-,27+,28+,29-,30+,31-,32-,33+,34+,35+,37+,38+,39-,40-,41+/m1/s1
SMILES:	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@@H]([C@@](C)(CO)[C@@H]5CC[C@@]34C)O[C@H]3[C@@H]([C@H]([C@H](CO3)O)O)O)O)[C@@H]2[C@H]1C)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501236
PubChem CID:	21635823
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	=	35.5	%	PMID[447742]

☑ 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 NPC179434 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	261
0.1-0.2	1734
0.2-0.3	5041
0.3-0.4	11575
0.4-0.5	10608
0.5-0.6	6154
0.6-0.7	4072
0.7-0.8	1945
0.8-0.85	626
0.85-0.9	307
0.9-0.95	140
0.95-1	234

Similarity Score	Similarity Level	Natural Product ID
0.9903	High Similarity	NPC473383
0.9903	High Similarity	NPC139894
0.9902	High Similarity	NPC474589
0.9902	High Similarity	NPC29069
0.9902	High Similarity	NPC56713
0.9902	High Similarity	NPC475296
0.9902	High Similarity	NPC199457
0.9902	High Similarity	NPC279554
0.9902	High Similarity	NPC127056
0.9902	High Similarity	NPC108709
0.9902	High Similarity	NPC68419
0.9902	High Similarity	NPC174679
0.9902	High Similarity	NPC90856
0.9902	High Similarity	NPC59804
0.9902	High Similarity	NPC270667
0.9902	High Similarity	NPC110139
0.9902	High Similarity	NPC164194
0.9902	High Similarity	NPC136877
0.9902	High Similarity	NPC102914
0.9902	High Similarity	NPC7870
0.9902	High Similarity	NPC75747
0.9808	High Similarity	NPC238935
0.9808	High Similarity	NPC473343
0.9808	High Similarity	NPC163183
0.9808	High Similarity	NPC475208
0.9808	High Similarity	NPC150400
0.9808	High Similarity	NPC73318
0.9808	High Similarity	NPC96641
0.9808	High Similarity	NPC134835
0.9806	High Similarity	NPC164419
0.9806	High Similarity	NPC30397
0.9806	High Similarity	NPC211798
0.9806	High Similarity	NPC473481
0.9806	High Similarity	NPC235841
0.9806	High Similarity	NPC297208
0.9806	High Similarity	NPC108748
0.9804	High Similarity	NPC306746
0.9804	High Similarity	NPC167383
0.9804	High Similarity	NPC237503
0.9804	High Similarity	NPC57362
0.9804	High Similarity	NPC127853
0.9804	High Similarity	NPC204407
0.9712	High Similarity	NPC139044
0.9712	High Similarity	NPC102439
0.9712	High Similarity	NPC48249
0.9712	High Similarity	NPC1046
0.9712	High Similarity	NPC256798
0.9712	High Similarity	NPC104400
0.9712	High Similarity	NPC257468
0.9712	High Similarity	NPC104071
0.9712	High Similarity	NPC10320
0.9712	High Similarity	NPC324875
0.9712	High Similarity	NPC276093
0.9712	High Similarity	NPC475504
0.9712	High Similarity	NPC469946
0.9712	High Similarity	NPC475516
0.9712	High Similarity	NPC471383
0.9712	High Similarity	NPC101744
0.9712	High Similarity	NPC473373
0.9712	High Similarity	NPC109079
0.9712	High Similarity	NPC128925
0.9712	High Similarity	NPC79718
0.9712	High Similarity	NPC80843
0.9712	High Similarity	NPC292677
0.9712	High Similarity	NPC116794
0.9709	High Similarity	NPC476880
0.9709	High Similarity	NPC269095
0.9709	High Similarity	NPC476884
0.9709	High Similarity	NPC476887
0.9709	High Similarity	NPC274507
0.9709	High Similarity	NPC476882
0.9709	High Similarity	NPC476881
0.9709	High Similarity	NPC476885
0.9709	High Similarity	NPC476883
0.9709	High Similarity	NPC78046
0.9709	High Similarity	NPC476886
0.9709	High Similarity	NPC220984
0.9706	High Similarity	NPC476123
0.9706	High Similarity	NPC177246
0.9706	High Similarity	NPC284807
0.9706	High Similarity	NPC28198
0.9619	High Similarity	NPC219180
0.9619	High Similarity	NPC251263
0.9619	High Similarity	NPC114304
0.9619	High Similarity	NPC114287
0.9619	High Similarity	NPC204458
0.9619	High Similarity	NPC271138
0.9619	High Similarity	NPC189884
0.9619	High Similarity	NPC241909
0.9619	High Similarity	NPC258885
0.9619	High Similarity	NPC295823
0.9619	High Similarity	NPC475467
0.9619	High Similarity	NPC138334
0.9619	High Similarity	NPC166422
0.9619	High Similarity	NPC133818
0.9619	High Similarity	NPC473826
0.9619	High Similarity	NPC475287
0.9619	High Similarity	NPC47063
0.9619	High Similarity	NPC151543
0.9619	High Similarity	NPC192600
0.9619	High Similarity	NPC174720
0.9619	High Similarity	NPC269315
0.9619	High Similarity	NPC309714
0.9619	High Similarity	NPC323341
0.9619	High Similarity	NPC155410
0.9619	High Similarity	NPC124296
0.9619	High Similarity	NPC46665
0.9615	High Similarity	NPC191763
0.9615	High Similarity	NPC31839
0.9612	High Similarity	NPC137917
0.9608	High Similarity	NPC473538
0.9608	High Similarity	NPC283849
0.9533	High Similarity	NPC473405
0.9533	High Similarity	NPC471547
0.9533	High Similarity	NPC300419
0.9528	High Similarity	NPC475633
0.9528	High Similarity	NPC293330
0.9528	High Similarity	NPC475140
0.9528	High Similarity	NPC67857
0.9528	High Similarity	NPC473714
0.9528	High Similarity	NPC475486
0.9528	High Similarity	NPC65105
0.9528	High Similarity	NPC204414
0.9528	High Similarity	NPC123199
0.9528	High Similarity	NPC70809
0.9528	High Similarity	NPC100639
0.9528	High Similarity	NPC41061
0.9528	High Similarity	NPC469782
0.9528	High Similarity	NPC54636
0.9528	High Similarity	NPC164389
0.9528	High Similarity	NPC119592
0.9528	High Similarity	NPC57484
0.9528	High Similarity	NPC4328
0.9528	High Similarity	NPC471385
0.9528	High Similarity	NPC161717
0.9528	High Similarity	NPC476068
0.9528	High Similarity	NPC60557
0.9528	High Similarity	NPC298034
0.9528	High Similarity	NPC202828
0.9528	High Similarity	NPC224381
0.9528	High Similarity	NPC305981
0.9528	High Similarity	NPC261506
0.9528	High Similarity	NPC227551
0.9528	High Similarity	NPC43550
0.9528	High Similarity	NPC236638
0.9528	High Similarity	NPC71065
0.9528	High Similarity	NPC79643
0.9528	High Similarity	NPC250247
0.9528	High Similarity	NPC471550
0.9528	High Similarity	NPC309907
0.9528	High Similarity	NPC76972
0.9528	High Similarity	NPC475160
0.9528	High Similarity	NPC294453
0.9524	High Similarity	NPC46388
0.9524	High Similarity	NPC37739
0.9524	High Similarity	NPC471967
0.9519	High Similarity	NPC242611
0.9515	High Similarity	NPC285576
0.951	High Similarity	NPC475611
0.9444	High Similarity	NPC237191
0.9444	High Similarity	NPC475899
0.9444	High Similarity	NPC471548
0.9439	High Similarity	NPC476992
0.9439	High Similarity	NPC471384
0.9439	High Similarity	NPC160415
0.9439	High Similarity	NPC288205
0.9439	High Similarity	NPC26626
0.9439	High Similarity	NPC37134
0.9439	High Similarity	NPC75287
0.9439	High Similarity	NPC161674
0.9439	High Similarity	NPC305267
0.9439	High Similarity	NPC51465
0.9439	High Similarity	NPC291903
0.9439	High Similarity	NPC58448
0.9412	High Similarity	NPC173583
0.9358	High Similarity	NPC477464
0.9358	High Similarity	NPC471577
0.9358	High Similarity	NPC473401
0.9352	High Similarity	NPC473824
0.9352	High Similarity	NPC33012
0.9352	High Similarity	NPC85154
0.9352	High Similarity	NPC309223
0.9352	High Similarity	NPC185466
0.9352	High Similarity	NPC68175
0.9352	High Similarity	NPC475209
0.9352	High Similarity	NPC470876
0.9352	High Similarity	NPC110633
0.9352	High Similarity	NPC69811
0.9352	High Similarity	NPC475119
0.9352	High Similarity	NPC473452
0.9352	High Similarity	NPC286457
0.9352	High Similarity	NPC475514
0.9352	High Similarity	NPC8524
0.9352	High Similarity	NPC148417
0.9352	High Similarity	NPC136768
0.9352	High Similarity	NPC191827
0.9352	High Similarity	NPC102505
0.9352	High Similarity	NPC220160
0.9352	High Similarity	NPC323359
0.9352	High Similarity	NPC123522

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 NPC179434 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	2040
0.2-0.3	3857
0.3-0.4	1946
0.4-0.5	621
0.5-0.6	270
0.6-0.7	141
0.7-0.8	22
0.8-0.85	9
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9057	High Similarity	NPD8132	Clinical (unspecified phase)
0.886	High Similarity	NPD8328	Phase 3
0.8829	High Similarity	NPD8295	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD8133	Approved
0.8182	Intermediate Similarity	NPD6412	Phase 2
0.8108	Intermediate Similarity	NPD6686	Approved
0.8	Intermediate Similarity	NPD7748	Approved
0.7966	Intermediate Similarity	NPD8377	Approved
0.7966	Intermediate Similarity	NPD8294	Approved
0.7944	Intermediate Similarity	NPD7902	Approved
0.7934	Intermediate Similarity	NPD7507	Approved
0.7899	Intermediate Similarity	NPD8380	Approved
0.7899	Intermediate Similarity	NPD8379	Approved
0.7899	Intermediate Similarity	NPD8378	Approved
0.7899	Intermediate Similarity	NPD8033	Approved
0.7899	Intermediate Similarity	NPD8296	Approved
0.7899	Intermediate Similarity	NPD8335	Approved
0.781	Intermediate Similarity	NPD7515	Phase 2
0.7742	Intermediate Similarity	NPD7319	Approved
0.7731	Intermediate Similarity	NPD7516	Approved
0.7664	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD7900	Approved
0.7661	Intermediate Similarity	NPD7736	Approved
0.7647	Intermediate Similarity	NPD7328	Approved
0.7647	Intermediate Similarity	NPD7327	Approved
0.7603	Intermediate Similarity	NPD8513	Phase 3
0.7603	Intermediate Similarity	NPD8517	Approved
0.7603	Intermediate Similarity	NPD8516	Approved
0.7603	Intermediate Similarity	NPD8515	Approved
0.7459	Intermediate Similarity	NPD7503	Approved
0.744	Intermediate Similarity	NPD8293	Discontinued
0.7368	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD8034	Phase 2
0.7315	Intermediate Similarity	NPD8035	Phase 2
0.7265	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6370	Approved
0.7232	Intermediate Similarity	NPD7638	Approved
0.7227	Intermediate Similarity	NPD8297	Approved
0.7227	Intermediate Similarity	NPD6882	Approved
0.7179	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7640	Approved
0.7168	Intermediate Similarity	NPD7639	Approved
0.7157	Intermediate Similarity	NPD7645	Phase 2
0.7143	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7492	Approved
0.7131	Intermediate Similarity	NPD6009	Approved
0.7097	Intermediate Similarity	NPD6054	Approved
0.7097	Intermediate Similarity	NPD6059	Approved
0.7097	Intermediate Similarity	NPD6319	Approved
0.7091	Intermediate Similarity	NPD6399	Phase 3
0.7087	Intermediate Similarity	NPD6616	Approved
0.7075	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6067	Discontinued
0.7059	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7078	Approved
0.7025	Intermediate Similarity	NPD4632	Approved
0.7009	Intermediate Similarity	NPD5739	Approved
0.7009	Intermediate Similarity	NPD6402	Approved
0.7009	Intermediate Similarity	NPD6675	Approved
0.7009	Intermediate Similarity	NPD7128	Approved
0.6975	Remote Similarity	NPD6373	Approved
0.6975	Remote Similarity	NPD6372	Approved
0.6937	Remote Similarity	NPD8171	Discontinued
0.6905	Remote Similarity	NPD6015	Approved
0.6905	Remote Similarity	NPD6016	Approved
0.6891	Remote Similarity	NPD6881	Approved
0.6891	Remote Similarity	NPD6899	Approved
0.6891	Remote Similarity	NPD7320	Approved
0.686	Remote Similarity	NPD6650	Approved
0.686	Remote Similarity	NPD8130	Phase 1
0.686	Remote Similarity	NPD6649	Approved
0.6855	Remote Similarity	NPD7115	Discovery
0.685	Remote Similarity	NPD5988	Approved
0.6847	Remote Similarity	NPD6411	Approved
0.6807	Remote Similarity	NPD5697	Approved
0.6807	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5701	Approved
0.6777	Remote Similarity	NPD6883	Approved
0.6777	Remote Similarity	NPD7102	Approved
0.6777	Remote Similarity	NPD7290	Approved
0.6769	Remote Similarity	NPD8074	Phase 3
0.6757	Remote Similarity	NPD46	Approved
0.6757	Remote Similarity	NPD6698	Approved
0.6727	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6847	Approved
0.6721	Remote Similarity	NPD6869	Approved
0.6721	Remote Similarity	NPD6617	Approved
0.6697	Remote Similarity	NPD3618	Phase 1
0.6696	Remote Similarity	NPD6084	Phase 2
0.6696	Remote Similarity	NPD6083	Phase 2
0.6694	Remote Similarity	NPD6014	Approved
0.6694	Remote Similarity	NPD6012	Approved
0.6694	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6641	Remote Similarity	NPD6921	Approved
0.6641	Remote Similarity	NPD5983	Phase 2
0.6638	Remote Similarity	NPD4225	Approved
0.6636	Remote Similarity	NPD3573	Approved
0.6636	Remote Similarity	NPD3667	Approved
0.6612	Remote Similarity	NPD6011	Approved
0.661	Remote Similarity	NPD7632	Discontinued
0.6591	Remote Similarity	NPD6033	Approved
0.6585	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6008	Approved
0.6574	Remote Similarity	NPD3669	Approved
0.6574	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD6336	Discontinued
0.6552	Remote Similarity	NPD4755	Approved
0.6549	Remote Similarity	NPD6079	Approved
0.6549	Remote Similarity	NPD7983	Approved
0.6545	Remote Similarity	NPD7521	Approved
0.6545	Remote Similarity	NPD7334	Approved
0.6545	Remote Similarity	NPD6684	Approved
0.6545	Remote Similarity	NPD7146	Approved
0.6545	Remote Similarity	NPD5330	Approved
0.6545	Remote Similarity	NPD6409	Approved
0.6519	Remote Similarity	NPD8449	Approved
0.6518	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6940	Discontinued
0.6504	Remote Similarity	NPD4634	Approved
0.6503	Remote Similarity	NPD7625	Phase 1
0.6496	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5778	Approved
0.6491	Remote Similarity	NPD5779	Approved
0.6491	Remote Similarity	NPD4202	Approved
0.6471	Remote Similarity	NPD8450	Suspended
0.6449	Remote Similarity	NPD7525	Registered
0.6441	Remote Similarity	NPD4700	Approved
0.6441	Remote Similarity	NPD5286	Approved
0.6441	Remote Similarity	NPD5285	Approved
0.6441	Remote Similarity	NPD4696	Approved
0.6429	Remote Similarity	NPD5737	Approved
0.6429	Remote Similarity	NPD6672	Approved
0.6429	Remote Similarity	NPD6903	Approved
0.6415	Remote Similarity	NPD6115	Approved
0.6415	Remote Similarity	NPD6118	Approved
0.6415	Remote Similarity	NPD6114	Approved
0.6415	Remote Similarity	NPD6697	Approved
0.6389	Remote Similarity	NPD1779	Approved
0.6389	Remote Similarity	NPD1780	Approved
0.6387	Remote Similarity	NPD5344	Discontinued
0.6379	Remote Similarity	NPD5695	Phase 3
0.6378	Remote Similarity	NPD6274	Approved
0.6364	Remote Similarity	NPD3665	Phase 1
0.6364	Remote Similarity	NPD3133	Approved
0.6364	Remote Similarity	NPD3666	Approved
0.6357	Remote Similarity	NPD7100	Approved
0.6357	Remote Similarity	NPD7101	Approved
0.6356	Remote Similarity	NPD5696	Approved
0.6343	Remote Similarity	NPD8337	Approved
0.6343	Remote Similarity	NPD8336	Approved
0.6333	Remote Similarity	NPD5224	Approved
0.6333	Remote Similarity	NPD5226	Approved
0.6333	Remote Similarity	NPD4633	Approved
0.6333	Remote Similarity	NPD5211	Phase 2
0.6333	Remote Similarity	NPD5225	Approved
0.6328	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD4697	Phase 3
0.6325	Remote Similarity	NPD5221	Approved
0.6325	Remote Similarity	NPD5222	Approved
0.6325	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6116	Phase 1
0.6311	Remote Similarity	NPD4767	Approved
0.6311	Remote Similarity	NPD4768	Approved
0.6281	Remote Similarity	NPD5174	Approved
0.6281	Remote Similarity	NPD5175	Approved
0.6279	Remote Similarity	NPD6335	Approved
0.6277	Remote Similarity	NPD8338	Approved
0.6271	Remote Similarity	NPD5173	Approved
0.626	Remote Similarity	NPD6908	Approved
0.626	Remote Similarity	NPD6909	Approved
0.625	Remote Similarity	NPD6868	Approved
0.625	Remote Similarity	NPD5223	Approved
0.6241	Remote Similarity	NPD8299	Approved
0.6241	Remote Similarity	NPD8342	Approved
0.6241	Remote Similarity	NPD8341	Approved
0.6241	Remote Similarity	NPD8340	Approved
0.6239	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5141	Approved
0.6228	Remote Similarity	NPD4753	Phase 2
0.6226	Remote Similarity	NPD6117	Approved
0.6216	Remote Similarity	NPD3668	Phase 3
0.621	Remote Similarity	NPD4730	Approved
0.621	Remote Similarity	NPD4729	Approved
0.6202	Remote Similarity	NPD6317	Approved
0.6195	Remote Similarity	NPD7524	Approved
0.6194	Remote Similarity	NPD8451	Approved
0.6186	Remote Similarity	NPD7732	Phase 3
0.6186	Remote Similarity	NPD7614	Phase 1
0.6186	Remote Similarity	NPD7839	Suspended
0.6174	Remote Similarity	NPD7838	Discovery
0.6165	Remote Similarity	NPD7830	Approved
0.6165	Remote Similarity	NPD7829	Approved
0.6154	Remote Similarity	NPD6313	Approved
0.6154	Remote Similarity	NPD6314	Approved
0.6154	Remote Similarity	NPD7641	Discontinued

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