NPASS Compound

Structure

CID120728 OpenBabel06191715472D 50 55 0 0 1 0 0 0 0 0999 V2000 4.5983 -1.2318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0934 -3.6637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9683 -6.0036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4260 -2.8647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2920 -4.3647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2920 -2.3647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1580 -3.8647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0366 -2.8675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5600 -4.3647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3036 -2.1874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1506 -5.4280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4260 -3.8647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1580 -2.8647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 -2.3364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9619 -3.8647 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6939 -3.8647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 -3.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1356 -4.4281 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 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1801 -4.1333 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2043 -5.7512 0.0000 C 0 0 0 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 -6.0622 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0241 -2.3647 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6939 -2.8647 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9095 -6.7067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8279 -4.3647 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -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 2.6045 -4.9510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 18 2 0 0 0 0 3 19 2 0 0 0 0 4 8 1 0 0 0 0 4 20 2 0 0 0 0 5 9 2 0 0 0 0 5 20 1 0 0 0 0 6 10 1 0 0 0 0 6 21 2 0 0 0 0 7 11 2 0 0 0 0 7 21 1 0 0 0 0 8 22 2 0 0 0 0 9 22 1 0 0 0 0 10 23 2 0 0 0 0 11 23 1 0 0 0 0 12 17 1 0 0 0 0 12 26 1 0 0 0 0 13 20 1 0 0 0 0 13 28 1 0 0 0 0 14 21 1 0 0 0 0 14 29 1 0 0 0 0 15 25 1 0 0 0 0 16 46 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 19 36 1 0 0 0 0 22 38 1 0 0 0 0 23 39 1 0 0 0 0 24 15 1 1 0 0 0 24 30 1 0 0 0 0 25 48 1 1 0 0 0 26 31 1 0 0 0 0 26 47 1 1 0 0 0 27 16 1 6 0 0 0 27 32 1 0 0 0 0 27 49 1 0 0 0 0 28 40 2 0 0 0 0 28 46 1 0 0 0 0 29 41 2 0 0 0 0 29 47 1 0 0 0 0 30 18 1 1 0 0 0 30 35 1 0 0 0 0 31 19 1 1 0 0 0 31 35 1 0 0 0 0 32 33 1 0 0 0 0 32 42 1 1 0 0 0 33 34 1 0 0 0 0 33 43 1 6 0 0 0 34 37 1 0 0 0 0 34 44 1 1 0 0 0 35 50 1 6 0 0 0 36 45 2 0 0 0 0 36 50 1 0 0 0 0 37 48 1 6 0 0 0 37 49 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	692.25
Volume:	679.805
LogP:	1.377
LogD:	1.959
LogS:	-3.034
# Rotatable Bonds:	11
TPSA:	198.51
# H-Bond Aceptor:	13
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.11
Synthetic Accessibility Score:	5.23
Fsp3:	0.432
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.227
MDCK Permeability:	1.732309647195507e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.922
20% Bioavailability (F20%):	0.606
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	80.77709197998047%
Volume Distribution (VD):	0.344
Pgp-substrate:	8.189162254333496%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.014
CYP2C19-inhibitor:	0.176
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.642
CYP2C9-substrate:	0.283
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.653
CYP3A4-substrate:	0.236

ADMET: Excretion

Clearance (CL):	5.129
Half-life (T1/2):	0.848

ADMET: Toxicity

hERG Blockers:	0.149
Human Hepatotoxicity (H-HT):	0.95
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.159
Rat Oral Acute Toxicity:	0.866
Maximum Recommended Daily Dose:	0.811
Skin Sensitization:	0.07
Carcinogencity:	0.067
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.182

Download Data

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

Natural Product: NPC120728

Natural Product ID:	NPC120728
*Common Name:**	Ixerochinoside
IUPAC Name:	[(2R,3S,4S,5R,6R)-6-[[(3aR,4R,6aR,8S,9aR,9bR)-4-[2-(4-hydroxyphenyl)acetyl]oxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-8-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate
Synonyms:	Ixerochinoside
Standard InCHIKey:	HMUFZGUGGDDWBV-ITNUQCNVSA-N
Standard InCHI:	InChI=1S/C37H40O13/c1-17-12-26(47-29(41)14-21-6-10-23(39)11-7-21)31-19(3)36(45)50-35(31)30-18(2)25(15-24(17)30)48-37-34(44)33(43)32(42)27(49-37)16-46-28(40)13-20-4-8-22(38)9-5-20/h4-11,24-27,30-35,37-39,42-44H,1-3,12-16H2/t24-,25-,26+,27+,30-,31+,32+,33-,34+,35+,37+/m0/s1
SMILES:	C=C1C[C@H]([C@H]2C(=C)C(=O)O[C@@H]2[C@H]2C(=C)[C@H](C[C@@H]12)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)Cc2ccc(cc2)O)O1)O)O)O)OC(=O)Cc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455771
PubChem CID:	11158258
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001770] Guaianolides and derivatives

*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
NPO10533	Ixeris chinensis	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[15635221]
NPO10533	Ixeris chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067155]
NPO10533	Ixeris chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10533	Ixeris chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10533	Ixeris chinensis	Species	Asteraceae	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
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[512023]

☑ 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 NPC120728 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	328
0.1-0.2	1131
0.2-0.3	2705
0.3-0.4	5706
0.4-0.5	10980
0.5-0.6	10388
0.6-0.7	9565
0.7-0.8	1803
0.8-0.85	81
0.85-0.9	6
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9859	High Similarity	NPC35097
0.9714	High Similarity	NPC194938
0.9306	High Similarity	NPC473147
0.8904	High Similarity	NPC296659
0.8904	High Similarity	NPC202391
0.8859	High Similarity	NPC96599
0.88	High Similarity	NPC240592
0.88	High Similarity	NPC117346
0.875	High Similarity	NPC257847
0.8707	High Similarity	NPC478250
0.8684	High Similarity	NPC478235
0.8681	High Similarity	NPC471345
0.8654	High Similarity	NPC208676
0.8654	High Similarity	NPC130489
0.8649	High Similarity	NPC184464
0.8649	High Similarity	NPC251062
0.8645	High Similarity	NPC187205
0.8618	High Similarity	NPC289021
0.8618	High Similarity	NPC158546
0.8592	High Similarity	NPC478255
0.8581	High Similarity	NPC186296
0.8544	High Similarity	NPC145847
0.8531	High Similarity	NPC471066
0.8531	High Similarity	NPC471095
0.8516	High Similarity	NPC475484
0.8511	High Similarity	NPC225307
0.8506	High Similarity	NPC229354
0.8497	Intermediate Similarity	NPC475379
0.8493	Intermediate Similarity	NPC469696
0.8491	Intermediate Similarity	NPC109990
0.8487	Intermediate Similarity	NPC478236
0.8472	Intermediate Similarity	NPC164172
0.8467	Intermediate Similarity	NPC475528
0.8462	Intermediate Similarity	NPC475378
0.8446	Intermediate Similarity	NPC137501
0.8446	Intermediate Similarity	NPC7518
0.8446	Intermediate Similarity	NPC154262
0.8446	Intermediate Similarity	NPC159387
0.844	Intermediate Similarity	NPC288416
0.8435	Intermediate Similarity	NPC31745
0.8435	Intermediate Similarity	NPC220936
0.8414	Intermediate Similarity	NPC169398
0.8411	Intermediate Similarity	NPC474268
0.8411	Intermediate Similarity	NPC475539
0.8411	Intermediate Similarity	NPC143246
0.8411	Intermediate Similarity	NPC320734
0.8411	Intermediate Similarity	NPC119773
0.84	Intermediate Similarity	NPC77922
0.84	Intermediate Similarity	NPC473281
0.8392	Intermediate Similarity	NPC17968
0.8392	Intermediate Similarity	NPC470122
0.8392	Intermediate Similarity	NPC469705
0.8389	Intermediate Similarity	NPC148080
0.8389	Intermediate Similarity	NPC469623
0.8387	Intermediate Similarity	NPC245615
0.8387	Intermediate Similarity	NPC115466
0.8387	Intermediate Similarity	NPC299706
0.8387	Intermediate Similarity	NPC61604
0.8366	Intermediate Similarity	NPC478234
0.8366	Intermediate Similarity	NPC161955
0.8356	Intermediate Similarity	NPC123988
0.8345	Intermediate Similarity	NPC28637
0.8333	Intermediate Similarity	NPC293154
0.8333	Intermediate Similarity	NPC40305
0.8333	Intermediate Similarity	NPC46137
0.8333	Intermediate Similarity	NPC235294
0.8333	Intermediate Similarity	NPC281798
0.8323	Intermediate Similarity	NPC194705
0.8312	Intermediate Similarity	NPC229882
0.8312	Intermediate Similarity	NPC158635
0.8311	Intermediate Similarity	NPC171134
0.8311	Intermediate Similarity	NPC328273
0.8311	Intermediate Similarity	NPC321184
0.8311	Intermediate Similarity	NPC321638
0.8301	Intermediate Similarity	NPC28776
0.8301	Intermediate Similarity	NPC473138
0.8289	Intermediate Similarity	NPC212808
0.8282	Intermediate Similarity	NPC21956
0.828	Intermediate Similarity	NPC38699
0.8278	Intermediate Similarity	NPC63304
0.8258	Intermediate Similarity	NPC474620
0.8252	Intermediate Similarity	NPC158673
0.8243	Intermediate Similarity	NPC469364
0.8243	Intermediate Similarity	NPC100558
0.8243	Intermediate Similarity	NPC101686
0.8243	Intermediate Similarity	NPC65262
0.8243	Intermediate Similarity	NPC310252
0.8243	Intermediate Similarity	NPC84789
0.8243	Intermediate Similarity	NPC302583
0.8239	Intermediate Similarity	NPC179914
0.8231	Intermediate Similarity	NPC263829
0.8228	Intermediate Similarity	NPC163635
0.8228	Intermediate Similarity	NPC478055
0.8224	Intermediate Similarity	NPC210330
0.8214	Intermediate Similarity	NPC471067
0.8212	Intermediate Similarity	NPC105005
0.8212	Intermediate Similarity	NPC152796
0.8212	Intermediate Similarity	NPC475213
0.8207	Intermediate Similarity	NPC254819
0.8207	Intermediate Similarity	NPC138777
0.8207	Intermediate Similarity	NPC476407
0.8207	Intermediate Similarity	NPC225384
0.8207	Intermediate Similarity	NPC246869
0.82	Intermediate Similarity	NPC46644
0.8194	Intermediate Similarity	NPC87630
0.8194	Intermediate Similarity	NPC179128
0.8194	Intermediate Similarity	NPC116292
0.8194	Intermediate Similarity	NPC162569
0.8194	Intermediate Similarity	NPC267469
0.8194	Intermediate Similarity	NPC35160
0.8188	Intermediate Similarity	NPC49597
0.8188	Intermediate Similarity	NPC62800
0.8188	Intermediate Similarity	NPC324262
0.8182	Intermediate Similarity	NPC103533
0.8182	Intermediate Similarity	NPC471881
0.8182	Intermediate Similarity	NPC35288
0.8182	Intermediate Similarity	NPC156692
0.8182	Intermediate Similarity	NPC173150
0.8182	Intermediate Similarity	NPC45224
0.8182	Intermediate Similarity	NPC469687
0.8182	Intermediate Similarity	NPC471882
0.8176	Intermediate Similarity	NPC226759
0.8176	Intermediate Similarity	NPC49173
0.817	Intermediate Similarity	NPC208293
0.817	Intermediate Similarity	NPC473867
0.8169	Intermediate Similarity	NPC126991
0.8169	Intermediate Similarity	NPC83218
0.8163	Intermediate Similarity	NPC34293
0.8163	Intermediate Similarity	NPC886
0.8163	Intermediate Similarity	NPC287597
0.816	Intermediate Similarity	NPC88176
0.816	Intermediate Similarity	NPC469396
0.816	Intermediate Similarity	NPC469458
0.816	Intermediate Similarity	NPC149002
0.816	Intermediate Similarity	NPC469459
0.816	Intermediate Similarity	NPC469419
0.8158	Intermediate Similarity	NPC296954
0.8158	Intermediate Similarity	NPC300894
0.8158	Intermediate Similarity	NPC141455
0.8158	Intermediate Similarity	NPC196063
0.8156	Intermediate Similarity	NPC470907
0.8156	Intermediate Similarity	NPC232454
0.8156	Intermediate Similarity	NPC178449
0.8153	Intermediate Similarity	NPC87403
0.8148	Intermediate Similarity	NPC471861
0.8146	Intermediate Similarity	NPC296643
0.8143	Intermediate Similarity	NPC469686
0.8141	Intermediate Similarity	NPC140151
0.8137	Intermediate Similarity	NPC477627
0.8121	Intermediate Similarity	NPC260425
0.8117	Intermediate Similarity	NPC473149
0.8113	Intermediate Similarity	NPC228357
0.8112	Intermediate Similarity	NPC471157
0.8112	Intermediate Similarity	NPC61181
0.8095	Intermediate Similarity	NPC114116
0.8092	Intermediate Similarity	NPC204644
0.8092	Intermediate Similarity	NPC89317
0.8089	Intermediate Similarity	NPC106818
0.8089	Intermediate Similarity	NPC478268
0.8086	Intermediate Similarity	NPC471850
0.8085	Intermediate Similarity	NPC52097
0.8079	Intermediate Similarity	NPC47471
0.8079	Intermediate Similarity	NPC476377
0.8077	Intermediate Similarity	NPC12006
0.8077	Intermediate Similarity	NPC69367
0.8075	Intermediate Similarity	NPC269668
0.8075	Intermediate Similarity	NPC138993
0.8072	Intermediate Similarity	NPC477617
0.8072	Intermediate Similarity	NPC222665
0.8072	Intermediate Similarity	NPC149502
0.8072	Intermediate Similarity	NPC271755
0.8072	Intermediate Similarity	NPC254071
0.8071	Intermediate Similarity	NPC160854
0.8071	Intermediate Similarity	NPC469703
0.8071	Intermediate Similarity	NPC469704
0.8071	Intermediate Similarity	NPC201402
0.8069	Intermediate Similarity	NPC214246
0.8067	Intermediate Similarity	NPC81515
0.8067	Intermediate Similarity	NPC68092
0.8067	Intermediate Similarity	NPC197316
0.8067	Intermediate Similarity	NPC220942
0.8067	Intermediate Similarity	NPC89105
0.8067	Intermediate Similarity	NPC472350
0.8067	Intermediate Similarity	NPC64141
0.8067	Intermediate Similarity	NPC476383
0.8067	Intermediate Similarity	NPC205195
0.8063	Intermediate Similarity	NPC4747
0.8063	Intermediate Similarity	NPC104275
0.8056	Intermediate Similarity	NPC106677
0.8054	Intermediate Similarity	NPC472132
0.8054	Intermediate Similarity	NPC470572
0.8052	Intermediate Similarity	NPC229505
0.8052	Intermediate Similarity	NPC291153
0.8052	Intermediate Similarity	NPC3982
0.805	Intermediate Similarity	NPC186316
0.8039	Intermediate Similarity	NPC471028
0.8038	Intermediate Similarity	NPC471874
0.8026	Intermediate Similarity	NPC65833
0.8025	Intermediate Similarity	NPC293568
0.8025	Intermediate Similarity	NPC471858

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 NPC120728 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	701
0.2-0.3	1573
0.3-0.4	2763
0.4-0.5	2361
0.5-0.6	1181
0.6-0.7	277
0.7-0.8	25
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
0.8067	Intermediate Similarity	NPD7266	Discontinued
0.8024	Intermediate Similarity	NPD7685	Pre-registration
0.7875	Intermediate Similarity	NPD8455	Phase 2
0.7836	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7228	Approved
0.7683	Intermediate Similarity	NPD6234	Discontinued
0.7669	Intermediate Similarity	NPD4967	Phase 2
0.7669	Intermediate Similarity	NPD4965	Approved
0.7669	Intermediate Similarity	NPD4966	Approved
0.7651	Intermediate Similarity	NPD3764	Approved
0.7628	Intermediate Similarity	NPD6190	Approved
0.7622	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD37	Approved
0.7532	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7199	Phase 2
0.7471	Intermediate Similarity	NPD3818	Discontinued
0.7452	Intermediate Similarity	NPD4628	Phase 3
0.7434	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6559	Discontinued
0.7399	Intermediate Similarity	NPD7240	Approved
0.7386	Intermediate Similarity	NPD6355	Discontinued
0.7368	Intermediate Similarity	NPD6663	Approved
0.7326	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6004	Phase 3
0.7261	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6005	Phase 3
0.7261	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6002	Phase 3
0.7256	Intermediate Similarity	NPD4380	Phase 2
0.7246	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5736	Approved
0.7202	Intermediate Similarity	NPD7075	Discontinued
0.7184	Intermediate Similarity	NPD7074	Phase 3
0.7168	Intermediate Similarity	NPD7799	Discontinued
0.716	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7054	Approved
0.7125	Intermediate Similarity	NPD8166	Discontinued
0.7115	Intermediate Similarity	NPD6653	Approved
0.7091	Intermediate Similarity	NPD7458	Discontinued
0.7086	Intermediate Similarity	NPD7472	Approved
0.7076	Intermediate Similarity	NPD8127	Discontinued
0.7073	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7097	Phase 1
0.7062	Intermediate Similarity	NPD7808	Phase 3
0.7045	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5647	Approved
0.7032	Intermediate Similarity	NPD6233	Phase 2
0.703	Intermediate Similarity	NPD1653	Approved
0.7027	Intermediate Similarity	NPD5126	Approved
0.7027	Intermediate Similarity	NPD5125	Phase 3
0.7024	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7680	Approved
0.7013	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6273	Approved
0.7007	Intermediate Similarity	NPD9545	Approved
0.7006	Intermediate Similarity	NPD7251	Discontinued
0.6993	Remote Similarity	NPD2861	Phase 2
0.6989	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6798	Discontinued
0.6951	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6797	Phase 2
0.6943	Remote Similarity	NPD230	Phase 1
0.6933	Remote Similarity	NPD1091	Approved
0.6923	Remote Similarity	NPD7930	Approved
0.6923	Remote Similarity	NPD7819	Suspended
0.6923	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7033	Discontinued
0.6914	Remote Similarity	NPD3750	Approved
0.6914	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD8434	Phase 2
0.6906	Remote Similarity	NPD8150	Discontinued
0.6895	Remote Similarity	NPD8320	Phase 1
0.6895	Remote Similarity	NPD8319	Approved
0.6894	Remote Similarity	NPD5958	Discontinued
0.6889	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5402	Approved
0.6882	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5403	Approved
0.6864	Remote Similarity	NPD6801	Discontinued
0.6863	Remote Similarity	NPD3094	Phase 2
0.6859	Remote Similarity	NPD7999	Approved
0.6859	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7028	Phase 2
0.6842	Remote Similarity	NPD7768	Phase 2
0.6832	Remote Similarity	NPD5762	Approved
0.6832	Remote Similarity	NPD5763	Approved
0.6829	Remote Similarity	NPD5058	Phase 3
0.6813	Remote Similarity	NPD2799	Discontinued
0.6805	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.679	Remote Similarity	NPD1549	Phase 2
0.6776	Remote Similarity	NPD1608	Approved
0.677	Remote Similarity	NPD2438	Suspended
0.677	Remote Similarity	NPD2935	Discontinued
0.6765	Remote Similarity	NPD1934	Approved
0.6759	Remote Similarity	NPD969	Suspended
0.6755	Remote Similarity	NPD7700	Phase 2
0.6755	Remote Similarity	NPD7699	Phase 2
0.6754	Remote Similarity	NPD7435	Discontinued
0.6753	Remote Similarity	NPD2797	Approved
0.6753	Remote Similarity	NPD6362	Approved
0.6747	Remote Similarity	NPD5401	Approved
0.6742	Remote Similarity	NPD5844	Phase 1
0.6742	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD2629	Approved
0.6728	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD1465	Phase 2
0.6723	Remote Similarity	NPD7473	Discontinued
0.6711	Remote Similarity	NPD3092	Approved
0.6709	Remote Similarity	NPD4062	Phase 3
0.6708	Remote Similarity	NPD1510	Phase 2
0.6707	Remote Similarity	NPD3400	Discontinued
0.6707	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4110	Phase 3
0.6707	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7411	Suspended
0.6705	Remote Similarity	NPD3749	Approved
0.6689	Remote Similarity	NPD3019	Approved
0.6689	Remote Similarity	NPD2932	Approved
0.6688	Remote Similarity	NPD3027	Phase 3
0.6688	Remote Similarity	NPD7095	Approved
0.6687	Remote Similarity	NPD6799	Approved
0.6686	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3751	Discontinued
0.6684	Remote Similarity	NPD6535	Approved
0.6684	Remote Similarity	NPD6534	Approved
0.6667	Remote Similarity	NPD4060	Phase 1
0.6667	Remote Similarity	NPD1481	Phase 2
0.6667	Remote Similarity	NPD1613	Approved
0.6667	Remote Similarity	NPD4140	Approved
0.6667	Remote Similarity	NPD6166	Phase 2
0.6667	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8151	Discontinued
0.6667	Remote Similarity	NPD7137	Phase 2
0.6667	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6232	Discontinued
0.6648	Remote Similarity	NPD3787	Discontinued
0.6647	Remote Similarity	NPD6599	Discontinued
0.6647	Remote Similarity	NPD3882	Suspended
0.6646	Remote Similarity	NPD3268	Approved
0.6646	Remote Similarity	NPD6674	Discontinued
0.6643	Remote Similarity	NPD6685	Approved
0.6633	Remote Similarity	NPD7874	Approved
0.6633	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD5494	Approved
0.6628	Remote Similarity	NPD5760	Phase 2
0.6628	Remote Similarity	NPD5761	Phase 2
0.6627	Remote Similarity	NPD7236	Approved
0.6626	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD5735	Approved
0.6624	Remote Similarity	NPD4908	Phase 1
0.6615	Remote Similarity	NPD6823	Phase 2
0.6605	Remote Similarity	NPD5588	Approved
0.6605	Remote Similarity	NPD3748	Approved
0.6604	Remote Similarity	NPD8032	Phase 2
0.6603	Remote Similarity	NPD2798	Approved
0.6601	Remote Similarity	NPD1610	Phase 2
0.6601	Remote Similarity	NPD1535	Discovery
0.6599	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD7783	Phase 2
0.6597	Remote Similarity	NPD6779	Approved
0.6597	Remote Similarity	NPD6782	Approved
0.6597	Remote Similarity	NPD6780	Approved
0.6597	Remote Similarity	NPD6781	Approved
0.6597	Remote Similarity	NPD6776	Approved
0.6597	Remote Similarity	NPD6778	Approved
0.6597	Remote Similarity	NPD6777	Approved
0.659	Remote Similarity	NPD3817	Phase 2
0.6588	Remote Similarity	NPD3455	Phase 2
0.6585	Remote Similarity	NPD4534	Discontinued
0.6581	Remote Similarity	NPD1283	Approved
0.6581	Remote Similarity	NPD1876	Approved
0.658	Remote Similarity	NPD7696	Phase 3
0.658	Remote Similarity	NPD7698	Approved
0.658	Remote Similarity	NPD7697	Approved
0.6579	Remote Similarity	NPD17	Approved
0.6564	Remote Similarity	NPD5408	Approved
0.6564	Remote Similarity	NPD5406	Approved
0.6564	Remote Similarity	NPD1551	Phase 2
0.6564	Remote Similarity	NPD5404	Approved
0.6564	Remote Similarity	NPD5405	Approved
0.6562	Remote Similarity	NPD2979	Phase 3
0.6556	Remote Similarity	NPD3091	Approved
0.6556	Remote Similarity	NPD7741	Discontinued
0.6556	Remote Similarity	NPD1894	Discontinued
0.6554	Remote Similarity	NPD7229	Phase 3
0.6549	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5765	Approved
0.6548	Remote Similarity	NPD2533	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